75% of Entrepreneurs Regret Their Exit. Here Are the 3 Things They're Missing.

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Key Takeaways

- Entrepreneurs often fail to create a personal plan, and even more fail to continually assess it.

- 75% of owners regret exiting their business — often due to a lack of personal planning.

- Use the assessment tools you’ve refined as a business owner to unlock personal planning success.

The best entrepreneurs are planners. For most who are achieving success, they already have the long game in mind: a multi-year vision for their business with clear milestones and metrics to measure success. Established methods guide their growth planning, and those who aren’t planning are left behind.

Similarly, entrepreneurs often have an eye on their personal finances. Informed by business growth, business owners often have metrics to assess their progress towards financial security.

In my role as President of the Exit Planning Institute®, I advocate for a three-pronged approach to planning an exit. Business and personal financial planning are two of the prongs, and there are many advisors and frameworks available to help entrepreneurs hit their goals.

What many owners find harder — and lack clarity on how to assess — is the third prong: a personal plan.

What is a personal plan?

A personal plan is a written plan, driven by your personal purpose and identity, that includes goals and objectives to fulfill your desired legacy.

At least once per decade, Exit Planning Institute surveys business owners nationwide through the State of Owner Readiness Report. In 2023, our latest report showed that only 44% of business owners felt ready to exit from a personal planning perspective. That number is probably a little high, since only 41% had a written, formal plan for what they would do next, and fewer still — 35% — had completed an assessment on their personal readiness.

A personal plan is more than how you’ll spend your time post-exit. Too many people think they’ll simply retire, and then struggle to fill the 50 or 60 hours per week they poured into their business. But it’s not only about time — it’s about meaning. Purpose matters. Working now towards a life of fulfillment is critical.

A personal plan includes:

- Purpose: Understanding the unique impact you make. You can’t identify what activities will fulfill your post-exit life until you understand this. Bonus: Being able to articulate your purpose will benefit you now as a business owner.

- Vision: In 10 years, how will you have moved closer to your personal purpose in every arena?

- Goals: What measurable progress can you achieve in one year towards your vision?

- Action: What are the key steps to achieve your one-year goal in the next 90 days?

What’s the risk of not crafting a personal plan?

Let me ask you a question: if I put you in a room with three other business owners, are you truly more exceptional than they are?

75% of business owners deeply regret exiting their business within one year of the sale. They spiral, realizing they’ve lost their sense of meaning in life and have no plan for finding it in their new context.

Remember the sacrifices and long hours I mentioned as part of being an entrepreneur? How have they impacted your relationships? Are you intentionally devoting time and energy to ensure those bonds remain solid for your post-exit life? Gray divorce — divorce among retirees — is on the rise, and no one is immune. What about your physical and mental health? Just like business outcomes, personal well-being requires constant work and monitoring. These results don’t just happen by themselves.

Thinking like a business owner: 3 phases of measuring your personal plan

Let’s say you are one of the committed entrepreneurs who has created a personal plan. Congratulations — you’re ahead of most.

However, as you know, a plan is nothing without constant work and assessment. You need to adapt, evolve, and continue to work your plan. To track your improvement, here are three ways to measure your progress:

1. Assess yourself. Cara Gray’s “Future Identity Snapshot” is one of the best tools for assessing your personal plan. In 15 minutes, this AI-enabled tool for owners uses 12 questions, a written reflection, and guided videos to help you explore who you are and how you want to live in your next phase of life.

2. Create a KPI for your time. My friend Tommy Breedlove, a best-selling author and speaker on personal planning, devotes two hours per day to his personal plan. For him, that means reading, working out, meditating or spending intentional time with his family. Two hours may not be the right number for you, but the point is that you need to set a daily goal with action items — and track your progress.

3. Assess your happiness. The Happiness Portfolio®, created by Marianne Oehser and Susan Latremoille of Next Chapter Lifestyle Advisors, targets eight specific areas of your life: pro