ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue 15 - The Plan You Don’t Have

Today’s issue begins The Meaning Plan series — five-articles on what you build inside your Golden Window, once you've seen it.

Somewhere in a drawer or a portal, you have a document that describes your retirement in detail. It has a date on it, and numbers, and someone has probably stress-tested it. What you almost certainly do not have is a different document entirely, one describing the life those years will contain. Most people never notice the gap, because the financial plan is so thorough that it feels like the whole plan.

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A Coaching Story

I worked recently with a couple who had done everything right.

She chairs a department at a large university in the Midwest and holds a national leadership role in her field. He was a financial advisor and has been retired for two years. Between them, they have a retirement financial strategy in better shape than most: modeled, stress-tested, and revisited on a schedule. He built it himself, the way he built them for other people his whole career.

When I asked what they could afford, the answer arrived fast and with numbers attached. They can live comfortably. The withdrawal rate is set, and there are contingencies for the contingencies.

When I asked what an ordinary Wednesday would look like the first spring after she steps down, something shifted.

She said she wants to stay engaged professionally and hold onto her national role. He said he wants to travel and see the grandchildren. Both answers were true and reasonable, yet neither had ever been articulated in quite those words. And neither of them could say what their answer really meant. What would “staying engaged” actually consist of, on a calendar? Which weeks would the travel take, and who would be in the house the rest of the time?

They had never built a detailed spending budget for retirement, and the reason was not carelessness. You cannot budget for a life you have not yet defined.

So we walked through the architecture of a week. Hobbies: neither of them has one they have kept up. Friends: their professional networks ran on separate tracks for most of their careers, and the two close couple-friends they have are consumed right now by serious health issues, so they are largely unavailable. The two of them are originally from the East Coast, and they live in a midwestern city they moved to for her job. Their children are bicoastal.

Every decision they’d made for their future had been a sound one. They were simply all focused on the money. They had given almost no thought to their daily life in their next phase.

(De-identified composite story does not represent the experience of any one person or organization.)

The Changing World of Work

Their situation is a common one. Only 11% of couples retire at the same time, and nearly two-thirds stagger their exits by a year or more. (Ameriprise Financial, “Couples, Money & Retirement,” 2024) Very few couples plan for that stretch of years, because on paper it reads as one person’s date moving rather than as a gap at all.

He saw the problem before she did, because he used to sit on the other side of that desk.

Among Americans in their 50s and 60s who work with a financial professional, 87% have discussed an investment strategy for retirement. Only 53% have discussed a budget for the activities they say they want to do. (Lincoln Financial Group, “The Action Plan,” 2024) Same client, same office, same hour. One half of that conversation is standard practice, and the other half of the planning is optional.

Here is what I did not expect. The largest study of its kind pooled 125 reports and data from 78,632 people. Of the five things it analyzed, social participation was the strongest predictor of how well people adjust after leaving work, and it outperformed finances by a statistically significant margin. Financial preparedness had a correlation coefficient of .07 and did not reach statistical significance at all. (La Rue, Haslam and Steffens, “A meta-analysis of retirement adjustment predictors,” Journal of Vocational Behavior, 2022)

Income and net worth were important, so let me be careful here: having enough money is real, and it matters. It was the planning — the part everyone dutifully does — that failed to predict how the years, and the satisfaction with life, would actually go.

And social participation, the study’s strongest predictor of adjusting well to retirement, is exactly what this couple has the least of. People rightly worry about purpose after retirement, but it’s the easier piece to rebuild, because a person can go looking for purpose alone. A life with people in it is the hard part. It requires other people, and at this stage of life they have to be recruited.

Work friendships are largely the reason. They run on passive contact: the same building, the same meetings, a shared project that supplies the conversation so neither person has to actively drive it. Take away that scaffolding, and many friendships do not survive the transition. In addition, the couple’s professional networks were never joined, so there is even less to build on.

This Week’s Resource

Take one page and draw a line down the middle.

On the left, write what your financial plan specifies. Be exact, because it should be exact. The date. The withdrawal rate. The accounts, the sequence, the tax treatment, the long-term care assumption, and the number the whole plan is built to protect.

On the right, write what a plan for what life will look like in those same years, and hold it to the same standard as the left column. Where you will be. What a typical week contains. Who is in the calendar, by name. What you must build that has not existed during your working years. What you would need to start now to ensure it’s ready when you are.

That last item has a price you can actually estimate. Research on how friendships form puts it at roughly 50 hours of shared leisure time to turn an acquaintance into a casual friend, and upward of 200 to make a close one. (Jeffrey A. Hall, “How many hours does it take to make a friend?”, Journal of Social and Personal Relationships, 2019) Those are hours of chosen time, not hours logged in the same building. If your right-hand column involves three of those friendships, you are looking at a multi-year build, and it has to start well before the date sitting in the left column.

Now, read the two columns side by side and notice how much of the right one you can fill in with the same confidence as the left.

That right column has a name. I call it your Meaning Plan. Almost no one has one, and the people with the best financial plans are often the furthest behind on it — because a good financial plan feels so much like readiness.

A Powerful Coaching Question

What does your first ordinary Wednesday of retirement look like, and who else is in that week's calendar?

Inspiration for the Week

Traveler, there is no path. The path is made by walking.

— Antonio Machado

Machado is describing how a path actually comes into being. Your path through retirement will not automatically be spelled out for you the way your portfolio will be. You have to create it, one step at a time.

Before You Go

This couple already had an excellent financial plan. What they were missing was a plan for the life that money was going to pay for. And they had no idea how much they needed it.

That gap is where this season is going. Over the next four issues, we are going to build the right-hand column I described in this week’s resource, one question at a time. Next week we start with the question that unlocks the rest, the one underneath the question everybody asks: what would you do if the money questions and concerns were already handled?

Before then, write me the one sentence your financial plan cannot answer. I am collecting them, and they will shape what I write for the rest of this season.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #14 - The Work We Don't Count

I’m writing this from my brother’s kitchen table. I’ve been here just over a week, and most of what I’ve done in that time will never show up on any record of my work. Visiting my mother in the hospital for three days while her doctors started a new medication. Arranging to pick up the prescription so she could stay on schedule once she got home. Sitting quietly in a chair while she slept.

I’m not telling you any of this for sympathy. I’m telling you because I’ve spent years coaching people through career decisions, and I keep finding the same thing beneath the choices that look irrational from the outside. There is a second job. Nobody counts it.

Photo by razi pouri on Unsplash

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A Coaching Story

A woman I coach turned down a promotion last spring. She told her boss she wasn’t ready.

That wasn’t true.

Here’s what was true: Her mother had started forgetting things. Her father had died two years ago. She was driving 90 minutes each way, twice a week, to sort pill boxes and argue with a Medicare rep. She was also raising a 12-year-old.

She was working two jobs. Only one of them had a title.

“I feel like I’m falling behind,” she said.

I asked her what she meant by that. Behind who, and by what measure? She started to answer, then stopped. She realized she was comparing herself to people who were not doing everything she was doing.

So we counted it. Actual hours, on paper. Roughly 22 hours each week of driving, calls, paperwork, and the particular exhaustion of managing someone else’s decline. When she saw the number she went quiet for a while.

She isn’t falling behind. She’s working harder than almost anyone I know. It’s just that half her work doesn’t count by any traditional measure.

That distinction was everything. Falling behind is a performance problem, and the fix for a performance problem is to try harder. Being overextended is a capacity problem, and the fix is that something comes off the plate or somebody helps carry it. She had been reaching for the first solution for two years while living inside the second problem.

She took the promotion three months later. Nothing about her mother’s situation got easier. What changed is that she stopped treating the caregiving work as a defect in her performance and started treating it as a fact of her life. Then she negotiated for what she needed to do the second job while also doing the first.

The Changing World of Work

In 2024, family caregivers in the United States provided 49.5 billion hours of unpaid care to adults. Valued honestly, that comes to more than $1 trillion in economic value, which is more than the country spent on Medicaid that year (AARP Public Policy Institute, Valuing the Invaluable 2026, 2026).

None of it appears in the nation’s GDP. None of it earns a pension. None of it goes on a résumé.

Roughly 59 million Americans care for an adult, and seven in 10 of them also hold a paying job (AARP & National Alliance for Caregiving, Caregiving in the US 2025, 2025). The average caregiving workload is 27 hours a week. That is a second job. It just isn’t on the org chart.

In the post-pandemic era, we took away much of the flexibility that helps with managing that second job. Two-thirds of CEOs say return-to-office mandates pushed a disproportionate number of women out of their jobs, and women are five times more likely than men to say caregiving is why they left the workforce (Forbes, RTO Mandates Force Caregivers Out Of Work, 2026).

But the data misses the bigger story. Most of these people don’t quit. They downshift. They take the job below their highest level of competence because the hours are predictable, and the spreadsheet records that as a personal choice.

This Week’s Resource

The Second-Job Audit

Here’s what I’ve seen work when someone is carrying an invisible load and calling it a personal shortcoming. Three moves, in order. The order matters.

One: count the hours. Not an estimate. For one week, write down every block of time that goes to care, coordination, or cleanup that nobody is paying you for. Driving, phone calls, forms, and the 20 minutes after a hard call when you can’t do anything useful. The number is not always easy to see, but it’s important. You cannot negotiate for something you have never measured.

Two: name the real problem. Look at the number and say which problem you actually have. If you are falling behind, it means you are underperforming, and the fix is to work harder. If you are actually overextended, it means you are at or above capacity, and the fix is to remove work or add support. Those two labels send you down completely different roads. We assume the first one almost every time, because we have been taught that care isn’t really work, so it can’t possibly be the reason we’re tired.

