Building a Business You Never Want to Retire From: Lessons from My Parents' 40-Year Journey

Last month, my parents retired after running their own business for four decades—essentially my entire life.

As I've watched them navigate the bittersweet process of selling and letting go of their life's work, I've grappled with two profound questions:

1. What does it truly mean to LOVE your work so much that retirement feels optional?
2. And how do you ultimately let go of something you've built from scratch and nurtured for 40 years?

The conventional wisdom about work is straightforward: it's a means to an end. We're told to spend our lives working and saving for that idealized future when we can finally sit back and enjoy the fruits of our labor. But after watching my parents' journey and now running my own business, I've learned that this narrative misses something crucial.

Anyone who's owned a business knows it's an uphill battle requiring dedication and perseverance that most people lack. Yet when done for the right reasons and thoughtfully adapted over time, running a business becomes more than just work—it becomes one of the best ways to do what you love every day instead of merely counting down the years until retirement.

When I use "love" to describe work, I'm not talking about something that's consistently easy, lucrative, or even traditionally fulfilling. Work I love:

• Challenges me daily to grow and evolve
• Holds me to a higher standard as a human being
• Forces me to take responsibility for both my actions and their rewards
• Gives me what my life needs, even before I recognize those needs myself

For my parents, self-employment meant being present for moments many of my friends' parents missed. They picked us up from school every day, spent summers with us, and showed up for countless "middle-of-the-day" events that mattered. But this flexibility came with trade-offs: Dad taking business calls during vacation, afternoons spent in their various offices after school, and weekend work becoming the norm.

The boundaries between work and life weren't just blurred—they were practically nonexistent. This meant I didn't just observe their business; I lived it. Their business partners became our vacation companions, my sister and I worked various roles throughout our school years, and when their office moved to our home, customer service became a family affair.

11-year-old me and my dad

Growing up, I never wanted to work for myself. While my parents were very successful, I saw the blood, sweat, and tears it took to weather up and down markets, be responsible for the livelihood of others, and still do your best to be there for yourself and your family. 

It wasn't until several years into owning my own business that I realized what my parents had known all along: No one can give you freedom, fulfillment, or purpose — you have to build it yourself.

When that happens, you no longer desperately dream of “retirement; " you live through your work every day. 

Hosting their retirement party became one of my proudest moments. It was deeply moving to see the culmination of everything they'd built, the lives they'd touched, and the challenges they'd overcome. 

The whole fam at the retirement party

But what struck me most was the symmetry of the moment—looking at old photos of my sister and me working alongside them, then watching the new family taking over the business, already including their own children in the journey.

My parents' legacy isn't just about the business they built—it's about showing that success can be achieved while maintaining family bonds and creating opportunities for the next generation. Their business will continue helping another young family realize the dream of building their own success story.

In celebration of their retirement, I'm sharing some of their wisdom that I first published almost a decade ago. The advice remains as relevant today as it was then, perhaps even more so in our rapidly changing business landscape.

To my parents: Congratulations on building something so meaningful that letting it go was the hardest part. You've shown me what it means to build a business we never want to retire from.

Business Advice from a Couple of 40-Year Pros

• Be ready to manage the downside. The upside tends to take care of itself.
• Errors of omission have greater consequences than errors of inclusion.
• Play the long game. If you stay in the game you can always stage a comeback.
• It is not how many times you say yes that will keep you in business, it is how many times you learn to say no.
• You make three promises to your customers: be on time, stay on budget, and provide customer satisfaction. The one you cannot break, without sacrificing the relationship, is number 3. If you blow it on 1 and 2, number 3 can bring it back around.
• Say thank you to your employees as often as you can and mean it. You wouldn’t have a business without them.
• Trust but verify.
• Always keep space in your life for time away from your business. It is part of your life but not all of your life.