For many women in their 40s, 50s, and early 60s, life feels like one long balancing act. And if you’re a business owner, you might be dealing with more than the usual stress: You’re leading a business, caring for aging parents, and possibly supporting adult children, all while thinking ahead to your own retirement.
But what happens when the business that has supported everyone for years becomes part of your next big transition?
An exit strategy isn’t just for entrepreneurs looking to cash out; it’s for any business owner who wants options, flexibility, and peace of mind when life inevitably changes. Whether you plan to sell, pass the company on to family, or simply step back, having a clear roadmap ensures that all your hard work pays off.
Start With Your “Why”
Before diving into the mechanics of selling or succession, clarify your personal goals. Do you want to fund your retirement? Transition ownership to your children or key employees? Reduce your workload while maintaining partial ownership?
Your “why” will drive the structure of your exit, financially and emotionally. Many women in the sandwich generation find their priorities evolving: a desire for flexibility, family time, or the ability to care for aging parents without the constant demands of running a business. Knowing what matters most helps shape every decision that follows.
If You THINK You’re Ready…Don’t Wait to Plan
The best transitions happen when you plan early. Ideally, you should begin thinking about your exit strategy three to five years before stepping away. That gives you time to:
- Identify and train a successor—whether that’s a family member, employee, or outside buyer.
- Document systems and procedures to make your business more turnkey.
- Clean up financials and operations to make it attractive to potential buyers or investors.
A first step might be getting a professional valuation of your business, which will help you see where you stand today and how to increase your company’s worth before selling or transferring ownership. Factors like recurring revenue, brand reputation, intellectual property, and leadership depth all play into your valuation. Many women undervalue what they’ve built, especially when their business success feels “personal.” A valuation reframes it as what it truly is - an asset that can fund your next chapter, whether that’s retirement, a new venture, or taking time off for caregiving.
Remember, if you want to keep the business in the family, conversations should start well before a health crisis or financial urgency forces your hand. Too often, women delay these talks while juggling caregiving responsibilities, only to find themselves making rushed decisions later.
Taxes and Retirement
Selling a business can come with major tax consequences like capital gains, depreciation recapture, and potential state-level taxes. The structure of the sale (asset sale vs. stock sale) will impact your after-tax proceeds significantly.
Working with a financial advisor and CPA early allows you to explore:
- Installment sales, which spread income (and taxes) over several years.
- Charitable remainder trusts (CRTs), which reduce taxes while supporting causes you care about.
- Qualified Small Business Stock (QSBS) exclusions, which may apply for certain C-corporations.
When it comes to running (and selling a business) you probably know by now that timing is everything. That’s true when it comes to retirement planning as well. Maybe your parents’ health needs are increasing. Maybe your children are launching (or relaunching). Maybe you’re simply ready to slow down.
Coordinating your business exit with these personal transitions helps preserve both your finances and your sanity. Consider:
- How the sale proceeds will support your long-term retirement plan.
- Whether you want to stay involved part-time or as a consultant.
- The emotional shift that comes with stepping back from a company that’s been central to your identity.
Who You Need on Your Team
The best exits are team efforts. You’ll want to assemble:
- A financial planner to integrate your business proceeds into your overall wealth strategy.
- A CPA or tax strategist to minimize tax exposure.
- A business attorney to structure the sale and protect your interests.
- A valuation expert or business broker to get you a fair price.
An exit strategy isn’t about walking away - it’s about walking forward with intention.
For women in the sandwich years, planning your transition early can mean the difference between reacting to life’s changes and shaping them. Whether you plan to sell, gift, or simply step back, your business deserves the same thoughtful planning you’ve always given everyone else.
Are you ready to start planning so you know all of your options? We’re here to help. CLICK HERE to make an appointment.