This article was written by guest contributor Reed Warren, CEO of iTValuations, which offers business valuation services, tax advisory, and sell-side and buy-side advisory services.
Most people know that small business leaders are under a lot of pressure. What isn’t talked about enough is the emotional pressure that goes along with being at the helm of the business, and along with that, the toll stepping away can take if you’re not prepared for it.
The Exit Planning Institute reports that 75% of business owners regret selling their company within a year, and it’s clear that emotional pressure plays a significant part in that number. Many owners sell their business and enjoy a honeymoon period for about six months. It feels amazing to get out of the fire and have some money in your pocket.
For many entrepreneurs, boredom and a sense of purposelessness settle in after the newness wears off. Suddenly, the attributes that worked for you as an owner and leader don’t anymore. You’ve stepped out of the company, and it kept chugging along, just like it was supposed to. You’ve gotten exactly what you wanted, but you’re unsure where that leaves you.
That’s why it’s so important to make sure you’re properly prepared to sell from not just a financial standpoint, but also an emotional one.
Beyond the Dollar Signs
Many entrepreneurs tend to equate their business’ value with their own self-worth, which can lead to a crisis of self and purpose post-sale. That means finding things outside of the business to pour your time and effort into. Hobbies and a social network will fill some of this gap.
That only scratches the surface though. Consider, does your sense of identity come from within, or is it externally validated?
Support from your community can help strengthen your internal sense of identity. This could include your spouse, a counselor, a peer group, or a social group. What’s important is finding people you can learn to be vulnerable and authentic with because oftentimes, our outward self isn’t very authentic. That wears on you over time, especially when you’ve been burying yourself in work to avoid these feelings.
Everyone’s journey is different. We don’t often admit it—and we certainly don’t admit we need help. I encourage you to find a safe place to start to explore those questions and discover what’s underneath.
The most important thing is to practice being open, honest, and authentic outside of the work environment. We spend most of our waking hours in the workplace. Taking time to figure out who you are before you step away from your business will help prepare you to walk into the next phrase.
Keeping the Stool Stable
Visualize yourself as a four-legged stool, with a leg for your emotional, spiritual, mental, and physical health. It’s important to care for each of those four areas equally; otherwise, the stool (you) will become unbalanced and start wobbling.
It’s important you integrate quiet and reflective time into your week, so you can identify when your stool gets wobbly. I don’t necessarily mean you need to meditate, but find things that quiet your mind and allow you to check in with yourself.
The more quickly you’re able to identify when your stool becomes unbalanced, the faster you’ll be able to develop strategies to find balance. This is a crucial skill as not only an owner/operator, but for someone preparing themselves emotionally for life post-transaction.
I’ll be the first to admit, as a business owner, finding this time is easier said than done, but being intentional in blocking time each week will pay off tenfold.
Intentionality, Community, Accountability
Intentionality is key to living an authentic life. Deliberately surrounding yourself with people of character, who love you more than your feelings, can make all the difference. What I mean by that is that I have a good friend of mine who loves me enough to tell me when I’m straying from my path, so I can take corrective action. As hard as it can be to hear, it’s because he cares enough to do that, rather than feeding me feel-good platitudes.
Seek out at least a handful of people who you know and trust, who are willing to tell you the truth in love. If there’s anything I’ve learned on my own journey, it’s that the times I ignore those people because I think I know better, I’ve gotten into the most trouble.
Must-Read Personal Development Books
Here are a few books I recommend to help you on this journey.
- Leadership and Self-Deception, The Arbinger Institute.
- The 5 Types of Wealth, Sahil Bloom.
- Wild at Heart, John Eldridge.
- The Emotional Side of Selling a Small Business, Jamison West.
The reality of being a leader is that if we were all willing to be transparent, we’d get through this journey smoother and more painlessly. We’re all afraid that people are going to walk away if we’re not the strong image we project. But I’ve found that when I’ve been vulnerable to the people around me, they become more endeared to me and willing to help out.
For more of the latest in M&A, check out how Evergreen Elevate helped MSPs boost value pre-sale.





