You’ve probably given a lot of thought to your business exit. Valuation methodology. Deal structure. Tax considerations. You might even have detailed plans covering various scenarios.
But what about you? What’s your Personal Strategy?
If the answer is “I’ll be fine” or “I’ll figure it out when I get there,” you’re could be joining the 75% who regret their exit within a year. Not because they got bad deals, because they planned the business exit brilliantly and the personal exit not at all.
Here’s what we’ve learned at Exitologists: your personal exit strategy needs as much thought as your business exit strategy. Possibly more, because getting the business bit right but the personal bit wrong doesn’t just cost you money. It costs you your health, your relationships, and your sense of self.
So here are the five pillars every personal exit strategy needs to address. Not theoretical concepts, actual frameworks you can work with. Not vague aspirations, specific questions you need to answer.
Because if you can’t answer these questions before you exit, Tuesday morning is going to be brutal.
Five Pillars. Skip One and Everything Collapses.
Over this series, we’re going to explore each of these pillars in depth. But first, you need to understand why all five matter, why you can’t skip any of them, and how they fit together.
Think of these as the load-bearing walls of your personal exit strategy. Remove one and the whole structure becomes unstable. Ignore one and you’ll pay for it later. Sometimes immediately, sometimes years down the line, but you’ll always pay for it.
Pillar 1: Identity Beyond The Business
The core question: Who are you when you’re not “the founder”?
After 10, 15, 20 years of being defined by your business, you’ve probably forgotten. Your introduction is your role. Your self-worth is tied to business performance. Your entire identity is wrapped up in this thing you’re planning to sell.
So what happens when it’s gone?
Founders who skip this work experience what we call “the imposter problem.” They walk into networking events six months post-exit, someone asks what they do, and they freeze. They’re not the founder anymore. They’re not anything. They feel like frauds.
Some spend years telling people they’re “consulting” because they can’t bear to admit they’ve sold up and have no idea what comes next. Others fall into depression because the thing that gave them identity and purpose has disappeared.
What you’ll learn in the deep dive: How to excavate who you are underneath the founder persona. The exercises that actually work for identity reconstruction. Why this work takes years, not weeks. And how to know if you’re doing real identity work or just fooling yourself.
Pillar 2: Financial Reality Check
The core question: What do you actually need versus what you think you need?
Most founders set their exit number using terrible methodology. Your competitor sold for £4 million so you need £5 million. Or it just sounds like “a lot of money” and therefore enough. Or you did a back-of-envelope calculation that ignored tax, inflation, and the fact that all your company perks disappear when you sell.
The result? You either chase an unrealistic number for years or take an inadequate number and regret it later.
What you’ll learn in the deep dive: How to do a proper lifestyle audit. What changes financially when you exit (it’s more than you think). How to calculate your actual “enough” number. The difference between needs-based and status-based exit numbers. And why chasing “more” when you’ve got “enough” wastes years of your life.
Pillar 3: Relationship Reconstruction
The core question: Have you asked your family if they actually want you present again?
You’ve been a ghost in your own life for years. Present physically perhaps, but mentally and emotionally you’ve been in the business. Your partner has built a life around your absence. Your children have adapted. Your friendships have atrophied.
Now you’re planning to suddenly be available. Have you asked them if they want that?
One founder we know sold his business planning to “finally spend time with the family.” His wife’s response? “I’ve spent 12 years raising these kids essentially alone. Where were you when I needed you?” They divorced 14 months post-exit.
What you’ll learn in the deep dive: How to have the difficult conversations before it’s too late. What your partner actually expects from exit (it might not align with your plans). How to rebuild relationships you’ve neglected. And why assuming your family will be thrilled by your return is dangerous.
Pillar 4: Purpose Rediscovery
The core question: What drives you when profit isn’t the scoreboard?
For years you’ve had crystal-clear purpose. Build the business. Hit the targets. Make payroll. The scoreboard is obvious: profit, growth, valuation. Every morning you wake up knowing exactly what you’re doing and why.
Then you exit. The scoreboard disappears. The purpose evaporates.
One founder described post-exit life as “winning the lottery and discovering money doesn’t actually solve the existential dread.” He had everything: financial security, time freedom, no obligations. And he was utterly miserable because none of it meant anything.
What you’ll learn in the deep dive: How to separate what you think you should want from what you actually want. Why “hobbies” aren’t the same as purpose. How to test sources of meaning whilst you’re still in the business. And what to do if you’re a builder who needs to build, because retirement will destroy you.
Pillar 5: Time Architecture
The core question: What does your day look like when nobody needs you?
You’ve spent years being needed. Your calendar is full. Your to-do list is endless. Your time has structure because the business creates it.
Then you exit. Nobody needs you. Nothing is urgent. Your calendar is empty. Complete freedom over your time, and if you haven’t prepared for it, that freedom becomes a void.
Some founders love this initially. The relief lasts about three weeks. Then the anxiety sets in. Then the depression. Other founders panic-fill every minute because they don’t know how to exist without being busy.
What you’ll learn in the deep dive: How to design time that works for you. The difference between productive rest and destructive drift. Why the first 90 days post-exit are the danger zone. How to test different time structures before you exit. And whether you need tight structure or loose structure to thrive.
Why You Can’t Skip Any Of These
Here’s what we’ve learned from our own failed exits: you can’t cherry-pick. These five pillars aren’t optional extras you add if you’ve got time. They’re the foundation.
Skip the identity work and you’ll have an existential crisis six months post-exit. Skip the financial reality check and you’ll chase the wrong number. Skip the relationship work and you’ll exit to find your family has moved on without you. Skip the purpose discovery and you’ll drift aimlessly. Skip the time architecture work and you’ll either panic-fill your calendar or sink into depression.
The founders who exit successfully (truly successfully, not just financially) are the ones who’ve worked through all five pillars before they sign the papers. They know who they are beyond the business. They’ve done the financial maths properly. They’ve rebuilt their relationships. They’ve discovered sources of purpose. They’ve designed how they’ll structure their time.
And they’ve done all of this whilst still running the business, so the transition is gradual rather than sudden.
What Comes Next
In future posts, we’re going to explore each pillar in depth. Not theory, practical frameworks, uncomfortable questions, and honest assessment of what this work actually looks like.
Each pillar requires real effort. There are no shortcuts, no hacks, no “one simple trick.” It’s deep work that takes time and introspection. But it’s the difference between exiting to freedom and exiting to crisis.
The choice is yours: do the work now whilst you’ve still got time, or join the 75% who discover too late that they weren’t ready.
We’ll start with the hardest one: identity. Because if you don’t know who you are without the business, nothing else matters.
Why These Five Pillars Are Harder Than They Look
You might be thinking: “Right, I’ve got the framework. I’ll work through these myself.” And you’re capable – you’ve built a business from nothing.
But here’s what we’ve learned at Exitologists: these five pillars are interconnected. Your identity work informs your purpose discovery. Your financial reality affects your relationship conversations. Your time architecture depends on understanding all the others. Working through them systematically, in the right order, with proper depth, makes the difference between genuine preparation and surface-level box-ticking.
The bigger challenge? You can’t see your own blind spots. We’ve watched founders who thought they’d done the identity work discover six months post-exit that they’d only scratched the surface. We’ve seen founders who believed they’d had “the conversation” with their partners realise they’d avoided the real issues.
I wish I knew about these pillars before my last exit. I’ve learned from others and I’ve got it wrong, so you don’t have to.