Three: ask for the fact, not the feeling. Don’t go into your manager’s office asking for understanding. Go in with the number and one specific structural request. My client’s version sounded like this:

“I’m managing my mother’s care, and it runs about 22 hours a week. I’m not asking to do less work. I’m asking to do it on a schedule that doesn’t collapse when she has a bad week. Two remote days and a hard stop on Thursdays would cover it.”

She got both. The public policy issues stayed exactly as broken as they were — she didn’t have to fix those. She just needed breathing room.

A Powerful Coaching Question

What are you doing this week that no system anywhere is counting? And what would change if you described that effort out loud to one person who could help you act on it?

Inspiration for the Week

“Attention is the rarest and purest form of generosity.”

— Simone Weil, letter to Joë Bousquet, 13 April 1942

Weil wrote that to a man lying in a hospital bed with a wound that never healed. She understood that paying real attention to another person costs something, and that we have never had a good way to measure that cost. You are spending that currency every week. It isn’t nothing just because nobody is counting it.

Before You Go

If you're carrying an uncounted second job right now, hit reply and tell me what it is. I read every email.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #13 - Nobody Left to Be Loyal To

A young lawyer I coach told me his parents keep giving him the same advice, and he cannot make himself take it.

“Hang in there.”

He is two years out of law school, in a job that pays badly. Everyone a year or two ahead of him leaves around the three-year mark. The partners above them treat that like a character flaw, assuming they are from a generation that won’t commit. And when he told me about it, what worried him most was that he might be proving them right.

I have made five major career transitions of my own, and nobody has ever accused me of failing to commit. (You can read more about them here.) So I went and looked at whether the accusation against his generation holds up.

The data says no. What I found instead was sadder, and it turned out to be about his father.

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A Coaching Story

He came to our session apologizing, which is its own tell. He said he felt restless, and he was worried that restless was just a nicer word for entitled.

I asked him how “hang in there” was supposed to benefit him.

He started to answer and then stopped. He said his father had given 31 years to one company and retired with a pension. His mother is still at the same hospital system where she started. When they say hang in there, they mean something specific: stay, the staying will be counted, and one day it will be paid back.

Then he said the thing that made this issue worth writing.

“I don’t think anybody is counting how long I’m staying at all, besides me.”

I want you to understand something about him, because it changes what this issue is about. He was sincere. He wants to give a firm 30 years. He would love for someone to want that from him. He simply cannot find the employer his parents keep describing, and he has started to suspect the deal they are pointing at was never available to him.

He is right, and this problem goes deeper than he knows.

The Changing World of Work

Start with the accusation, because it collapses on contact.

Young workers are not job-hopping more than their parents did. Today, workers aged 25 to 34 stay in a job a median of 2.7 years. Back in 1983, when that same age bracket was entirely Baby Boomers, it was 3.0 years. Three months of difference across four decades. They are also just as committed as anyone else: among workers in their first year on the job, intent to quit has been falling, from 37% in 2023 to 32% in 2025, closing in on the 30% of people who have been with an organization three years or more.

What the data shows instead is quieter, and it’s worse.

The bottom rung of the ladder is gone. A year after graduating, 52% of the class of 2023 were working in jobs that did not require their degree. Meanwhile the market has frozen shut. Layoffs are running at 1.1%, below where they sat in 2019. Almost nobody is being pushed out, which sounds like good news until you notice the other half of it. Nobody is leaving, so nobody new gets in. The people locked outside are the ones who never got a seat.

And the employer’s half of the bargain has been visibly disappearing. Since 2020, the share of American workers who agree that someone at work cares about them as a person has fallen from 54% to 41%. Having opportunities to learn and grow fell from 48% to 37%. My young lawyer is being lectured about commitment by an institution that is quietly withdrawing its dedication to him.

Then there is the pension, which is where his father comes in.

Defined-benefit pension participation in the private sector peaked in 1984 and has fallen ever since, from roughly 30 million active participants to 11.1 million by 2023. Today, at companies with fewer than 100 employees, only 6% of workers even have access to one. The deal his parents describe was gone before he was born.

But look at how that deal actually worked, because this is the part that undid me. Before 1974, pension plans commonly used what was called cliff vesting: no benefits at all if you left before 10 years of service. Some required you to reach age 40 and 15 years. Some had no vesting whatsoever.

Nine years and eleven months bought you nothing.

That system did not reward loyalty so much as make leaving unaffordable, which is a different strategy wearing the same coat. And it is still how staying works for an enormous number of people: 43% of American workers say they stay mainly because leaving would be too difficult or costly. Of those, 69% cannot afford to lose the pay or benefits.

His father gave 31 years and called it loyalty. His father may have been measuring the price of the exit while believing the promise.

But there is one more turn, and it is the one that changed how I read this whole story. In 15 years of this work, I have noticed that the people who feel this loss most sharply are rarely the young ones. They are the ones who believed the promise. My client’s father was told, in effect, give us your time commitment and we will keep you financially safe. He arranged 31 years around that agreement. My client was never told any such thing. He arrived expecting nothing, so for him, no deal was broken.

That rearranges the whole family narrative.

The wounded one in this story is my client’s father. He believed the promise, gave it 31 years, and has spent the time since living with whatever the answer turned out to be. And when he tells his son to hang in there, he may not be giving advice at all. He may be defending the thing he already paid for. Because the alternative is to look at 31 years and ask what they bought for him and his family. No one should have to do that at 68.

“Hang in there” might be his father’s grief.

This Week’s Resource

My client asked me the obvious question. If not the firm, then what?

That question deserves a real answer, because loyalty does not evaporate when its target disappears. It sits there, looking for somewhere to go. Most of the committed young people I work with have loyalty to spare — and nowhere to spend it.

So I told him what I have come to believe: loyalty didn’t die, it changed targets. There are four targets for your loyalty, and every one of them belongs to you.

Your craft. You can be loyal to the quality of what you make, whether or not anyone above you notices. Your craft and its quality travel with you. No reorganization touches it.

Your people. The actual humans you have worked beside and learned from, rather than the org chart. Those personal bonds outlast every employer, and they are usually the relationships that get you to whatever comes next.

Your profession. My client is a lawyer, and that is older and bigger than whoever signs his check this year. The profession does not end when the job does.

Your values. What you will and won’t do, no matter who is asking. I call these your bright red lines, and I have written about them here.

All four loyalty targets have something in common, and that is the whole point. Nobody assigned them to you, and nobody can fire you from them. None of them holds you by making leaving expensive. You stay because you want to, which is the only version of loyalty that was ever worth the name.

I want to be honest about one thing, because I think about it every time I offer this concept to a client or a colleague. Choosing where your loyalty goes is easier when you have somewhere else to be. My young lawyer has a license and options, and that is leverage a lot of people his age do not have. If you are reading this from a job you genuinely cannot afford to leave, the four targets are still yours, and I am not going to pretend that naming them pays your rent. Start with the one that costs nothing. The highest-yield, lowest-cost target is the people and relationships you are building with them.

A Powerful Coaching Question

Think about where your loyalty goes by default right now. Are you staying because you want to be there, or because leaving would cost too much? And if you already know the answer, what are you doing with all the loyalty you have left over?

Inspiration for the Week

“Before you tell your life what you intend to do with it, listen for what it intends to do with you.” — Parker Palmer, Let Your Life Speak

My client’s parents are telling him what to do with his life. They love him, and they are working from the only career roadmap anyone ever handed them, with their own grief folded into it. But listening to them is not the listening Palmer means. That one is his job, and he is young enough that it still costs him almost nothing. It will yield a great deal in satisfaction and self-direction over the years to come.

Before You Go

If you are early in your career and someone has told you that your generation won’t commit, I would genuinely like to hear about it. Write back and tell me what they said, and what you wish you had said back. I am collecting these anecdotes. I’m traveling for the next week or so, and it may take me a few days, but I’ll respond.

And if you are further along and you heard your own voice in my client’s father, I hope this landed gently. You kept your side of an agreement, and you kept it well. Being naive was never the problem here. The person who left the table was never you.

P.S. If you know someone two or three years into a career who has been made to feel like they are the problem, forward this newsletter to them. It may be the first time anyone has shown them the numbers to refute the claim that they won’t commit. And if you know someone who gave a company 30 years, it might be worth asking them what they think they got in return. They may have been waiting a long time for someone to ask.

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Until next week,

The task sounded administrative. I was to complete personnel evaluations for the people who reported to me, rate them on a bell curve, and submit them to central management without showing them to the people I had evaluated. Management would then rescale the scores, rewrite my summaries, and hand them back to my people as though the revisions were mine.

My name. My words, replaced. My people, reading a version of my judgment I had never made.

I brought a box to work that day.

I told my boss we had two choices. Either I would share my original evaluations with each person, and the organization could do whatever it wanted afterward, or he could walk me out. I offered to have my office packed in 30 minutes.

He took the first option. He told me I was right. And then he said something I have never forgotten: “I wish I had your courage to do the right thing.”

I have thought about that sentence for years. He knew exactly what the right thing was. He had simply never decided, in advance, what he would not do.

I call these moments Bright Red Lines — the things that, if you are asked to do them, could cause you to leave your role, your job, or your organization. Most of us never name ours until we are already standing on one.

What a Bright Red Line is not

It is not merely a hard thing. Cutting someone’s job can be brutal and still be a legitimate part of your leadership role. A conversation you are dreading is not grounds for quitting — it’s a core skill. Difficulty is not the test.

How you will recognize one

A Bright Red Line keeps you up at night, and it arrives with a specific physical feeling: a queasiness low in your gut that does not match the size of the task. Your intuition starts buzzing. Dread feels like reluctance. This feels like nausea.

What to do about it

Three things, and the first matters most.

Know that Bright Red Lines exist, and that you are the one who sets your own moral compass. People who have never considered this are genuinely shocked when they meet a situation like this, and shock is a terrible state to negotiate from.

