Posted in Triplett & Carothers on October 28, 2025
Retiring from a business you founded isn’t like leaving a job. It’s a personal, financial and emotional process that takes time and coordination. Whether you want to sell, pass the business to family or simply step back, the best outcomes follow thoughtful preparation.
Start with a clear plan
Begin by asking key questions: When do you want to retire? Do you want to sell, transfer ownership or wind down operations at your business? Do you have a particular person in mind to take over? The answers will shape everything from your tax strategy to your lifestyle goals.
Get a professional valuation of your business, assets and investments so you know what you’re working with. If a sale is likely, make sure your financial records are clean and your management team is stable; buyers will pay more for a business that can run smoothly without you. You could also ask trusted employees to sign retention agreements to reassure potential buyers by protecting continuity.
Decide how you’ll exit
If you plan to sell, work with your financial and tax advisers to coordinate the sale with your broader retirement strategy. You’ll need a tax-smart withdrawal plan that covers both personal and business assets so that neither your retirement income nor your company’s value takes an unnecessary hit.
If you’d rather stay involved, consider scaling back instead of stepping away completely. Many founders shift into advisory or consulting roles, providing high-level insight without being involved day-to-day. This approach preserves connection and purpose while giving you more freedom, but your ongoing commitment may delay the financial rewards of a full sale.
Family succession is another path. Passing the business to children or other relatives can create a legacy, but it requires early and open discussions. Make sure potential successors want the role and understand its responsibilities. If multiple family members are interested, try to prevent conflict by establishing clear ownership and leadership structures. Remember that transferring ownership as a gift may trigger gift tax obligations for you and potential tax consequences for your successor, so plan these transitions carefully.
If no suitable buyer or successor emerges, closing the business may be the right option. Creating a realistic timeline lets you notify clients and employees, meet all legal requirements and extract maximum value from the remaining assets.
Take it slowly
Gradual transitions often work best. Reducing your work hours, delegating responsibilities and mentoring future leaders together ensure continuity for your team and your clients. A slow handoff lets you pass along institutional knowledge and ease into retirement emotionally as well as financially.
Outside the office, consider what you’re retiring to, not just what you’re leaving behind. Many founders find fulfillment by serving on boards, mentoring startups or investing in interesting ventures. Channeling your experience into fresh projects can replace the structure and sense of purpose your business once provided.
You’ve spent years defining yourself through your company’s success. A deliberate, well-planned transition allows you to preserve that legacy even as you build a new life focused on curiosity, connection and independence.
Reach out to Roz Carothers and her team at Triplett & Carothers to learn more.
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