Dear Friends,
To anyone who found their way here recently — welcome. You showed up at an interesting moment.
Something shifted this week.
Scott Snider, President of the Exit Planning Institute, published a piece in Entrepreneur magazine. The headline alone stops you: 75% of business owners deeply regret exiting their business within a year of the sale. Not a small percentage. Not an outlier finding. Three out of four.
The reason, Snider argues, isn't financial. The money was often there. The reason is that they had no personal plan. No map for who they were going to be on the other side. No language for what they were walking into.
I've been saying a version of this for years. But here's what struck me about seeing it in Entrepreneur, under the byline of one of the most respected voices in the exit planning world: the field is catching up. The conversation is changing. What was once treated as the soft, optional, figure-it-out-later piece of an exit is starting to be named for what it actually is — the piece most likely to determine whether a person thrives or spirals after one of the biggest transitions of their life.
Snider frames exit planning as a three-pronged approach: business planning, financial planning, and personal planning. The first two have entire industries built around them. Frameworks, advisors, methodologies, benchmarks. The third — the personal plan — has been the orphan of the process. Owners know they need one. Few have one. Fewer still have done any real assessment of their personal readiness.
This is the Identity Gap.
I've written about it before, but it's worth naming again here. The Wealth Gap costs money when left unaddressed. The Identity Gap — the distance between who you've been and who you're becoming — costs something harder to recover: meaning, relationships, health, and purpose. Over thirty years of post-exit life, that gap compounds quietly, and expensively, in ways that no financial plan anticipates.
What Snider's article signals is that the exit planning ecosystem is starting to take this seriously. Not as a wellness add-on. Not as a nice-to-have conversation after the real work is done. As a planning imperative — something that belongs in the same room as the business valuation and the wealth transfer strategy.
I was honored that he named the Future Identity Snapshot as the lead tool in his personal planning framework — the first resource he recommends to business owners who are ready to do this work. The Snapshot was built precisely for this moment in an owner's life: the window before or just after an exit, when the financial picture is coming together and the personal picture is still blurry. It's a reflective assessment, not a personality quiz. It helps people find language for where they are, and orientation for what deserves attention next.
But the larger point isn't about the tool. It's about what Snider's article represents.
The exit planning world has always known that something was missing. Advisors see it in their clients. The 75% figure isn't surprising to anyone who works in this space. What's changing is the willingness to name it, frame it, and build it into the process before it becomes a crisis.
That's the shift. And it matters — not just for the owners navigating this transition, but for the advisors, planners, and partners who are trying to help them get to the other side with their sense of self intact.
And while Snider is writing for business owners, I want to be direct with those of you reading this who aren't: this isn't someone else's conversation.
The identity gap doesn't require a business sale to open up. It opens when a career ends. When a title disappears. When the structure that organized your days, your relationships, and your sense of purpose is suddenly gone — whether you sold a company or cleared out an office on your last day of work. The mechanism is the same. You spent decades building something, becoming someone, earning a place in a world that knew exactly who you were. And then, almost overnight, that world reorganizes itself around your absence.
What the exit planning field is finally naming — loudly, in Entrepreneur magazine — is something most people in transition discover quietly, on their own, months or years after the fact. The financial plan was solid. The calendar was full, for a while. And still something felt unresolved. Not broken. Not ungrateful. Just — unfinished.
That's the gap. And it's worth addressing before it widens.
If you want to read Snider's full piece, it's worth your time. I'll link to it below.
And if you've been wondering whether the questions you're sitting with — about identity, about what comes next, about who you are outside of the role you've held for decades — are worth taking seriously: they are. The field is finally saying so out loud.
The Future Identity Snapshot is the tool Scott Snider recommends. You can take it at goodmorningfreedom.com. And you can read his full Entrepreneur article here: https://www.entrepreneur.com/leadership/75-of-entrepreneurs-regret-their-exit-here-are-the-3/504265
Warmly,
Cara
Future Identity Strategist
Founder, Good Morning Freedom