One of Sandy Kapell’s clients, a woman in her late twenties, arrived at a conclusion about her own career that stopped Kapell cold. The lesson she believed she was supposed to learn, she said, was to be quiet. She had been observing things at work that needed to be said, and somewhere along the way she had absorbed the message that saying them was the problem. “That’s actually not the lesson,” Kapell said. “But that’s the message she’s getting.”
Sandy Kapell is the CEO and founder of Trakehner Leadership, where she works with leaders and organizations moving through change, restructuring, and growth. Her expertise sits at the intersection of human resources, operations, and transformation, built across senior roles at Madison Square Garden Entertainment and the Metropolitan Opera, with earlier leadership positions at Cablevision, MetLife, and AIG. She has spent decades studying how large groups of people respond when the ground shifts under them, and she has come to believe the same principles explain something far more personal: why so many capable women hit a season of their working lives and conclude, wrongly, that they are failing.
The Working Life Has Seasons, and Each One Has Different Rules
Kapell rejects the standard generational framing, which she says is both too broad and too prescriptive. “Generations are broad, and they’re twenty years, and they’re also telling you what you are,” she said. Her alternative organizes a working life by decade, and each decade carries a different assignment.
The 20s, in her framing, are for exploration. Most people leave college certain they know what they want, enter the workforce, and discover it was not what they pictured. Kapell wants that experience treated as information rather than failure. The 30s are for picking a direction, not necessarily the permanent one, and beginning to build real expertise inside it. The 40s are what she calls “unlocking ambition,” the decade when accumulated skill finally registers as competence and many women realize for the first time that they have it. The 50s open a space between career and other possibilities, when freedom expands, and legacy starts to surface as a question. The 60s she describes as a second learning peak, a second twenties, when the hobby that got postponed for family or career or profession finally has room. And the seventies, in her view, deserve celebration. “I wish every woman in their seventies was walking around with a crown,” she said.
The practical value of a map like this is that it turns a private crisis into a predictable transition. A woman at 47 who suddenly wants more is not malfunctioning. She has arrived at the decade where that is supposed to happen.
Real Expertise Is the Foundation Most People Skip
When asked what people miss when they set out to build something, Kapell answered with two halves, and the first one was permission. She has heard accomplished women say publicly that they have no fear and take risks freely, and she wanted to complicate that. “I have a ton of fear, and I do worry about failing, and that’s okay,” she said. Fear is the norm rather than the exception, and the useful skill is not eliminating it but acting while it is present.
The second half was a warning about depth. Kapell urges women not to shy away from developing genuine expertise in something they care about, and she draws a hard line around what that means. “Really become an expert and not an internet expert,” she said. Her definition is specific and demanding. Read seriously on the topic. Talk to people who work in it. Put yourself physically inside it. Then find the hardest examples available and study what failed alongside what succeeded, because failure carries information that success usually hides. Kapell noted that women often do not receive the message that it is acceptable to be the expert in the room, and that the absence of that message costs them years.
What Reorganizing a Company Teaches You About Reorganizing a Life
Kapell has led organizational change at scale, and she named three conditions that determine whether it works. The first is clarity. The organization has to be unified and specific about what it is moving from, what it is moving to, the timeline, and how the change will actually operate day to day. If leaders send contradictory signals, the change fails regardless of how good the plan is.
The second condition is feedback loops. Leaders slide into echo chambers with very little effort, and the only defense is deliberately building channels that deliver honest information about what messaging is landing and what is not. The third condition is the recognition that people do not check themselves at the door. As Kapell put it, if someone is having a problem in a relationship, if a child is sick, if a parent is in a nursing home, if there is a serious illness in the family, all of it walks into work with them.
Each of these translates directly to a woman managing her own transition. Clarity means knowing what you are moving from and toward rather than only knowing you are unhappy. Feedback loops mean having people in your life who will tell you the truth rather than reflect your own reasoning at you. And the third condition is permission to be a whole person while you do it.
The Three Second Pause That Prevents Most Bad Reactions
One of the most immediately usable ideas Kapell offered concerns what happens in the seconds after someone says something that lands badly. Her observation, drawn from her clients and from research she has read, is that women move very quickly to self-blame. The comment arrives, and the internal verdict is that it must be about them.
Her alternative costs three seconds. “In my experience, a lot of times when people make a comment, the smartest thing to do is ask a question about why the comment before you react,” she said. “Because if you can get them to explain why, they’re gonna give you the answer you need.”
“Is this about me? Or is there a question I can ask about why? Because maybe this has nothing to do with me.”
~ Sandy Kapell
Kapell also connects this pattern to a broader one she has watched play out at senior levels for years. The self-talk she hears now from her clients is the same self-talk she heard from extremely successful women when she worked in human resources, and it runs on a loop about whether they belong in the room. “We undermine ourselves pretty successfully without anybody saying anything,” she said.
How to Tell Why You Feel Stuck
For the woman who feels stuck or off course, Kapell resists offering a single answer because, in her experience, “stuck” is a symptom with at least three different causes, and each one requires a different response. She frames it as a moment for radical candor with yourself.
The first possibility is that your ladder is leaning against the wrong building, that your heart is genuinely no longer in the work, and the task ahead is building the courage to change buildings. The second is that other people are holding you back, which is a political and strategic problem rather than an emotional one. The third is that you are holding yourself back, which is the hardest to see and the most common in the pattern Kapell described earlier.
The instruction she gives is to run the diagnostic before choosing the solution, because acting on the wrong cause produces motion without progress. A woman who quits a job she actually loves because she mistook her own self-doubt for a bad fit has solved a problem she did not have.
Kapell also made a point about change itself that reframes the whole question. The more you understand how change works as a process, including how people react emotionally to it and that those reactions follow a cycle, the more control you have. She illustrated it with a deliberately mundane example from corporate life. Move a payroll cycle from Thursday to Friday, and people react strongly, and the conversation gets stuck on Thursday versus Friday. Address what people are actually worried about underneath, and by her estimate the objection dissolves for 75% to 80% of them. The thing changing is rarely the real issue. The same is true when the organization in question is your own life.
You Are Not Behind, You Are in a Different Season
Sandy Kapell told a story about asking everyone she and her team knew a simple question while building their program: who do you know, outside your own family, who is in their sixties or seventies and whom you feel close to? Almost no one had an answer beyond their boss’s boss. That gap, she said, leaves an enormous amount of accumulated wisdom sitting unused, and it runs in both directions, because women in their fifties and sixties have just as much to learn from women in their twenties about how the working world now operates.
If there is one thing to carry out of this, it is the diagnostic. The next time the feeling arrives that you are behind or that something has gone wrong, run Kapell’s question before you run the story. Is this about me, or is there something else happening here? Then ask which kind of stuck you actually are.
Kapell’s larger point is that a career was never meant to be a straight line, and the women who do well are not the ones who avoided the shifts. They are the ones who recognized which season they had entered and adjusted the rules accordingly. After a career spent moving organizations through exactly this kind of change, Sandy Kapell is making the case that individuals deserve the same clarity companies get.