Then name the things that are bright red lines for you in advance. Not a long list — a handful of things you already know you would not do. Write them down somewhere. It is startling how much steadier you feel having decided before the moment arrives.

Finally, have a plan. Who would you need to negotiate with? What exactly would you say? Who else would need to know?

A Bright Red Line rarely requires you to quit. It requires you to be genuinely willing to.

That was the whole difference in my story. The box was real, and I would have used it. That is what made the first option available.

If you have had a Bright Red Line moment, I would like to hear what you learned from it. And if you know someone who has not met one yet, send this to them. The time to decide is before you are standing there.

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #12 - Before the Next Thing

I have made five career transitions of my own. (You can read more about them here.) Each time, the hardest part was noticing, early enough for it to matter, that something in me had started to want a different life. We are taught to want the next thing, and we get so good at chasing it that we rarely stop to ask whether wanting it is still our truth.

This week, I want to talk about the pause that shows up right after a win, when you expected to feel triumphant and instead feel something you can’t quite name. It is one of the most important signals in a career, and it usually arrives well before we think it should.

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A Coaching Story

A client I worked with recently had just been named chief medical officer of her health system. She was in her mid-40s, which put her a good 10 years ahead of the usual timeline for that role. By every external measure, she had won. The board had chosen her, and she was genuinely excited about the work.

She was also anxious in a way she could not explain.

We spent the first part of our session exploring that anxiety. This wasn’t impostor syndrome. She had earned the role, she knew it, and she loved the work. But something about the moment felt off, and the harder she tried to name it, the more she couldn’t find the words.

So I asked her what she already knew about what felt off, even if she couldn’t name the feeling just yet.

She sat with that for a moment. Then she said, “I don’t think I want to still be chasing the next thing when I’m 60.”

There it was. She had spent her whole career excelling at climbing the next rung on the ladder. That ambition was the engine that got her where she had just landed, years earlier than most. She had leaned in, exactly as she was taught. And now, absorbing the reality of the win, she was wondering for the first time whether this was what she had really wanted, or a script she had internalized so young she had never thought to question whether it was for her.

The dissonance was about the pattern, not the job itself. She could see, clearly, a version of herself at 60 still climbing the ladder out of pure momentum, still saying yes to the next thing because saying yes was the only mode she knew. And she did not want to be that person.

The good news is that she noticed at 45, not at 60. That gap was everything.

The Changing World of Work

A single number from the Bureau of Labor Statistics reframes this whole issue. The average American born in the later Baby Boom held about 12.9 jobs between the ages of 18 and 58, and younger workers are on pace to match or beat that. Movement is the structure of a modern career, not an exception.

Which means the real question was never whether my client would keep changing roles. She would, and so will the rest of us. The question is whether each move is chosen intentionally, or simply accepted as the next available (and expected) rung, reached for out of habit. Motion is easy to mistake for direction. You usually can’t tell them apart from the outside, and often, you can’t tell from the inside either. The difference tends to surface later, right around the time you notice how much of your finite, high-function window has already gone into getting somewhere you never actually decided to go.

This Week’s Resource

I gave my client a simple practice, one I offer a lot of ambitious people who feel that same tug. I call it the Direction Check. Before you say yes to the next big move, whatever form it takes, sit with three questions.

First: Am I moving toward something I actually want, or just away from the discomfort of standing still? Ambition and avoidance can wear the same suit.

Second: Whose ambition is this? Did I choose this particular rung to climb, or did I absorb, somewhere early, the belief that I am supposed to want it? Naming the source doesn’t make the ambition wrong. It just makes it yours to decide about.

Third: If I picture myself climbing this same way at 60, what comes up, pride or fatigue? Your body often knows before your resume does.

None of these questions tell you to stop climbing. Plenty of people run the Direction Check and give a full-throated yes to the next thing, then climb with more freedom afterward because they chose it on purpose. The goal of the Direction Check is simply to make sure your ambition is aimed at a life you actually want to be living, while you still have decades of good years to live it.

A Powerful Coaching Question

When you picture yourself 15 years from now, still reaching for the next rung the same way you reach for it today, does that feel like a life you are choosing, or one you are defaulting into?

Inspiration for the Week

Find out who you are and do it on purpose.

Dolly Parton

The chasing only costs you when it comes from someone else’s idea of a life. So find out whose ambition you are actually running on. If it turns out to be yours, chase it with everything you have. If it isn’t, you’ve just uncovered the most important thing you’ll learn all year, and you found it with time to spare.

Before You Go

If that question landed somewhere tender, reply and tell me: when you picture 60, are you still climbing? I read every response, and I love hearing from readers.

P.S. That finite, high-function window has a name. I call it the Golden Window: the stretch of years when you’re healthy and able enough to do the things that matter most to you. You’re likely decades from any hard decision about it, and that’s the point. The best time to learn your Golden Window exists is long before the decisions about it get hard. When you’re ready to look, it will be here.

Until next week,

Quick note about something you’ll notice on the newsletter this week.

I’ve turned on payments.

Before you raise an eyebrow: nothing gets locked. Every post stays free, exactly the way it’s always been. You won’t hit a paywall here, and you won’t get the “subscribe to keep reading” cutoff halfway through a piece.

Substack now lets any of you who want to support the work do that. Think of it as a tip jar by the door, not a toll booth. If these essays help you think through your own work and career, and you’d like to chip in, there’s a button for that now.

If you’d rather read along for free, that’s genuinely fine. It’s what most people will do, and I built it that way on purpose. But a couple of you expressed interest in supporting this work before I’d even set it up. That’s what nudged me to do it. Thank you.

I keep this space free on purpose. This newsletter is where I get to think out loud with people moving through the same shifts in work that I am. Sometimes, it’s where we start working together more directly. What I care about is the conversation. The money is beside the point.

So nothing on your end changes. Read it, reply, forward it to someone who needs the message you find here. And if you ever feel like dropping something in the tip jar, I’ll be grateful and even delighted. But I won’t have expected it.

One more thing while I have you. I also send a free monthly email called Field Notes — a more personal letter that doesn’t live here on Substack. Sign up, and as a thank-you, I’ll send you my What Matters Most to You workbook, a fillable guide for clarifying your values, so you can use them to shape your next career decision. You can grab it, and get access to the newsletter, right here:

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More soon.

Quick note about something you’ll notice on the newsletter this week.

I’ve turned on payments.

Before you raise an eyebrow: nothing gets locked. Every post stays free, exactly the way it’s always been. You won’t hit a paywall here, and you won’t get the “subscribe to keep reading” cutoff halfway through a piece.

Substack now lets any of you who want to support the work do that. Think of it as a tip jar by the door, not a toll booth. If these essays help you think through your own work and career and you’d like to chip in, there’s a button for that now. If you’d rather read along for free, that’s genuinely fine. It’s what most people will do, and I built it that way on purpose.

A couple of you expressed interest in supporting this work before I’d even set it up. That’s what nudged me to do it. Thank you.

I keep it free on purpose. This newsletter is where I get to think out loud with people moving through the same shifts in work that I am, and sometimes it’s where we start working together more directly. What I care about is the conversation. The money is beside the point.

So nothing on your end changes. Read it, reply, forward it to someone who needs it. And if you ever feel like dropping something in the tip jar, I’ll be grateful and delighted.

One more thing while I have you. I also send a free monthly email called Field Notes — a more personal letter that doesn’t live here on Substack. Sign up, and as a thank-you, I’ll send you my What Matters Most to You workbook, a fillable guide for clarifying your values, so you can use them to shape your next career decision. You can grab it, and get access to the newsletter, right here:

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More soon.

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue 11 - The Golden Window

For most of your career, money was the constraint. You made decisions around it. You measured yourself by it. But at the senior stage, something shifts, and almost no one tells you when it happens.

The scarce resource stops being money. It becomes time. Not time in the abstract, the someday-I’ll-retire kind. Healthy time. The specific, finite span of years where you still have the energy, mobility, and clarity to embrace a next chapter, instead of just paying for one.

I call that span the Golden Window. It is open right now. It will not stay open forever. And “one more year” spends it down, regardless of whether you realize it.

This is the last of five articles in this series. We started with what people regret when they wait too long, then the costs that never show up on a balance sheet. We looked at why the people most able to leave are the ones who don’t, and at what one more year actually costs when you stack the years. This issue is where those add up to a number. Not money. Time.

A Coaching Story

She was a chief medical officer in her early 60s, with eight years at the top of an organization she was proud of. The compensation was extraordinary. Her financial planner had told her, in plain language, that she could retire any time she wanted.

She did not come to coaching to talk about money. She came because she felt stuck and could not explain why, given that by every measure on paper, she had won.

I asked her to rate her experience in the role from one to 10. She said it was a 10, easily.

Then I asked her to rate her enthusiasm for it. She sat with that one. “A three,” she said. “Maybe.”

High experience, low enthusiasm. People call that burnout, but it isn’t. It is a chapter that has reached its logical conclusion, yet it continues. On and on and on.

So, I asked my client the question her financial planner never had. Not “what would leaving cost you?” Instead, I asked: “What is this role costing you, in the years you can still do something with?”

She told me about volunteer health care work she had wanted to pursue for a decade. Hands-on, demanding work — the kind that needs working knees and real stamina. Every year, she had filed it under “later.”

Yet, “later” kept moving further out on the calendar. And the version of her that could actually embrace that dream had a shelf life — one she had never once put on a spreadsheet.

She was not being reckless by wanting this dream. She had been reckless by assuming the window to embrace it would stay open for her.

