To My Small Business: Well, I've Been Afraid of Changin', 'Cause I've Built My Life Around You
While thinking about succession planning might feel like anticipating a landslide (here's to you, Fleetwood Mac), there are strategies you can implement to manage the uncertainty and the transition.


The aging of the American population continues to accelerate, and more small and midsize business owners are wondering: What do I do with my life’s work when I retire?
Many business owners reaching retirement age are considering handing off their business to the next generation, whether a family member, a colleague or an outside interest.
Data from the U.S. Census Bureau shows that just over half (52.3%) of U.S. employer-businesses are owned by people who are at or near retirement age, while 51% of the current American business market is owned by Baby Boomers, who are set to transition within the next 10 years.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.

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.
The Kiplinger Building Wealth program handpicks financial advisers and business owners from around the world to share retirement, estate planning and tax strategies to preserve and grow your wealth. These experts, who never pay for inclusion on the site, include professional wealth managers, fiduciary financial planners, CPAs and lawyers. Most of them have certifications including CFP®, ChFC®, IAR, AIF®, CDFA® and more, and their stellar records can be checked through the SEC or FINRA.
According to Barlow Research, 41% of small businesses (with revenue between $100,000 and $25 million) plan to transition the ownership of their company in the next five years. Of these, 28% plan to sell or transfer to a family member.
This rapidly advancing retirement cliff demands that business owners begin implementing a focused, holistic succession plan, yet many are unprepared.
Owners of roughly half of U.S. businesses surveyed either plan on closing their business or do not have a plan. This is especially prevalent for small businesses, with only 30% of small business owners having a succession plan.
Why succession planning is so important
Why is a plan so important? The long-term survival of a business and the legacy of the owner depend on it. Only 30% of family-owned businesses survive from the first to the second generation, dropping to 12% from the second to the third generation.
This high rate of failure can be attributed to a number of factors. Some business owners are unwilling to prepare in advance.
In some circumstances, the emotions that come with selling one’s life's work overwhelm their ability to put a plan into action.
Finally, some owners may believe that they can easily undertake their succession themselves.
Yet we frequently see that these individuals and their families move too quickly and emotionally, without considering the multiple dynamics at play.
Calling your accountant or banker from the signing table may open a can of worms that should have been dealt with in advance of signing a deal.
In other cases, perhaps you haven’t dealt with your personal finances, and your lifestyle will change due to a different income level without the business’ income (even if it’s sold for a substantial dollar amount).
However, the challenges are by no means insurmountable. By working alongside a trusted financial professional who specializes in the ins and outs of succession planning, business owners can be confident that they are well prepared for the transition to retirement.
Elements to consider when succession planning
Finding that support is crucial when working through the numerous dynamics that we routinely see throughout the succession process, including:
Timing your exit. The ideal timeline for exit planning is 18 to 24 months, allowing for comprehensive planning and taking advantage of tax benefits. Planning should start as soon as possible, even if the business owner is not ready to exit immediately.
This includes creating contingency plans and bringing in key personnel to ensure the business can continue in the event of unforeseen circumstances.
Looking for expert tips to grow and preserve your wealth? Sign up for Building Wealth, our free, twice-weekly newsletter.
Identifying the right successor or buyer. Sometimes, owners are approached unexpectedly by brokers or private equity firms, triggering rushed transitions that can disrupt family dynamics and financial stability.
Having a succession plan in advance is a key part of building long-term wealth and business health.
Managing the culture of the business and family members. Family governance is crucial when involving family members in the business. Open, honest conversations are necessary to align everyone's values and expectations.
Trust and communication are key to successful transitions, and experienced advisers can help navigate these complex situations.
Regular planning. Ongoing financial planning is essential, as circumstances can change. Regular check-ins and reevaluations are necessary to adapt plans as needed.
This includes considering the impact of increased costs or changes in family dynamics on the overall financial plan.
A trusted partner can be the difference between a successful and failed succession. Leveraging the experience of specialists can help ensure that decades of work are rewarded to their full extent, and the next generation is primed to build on an owner's legacy.
Related Content
- Succession Planning: Three Strategies for a Smooth Transition
- Seven Essentials When Preparing to Sell Your Business
- You’ve Just Sold Your Business: Now What?
- Five Tax Breaks Business Owners Might Not Know About
- Here’s How You Can Avoid Succession Drama at Your Company
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.

Mark Valentino is President and Head of Business Banking at Citizens. Under his leadership, the Business Banking team brings comprehensive advice and solutions to help small businesses operate at every stage of their journey. Mark rejoined Citizens in October 2023 after leading a privately owned healthcare provider in Southern California. During that time, including his role as CEO of LA Downtown Medical Center, he dedicated his energy and efforts to expanding mental health access to the underserved communities of greater Los Angeles.
-
$40,000 CD vs $40,000 High-Yield Savings Account - 3 Things Savers Should Consider Now
Both options offer risk-free methods to grow your savings. Learn how much you can earn with each, how they differ and which one suits you best.
-
I'm 51 and my portfolio is up. I'm planning to retire at 60 and want to start moving out of stocks. Is that smart?
We ask financial experts for advice.
-
Gray Divorce Can Throw Your Retirement a Curveball: What to Know
If you're entering retirement and going through a divorce at the same time, you've got some work to do to shore up your long-term financial security.
-
I'm a Real Estate Investing Expert: Optional 721 UPREIT DSTs Can Be the Best of Both Worlds
Before investing in any 721 UPREIT exchange, look for one that offers a straightforward, investor-friendly exit.
-
Markets Are Quiet Ahead of Fed Day: Stock Market Today
Investors, traders and speculators appear to be on hold amid an unusually fraught Fed meeting.
-
5 Multibagger Stocks With Amazing Returns in 2025
multibagger stocks As the term suggests, multibagger stocks multiply your money – gains of 1,200%, for example. Here's where to look for that kind of performance this year.
-
Investing Freebies: Perks You Get for Owning These Stocks
While the biggest investing returns come over the long term, these companies offer instant gratification for investors with several freebies and perks.
-
How an Expired Passport Thwarted Blackmail (and What Other Important Documents You Should Keep)
An optometrist produced his expired passport to foil a blackmail attempt by the daughter of a former employee. After proving he was out of the country on the date of a forged diary entry, he took it a step further.
-
Optimize, Grow, Retain: The Power of Annual Client Reviews
Financial advisers can use annual reviews to help enhance client outcomes, strengthen relationships and build their practice.
-
I'm a Real Estate Investing Pro: This Is What Investors Should Know About Truck Stop Investments
Truck stops might seem like good investments, but they can actually be a risky gamble due to unstable fuel prices, unreliable operators and coming changes in transportation. Instead, consider safer options like industrial or residential properties.