Commentary April 29, 2025
The Exit Strategy Blueprint: How To Avoid Seller’s Remorse
It’s natural to have regrets after you sell your business, but you can ease your transition by mapping the next stage of your career and life.
For entrepreneurs, most of their adult lives have been about making sacrifices to build their businesses, create jobs and provide a good life for their families. Sooner or later, though, the day will come when you need to exit your business, either by choice or circumstance, depending on your planning. The question is, are you emotionally ready for this massive change in your life? Unfortunately, most aren’t.
There are several key questions to consider. What will you do after the sale? How and where will you spend your time? Who will you hang out with? (Remember, if you exit early, many of your friends will still be working.) How will your significant other feel about your lifestyle change? Let’s dive into some of these issues.
This is the sixth and last column in The Exit Strategy Blueprint series written by Anup Gupta, a professional speaker, author, consultant and small-business trainer with a passion for helping entrepreneurs grow their businesses with a focus on the bottom line, paving the path toward exiting successfully. Anup started his distributor business at the age of 28 and reached a peak revenue of over $3.6 million. He attained financial independence at 49, and exited his business at 53. Contact him at agconsultingusa@gmail.com or 330-554-2152 (call/text).
Avoiding Seller’s Remorse
Seller’s remorse is bound to set in after the sale. Some of the excitement of the big payout wears off when you feel lost and unsure of how to spend your time. You miss interactions with your clients/suppliers and the camaraderie of co-workers.
The best way to avoid seller’s remorse is to have a written plan in place years before the sale. If you have read my previous column, you know that you should be working on a financial plan simultaneously while running your business. In this case though, I’m referring to your personal plans. Write down what you intend to do professionally to stay busy, along with some pleasure activities you desire. Business activities can include taking classes online or at a local college, consulting, speaking, writing, joining nonprofit boards, mentoring, etc. Personal pleasure activities could be traveling, golfing, taking lessons, spending time with family – any activity you always enjoyed but couldn’t make as much time for.
Work on improving your physical, emotional and mental health. Yoga, meditation, joining like-minded groups, and spending more time with your spouse/partner and other family members and friends are just a few examples. For most of your adult life, you’ve been running around like crazy for everybody else. Now is the time for you to put the spotlight on yourself, your well-being and happiness.
Be sure to read Anup’s previous column, Am I Financially Ready To Retire?. Many business owners tie the sale of their business to their retirement, but that can be a mistake.
At this stage, dedicate time and energy to your passions and those of your spouse/partner. This will bring purpose and fulfillment and enrich your lives. Be intentional. Warren Buffett, one of the greatest investors of our time, says, “When you are living a life of passion and obsession, there are no limits.”
Maybe you’ve always yearned to make a difference in other people’s lives and leave a lasting impact on the world. If philanthropy is near and dear to your heart, now is the time to pursue those endeavors. In a recent conversation with a fellow retiree from California, she shared how, in her 60s (after buying an oceanfront property to pamper herself), she embraced supporting specific social causes. She donated over a million dollars to more than 20 causes. In the process, she made dozens of friends. Not a week goes by that she doesn’t hear from somebody who has benefited from her generosity.
As you near the day when the deal consummates, all the memories and emotions come flooding back: toiling those late nights, building the business one happy customer at a time, the adrenaline rush of winning a big contract, interacting with the whole team. Once the contract is signed, it all becomes a part of history. Being pulled in 10 different directions by customers, suppliers, employees and other operational responsibilities – it all comes to a screeching halt. Feeling that loss of identity when you go from head honcho to a nobody? You bet!
For entrepreneurs, your name became synonymous with your company and the title you held throughout your business life. Separating from it takes time – a lot of time for some, sadly. Be prepared for it but also give yourself grace to get through it.
Rewiring, Not Retiring
I want to share the story of my exit for perspective. After selling my business and handing over the reins to the new owners in March 2022, I worked there until December for a smooth transition. I took it easy for a week, then my wife and I flew to Las Vegas and had a wonderful time. For the first time, I didn’t need to check my phone for emails or calls, or bail out a client for their poor planning. Our adult children were shocked to learn that their parents, who had always planned for months for any trip, had packed and just left for vacation. Why not? We had earned this freedom after putting in 26 years of hard work.
Within a few weeks, we decided to visit our families in India. I will never forget a comment my mother made to me. She said this was the first time she felt I was there with her. Why? Because I was able to spend quality uninterrupted time with her. That one statement cemented my belief that I had made the right decision by selling my business. My parents aren’t getting any younger. I want to spend as much time as I can with them. I want to go places with them, laugh, hear my childhood stories, catch up and be there for them.
Post-exit, I started my consulting business, working with other entrepreneurs to help them increase profitability and put the pieces together for a successful exit. I’ve been a published author and speaker for over a decade, which I enjoy immensely. To further this passion, I’ve been fortunate to write for two publications and speak at several business organizations. To fulfill my philanthropic aspirations, I joined SCORE as a mentor to coach my fellow business owners. Last year, the local Black Chamber of Commerce approached me to sit on their board, which I graciously accepted.
“Why can I enjoy my time after exiting without remorse? With my wife’s input, I documented our reasons for exiting and goals after the exit. If feelings of nostalgia or sadness ever start to creep in, I look at that list.”
At this stage of my life, I work as much or as little as I want. I have the time to pursue my hobbies and spend quality time with my wife and two children. When I’m not out at a speaking engagement or a meeting, I love spending time in our newly built sunroom.
Why can I enjoy my time after exiting without remorse? With my wife’s input, I documented our reasons for exiting and goals after the exit. I divided them into three categories: financial, business and personal. If feelings of nostalgia or sadness ever start to creep in, I look at that list, which is very prominently taped in my home office.
Also, I don’t call this the retirement phase, which, to me, implies it’s all over. I call it “rewiring.” I am rewiring from the phase of “must-do” activities to “want-to-do” activities.
Remember this simple fact: You must exit your business one day. The only unknown is who holds the key to the lock – the circumstances or you? Plan it right so it can be on your own terms.
To my fellow hardworking entrepreneurs, I wish you a successful and happy exit. If I may assist you in your journey, contact agconsultingusa@gmail.com. Your questions and comments are always welcome.