The Changing World of Work

Americans now live an average of 12.4 years in poor health at the end of life, the largest gap between lifespan and healthspan of any of 183 countries studied. That figure has grown from 10.9 years since 2000. (JAMA Network Open, Global Healthspan-Lifespan Gaps Among 183 WHO Member States, 2024)

Read that as a planning fact, not a health scare. Your lifespan and your healthspan are two different numbers, and they are drifting further apart. The years at the very end are increasingly years that people can fund but not fully use.

That means the window for doing — not just affording — a next chapter is narrower than your retirement projections assume. Your financial plan draws on your projected lifespan. Your real choices are influenced by your healthspan. The gap between those two lines is exactly the cost no one is modeling.

The executive with the extraordinary package had planned beautifully — but for the wrong number.

This Week’s Resource

The Meaning Plan

You have a financial plan. Most senior professionals have had one for years. Almost no one has its companion.

I call it a Meaning Plan. A financial plan answers, “can I afford the next chapter?”

A Meaning Plan answers “what is the next chapter for?” It governs the financial plan, not the other way around. The money is the fuel. This is the destination.

Three questions to start one this week:

1. What would I do with the window if money were already handled? My client’s planner had given her permission to leave. She still needed permission to want something different. What would you do in her circumstances?

2. Who carries this work forward after me? At the senior stage, your value shifts from being the person who does the work to being the person who develops the people who will do the work. My client named two potential successors before she changed anything else. That single move turned “leaving” from a loss into a handoff.

3. What is one small prototype I could run in the next month? Not a leap. A test. My client ran one conversation with someone already doing the work she was drawn to. One conversation told her more than a year of deliberating had.

Your very next action: pick one of the three questions. Answer it on paper this week.

The Meaning Plan is where you start. The Golden Window course is where you finish the thought: a five-day walk-through that puts a real number on what staying is actually costing you in healthy years, not only dollars, then hands you the step-by-step for what comes next.

Get the Course Now

A Powerful Coaching Question

Here is the question I would put to you if you were sitting across from me:

You know almost exactly what one more year in your role will pay you. Do you know how much it will spend, in the years you can still use fully?

Inspiration for the Week

“The soul would much rather fail at its own life than succeed at someone else’s.”

— David Whyte, The Heart Aroused (1994)

The window does not close all at once. It narrows quietly, a year at a time, while you are busy being responsible. The good news is that the window responds to attention. See it, and you can start spending it on purpose.

You are no longer drifting. You are designing.

Before You Go

If the Golden Window named something you have been putting off, hit reply and tell me what it is. I read every response, and they shape what I write next.

The Golden Window course is open.

If this issue named something real, the course is the full version of it: the diagnostic that scores where you stand, and the plan for the chapter ahead. It’s open now at the founding price of $197. It goes to $297 after July 23.

Open Your Golden Window

Until next week,

You’ve been reading More Than Work since close to the beginning, and that means something to me. So before I tell anyone else, I want to share this with you.

The thing I’ve been building has a name: The Golden Window. It’s a five-day course an online calculator tool that puts a real number on what staying in a role is costing you, measured in healthy years rather than dollars. It’s the calculation underneath a lot of what I’ve been writing here.

It opens to everyone on July 9. You’ve been here from the start, so you get in first. That means the founding price of $197 is yours, before it’s available to the public.

I’ll share the link to the course when we go live on Thursday.

One scheduling note: More Than Work usually arrives on Tuesday. This week, with the holiday and the launch, I’m holding it until Thursday, when the new issue and the course open together.

Founding members of the course also get a live group Q&A with me later this summer. Call it my thank-you for being early — to this newsletter and to The Golden Window.

With gratitude,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #10 - One More Year

“One more year.” It is the most reasonable thing a senior professional ever says. The bonus vests in the spring. The reorganization needs a steady hand to complete it. And the successor, everyone agrees, is not quite ready. Each reason is valid. Each year is defensible on its own.

That is exactly what makes it dangerous.

The cost of waiting was never about any single year. It is in all of them, stacked one sensible decision at a time. The stack stays invisible until you turn around one day and it is five years tall.

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A Coaching Story

He had built a company over 30 years and was ready, on paper, to step back. He was more than ready, really. He had hit his financial comfort number twice over.

He came to coaching after he finally sold his business, expecting to feel relief. Instead he felt something he could not identify, and it was bothering him more than any quarter’s results ever had.

We traced it back. Three times over the last decade he had set a date to step away. Three times he had moved it. Once, he stayed for an acquisition he wanted to see through. Another time, the market was good, and one more year of growth would pad the sale. Most recently, he didn't know who he'd be on the other side of selling and retiring, and another year of work let him avoid finding out.

Each delay made sense. He would make the same calls again with the same information.

But while he was heads-down hitting the number, the things he had been saving for had quietly changed. The long treks he and his wife had planned now bothered his knees. His appetite for big, ambitious travel had cooled into a preference for the familiar. The friends he pictured doing all this with had scattered, or slowed or were managing their own health.

He had not failed. He had retired exactly as planned, with more than enough financial resources. He was just late. Not tragically late, just late enough that the chapter of life he thought he'd bought began after the version of him who could fully enjoy it had started to disappear.

That is the quiet grief of an on-time retirement. The money was there. The life it was meant to enable was no longer feasible. The retirement he'd once envisioned was out of reach.

The Changing World of Work

The retirement plan has one part almost everyone gets wrong.

“One more year” assumes the choice will still be yours next year. For nearly half of people, that assumption would be wrong. 46% of workers who retired in 2025 left earlier than they had planned, and more than three-quarters of those early exits were driven by unexpected circumstances: health problems, a disability, a layoff, a parent who needed care. (EBRI, 2025 Retirement Confidence Survey)

Consider that fact in your decision process. If you’ve set a date, you likely assume you will arrive in that moment on your terms, in the shape you are in now. Almost half the time, life has a different plan.

Waiting feels like the safe, responsible move. It is actually the gamble. Every “one more year” decision is a bet that the future you are counting on will still be available when you finally decide to claim it.

Sometimes people win that bet. Often, they don’t.

This Week’s Resource

The Cost-of-Waiting Audit

Most senior professionals can tell you the exact date or financial goal they are waiting for. Very few have said out loud what they are assuming will still be true when it comes.

This is a short, uncomfortable exercise. Do it on paper.

1. Name the milestone. The vesting cliff, the birthday, the milestone, the “after the reorg.” Write down the specific thing you are waiting for. Be honest about whether it is one date or a date that keeps moving.

2. Name what you are assuming. Write down what you are quietly counting on still being true when that milestone arrives. Your health. Your energy. Your spouse’s health. The friends you pictured in this chapter of your life. The appetite to do the thing, not just pay for it.

3. Ask one question of each assumption. Is this guaranteed, or am I treating a hope as a fact?

That is the whole exercise. It is not meant to scare you out of waiting, because sometimes waiting is right. The point is to acknowledge the bet you are making, so that if you choose to wait, you are choosing it with your eyes wide open.

Your very next action: write down the milestone. Just the milestone. Most people have never actually put it on paper.

A Powerful Coaching Question

If you were sitting across from me, this is what I’d ask:

Name the milestone you've been waiting for. Now acknowledge what you're assuming will still be true about you when it arrives.

Most people have never said the second part out loud.

Inspiration for the Week

“It is not that we have a short time to live, but that we waste much of it.”

— Seneca, On the Shortness of Life (c. 49 CE)

2,000 years later this wisdom still resonates, because the trap of a finite life has not changed. We do not lose the time in one dramatic stroke. We spend it, one reasonable year at a time, always counting on more time to come.

Before You Go

So what does one more year actually cost you, specifically, in your situation? That is the real question, and it deserves a real number. Next week, we put one on it.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #9 - The Cage is Made of Gold

The most trapped people I coach are the ones who could walk away tomorrow and never work again.

It should not make sense. We assume the people with the most options feel the most free, with more money, more standing and more open doors than they could ever use. And yet, the ones who could leave without a second thought are often the ones who cannot picture leaving at all.

This week is not about whether you should go. It is about something quieter: why the door is right there, unlocked, and you still do not walk through it. The reason is rarely loyalty. It is usually something you would never say out loud.

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A Coaching Story

He is a managing partner in his mid-sixties, at a law firm he spent 30 years helping build. His name is on the door, and he has the kind of standing in his city that ensures his calls get returned within the hour. By every measure that fits on a résumé, he has arrived.

He came to coaching for a reason he could not quite identify. A few weeks earlier, at a firm event, a younger colleague introduced him as “our longtime managing partner.” The introduction was warm, admiring, completely kind. And for half a second, standing in front of the room, he caught himself wondering what they would call him next year. The thought frightened him more than any case ever had.

When we talked, he gave me all the right reasons for staying. He was not ready. The firm needed him to help navigate a leadership change. He still loved the work. Each reason was true, yet none of them was the truth.

So I asked him something else. Who are you, when you are not the managing partner?

He answered with his résumé: the cases he had won, the lawyers he had trained, the clients who would work with no one else. I let him finish, then said gently that he had told me what he does. I asked again who he is.

The room went quiet. Sitting in that silence, he saw it. He was not staying for the law anymore. He could barely remember the last legal matter that genuinely lit him up. He was staying because his title told him who he was, and the office told the world he still mattered. Take those away and he did not know what would be left.

That was the cage. Somewhere along the way, the work stopped being what he did and became who he was. And the bars were never iron. They were made of gold: the title, the standing, everything he had earned.

The Changing World of Work

When researchers studied more than a million burned-out employees, the phrase they reached for most to describe what made their workplace great was “golden handcuffs.”

Across 1,734,443 employee surveys, “golden handcuffs” was the single most common phrase burned-out workers used to describe what makes their workplace great. Great Place to Work, Golden Handcuffs: What Employee Survey Responses Reveal About Burnout, 2023

People who were exhausted and quietly miserable were asked what they liked about where they work. The answer that rose to the top was the very thing keeping them there against their own wishes. They named the trap as the perk.

