The Shocking Regret Most Entrepreneurs Have (And How to Avoid It)

In the world of business, it’s easy to get caught up in the push for growth, whether you’re scaling, pursuing mergers and acquisitions, or preparing for an exit. But when was the last time you paused and asked yourself: Is this path I’m on truly aligned with the life I want to live?

Take the story of a man named John. He’s 46 and spent most of his life following the “safe” path. He worked a steady 9-to-7 job, six days a week, for 26 years. But now, he’s filled with regret. As he puts it: “All my dreams, my passion, gone in a steady job. I repeatedly chose the safe path for everything, which eventually changed who I was.”

John reflects on his sacrifices, such as missing his father’s funeral, failing to complete his novel, and not traveling or helping others like he once dreamed. Now, he feels distant from his son, is in a rapidly declining marriage, and he’s left questioning how he spent his life. “If my younger self had met me today, I would have punched myself in the face,” he says. His message to others is clear: “Don’t procrastinate. Do something with your life while you’re young. Do not waste your life like I did mine.”

This story is a stark reminder of what happens when you lose agency—when life happens to you instead of being shaped by you. It’s easy to get caught up in the security of work, but at what cost? How can we avoid the trap of waking up one day filled with regret?

The Concept of Life Planning

Life planning is about asking yourself the big questions, the ones we often push to the back of our minds—especially when we’re scaling businesses, negotiating M&A deals, or planning an exit:

• If you were financially set for life, would you keep doing what you're doing, or would you change direction?

• If you had five to ten years left to live, how would you adjust your business and personal life?

• If you had only 24 hours left, how would you spend them?

These questions aren’t just theoretical exercises. They’re designed to force us to reflect on whether the decisions we’re making today will lead to fulfillment or regret down the road. Too many entrepreneurs, like John, get caught up in the grind, scaling their businesses, chasing deals, and working long hours, only to look back and realize they missed out on the things that truly mattered to them.

The Dangers of Losing Agency in Business Decisions

John’s story highlights the dangers of living without agency, when life feels like it’s happening to you, rather than being shaped by you. This is especially true when entrepreneurs make significant business decisions, whether it’s pursuing an acquisition, selling their business, or pushing for rapid growth. It’s easy to get caught up in the momentum of these big moves without considering how they align with your personal goals.

For example, when considering a merger or acquisition, the focus tends to be on financial metrics, valuation, synergy, and profitability. But before jumping into a deal, ask yourself: Is this acquisition helping me build the life I truly want, or is it just adding more complexity? Similarly, rapid scaling can lead to burnout if it’s not aligned with personal fulfillment.

Maintaining personal agency, taking control of your life and business decisions, is critical. Without it, you may find yourself on a path that leads to financial success but personal dissatisfaction. Reflecting on the why behind your business decisions can prevent you from waking up one day and realizing you’ve been living someone else’s version of success, not your own.

Balancing Work, Scaling, and Personal Fulfillment

A major challenge entrepreneurs face is balancing business growth, especially scaling, with personal life. It’s easy to convince yourself that you’ll make time for family and personal passions after hitting the next big milestone, whether that’s scaling to a certain revenue figure, selling the company, or closing a major acquisition. But in the meantime, life is happening.

Scaling a business doesn’t have to come at the cost of personal fulfillment. It’s about making intentional choices. Even during the busiest weeks, making small decisions is possible, like setting aside time for a family dinner or indulging in a personal passion that keeps you grounded and aligned with what truly matters.

What Would You Do If You Had Five Years Left?

One of the most powerful questions you can ask yourself is: What would I do if I only had five to ten years left to live?

This question is especially relevant when considering major business decisions like preparing for an exit. If you knew your time was limited, would you continue pursuing your current growth strategy or change direction? Would you focus on building lasting assets, spend more time with family, travel, or focus on experiences?

It’s not about abandoning work altogether, most entrepreneurs find fulfillment in what they do, but about making sure that the work you’re doing is aligned with the life you want to lead. If you wouldn’t keep doing what you’re doing under those circumstances, it’s worth asking why.

Work as a Source of Fulfillment

For many entrepreneurs, work is more than just a way to make money—it’s a source of purpose. The thrill of building something, solving problems, and creating value is deeply rewarding. But it’s important to remember that while work can bring fulfillment, it shouldn’t consume your life at the expense of everything else.

This is particularly important during mergers or acquisitions. These deals often require intense focus and energy, but they shouldn’t come at the cost of the personal life you’re trying to build. The same is true for scaling. You can grow your business while still making time for family and personal growth. It’s about creating a business that serves your life rather than allowing your life to be consumed by your business.

What Would You Do with 24 Hours Left?

Another essential life planning question: What would you do if you only had 24 hours left to live? This question forces you to distill what’s truly important.

If today was your last day, chances are you wouldn’t spend it working on a deal or stuck in meetings. Instead, you’d want to spend it with the people you love, doing the things that bring you the most joy and fulfillment. It’s a reminder that while work provides structure and meaning, the relationships we nurture and the memories we create matter most.

This perspective can be especially helpful when deciding whether to exit a business. An exit strategy shouldn’t just be about the financial gain. It should reflect what you want from life after the exit. If the exit doesn’t lead to the life you envision, it may be time to rethink your strategy.

Building a Life Without Regret

Entrepreneurs often face the challenge of balancing the demands of growing a business and pursuing personal fulfillment. By integrating life planning into your decision-making process, whether you’re scaling, merging, or planning an exit, you can ensure your business success doesn’t come at the cost of your personal happiness.

Ask yourself: Am I living with intention? Am I building a business that serves my life, or am I sacrificing my life for my business? By reflecting on these questions and making choices that align with your values, you can build a business and a life without regrets.

On The Business Lunch Podcast: Beyond Expertise: Hiring Leaders for Growth - Listen on Apple Podcasts I Spotify 

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