What I’ve Learned from 20 Years of Working with Business Owners on the Edge of Retirement
What I’ve Learned from 20 Years of Working with Business Owners on the Edge of Retirement
By Shawn Todd, CFP
There’s something humbling about sitting across the table from a busines
s owner who’s built something from scratch. Maybe it’s a thriving construction company, a medical practice, or a family-run restaurant. The business might be wildly successful or just finally gaining traction—but in almost every conversation, I hear the same thing:
“I wish I had started planning for myself sooner.”
It’s something I understand not just professionally—but personally.
I grew up surrounded by business owners. My mother and stepfather both ran their own businesses. My dad built a business on the side. My sister has run several successful businesses. My cousin started a very successful & growing online company. I started a business with my stepfather, my uncle was a business owner, and my grandfather ran two farms. I incorporated my first business at 26, after drawing up a logo on the back of a business card and getting a small $7,000 loan. How hard could business ownership be?
In short, entrepreneurship is part of my DNA. But so is seeing the cost when financial planning gets pushed to the back burner.
After 20 years of walking alongside business owners approaching retirement, here are some of the most important lessons I’ve learned—lessons I wish more people talked about earlier in the journey.
1. You’re Not Just Building a Business—You’re Building a Life
Too many business owners spend their best years reinvesting in the company, skipping vacations, and putting off key conversations at home because “the business needs them.” But if you don’t align your business with your life goals, you risk waking up one day with money and no map.
The best outcomes happen when business and personal goals are planned in sync—when you view your company as a tool to fund your freedom, not just your workload.
2. Your Business Can Be a Legacy—or a Liability
I’ve seen it too many times: someone’s poured 30 years into a business… only to have no plan to exit, no valuation, and no buyer. That turns a potential legacy into a long list of regrets.
Business succession isn’t just a legal conversation—it’s a deeply emotional one. Who will carry on what you’ve built? Is it a partner? A child? An external buyer? Starting early gives you the most options—and peace of mind for everyone involved.
3. Cash Flow and Profit Aren’t the Same as Financial Clarity
Many owners think, “I must be doing okay—I’m not struggling to pay the bills.” But clarity goes beyond surviving.
It means understanding:
- What you own (and what it’s worth)
- What your business contributes to your retirement
- What your tax exposure really looks like
- And what your family needs from all this
You don’t need to be an expert—but you do need a clear picture. Without it, every decision feels like a guess.
4. Your Family Is Watching—and Waiting
Business owners often carry the weight alone. Your spouse may not ask, the kids don’t know what to say, and you assume silence equals peace.
But silence usually equals stress.
When I meet with families, I hear the same fears:
- “What happens if something happens to them?”
- “Is the business our retirement plan?”
- “Are we safe if they step away?”
One of the greatest gifts you can give your family isn’t money—it’s clarity and communication. As I’ve grown my business – I’ve learned that really good conversations and insight come from home. My spouse Michele has often been a great sounding board for some of my ideas, and has been the provider of great wisdom over many years. It’s a relationship & dynamic that I truly appreciate.
5. Your Network Is Gold—So Learn from It
I’ve learned more from business owners in real conversations than I ever did in textbooks. I’ve seen what works, what fails, and what haunts people.
Some of the best business owners I’ve met I either was lucky to work for, or work around. I learned tons of lessons on quality of work, discipline, and belief in your vision.
When Corey & I started the podcast – we originally wanted to open the dialogue to include some of the amazing business owners we meet. Let them tell their stories. Since then, some of these incredible conversations have turned into really great and valuable lessons for us both.
So, take the time to talk to the people around you. Ask your peers what they regret. Ask what they wish they did differently. And if you don’t have someone you trust to ask… then find one.
Because at the end of the day, you don’t have to figure this out alone.
Final Thought: It’s Never Too Late, But Sooner is Always Better
Whether you’re 10 years from retirement or 6 months from a deal closing—clarity brings peace. And clarity comes from planning.
If you’ve spent your career building a business, maybe it’s time to start building your future with the same level of intention.
