You’ve Just Sold Your Business: Now What?
The transition into a new phase of life after selling your baby can be difficult, especially if you were reluctant to sell, but here’s how to refocus.


After years of caring for, making personal sacrifices, building your team, instituting workflows and processes, burning the candle at both ends day after day, the time has come where you have sold your business. It feels like you just sold your baby.
Many thoughts and emotions may be circling your mind like a shark circling its prey. It is critical that you are not captured by the shark-like thoughts and that you focus your time and attention on your future. Focusing on your past and those decisions that you cannot change can and will create angst that you simply do not need to complicate your frame of mind. Take this time to focus on your new chapter.
My great-grandfather would often tell me that you can control only the “controllables.” Trying to do otherwise is going to cause frustration, and in his deepest wisdom, he would look me in the eyes and say, “Where is your time best spent — in the here and now or in the past?”

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Consummating your business sale surely was no easy feat. Frankly, selling a business is no easy endeavor and requires a strong mental awareness, including extensive amounts of due diligence, sleepless nights, daily mind games of running what-if scenarios (which most of the time are overestimated and rarely play themselves out), contemplation of ideal deal terms, trying to read the buyers and so on.
After working with entrepreneurs since 1996, my business partner and I have narrowed down three common denominators that seem to be true of those individuals who have sold their businesses.
1. Transitions are easier for entrepreneurs who wanted to sell.
Those who have most successfully transitioned from selling their business made the decision because they knew it was the right time for them to sell. In contrast, those who struggle with transitioning typically did not make their decision solely on their own. Regardless of your occupation and/or business, we cannot stress enough the importance of doing this for you. Is this what you want?
You don’t want to end up with seller’s remorse, a feeling of sadness or regret after selling something the seller values emotionally or financially.
We see this scenario often: An entrepreneur hears that a friend or competitor sold their business or hears rumors about the terms someone else received. This leads to them thinking, “Should I sell my business?”
Teddy Roosevelt once said, “Comparison is the thief of joy.” Remember that those other deals came about after an ample amount of time was devoted to:
- Preparing valuations
- Updating and ensuring accuracy of financial records, such as balance sheets, income statements, income tax returns and personal financial statements
- Following and resolving legal, regulatory and transition issues
- Negotiating
2. Once you sell your business, make an effort to stay relevant.
Selling your business is a time in your life to transition into a new phase of life, and it is exciting. What an amazing time to reinvent yourself, stay connected or reconnect, and engage with others.
Here is a great example of someone who did just that. My business partner and I considered buying a financial advisory practice in Naples, Fla., in 2017. After doing an extensive amount of due diligence, we reached out to SCORE.org for some mentoring advice. Out mentor provided a unique perspective, having years of business experience, and had a genuinely sincere interest in helping us to understand from his perspective the fairest deal terms. The most memorable part of our experience: Our mentor was 93 years old and sharp as a tack.
With your newfound free time, take an interest in discovering new opportunities, share your experiences and begin to learn something new for future growth. Some ways to do that include:
- Join social groups such as local clubs, interest groups or community organizations that relate to your hobbies and special interests
- Tap social media sites such as Facebook and LinkedIn to connect with old friends, colleagues and family connections
- Give of your time and expertise and share your connections. Perhaps you can be a mentor as illustrated above
3. Don’t be afraid to pursue risk and adventure.
Entrepreneurs often tell us what they are going to do once they sell their business, but very few act on those ideas that really got their hearts pumping while working. Once you’ve sold, why not take the time now to venture into your bucket list? Maybe you’ll find inspiration in these ideas:
- Book a dog sledding expedition and an overnight stay in the wilderness
- Raft down the Amazon River
- Go on an African safari
- Scuba dive on the Great Barrier Reef
- Drive a race car
- Learn to fly an airplane
- Learn to sail
- Learn a new language
- Take a polar bear plunge
- Snowshoe through the Rocky Mountains
- Sleep under the stars
- Learn beekeeping
- Take a cooking class in France or Italy
Congratulations on your success. Although it feels like you sold your baby, this is now a time to reinvent yourself. You can control only the controllables, so it is up to you to find fulfillment beyond the realm of entrepreneurship.
What a privilege and opportunity to invest time with your loved ones, explore your personal interests and consider new adventures. To your future!
Content in this material is for general information only and is not intended to provide specific advice or recommendations for any individual.
related content
- For Business Owners, Estate and Exit Planning Join Forces
- Five Ways to Get Key Employees to Ride Out Big Changes
- How Should a Small Business Plan for Rising Taxes?
- Marketing to Women Could Be a Business Owner’s Best Decision
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Dennis D. Coughlin, CFP, AIF, co-founded CG Capital with Christopher C. Giambrone in 1999. He has been in practice since 1996 and works with individuals nearing retirement and those whom have already retired. Proud of his humble upbringing, Dennis shares his advice with the same core principles that he was raised with. When not in the office, you will find him with his family enjoying the outdoors.
-
What Trump's EU Trade Deal Means for Your Wallet
Trump's trade deal with the EU averted the worst case scenario, but US consumers might still see price hikes on some key goods.
-
July Jobs Report Renews Rate-Cut Hopes: What the Experts Are Saying
The July jobs report shows weakening in the labor market and lifts expectations for a September rate cut.
-
How Much Income Will an Indexed Annuity Get You? An Annuities Expert Lays Out the Numbers
Guaranteed lifetime income sounds great, but how much will it be? Several factors determine your future payout on indexed annuities with an income rider.
-
Financial Fact vs Fiction: Why Inflation Is Lower, But Prices Are Not
Do you think bonds protect you from stock losses? Are you confident your assets will go to your intended heirs if all you have is a will? Think again — and read on for other myths that could be leading you astray.
-
I'm a Personal Finance Expert: Here's the Truth About Using AI to Plan Your Retirement
AI can be a useful tool, but it often gets important financial information wrong. It also can't emulate the empathy, judgment and personal connection you can get with a human being.
-
You Don't Have to Be Wealthy to Need a Wealth Manager
Navigating complex financial decisions is hard on your own, no matter how much money you have. A wealth manager can provide comprehensive financial planning, investment management, risk management and more.
-
Despite Tariffs, These Investment Experts Are Bullish on European Equities
European equities were one of the better-performing investments during the first half of 2025. They could be a good long-term prospect for U.S. investors needing to diversify, according to these investment managers.
-
How Do You Know You Are Ready for a Gray Divorce? 15 Yes-or-No Questions
As more people 50 and older get divorced, many splits are initiated by women who want a new path. Answer these 15 questions to see if you might need to think about how you should move forward.
-
'Buy Now, Pay Later' for Everyday Spending? This Financial Pro Thinks It's Risky
'Buy Now, Pay Later' apps can get you out of a jam when you need money quickly. But using them regularly for small purchases could create problems.
-
Five Things to Consider Before Rolling Your 401(k) into a Roth IRA
Converting at least some of an old 401(k) to a Roth IRA can offer long-term tax benefits and retirement flexibility, especially if you anticipate being in a higher tax bracket later or wish to leave a tax-free legacy.