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“Being a world traveler or the best golfer at the club aren’t sufficient attributes of a new identity to be sustainable because they don’t provide an outlet for tackling and resolving problems.”

James Fitts, CFP®

Managing Director, Business Owner Services & Senior Family Wealth Advisor

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Not an End but a Beginning: A Business Owner’s Guide to Retiring Well

As Appeared in Small Biz Daily

Business owners by nature are problem solvers. Driven by a need to be in control of their destiny, they start businesses that solve their clients’ problems, but that is just the beginning. Running the business creates daily opportunities to problem solve— from hiring and training the right people, to negotiating favorable terms with suppliers and managing cash flow, to anticipating competitive changes that could disrupt the business model and managing margins so the business reaches and retains profitability—business owners are problem solvers.

But after years of successfully meeting these challenges, there comes a time that every business owner has to move on. Ownership transition is inevitable: embracing it and taking control of the process will lead to better outcomes for you and your family. The successful transition of ownership in your business is your crowning achievement as an owner, and you want to leave it healthy, prosperous and ready for the future.

Where will you direct your energies?

We advocate that you should transition out of your business before you realize you’ve stayed too long. This strategy is overwhelmingly positive, but it does have one downside: without thoughtful planning, all the entrepreneurial energy that led you to start and run the business for years won’t have an outlet. For many, this can lead to feelings of regret, and stifle what should otherwise be a productive and joyous time of life.

What will you do?

We highlight this question by saying that you should retire to something, not from something. The single largest reason owners delay the transition of their business is because they can’t answer the question, ‘What will I do?’ The answer eludes them because it hasn’t been confronted, and it’s easier to stay with the business because it’s comfortable and known, then to face an uncertain future.

This dilemma manifests itself repeatedly when a transition occurs without thought to the future. Sometimes thinking they will have plenty of time to figure it out, the owner pushes through a sale only to be spit out of the other side with a large bank account and the dawning realization that fulfillment was left behind. This can cause real emotional distress and undermines the owner’s very sense of themselves as a person.

The identity of an owner is wrapped up tightly in their business, the role they play in the community, and the recognition they receive from being successful. Their social connections have grown out of the business because it is central to the family’s role in the community. When the business goes away, all of the structure they had and knew needs to be replaced. It’s no wonder owners avoid a transition as long as possible. Without a clear destination after the sale, it’s easier and more comfortable to hang on.

What will you retire “into”?

The key to avoiding (or at least, minimizing) the emotional upheaval of a sale, is reinvention. When an owner can successfully imagine, and then put into practice, a new identity not dependent on the business, they have something to look forward to, to retire ‘into’. The more clearly we are able to see the future, the more that our behavior is rewarded with feelings of excitement and anticipation for what’s to come. We feel safe. With a redefined persona waiting, the owner can proceed to realize their new goals. The energy and passion once directed at making their business successful now has a new outlet, and instead of avoiding a business transition, the future is an incentive to move forward with confidence.

Who will you be?

To work well, this new identity must include a challenge. Being a world traveler or the best golfer at the club aren’t sufficient attributes of a new identity to be sustainable because they don’t provide an outlet for tackling and resolving problems. Your reimagined identity must also have purpose, and a great way to start thinking about purpose is to ask yourself, “How do I want my family, friends and community to remember me?” You have likely built the foundation of a legacy through your business life, but is there more? What did you leave behind that you now have time to develop? What goals remain incomplete? What will your eulogy include?  In these answers you will find purpose, new problems to solve, a destination to retire into, and a reason for embarking on the next chapter in your life with confidence and excitement.


James Fitts, CFP®, Managing Director, Business Owner Services Senior Family Wealth Advisor

Jim is an experienced investment professional who consults with families on intergenerational gifting strategies, family wealth education, governance and philanthropy. He has extensive experience in assessing personal and business financial positions and advises family-owned businesses on ownership and management succession. He is coauthor of Your Next Adventure: Planning for Life After the Sale of Your Business. He also speaks at conferences and events about the human and emotional process that many business owners overlook when transitioning out of their businesses.

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