The pattern holds all the way up the org chart. Nearly 40% of senior executives say they weighed leaving in the past year, and the reason was rarely money. It was frequently burnout and the wish for a more balanced life. TopResume via CFO Dive, 2026

When a reward becomes the bars of a cage, you stop seeing it as a reward, and you stop seeing the cage. You just call it a good job and keep showing up.

This Week’s Resource

The Five Bars of the Cage

Last week I wrote about the cost of staying too long. This week, I’m zeroing in on a way to see what is actually holding you in place. This is a checklist, not a score. Read each one slowly. If you are staying mainly for that reason, it is a bar, not a strategy. It is keeping you trapped.

1. The Scoreboard. “I’d be walking away from money I’ll never make again.” The compensation stopped being about need a long time ago. Now it is proof, in a number, that you still matter, a scoreboard you cannot quite stop checking.

2. The Title. “Who am I if I’m not the managing partner, the chief, the founder?” If the honest answer is that you do not know, notice what that means. You have let the title quietly become the person.

3. The Room. “Without this seat, the calls stop coming.” You are staying for the access, the being known, the somebody-ness. All of it is real, and all of it is rented. It belonged to the chair, and the chair was never yours to keep.

4. The Save. “It’ll fall apart without me.” Being needed feels like meaning. Often it is just about a place your importance is guaranteed. Ask yourself honestly whether your workplace would actually fall apart if you left, or whether it’s you who might crumble.

5. The Mastery. “I’m the best in the building at this.” You probably are. But staying because you have mastered something means choosing the comfort of being excellent over the risk of being a beginner again. The cage is gold because you earned it. And it’s still a cage.

How to read this list: You will see yourself in more than one of these, and that is normal. Pay attention to the one you would rather not look at too closely. The bar you most want to explain away is usually the one that holds the lock on the cage.

The managing partner in the story went quiet on two of them: the Title and the Room. He had spent 30 years feeling sure he was staying because of the work.

A Powerful Coaching Question

Here's what I'd ask you if you were sitting across from me: if one reward of this role disappeared tomorrow and you felt relieved to walk away, which reward would it be? Consider why that one has such a hold on you.

Inspiration for the Week

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

— Bronnie Ware, The Top Five Regrets of the Dying (2012)

Ware heard that regret more than any other, from people at the very end. Notice where it lands for you. It is about whose life you were living, and whether it was ever your own. The cage is comfortable enough to stay in for years. The only question that matters is whether it is yours.

Before You Go

If one of those five bars made you wince, hit reply and tell me which one. I read every response, and they shape what comes next.

Next week: the most expensive sentence in a senior career.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #08 - The Cost That Isn’t Money

Careers move in cycles. We are taught to see a career as one long climb, but it runs more like a series of chapters, each with a beginning, a productive middle, and an end that arrives whether or not we are ready to acknowledge it.

At the senior stage of career, the riskiest move is rarely leaving too soon. It is staying long past the end of a cycle, for reasons that look like prudence from the outside.

Staying too long carries a cost, and it’s not the one your financial planner models. It’s a quieter cost, measured in years rather than dollars, and almost no one is taught to count it.

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A Coaching Story

She was a senior executive at a company she had helped build, in her early sixties, with the kind of compensation package that makes leaving feel irresponsible. A vesting cliff that was 18 months out. A title that still opened every door. By every external measure, staying was the only sane choice.

She arrived at our session with a spreadsheet. She had modeled the cost of leaving down to the decimal: the unvested equity she would forfeit, the bonus she would miss, the months of income between this role and whatever came next. She knew exactly what walking away would cost her. She wanted me to tell her the number was too big to argue with.

I asked her a question her financial planner never had. It wasn’t about the cost of leaving. It was this:

What does staying cost you?

She started to answer in dollars again. I stopped her.

Not in dollars.

She went quiet. Then she told me her husband had been asking for two years to take a long trip, the kind that needs working knees and real stamina, while they both still had that capacity. Every time, she had said to him:

After the next milestone.

But the milestone kept moving. Last year, it was a reorganization. This year, the vesting cliff. Next year, there would be something else, because there is always something else.

There was another figure that mattered, but it wasn’t on her spreadsheet. It was the number of good years she was spending to earn money, when she already had enough.

She was not being reckless, and she was not being sentimental. She was the most rigorous person in every room she walked into. That was exactly the problem. The most rigorous people run the numbers they were trained to run. They don’t always stop to ask which other numbers they should be tracking.

What she had been calling discipline was a career cycle that had ended some time ago and stayed open because the only ledger she trusted was the financial one. The cost of staying was never going to show up there. That cost was being tallied somewhere her training had never taught her to look.

The Changing World of Work

Nearly a quarter of workers over 50 planned to change jobs in 2025, up from 14% the year before. [AARP, More Americans 50-Plus Seek to Make a Job Change in 2025, 2025 — https://www.aarp.org/pri/topics/work-finances-retirement/employers-workforce/older-job-seekers-age-discrimination-artificial-intelligence/]

That is a 71% jump in a single year. The people around you are not winding down. They are making moves.

The next chapter is promising, meaningful, and rich in the ways that matter most. And people your age are stepping into it right now. The thing standing between most senior professionals and that chapter is rarely money. It is the assumption that there will be time later, and the energy to enjoy that time when it comes.

That assumption is the most expensive one a senior professional makes. The executive with the spreadsheet had modeled every dollar and none of the years. The chapter she kept deferring has a waiting room, and the cost of delay is paid in vitality she is spending somewhere else.

This Week’s Resource

Last issue, I named the concept of Regret Risk, the slow cost of staying in a role past the point where it is still building the life you want next. This week, you can score your own Regret Risk.

The Career Cycle Diagnostic is the tool I use with senior clients who arrive at coaching with some version of should I stay or retire? The tool has four steps, and it takes about 15 minutes to complete.

You start by placing yourself on a four-quadrant grid based on whether you are still gaining or growth has plateaued, and whether your enthusiasm for the work is high or fading.

Then you rate yourself on four measures of whether this chapter is still giving something back to you. Those four add up to a Regret Risk Score. A fifth measure, Forward Pull, is scored separately, because wanting what comes next is different from being done with what you have.

The Regret Risk Category (determined by your Regret Risk Score, and adjusted if needed by the Forward Pull) tells you where you stand: low, moderate, high, or critical levels of Regret Risk. Then the tool turns the question around and asks what staying is costing you. Then it ends by asking you to name what you will do with this information.

There is one question inside this tool that I ask every senior client. It stops them cold, every time. I am not going to spoil it by sharing it here. It works best when you meet it on your own.

The score and category show you where you are. Calculating the full cost of a cycle that has run its course takes more than a newsletter, but this tool will point you toward what comes next.

A Powerful Coaching Question

Here is the question I would put to you if you were sitting across from me:

You know almost to the dollar what one more year in your current role pays you. Have you ever once calculated what it costs you, in years and vitality that you will not get back?

Inspiration for the Week

“How we spend our days is, of course, how we spend our lives.”

— Annie Dillard, The Writing Life (1989)

We treat our days as if they are a rehearsal for some later, more real chapter. They are not. The chapter you are in is your life. The only question is whether you are spending it on a cycle that is still giving something back to you, or one you have simply not gotten around to closing.

Before You Go

If the cost that isn’t money named something you have been avoiding, hit reply and tell me what surfaced. I read every response. They shape what comes next.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #07 - REGRET RISK

A client sat across from me last month. Accomplished, well-compensated, three years from the retirement he had been planning since his forties. We had cleared the morning for our session, and a few minutes in he said, very quietly, “I don’t know if I’ll still want this when I get there.”

He didn’t tell me what “this” meant. He didn’t need to.

Forty percent of C-suite leaders considered leaving their roles in the past 12 months. Almost none of them actually did. That gap, between the thought and the action, is where Regret Risk lives.

It is the most expensive quadrant on the grid I draw for clients. And from the outside, the people who are there look like the most successful people you know.

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A Coaching Story

She is a senior physician executive. Mid-sixties. Chief of a clinical service line at a large health system. Compensation excellent, board seat lined up for the post-retirement chapter. By every external measure, she is the picture of late-career success.

She arrived for our session and forgot why she’d booked it.

Her question for me was the one she’d been bringing to her CFO and her financial planner for years. When should she retire?

The real issue took longer to surface. She had been answering the retirement question by saying, “in three years,” for five years. Every January, her years to retirement reset. She wasn’t lying to anyone, not even herself. She was treating “in three years” the way she’d been trained to treat every clinical decision: as a position to defend, not a question to keep open.

I drew the Stay/Go Grid on a piece of paper and turned it toward her.

She placed herself in Stay & Survive within 90 seconds. The placement was easier than the year of conversation it took to get there.

I asked her to walk me through the Four Es of her current role. Education had gone quiet two years ago. She could not remember the last clinical or leadership concept that had genuinely changed her thinking. Experience was still abundant on paper, but she had stopped gaining meaningful benefit. Exposure was at a ceiling: everyone who needed to know her name already knew it. Enthusiasm was the tell. When I asked her for a number out of 10, she said “a four,” then sat back as if saying it out loud had cost her something.

Then I asked the question we really needed to explore.

“If you knew this was the last good year you’d have — the stamina, the clinical acumen, the love of the work — what would you spend it doing?”

She didn’t have an answer. That was the answer.

What she had been calling discipline now had a name. Regret Risk is the cost of staying past the point where the work is still helping you build the life you want next. And the people most at risk are the ones whose careers look, from the outside, the most enviable.

