Due Diligence on Yourself

Deal psychology for people who’d rather not discuss their feelings 

We all carry a few identities at once. Spouse, parent, child, professional, guy with strong opinions about his fantasy football roster. For entrepreneurs, one of them tends to crowd out the rest. A very large part of who we are is bound up in the business we built. Mine included. I know a handful of owners who hold this in healthy balance, and I’d call them the exception. I also suspect two of them are lying. 

This fusion with your company usually works fine right up until you sell. 

Then an exit can feel less like a business transaction and more like a divorce from part of yourself. Left alone, that feeling makes owners second-guess their decision, regret it after closing, or blow up an economically sound deal in the ninth inning.  

I’m sure the brochure you have in your mind about post-sale life is appealing: less stress, more golf. The real-life documentary version, however, might catch you reorganizing the garage for the third time simply for something to do. And yes, that’s a true story from my first attempt at an exit, when I didn’t have a clear picture of what would come next. 

Money is very good at solving money problems. Its record against boredom on a Tuesday afternoon is poor. 

How identity shows up in a deal 

This pattern has emerged over time and again in my work with entrepreneurs. A deal that pencils cleanly stalls out because the seller has developed sudden and passionate views about a minor term. 

When an owner who spent thirty years refusing to read the fine print becomes a working capital scholar six weeks before close, the issue is not working capital. It’s the question of who they will be when no longer CEO. The close date starts reading as an ending rather than a milestone, so they go looking for an off-ramp. Nobody wants to become unmoored. 

Late realizations are expensive. Months of grinding diligence, advisory fees that are not refundable, management bandwidth you never get back, and a team that worked a second full-time job all year for nothing. And the bill lands on your health and your business at the same time. 

Grieving it properly 

Walking away from something you built creates real mourning, and it takes away the structure of your day. Waking up without purpose is no joke. 

Owners skip this work because M&A advisors aren’t therapists. We bill more and hug less. We have crisp playbooks for the financial planning and the legal mechanics, and nothing structured to help with the fear that keeps people awake at two in the morning. So it goes unaddressed until it surfaces as resistance, usually wearing the costume of a term sheet objection. 

Ambivalence isn’t weakness, and it isn’t evidence that something’s wrong with the deal. It’s a normal response to a large life transition, and it deserves the same intentionality you’d give a quality of earnings report. 

A better question 

Class VI’s new Is It Time? report makes the case for changing the question. Most owners ask what they’re leaving behind. The more useful question is what they’re moving toward. With a plan for the next chapter, the deal becomes a transition between two legitimate identities instead of the end of your primary one. It’s what I tell owners at our first meeting: run TO something, not FROM something. 

I’ve watched people land beautifully in philanthropy, in family time, in board seats that keep them near the game, or in some new hobby. There’s no correct answer, only a chosen one. “I’ll figure it out later” is a plan the same way “lose weight” is a diet. 

Three questions before you launch 

Identity work, in this context, is an honest self-assessment of personal readiness. Three questions I ask entrepreneurs to sit with: 

• Who am I outside of work, and do I want that person to have more of my calendar? 
• What fills the space where the company used to be? 
• Am I excited about the next stage, or dreading it? 

Then take the answers to people who will tell you the truth. A spouse, a coach, a trusted advisor. Your spouse, I’d note, has been quietly compiling research on this question for years and will be delighted to present findings. We all have blind spots. Better to bring them to light now than when the bankers and lawyers are at the table and the meter is running. 

Treat it as risk mitigation rather than soul-searching. Resolving any qualms early protects your timeline and your peace of mind afterward, and it belongs on the prep list next to the financial model and the growth story. 

Personal readiness is deal prep 

Financial and operational tuning gets a deal to the table. Identity readiness decides whether it closes cleanly, and whether you’re glad it did. Plenty of entrepreneurs say they regret selling. That club meets weekday mornings at the golf course, and the conversation is worse than the golf scores. 

Work through the questions above, and the rest of them in Is It Time? If it feels like your moment has arrived, I wish you all the best on the other side.