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By Diane Bourdo, CFP®
You’ve built something meaningful. Something real. Whether your business started as a spark of inspiration or a strategic move, it’s grown into an extension of your identity. Now, as you begin thinking about what’s next, whether that’s stepping away, slowing down, or shifting roles, the question isn’t just when you’ll retire from your business, but how.
According to research conducted by the Exit Planning Institute, many baby boomers have yet to develop an exit strategy, despite owning 51% of privately held businesses. And time isn’t slowing down. In ten years, the youngest baby boomers will be 71. The majority are already well into their 70s. Yet millions of these businesses are still operating without clear succession plans or retirement blueprints.
Gen X and millennial business owners are generally taking a different approach. They’re planning ahead, thinking long-term, and aligning their financial strategies with their life goals. They’re proving that proactive preparation doesn’t just ease transitions, it maximizes opportunities.
For lifelong innovators, retirement isn’t about walking off into the sunset but transitioning with intention. It’s about designing a future that honors what you’ve built and gives you the freedom to shape what comes next. Whether you’re preparing now or still just considering retirement down the line, it’s never too early (or too late) to plan with both purpose and process.
Too often, business owners focus on the technical aspects of retirement—valuations, tax implications, legal structures. And while those are absolutely important (we’ll get to that), purpose should come first.
What do you want your life to look like after you retire from your business? That’s not a rhetorical question. It’s the foundation of a successful transition. Are you stepping away to spend more time with family? To pursue a new venture or creative pursuit? To rest? To travel? To give back? Knowing your “why” creates clarity in your decision-making and helps ensure that your retirement isn’t just financially sound but emotionally fulfilling.
Many founders experience a loss of identity after leaving their business. But if you reframe this next chapter as a new arena for innovation, the possibilities open wide.
Once you’ve clarified your purpose, it’s time to focus on the process. Selling or stepping back from a business isn’t a single event but a series of decisions that build on one another. The proper process protects your wealth, legacy, and peace of mind.
Here’s what a thoughtful transition might include:
The earlier you start preparing, the more options you have. Ideally, business succession planning starts three to five years before your target transition date, giving you time to identify successors, maximize the value of your business, and coordinate your personal financial plan with your business exit.
What is your business truly worth and what will it take for that value to support your next chapter? A professional valuation (updated regularly) helps clarify your options and identify areas for improvement before you sell or transfer ownership.
You don’t have to sell to the highest bidder. Options like employee stock ownership plans (ESOPs), family transitions, management buyouts, or partial sales can align more closely with your values and goals. The right strategy all ties back to your purpose and what you care most about: legacy, liquidity, control, or continuity.
Many business owners have wealth tied up in the business, whether through retained earnings, stock, or real estate. A transition plan should include a personal financial strategy: income replacement, tax planning, risk management, and investment alignment that reflect your new reality.
You don’t have to do this alone. A transition touches so many parts of your life—emotional, financial, professional. Surrounding yourself with advisors who understand the big picture helps ensure your decisions reflect your values and goals.
At Treehouse Wealth Advisors, we work with innovators every day. We know how much care, courage, and creativity it takes to build a business, and we bring that same energy to helping you navigate what comes next.
Retiring from your business isn’t an ending but a transformation. Whether you’re just beginning to think about life beyond your business or are deep in the planning stages, we’re here to help. Let’s build a retirement strategy that honors what you’ve created and sets you up to thrive long after the business cards are put away. Reach out to our team today.
Garrison Point Advisors, LLC doing business as “Treehouse Wealth Advisors” (“TWA”) is an investment advisor in Walnut Creek, CA registered with the Securities and Exchange Commission (“SEC”). Registration of an investment advisor does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the Commission. TWA only transacts business in states in which it is properly registered or is excluded or exempted from registration. A copy of TWA’s current written disclosure brochures, Form ADV Part 1 and Part 2A, filed with the SEC which discusses among other things, TWA’s business practices, services, and fees, is available through the SEC’s website at: www.adviserinfo.sec.gov.
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