Before You Prepare Your Business for Sale, Prepare Yourself
Why personal readiness determines whether your exit becomes a launchpad or a landing.
When I sold my company in 2013, I knew my numbers cold. I could tell you our trailing twelve-month EBITDA, our growth rate, and the multiples comparable companies had fetched. I had spreadsheets. I had projections. I had advisors.
What I couldn't tell you was what I wanted to do with the rest of my life.
The wire hit. The deal closed. And instead of the triumph I'd expected, I felt disoriented. For over a decade, I'd known exactly who I was—the founder of my company. I had a title, a team, a purpose. Every morning, I woke up knowing what I was supposed to do. Suddenly, all of that was gone.
My calendar was empty. The skills I'd spent years developing—managing teams, closing deals, solving operational problems—had no immediate application. I found myself saying yes to opportunities I should have deferred, searching for something to fill the void. I almost made several bad decisions in those first few months, not because I lacked intelligence or experience, but because I lacked clarity about where I was going.
I call this the Clarity Gap—the strategic disadvantage created when founders lack a clear post-exit vision. It's one of the most expensive mistakes I see when coaching founder-CEOs through business exit strategy, and it's almost entirely preventable.
When the Number Is Clear But the Vision Isn't
The Clarity Gap doesn't announce itself. It hides behind busy schedules and pressing deal mechanics. Here's how it typically shows up:
You can articulate your financial targets in precise detail. You know your minimum acceptable price, your ideal multiple, and your walk-away number. You've thought through deal structures and tax implications. But when someone asks what you want to be doing three years after the close, you give a vague answer about "spending time with family" or "maybe doing some advising."
You evaluate deals primarily on financial terms. When comparing offers, you focus on purchase price, earnout structures, and payment timing. Questions about post-close involvement, cultural fit with the buyer, or how the deal serves your longer-term goals feel secondary—nice to consider, but not decisive.
You haven't told many people you're considering an exit. You're keeping the process close, partly for legitimate confidentiality reasons, but also because you haven't fully processed what selling means for your identity. Talking about it makes it real in ways that feel uncomfortable.
You're running hard toward the transaction without a clear picture of where you're running to. The exit has become the goal rather than a means to enable something bigger.
Why Clarity Is So Hard to Find Before the Exit
The Clarity Gap isn't a sign of poor planning or lack of sophistication. It's actually a predictable consequence of how founders operate.
First, founders are trained to focus on what's in front of them. Building a company requires intense present-moment focus—solving today's problems, closing this quarter's deals, managing this week's crises. Looking too far ahead can feel like a luxury you can't afford. When exit planning begins, that same orientation kicks in: focus on the deal mechanics, the due diligence, the negotiation. Post-exit life feels abstract and distant compared to the concrete work of getting the transaction done.
Second, identity and role become fused over time. After a decade of being "the founder," it becomes hard to imagine yourself as anything else. The question "What do you want to do after you sell?" is really asking "Who are you when you're not this?"—and that's a much harder question. Most founders unconsciously avoid it by staying busy with deal details.
Third, the advisory ecosystem reinforces the gap. Investment bankers, M&A attorneys, and accountants are paid to close deals. They're excellent at optimizing transaction terms but rarely equipped to help you think through what the transaction should enable. Exit planning often becomes purely financial and legal—a contract to be negotiated rather than a life transition to be designed.
Fourth, there's a pervasive assumption that money solves everything. Many founders believe that once they have sufficient financial resources, the rest will figure itself out. This assumption is wrong. Research shows that 75% of business owners experience profound regret within 12 months of selling—not because the deals were bad, but because they weren't prepared for what came after.
What Unclear Vision Costs You During the Exit
The costs of the Clarity Gap show up in several ways, often simultaneously.
You make suboptimal deal decisions. Without clarity about what you want post-exit, you have no basis for evaluating whether a deal actually serves your goals. You might accept an earnout that keeps you involved for three years when you really wanted a clean break. You might choose a buyer who offers the highest price but has values fundamentally misaligned with yours. You might agree to a role in the combined company without thinking through whether that role fits your vision for your next chapter.
You lose negotiating leverage. Buyers can sense when a founder lacks conviction about what they want. That uncertainty shows up in negotiations as hesitation, inconsistency, or willingness to compromise on terms that should be non-negotiable. Founders with clear post-exit visions negotiate more effectively because they know exactly what they need from the deal and what they're willing to trade away.
You experience post-exit regret even when the deal succeeds financially. This is the most common and most painful cost. The founder who didn't think through life after the exit often finds themselves wealthy but directionless. They've optimized for the transaction without considering what the transaction was supposed to enable. The money lands, and then the hard part begins.
The personal toll is significant but often invisible from the outside. Depression is common among founders in the first year after exit. Relationships strain under the sudden change in identity and routine. Health issues emerge as the adrenaline of building wears off and accumulated stress catches up.
How Post-Exit Clarity Changes Everything
Founders who navigate exits well do something fundamentally different: they start with where they're going, not what they're leaving.
This begins with what I call the Exit Blueprint—a written document that articulates your post-exit vision before you engage with the transaction process. The Exit Blueprint addresses several key questions: What do you want your life to look like in three years? What activities, relationships, and accomplishments would make those years meaningful? What role, if any, do you want in the company after the sale? What constraints or requirements does your post-exit vision place on the deal structure?
