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Most exit planning covers valuation, deal structure, and taxes…
But almost none of it covers what happens to you the morning after the wire clears.
Jo Swann has spent years on that problem.
She's a licensed strategic psychotherapist and clinical hypnotherapist who works with founders and high performers after they've achieved everything they set out to achieve.
She calls herself "patient zero": after making her money in the IT industry in the '90s and moving to an oceanfront apartment in Malaysia, she hit the goal and promptly fell into an existential crisis.
"I had achieved the dream," she told John Warrillow on Built to Sell Radio. "And then, what now?"
If you're building toward an exit, her conversation with Warrillow about identity is worth your attention now, not after closing.
Here are 6 insights from it:
1. The story you've told yourself about who you are will collapse with the deal
Swann's central warning is blunt: the identity you've constructed as a busy, in-demand, driven operator is not the whole picture.
When the business sells, that construct falls apart, and you're left with 2 questions you may never have seriously asked.
Who are you? And what do you want?
This isn't a fringe problem…
Warrillow, who has recorded 500 episodes of his show, says one of the most consistent themes among entrepreneurs is a deep need to prove something to somebody: a doubting parent, an old boss, an ex.
He recalled interviewing a founder from a family of doctors who choked up describing the moment he told his mother about his exit. That drive builds companies. It also doesn't switch off when the company is gone.
Swann traces it back further…
Between birth and about age 7, we learn that doing what earns praise gets us love. If achievement was the price of affection in your childhood, you're likely still running that program decades later. The exit doesn't delete it.
2. "When I..." is the red flag phrase to listen for in your own speech
Swann's most practical diagnostic costs nothing. Listen for the phrase "When I."
When I sell the business, I'll spend time with my family.
When I hit my number, I'll get healthy.
When I've written the book, I'll relax.
Any sentence that places your happiness in the future is, in her words, one of the biggest traps in life.
Your imagination is limitless, so the post-exit life you're picturing will always outperform the real one. The deal closes, and what follows is an anticlimax.
Her prescription is to drag yourself back to today. Of everything you plan to do after the exit, what could you do this week? The coffee on the balcony, the afternoon in nature, the call with an old friend. If your values only exist in your imagined future, you're deferring them.
3. Your number is fine. Your reasons might not be.
Swann is careful here, because this is where skeptical listeners tune out...
She isn't anti-money. She likes flying first class and says so. If your number is $20 million, go get it.
The distinction she draws is between enjoying wealth and expecting it to fix you.
"You can never get enough of what you don't really need," she says.
Nobody actually needs the jet or the validation that comes with posting it on LinkedIn. What people crave underneath is acceptance and peace, and no purchase price delivers those. Chase the number for the adventure, not the cure.
4. The good life is boring, and that's a skill problem
Swann says the post-exit "good life" bores driven people almost instantly.
How long can you actually sit on a beach? For most founders, not even 5 minutes.
Her answer isn't to fill the void with new projects. It's to deliberately increase your tolerance for boredom and discomfort, without reaching for a phone, a drink, or a new deal.
She argues that phones and feeds have hijacked hardwired biological drives, including our low tolerance for discomfort and a built-in dissatisfaction that never fully resolves. You can't rewire those ancestral drives, but you can become aware of them and stop letting them run you.
Sitting with boredom, she says, is what opens the door to whatever comes next.
5. The second half of life runs on a different engine
Swann leans on Carl Jung's idea that life has two halves…
The 1st half is for carving out your place: building wealth, earning respect, raising a family. The ego drives it, and she doesn't villainize the ego. It's a fire starter.
The 2nd half asks for something else: to create, expand, and express.
In her practice, the clue is usually buried in childhood. She described a client who sold his company for $200 million after decades of grinding. When she asked what he loved as a kid, the answer was making things out of wood. Her advice: go collect some wood and make something. Another client, a wealthy estate owner, rediscovered a pull toward old paintings in antique shops and turned a room into an art studio, painting new work over them.
None of that was on their radar. It had to be uncovered, because decades of first-half striving had buried it.
6. Beware of striving dressed up as purpose
Warrillow raised an uncomfortable pattern: the post-exit founder who writes the book, joins the boards, and launches the academy "to give back," when what's really happening is the same old need for validation wearing a purpose costume.
Swann agreed it happens, and offered the same test as before.
If you catch yourself saying "when I've written the book, then I'll be happy," it's the ego talking, not a calling. Genuine purpose doesn't park your fulfillment in the future. The other tell is your body: poor sleep, heavy drinking, health problems.
"Our body is a great communicator," she says. Hers was the first thing to warn her she was on the wrong train.
The takeaway
Don't wait for the wire to hit before asking what you want and why.
Write down your values, then audit an ordinary week against them. Count how often you say "when I."
And if you have kids, Swann offers one piece of parenting advice for high achievers worried about raising strivers or slackers: praise curiosity and creativity, not just achievement, so love never gets welded to performance.
The deal is meant to be a milestone, not the destination.
Thanks for reading Acquiring & Exiting
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Ross Tomkins has nearly 20 years of entrepreneurial experience, which includes 20+ deals and 6 businesses scaled over $1M. He invests in, mentors, and advises business owners aiming to scale to 7 or 8 figures.
Find out more here.

Michael McGovern is an investor, business advisor, and direct-response marketing pro from California. His company - Relentless Growth Group - invests in, helps grow, and acquires American businesses in multiple sectors. Get in touch via his email newsletter: The Wildman Path.

Len Wright has 35+ years in entrepreneurship, specializing in bolt-on acquisitions, M&A, and business growth. He has founded, scaled, and exited 4+ ventures, and is the founder of Acquisition Aficionado Magazine - connecting a vast network of experts in buying, scaling, and selling businesses through strategic alliances.
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