The Changing World of Work

Forty percent of C-suite leaders said they considered leaving their roles in the past year, and half of them said they think about it “very often.” [HR Dive, March 2025] CEO turnover hit an eight-year high in 2025, with 234 chief executives exiting their roles globally. [Russell Reynolds, Global CEO Turnover Index 2025]

The story those numbers tell is not a labor market story. It is a finite-life-energy story.

Senior leaders are doing math their advisors never asked them to do. They are calculating in years and in capacities, not in dollars. They are looking at the trajectory of the next chapter and asking whether one more year at this level is worth the year of life they will spend to get it.

The financial plan was built the way most of them were taught. It assumed time was infinite and identity was portable. Both of those assumptions are wrong, and the cost of the second one is what no one is teaching them to count.

This Week’s Resource

The Stay/Go Grid is the tool I use with every senior client who comes to coaching with a “should I stay?” question. Two axes. Four quadrants.

• Stay & Thrive — high enthusiasm, still gaining at least one of the Four Es. Stay as long as that’s true.

• Stay & Survive — biding time for a financial milestone; growth has ceased. This is a dangerous quadrant. It looks like discipline. It costs like delay. This is where Regret Risk compounds quietly.

• Go & Thrive — actively designing the next chapter with intention. The healthy exit.

• Go & Survive — leaving without a thoughtful plan. Identity-loss risk runs highest here.

Before you decide which quadrant you’re in, run the diagnostic that goes with it.

📋 The Four Es — Senior Career Self-Assessment

Rate yourself 1–10 on each.

1. Education — Am I still learning new skills, concepts, or domains in this role?

2. Experience — Am I still gaining value from the leadership work itself, not just the title?

3. Exposure — Am I still being seen and known by the people who will matter to my next chapter?

4. Enthusiasm — When I picture doing this for another three years, how much of me leans in?

How to read it: Enthusiasm is the pivot point. If Enthusiasm is below a 6 and at least one other E is below 7, what you are calling strategy is stalling. That is Stay & Survive.

The executive in the story above placed herself within 90 seconds. So can you.

⬇ Go deeper — download the Stay/Go Grid

If those four numbers got your attention, the full Stay/Go Grid walks you through what to do with them next. It is the same tool I use in coaching, formatted for self-guided use.

A Powerful Coaching Question

If you knew this was the last year you would be at full strength — same energy, same clarity, same capacity — would you spend it the way you are spending it now?

Inspiration for the Week

“Tell me, what is it you plan to do with your one wild and precious life?”

— Mary Oliver, The Summer Day (1990)

That line of poetry is overused for a reason. At a certain career stage it stops being inspiring and starts functioning as a deadline. The question itself is the asset. What you do with it, this season, is the test.

Before You Go

If "Regret Risk" named something for you, hit reply and tell me what surfaced. I read every comment. They shape what comes next.

Until next week,

I’m writing to let you know that I’m publishing several days a week on Substack Notes, and would love for you to join me there!

Here’s the most recent note I’ve put out:

Notes is a space on Substack for us to share links, short posts, quotes, photos, and more. I plan to use it for things that don’t fit in the newsletter, like work-in-progress or quick questions.

Go to Notes

How to join

Head to substack.com/notes or find the “Notes” tab in the Substack app. As a subscriber to More Than Work, you’ll automatically see my notes. Feel free to like, reply, or share them around!

You can also share notes of your own. I hope this becomes a space where every reader of More Than Work can share thoughts, ideas, and interesting quotes from the things we're reading on Substack and beyond.

Why Substack Notes

Fellow writers and readers are spending time in Notes for a variety of reasons.

Ted Gioia sees Notes as a forum for dialogue.

The idea behind Notes is simple. Millions of people now participate in Substack as writers and readers—but much of this is built on long articles and essays. We now have a forum for dialoguing and sharing shorter posts.

Chris Ryan is drawn to Substack as an alternative for legacy social media.

One of my main reasons for joining Substack was to wean myself off exploitative social media platforms. I’m hoping this is going to help move us along on that journey!

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I’m going to focus on being positive, with my own thoughts and photos and by linking to songs, stories, poems from around the web and from other Substacks.

If you encounter any issues, you can always refer to the Notes FAQ for assistance. Looking forward to seeing you there!

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ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

ISSUE #6 - THE PROFESSIONAL PRECARIAT

I’ve been thinking about a term that doesn’t fit anymore.

“Gig worker.” The term conjures a driver, a delivery person, someone picking up shifts. They don’t picture the radiologist reading scans from a contractor portal. The attorney billing by the project. The consultant who’s done more good work this year than she ever did as an employee — and who hasn’t had a sick day she could actually take.

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Economists call them the precariat — workers whose income is contingent, benefits are nonexistent and professional identity is untethered from any institution. The precariat has evolved. It has a LinkedIn profile now. It has a graduate degree and a client list and a level of expertise that should, by every reasonable measure, come with some kind of safety net.

It doesn’t.

A COACHING STORY

A de-identified composite scenario based on my coaching experiences. This story does not reflect the experience of any particular individual or organization in any way.

She came to coaching with a concern she couldn’t quite articulate, but was really troubling her.

Fifteen years into medicine, she was doing work she believed in, but something had shifted in how it felt. The model had changed around her. Fewer staff privileges. More contracted hours. Patients seen in slots, listed in templates, billed in units, documented in an electronic medical record. She was good at her job. She also felt, increasingly, like a piece of a machine she hadn’t agreed to be part of.

The thing that cracked something open wasn’t a bad day. It was a conversation with a trainee.

They were talking about career planning — the kind of conversation she’d had a hundred times, the kind she’d once found energizing. The trainee was thoughtful, capable, clearly going to be excellent. And when the subject of job security came up, the trainee said something that stopped her cold:

“I never really expected that kind of career. My work is piecework. I treat it that way.”

She heard it as resignation. The trainee meant it as clarity.

That space between what she heard and what the trainee meant was what she brought to coaching. Not the trainee’s attitude, but her own grief. The career she’d been promised, or had promised herself, was her father’s career. A physician of a certain era. The kind of career that was stable, that built on itself, that earned something beyond a paycheck. Respect, autonomy and financial security were the bedrock of that kind of career.

“What if that career doesn’t exist anymore?” I asked. “Not just in medicine. Anywhere.”

She sat with that for a while.

“Then what are we supposed to be building instead?”

It’s a real question. And the honest answer is: the institutional structures that would answer it haven’t been built yet. What we have instead is a $1.27 trillion economy of people navigating that gap on their own.

THE CHANGING WORLD OF WORK

The global gig economy was valued at $556.7 billion in 2024. It is projected to reach $1.847 trillion by 2032 — more than tripling in under a decade. [World Economic Forum, November 2024] In 2023, 64 million Americans worked on a freelance basis, contributing $1.27 trillion to the US economy. [Upwork, Freelance Forward 2023] Among them: 11.2 million skilled independent professionals providing services to businesses — up 50% since 2020. [MBO Partners, 2024 State of Independence]

It is the economy — for a growing slice of workers who chose independent work and professional workers who were pushed into it.

But those numbers leave out everything that once came bundled with a job:

• Pension

• Employer-sponsored healthcare

• Sick pay

• Parental leave

• Short-term disability

The social contract — every protection that used to come bundled with employment — gets unbundled the moment you leave it. And the system hasn’t caught up. New institutional supports exist: portable benefits that travel with the worker, platform cooperatives, professional guilds for freelancers (sometimes called “proficians”). None of these systems are operating at scale.

So, the expertise got unbundled, but the protection didn’t come with it.

THIS WEEK’S RESOURCE

The Generational Precariat: Three Coaching Archetypes

One of the more useful frames I’ve encountered for coaching independent professionals is that precarity looks different depending on where you are in your career — and so does what actually helps with navigating this complexity.

Research on the professional precariat (drawing on sources including the WEF Future of Work series and Guy Standing’s foundational work The Precariat: The New Dangerous Class) points to three distinct generational patterns, each with its own challenge and its own lever for growth.

Boomers and Senior Professionals: The Bridge to Independence

The central challenge is what researchers call the “Zone of Fear” — the worry that leaving institutional employment means losing professional identity, not just income. The lever for growth for this group is reframing accumulated expertise as consultative capital. What you know isn’t locked inside an organization. It travels with you. It's important that senior professionals recognize that, so their next move can be rooted in opportunity, rather than fear.

Gen X and Millennials: The Contract Strategist

This group faces the “Flexibility Paradox” — the freedom of independent work that quietly expands to consume every waking hour; it looks like freedom but doesn't feel that way. For these professionals, the growth lever is setting firm time boundaries before any single client fills all available space, and building enough contract diversification that no client can operate as a de facto employer without the protections employment offers.

Gen Z: The Competency Translator

“Status frustration” is the defining tension here — high educational investment, unstable returns and a labor market where credentials don’t lead to security. The lever for growth among this group: translating academic achievement into durable, transferable competencies, and shifting from individual hustle toward collective voice. The emerging professional guilds are, in part, a Gen Z response to a system that hasn’t delivered what it promised.

The common thread across these archetypes? The gap between what independent work offers and what it protects against. Coaching into that gap is some of the most important work I do.

A POWERFUL COACHING QUESTION

If your income disappeared tomorrow, how many months could you sustain your life — and what does that number tell you about the choices you still have time to make?

INSPIRATION FOR THE WEEK

“Anxiety is the dizziness of freedom.”

— Søren Kierkegaard, The Concept of Anxiety (1844)

That line has been sitting with me all week. Not a warning. More like a precise name for exactly what that unsteadiness is. If you’re doing independent work and it sometimes feels unsteady, it may be the exact sensation of being free, without a safety net.

BEFORE YOU GO

I’ve created two infographics to share with you this week.

Both files are below — download the one that fits, or take both.

Until next week,

Today I’m announcing a brand new addition to my Substack publication: More Than Work subscriber chat.