The Exit Blueprint serves as a filter for every decision during the exit process. When you're evaluating buyers, you can assess them against your post-exit requirements, not just their financial offers. When you're negotiating terms, you know which elements are essential and which are tradeable because you've defined what the deal needs to enable.
Effective exit planning also requires what I call identity work—the deliberate process of reconnecting with who you are beyond your founder role. This means identifying your portable capabilities (skills and strengths that transfer beyond your current company), your values and interests that exist independent of your business, and the relationships and roles in your life that will remain after the exit.
The goal isn't to minimize the significance of your identity as a founder—that identity is real and earned. The goal is to ensure it's one facet of a multidimensional identity, not the whole thing. Founders who do this work are less likely to cling to their role past its expiration date and more able to embrace whatever comes next.
Finally, founders who close the Clarity Gap adopt what I call the Sell-Keep Mindset: run your business as if you'll own it forever while ensuring it's structured to sell at any time. Always ready, never desperate. This mindset removes the urgency that leads to bad decisions. You're not racing toward an exit—you're building optionality that lets you choose when and how to transition.
Testing Your Own Clarity
Here's a quick diagnostic to assess your own Clarity Gap:
Write down, in specific terms, what you want to be doing professionally three years after your exit closes. Not vague aspirations—concrete activities, commitments, or ventures. If you struggle to fill a page, you have a Clarity Gap.
Consider your current exit planning activities. What percentage of your time goes to financial and legal mechanics versus clarifying your post-exit vision? If it's heavily weighted toward the former, you're probably building a Clarity Gap.
Ask yourself: If I received an offer tomorrow that met all my financial requirements but required a three-year earnout with full-time involvement, would I know immediately whether that worked for my life? If you'd need to "think about it," you haven't done the clarity work.
Finally, talk to founders who have exited. Ask them what surprised them most about life after the sale. Listen for the gap between what they expected and what they experienced. Their answers will illuminate the blind spots you might be carrying.
Where to Start
Begin by blocking time—real, protected calendar time—to work on your Exit Blueprint. This isn't work you can do in the margins between deal calls. It requires focused attention and honest reflection. Start with a full day and plan to revisit it quarterly.
During that time, answer these questions in writing: What aspects of my current work give me energy, and which drain me? What would I do if I didn't need to make money? What relationships and activities have I neglected that I want to restore? What do I want to be known for in the chapter after this one?
Resist the urge to immediately translate your answers into action plans. The first goal is clarity, not optimization. Sit with what emerges. Let it inform your thinking about the exit rather than rushing to incorporate it into your deal strategy.
Share your Exit Blueprint with trusted advisors and mentors who know you well—not just your transaction team. Get feedback on whether your vision aligns with who they observe you to be. Often, others can see blind spots in our self-perception that we cannot.
And remember: the best time to do this work is before you're in an active deal process. Once term sheets are flying and due diligence is underway, it's much harder to pause and do the deep thinking required.
Questions for You and Your Team
Before moving on, take a few minutes to reflect on these questions. The goal isn't to have perfect answers—it's to surface whether the Clarity Gap might be affecting your exit planning.
If you sold your company tomorrow and someone asked you in three years whether the exit achieved what you hoped for, what would you need to be doing to answer "yes"? This question forces you to define success beyond the financial transaction.
What parts of your founder identity would be hardest to let go of—and have you thought about what replaces them? The things that are hardest to release often reveal the deepest identity fusion, which is where post-exit regret tends to originate.
If your ideal buyer offered 20% less than your target price but guaranteed complete alignment with your post-exit vision, would you take it? If you don't know the answer, you haven't clarified what that vision is worth to you.
Take the Next Step
If you want to see where your business stands on the dimensions buyers scrutinize most closely, take the Exit Readiness Assessment. It's a free 15-minute diagnostic that scores your business across six dimensions—and helps you understand what would move your valuation.
Take the Exit Readiness Assessment
If you'd like help thinking through your exit strategy—whether that's interpreting your assessment results, developing your Exit Blueprint, or preparing for a transaction—I offer a free 60-minute consultation.
The Exit Planning Book for Founder-CEOs
Why do 75% of founders regret their exit within a year—even when they hit their number? Because most exit planning ignores what actually matters: personal readiness, life after the transaction, and building a business that sells on your terms.
SPRINGBOARD: A Founder's Guide to Selling Your Company With Purpose, Clarity, and a Vision for What's Next provides a comprehensive framework for planning exits that serve your life goals, not just your financial targets. It covers the four phases most founders miss: preparing yourself, preparing your business, executing the transaction, and navigating what comes next.
The first three chapters are available now.
About the Author
Bruce Eckfeldt is a strategic business coach and exit planning advisor who helps founder-CEOs of growth-stage companies scale systematically and exit successfully. A former Inc. 500 CEO who built and sold his own company, he brings real-world operational experience to strategic planning and leadership development. He's a certified ScalingUp and 3HAG/Metronomics coach, Certified Exit Planning Advisor (CEPA), an Inc. Magazine contributor, and host of the "From Angel to Exit" podcast. Bruce works with growth companies in complex industries, guiding leadership teams through growth challenges and exit preparation. Reach him at bruce@eckfeldt.com with any questions or if you want more information or to book a call with him.
