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.
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.
You are now subscribed
Your newsletter sign-up was successful
Want to add more newsletters?
Delivered daily
Kiplinger Today
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more delivered daily. Smart money moves start here.
Sent five days a week
Kiplinger A Step Ahead
Get practical help to make better financial decisions in your everyday life, from spending to savings on top deals.
Delivered daily
Kiplinger Closing Bell
Get today's biggest financial and investing headlines delivered to your inbox every day the U.S. stock market is open.
Sent twice a week
Kiplinger Adviser Intel
Financial pros across the country share best practices and fresh tactics to preserve and grow your wealth.
Delivered weekly
Kiplinger Tax Tips
Trim your federal and state tax bills with practical tax-planning and tax-cutting strategies.
Sent twice a week
Kiplinger Retirement Tips
Your twice-a-week guide to planning and enjoying a financially secure and richly rewarding retirement
Sent bimonthly.
Kiplinger Adviser Angle
Insights for advisers, wealth managers and other financial professionals.
Sent twice a week
Kiplinger Investing Weekly
Your twice-a-week roundup of promising stocks, funds, companies and industries you should consider, ones you should avoid, and why.
Sent weekly for six weeks
Kiplinger Invest for Retirement
Your step-by-step six-part series on how to invest for retirement, from devising a successful strategy to exactly which investments to choose.
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?”
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free 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.
-
How to Turn Your 401(k) Into A Real Estate EmpireTapping your 401(k) to purchase investment properties is risky, but it could deliver valuable rental income in your golden years.
-
My First $1 Million: Retired Nuclear Plant Supervisor, 68Ever wonder how someone who's made a million dollars or more did it? Kiplinger's My First $1 Million series uncovers the answers.
-
How to Position Investments to Minimize Taxes for Your HeirsTo minimize your heirs' tax burden, focus on aligning your investment account types and assets with your estate plan, and pay attention to the impact of RMDs.
-
Don't Bury Your Kids in Taxes: How to Position Your Investments to Help Create More Wealth for ThemTo minimize your heirs' tax burden, focus on aligning your investment account types and assets with your estate plan, and pay attention to the impact of RMDs.
-
Are You 'Too Old' to Benefit From an Annuity?Probably not, even if you're in your 70s or 80s, but it depends on your circumstances and the kind of annuity you're considering.
-
In Your 50s and Seeing Retirement in the Distance? What You Do Now Can Make a Significant ImpactThis is the perfect time to assess whether your retirement planning is on track and determine what steps you need to take if it's not.
-
Your Retirement Isn't Set in Stone, But It Can Be a Work of ArtSetting and forgetting your retirement plan will make it hard to cope with life's challenges. Instead, consider redrawing and refining your plan as you go.
-
The Bear Market Protocol: 3 Strategies to Consider in a Down MarketThe Bear Market Protocol: 3 Strategies for a Down Market From buying the dip to strategic Roth conversions, there are several ways to use a bear market to your advantage — once you get over the fear factor.
-
For the 2% Club, the Guardrails Approach and the 4% Rule Do Not Work: Here's What Works InsteadFor retirees with a pension, traditional withdrawal rules could be too restrictive. You need a tailored income plan that is much more flexible and realistic.
-
Retiring Next Year? Now Is the Time to Start Designing What Your Retirement Will Look LikeThis is when you should be shifting your focus from growing your portfolio to designing an income and tax strategy that aligns your resources with your purpose.
-
I'm a Financial Planner: This Layered Approach for Your Retirement Money Can Help Lower Your StressTo be confident about retirement, consider building a safety net by dividing assets into distinct layers and establishing a regular review process. Here's how.