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ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue # 05 - THE CAREER STALL

I see a lot of coaching clients who feel stuck. The reasons vary, but the emotional weight is the same: a sense of boredom, the realization that there’s no growth opportunity, or just a feeling that something is “off” and a shift is needed. And almost always, there’s anxiety, depression or fear. Or all three.

I’ve seen this across age groups, genders, career stages and industries. It feels bigger than any one client’s experience. It’s a real trend worth paying attention to.

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A Coaching Story

My client was a mid-career engineer and leader at her organization. She had checked every box that indicated a strong career trajectory: a history of strong performance reviews, a resume showing progressive leadership responsibility, 12 years of loyalty to one organization, and consistent messages that she was “on track.”

She had been passed over for promotion three times. When she finally asked why, the answer was stunning.

Her performance was evaluated highly. Her potential to advance was not. No one could tell her why, or would.

In our coaching sessions, we talked through what that brought up: frustration, anger, shame and a sense that the goalposts hadn’t just moved. She wasn’t even playing in the same game as her peers who were advancing.

I asked her what she thought the problem was. She paused for a long time. “I’m not sure I’ll ever get promoted here,” she said. “Maybe I need to look elsewhere.”

We spent several sessions working through the pros and cons of staying versus leaving, and what was really driving her sense that she needed a change. In the end, she chose to search for a new role at a higher leadership level, at a different organization. She found one, and took it with more excitement than she’d felt in years.

The Changing World of Work

Her story isn’t unusual. Not even close.

65% of professionals say they feel stuck in their current roles heading into 2025. That’s 2 in 3 workers. Among women, it’s 68%. Among men, 62%. In tech, 73%. Career opportunity ratings on Glassdoor dropped 3% from 2022 to 2024, suggesting the stall is getting worse, not better. (Glassdoor Worklife Trends 2025)

That number flattens something important. The stall looks completely different depending on where you are in your career. (Nordic Journal of Transitions, Careers and Guidance)

Early career: AI is already eliminating entry-level roles. 51% of organizations say generative AI has already reduced their need for junior positions. Fewer on-ramps means fewer mentorship pipelines. The bottom rung is disappearing before people even get a foothold.

Mid-career (35–55): Organizations have flattened dramatically since COVID, cutting middle management and eliminating the promotion rungs that used to exist. Add the performance-versus-potential gap (women score 8.3% lower on assessments of potential to advance, despite strong performance ratings, making them 14% less likely to be promoted) and you get an invisible plateau that is genuinely difficult to name, let alone fix. (MIT Sloan Management Review)

Senior (50+): What was once a headwind becomes structural. 64% of workers over 50 have witnessed or experienced age discrimination. 16% have been passed over for promotion in favor of less-experienced younger colleagues. (AARP Age Discrimination Survey 2025/2026)

The word “stall” covers three distinct problems. Each calls for a different response.

That matters, because the strategies that help someone early in their career find traction look nothing like what works for someone who has been doing excellent work for 15 years and still isn’t advancing. Getting the diagnosis right is the first move.

This Week’s Resource

The performance-versus-potential gap is one of the least-talked-about forces in professional advancement. Women in mid-career feel it most acutely. This MIT Sloan piece names the mechanism clearly. Once you see it, it’s hard to unsee it.

Women Are Less Likely Than Men to Be Promoted. Here’s One Reason Why. — MIT Sloan Management Review (This is a great article to learn more about the performance-versus-potential gap.)

A Powerful Coaching Question

Stepping back from the day-to-day: over the past two or three years, have you been building toward something? Or just holding steady and calling it strategy?

Inspiration for the Week

“The most common form of despair is not being who you are.”

Søren Kierkegaard

Before You Go

I'm curious: what kind of career stall are you seeing most right now, in yourself or in the people around you? Hit reply and tell me.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue # 04 - The Expertise Trap

There is a question I ask most mid-career clients at some point in our work together. “Tell me what you want next.”

The answers follow a familiar pattern.

More scope. A stronger team. A title that finally matches the responsibility they’ve been carrying for years. Higher pay, a better organization, a manager who actually sees them.

None of those things are wrong to want. But when every option someone can generate is a variation on the same theme, when a bigger version of the job they already have is the only path they can picture, that pattern is worth a closer look.

This issue is about that pattern.

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A Coaching Story

He had been in his field for fifteen years. Senior director at a well-regarded company, the person his team called when something complicated landed on their desk. His performance reviews used words like “indispensable.” His manager had told him, more than once, that he was being considered for the next level of leadership.

He came to coaching not because anything was acutely wrong. He had the nagging sense that he wasn’t going anywhere, and he couldn’t explain why. “Stuck” was the word he kept using.

When I asked what he wanted next, he didn’t hesitate. “Something bigger with more scope. A VP role, ideally. I’ve been doing the work for a while.”

“Okay,” I said. “What else?”

He looked at me. “What do you mean, what else?”

“If the VP role doesn’t materialize, if the timing is off, or the organization isn’t moving that direction, what else are you considering?”

The pause lasted long enough that I let it sit.

“I guess,” he said finally, “I’d look for this same kind of role somewhere else. Somewhere better.”

That was where his real work started.

He wasn’t wrong to want a VP role, he may well have earned one. But every path he could picture was a variation on the one he was already on. Fifteen years of deep expertise had become the only lens he could see through. That was the trap. Not the job, not the organization. The trap was the narrowness of what he could imagine next.

A few sessions later, I walked him through a diagnostic I call the Four E’s, four questions about what any role is actually giving you. We went through each one. His silences got longer as we went.

When we got to the last question, he said, “I’ll be honest: that one’s been missing for a long time.”

Once he could name which E had gone flat, what to do next became much clearer. The answer wasn’t a job search, not yet. He just needed one targeted move to start replenishing what had quietly run dry. It was a smaller step than he expected, and more clarifying than two years of feeling stuck.

The Changing World of Work

A Harvard Business Review analysis from February 2026 found that AI is not reducing the cognitive load on knowledge workers, it is intensifying it. The expertise mid-career professionals have spent years developing is being both replicated and accelerated by the same tools, at the same time. Harvard Business Review, “AI Doesn’t Reduce Work — It Intensifies It,” February 2026

There is a counterintuitive finding buried in recent McKinsey research worth sitting with: heavy AI users report the highest intent to quit of any group of workers. The most capable knowledge workers, the ones who adopted AI earliest, are the most likely to be looking for a way out.

What the data shows is more specific: AI is hitting hardest at professionals who built careers on deep expertise, knowledge workers whose entire identity is tied to cognitive work they spent decades developing. When a tool starts doing the thinking you’re known for, the question isn’t whether your expertise still has value. It’s whether you’ve been growing in all four dimensions of your work, or deepening just one while the other three went quiet.

McKinsey & Company, “How AI is — and isn’t — changing the future of work,” 2026

This Week’s Resource

The Four E’s: A Diagnostic for What Your Career Is Actually Giving You

I developed this framework for my book Professional Careers By Design, and I use it with coaching clients when someone knows something is off but can’t name what. Think of it as a diagnostic, not a test of whether to stay or go. It’s four questions about what your current role is actually giving you right now, and what it isn’t.

Education. Are you actively learning something genuinely new? Not just getting better at what you already know, but encountering new skills, new ideas, new ways of thinking.

Experience. Are you building experience in new contexts, a new kind of challenge, a new level of leadership, a new type of organization? Or are you accumulating more of what you’ve already mastered?

Exposure. Are you being seen by people outside your current circle, stakeholders, peers or leaders who could open doors you don’t currently have access to?

Enthusiasm. Is there still a part of your work that lights you up and that carries genuine meaning beyond the deliverable?

With clients, I ask them to go through each question in the context of their current role. What’s actually true today, not what they wish were true.

In my experience, one or two E’s have gone quiet for clients at this stage. Gradually, in a way that’s easy to rationalize, and even to miss. That depleted dimension becomes your very next action. It doesn’t have to be a new job search, just one targeted shift. A new learning commitment, a new context, a new relationship, a project that reminds you what enthusiasm feels like.

What you can steal from this: my client from the story above knew within minutes which E had been flat for two years. It was enthusiasm. Naming it was more clarifying than anything else he’d tried. And he was stunned at how easy it was to regain that sense of joy with just a small shift. He asked to be part of a new team forming to assess the role of AI in their company, and he became the voice of senior folks there who were interested, not skeptical. His voice was valued, he learned new AI skills and became visible doing so. And his joy returned. He eventually stayed with that company and evolved that team assignment into a new role for himself outside the lane he had been imagining.

🔻 The full Four E’s worksheet — the same tool I use with coaching clients — is available as a free download here. It takes about 15 minutes to complete and most people find it uncomfortably useful. 🔻

A Powerful Coaching Question

Which of the four E's has been missing the longest for you? New learning, new experience, new visibility or genuine enthusiasm? And what have you been telling yourself about the reason for that?

Inspiration for the Week

“The only way to make sense out of change is to plunge into it, move with it, and join the dance.”

— Alan Watts

The trap isn’t expertise. Expertise is real and earned and worth protecting. The trap is deciding that because you know what you’re good at, you no longer need to ask where you’re growing. The Four E’s aren’t a one-time inventory. They’re a practice, and mid-career professionals are exactly the ones most likely to stop practicing those questions at the moment they need them most.

Before You Go

Run through the four questions this week. Then reply and tell me which E came up empty. You don’t need the full answer yet about what to do next. Just name what’s missing.

That’s where your next chapter starts.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

The career advice your parents gave you wasn’t wrong. It was written for a job market that closed before you graduated.

Last week I looked at this from a manager’s side: the VP of Operations who couldn’t fill the job she had at 25, because the pipeline that trained her had quietly closed. A lot of managers recognized themselves in that story.

This week is the other side of the same situation. Because Gen Z professionals aren’t just navigating a structural shift. They’re living the emotional reality of doing everything right and still hitting a wall. Same landscape. Different seat at the table.

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She was four years out of her graduate program. Solid performance reviews. A manager who’d told her, twice, that she was “being considered” for the next step up. She’d done what she was supposed to do: showed up, worked hard, said yes to the projects nobody else wanted, waited.

And then the rug came out.

Her manager left. A hiring freeze went into effect two quarters running. The informal promise of a promotion, the one nobody had put in writing, simply evaporated. There was no official cancellation, no conversation. It just disappeared.

This happens a hundred different ways. The supervisor who championed you moves to a new company. The promotion goes to someone hired from outside. A reorg eliminates your entire function. A new leader comes in with their own people already in place. The specific mechanism changes, but the experience is the same: you played by the rules of a game that changed without anyone telling you.

She wasn’t there because she was angry, though that would have been fair. She came because she didn’t know what to do next. She’d been building toward something that no longer existed, and nobody had said so out loud.

Early in our work together, I asked her what she was building.

She paused for a long time. “I thought I was building toward a promotion,” she said.

“Okay,” I said. “What else?”

She didn’t have an answer. That was the moment.

For four years she’d done everything the old rules rewarded: stayed, performed, waited. But tenure isn’t career capital. Career capital is the skills, relationships and story that belong to her, no matter what any one employer decides.

By our fourth session, she had a different answer. The difference between the first session and the fourth: she stopped waiting and started building. And the plan worked whether the promotion came or not.

Gen Z professionals average just 1.1 years in each role during their first five years of work, less than half the tenure of Baby Boomers in the comparable period of their careers. Entry-level job postings have dropped roughly 29% since January 2024. And according to recently published research, companies automating entry-level roles may be hollowing out the talent pipeline they’ll need within five years.

Randstad, Gen Z Workplace Blueprint, 2025 | Fortune/MIT, May 2026

That 1.1-year average tells a different story than most people assume. It’s what a lot of quiet disappointments look like in aggregate. The promotion that evaporated. The manager who left. The reorg that came through without warning. When the path forward isn’t visible from where you’re standing, people move. Short tenure is often what that looks like in the data.

The professionals adapting fastest aren’t waiting for the structure to return. They’re doing something specific: they’re making themselves legible. Building a record of what they can do, owning the story of where they’re headed, and practicing telling that story out loud, so when the next door opens, whether internal or external, they’re ready.

One Framework. Whether You’re Going for the Promotion or the Exit.

The old career playbook said: perform well, wait your turn, let your work speak for itself.

The work still has to speak. But “for itself” is doing too much lifting in that sentence. In a market where 29% of entry-level roles have disappeared and AI is absorbing routine output, nobody is managing your career except you. The work doesn’t speak unless you do.

Collect your stories.

A STAR story is a short, structured account of a problem you solved: Situation, Task, Action, Result. Doing the work and describing the work are two different skills. That gap shows up in interviews, in performance reviews, in every conversation with someone who could open a door.

Your next action: Start a running log of problems you’ve solved and contributions you’ve made. Three stories from the last year. One place. This is your STAR Story Bank, and it belongs to you regardless of where you work next.

Own your story.

Your job title is not your story. Titles change, companies restructure, roles disappear. The ability to articulate what you’re building, in two clear sentences, is portable in a way a job description never is.

Your next action: Write two sentences: what capability you’re developing right now, and what you’ll be able to do with it in a year. This becomes the center of every conversation about your next move, for a promotion conversation or a job search.

Tell your story.

Visibility is career capital. In a market where informal apprenticeship has been contracted away and proximity to senior people is harder to come by, you build it by making your work findable: an article, a post, a contribution in a professional community that shows what you know and how you think.

Your next action: Identify one skill you’re actively building. Find one low-stakes public way to demonstrate it this week. Start small. Make it visible. Tell your story.

<aside>

Are you building something right now, or are you waiting for someone else’s decision to tell you what you’re worth?

Once you stop looking for the ladder, it matters a lot less that it’s gone. The professionals who navigate this well aren’t the ones with better markets or better connections. They’re the ones who decided to start building something tangible before they felt ready. You don’t need a better market. You need a next move.

The promotion that didn’t come, the reorg that caught you off guard, the manager who left before putting anything in writing: none of that is a verdict on you. It’s the same wall everybody your age is standing in front of.

Before you close this: grab the free STAR Story Bank from the link above and fill in one story. Then share it in the comments below. That’s you telling your story in public. I read every one.

Until next week,

ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK

Issue #2 - Work as Need and Craft

I read a New York Times piece on a Sunday morning in April and couldn’t put my phone down. Not because the numbers were new to me — they weren’t. Because of what the graduates were doing instead: freelancing, piecing together gig work, picking up trades, starting small businesses before they’d ever held a real job. Finding ways to build a craft when the conventional on-ramps had closed.

The professionals who should care most about this aren’t 22. They’re the ones managing teams, building organizations, and quietly wondering where the next generation of capable people is going to come from.

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She was 58, a VP of Operations at a regional healthcare organization, two decades into leading teams. Good teams. The kind where someone always stepped up.

For the first time in her career, she was struggling to fill a role she described as “the job I had at 25.” Not senior. Not technical. Just a smart, trainable position for someone who wanted to learn the business from the ground up.

“We’ve posted it three times,” she told me. “The middle is gone.”

She wasn’t describing a salary problem or a location problem. She was describing a formation problem. The professionals she’d always hired had something in common: they’d been somewhere before they got to her. Somewhere hard, somewhere instructive, somewhere that had knocked the edges off. Those places were closing.

We spent most of our session on what she called “the pipeline question.” Not just her hiring gap, but the structural shift underneath it. She’d built her own career on an entry-level role that no longer exists at her company. The work had been absorbed — automated, contracted out, reorganized away. She couldn’t name the moment it happened. It just had.

By the end, she’d moved past the hiring problem. The real question she was sitting with was harder: if the pipeline that formed her has closed, what does that make her responsible for?

She didn’t have an answer. She’s still working on it.

51% of organizations say generative AI is already reducing their need for entry-level roles. Job postings for new graduates are still down 12% from pre-pandemic levels. More than 60% of the class of 2026 is pessimistic about their career prospects.

McKinsey, How AI Is and Isn’t Changing the Future of Work, April 2026 | Handshake, Class of 2026 Workforce Outlook

Most coverage frames this as a Gen Z problem. It’s not. Or not only.

Work has always served two functions that tend to get collapsed into one. There’s work as need — the income, the structure, the identity that a job title carries in a culture that still asks “what do you do?” within minutes of meeting someone. And there’s work as craft — the skill that develops through repetition, the judgment that builds through proximity to people who’ve done it longer, the professional formation that happens slowly through a thousand small decisions.

Entry-level jobs served both. They paid a beginning wage, and they transferred craft. When AI absorbs those roles, it addresses only the efficiency side — it can generate the output without building the person. What it quietly dismantles is the process by which capable professionals got built: the informal apprenticeship, the thousand small corrections that happened when junior staff sat near people who could catch a mistake before it became a habit.

The class of 2026 graduates picking up trades and starting businesses? They’re finding craft somewhere. They’re the resourceful ones. What’s harder to replace is what happens inside organizations — the knowledge passing from senior to junior people in ways most managers didn’t realize they were running until it was gone.

Gen Z’s financial insecurity jumped from 30% to 48% in a single year. That’s the need side breaking down in real time. The craft side is breaking down more slowly, more quietly. And the people who’ll feel it most aren’t the ones struggling to find their first job.

They’re the ones who have to build the next generation without the system that built them.

Deloitte, 2025 Gen Z and Millennial Survey

The Knowledge Transfer Audit

If your organization has been trimming entry-level roles — or if AI has started absorbing work that used to go to early-career people — three questions worth sitting with.

Question 1: Where does knowledge actually transfer on your team?

Not the formal version. Not the onboarding deck. Where does the real stuff pass — the judgment calls, the unwritten rules, how to read a room when a project is in trouble? In most organizations, that happened through proximity. Junior people watched, asked, made small mistakes near someone with the experience to notice. If that structure is thinner than it used to be, your institutional knowledge is aging out faster than you realize.

Question 2: Are you hiring for what exists, or what you need?

Skills-based hiring is gaining traction for good reason. The credential pipeline is changing — community colleges, bootcamps, non-traditional paths are producing capable people who don’t look like traditional candidates. The question isn’t whether someone had a conventional entry-level experience. It’s whether they have the raw material to grow. Are your job descriptions set up to find that?

Question 3: What gap are you responsible for closing, even if you didn’t create it?

The pipeline narrowed because of forces well above any one manager’s pay grade — markets, automation, efficiency drives that optimized for now at the cost of later. The organizations that navigate this well will be led by people who decided to act anyway — who mentored outside their direct reports, who built apprenticeship structures where none existed, who made early-career formation part of their own job description.

The VP from the story above started small. One mentorship arrangement. Informal office hours for early-career people in her network. Not a program. Just a practice.

She called it “paying for something that was given to me for free.”

The questions, if you want to sit with them:

1. Where does knowledge actually transfer on your team — not the formal version, but the real thing?

2. Are you hiring for what exists, or what you need?

3. What gap are you responsible for closing, even if you didn’t create it?

What did your first job teach you that couldn't have been taught in a classroom — and who's making sure the next generation gets that?

“If you are free, you need to free somebody else. If you have some power, then your job is to empower somebody else.”

~ Toni Morrison

The VP from the story wasn’t waiting for her company to build a program. She just started. That’s usually how it works.

If this found you at a useful moment, More Than Work lands in your inbox every week: one story, one signal, one tool, one question. Subscribe free below.

Until next week,