by Pat Alacqua, author of “Obstacles to Opportunity: Transforming Business Challenges into Triumphs“
People often ask me, “Why haven’t you retired?” And when I say, “I already did,” they laugh.
They respond, “Well then you’re terrible at it.”
From my perspective, retirement was never about walking away, unplugging, or fading out. It was about choosing. I wake up every day since selling my tradeshow and event business with a choice.
I didn’t win the lottery. I didn’t luck into that choice. When I sold that business at a time in my life when most people are still ramping up their careers, I found myself in a position I never really aimed for but one I was grateful to be in: I had options.
That changed everything. I had to ask myself: What now?
Some people walk away, and I respect that. But for me, walking away didn’t feel like the point. I enjoyed the work so much that I could choose to continue. I loved tackling challenges that move companies and leaders forward faster.
I didn’t retire. I just kept choosing.
That one statement defines how I think about success and leadership. And that idea — choice — has become the lens through which I see leadership and business building. That shift from being at the center of everything to building something that could thrive without me is the same shift I help other leaders make today.
Whether you’re a founder or someone leading inside an organization, it’s not about whether you plan to sell a company. It’s about whether you’re building something with real value. And alongside that value, you create options and a sense of security, ensuring you’re prepared for what the future may hold.
People often misunderstand what I mean when I say, “We help you grow your business and prepare it for sale.” They think we’re trying to talk them into selling. We’re not. In fact, many leaders don’t want to sell and may never do so. We don’t help leaders grow companies so they can sell. We help them prepare, so they’re never forced to.
You don’t have to sell. But one day, you might want to. And if that day comes and the business can’t survive without you, you don’t have a choice. You have a job you can’t leave.
That’s not freedom. That’s dependence. And for many smart, hardworking leaders, it’s a trap they never saw coming.
And that’s not just an entrepreneur’s issue. Inside large organizations there are leaders whose teams only move when they push. That’s not leadership. That’s weight. And it doesn’t scale.
One of the clearest comparisons I use for scaling a business or leading a team is that it’s much like raising kids. At first, you’re everything. You’re hands-on. You’re involved in every detail. The fundamental shift is that success eventually means you’re not needed in the same way. They’ve grown. They’ve matured. They can stand on their own. And when they do, your role shifts. You’re still there, but you become a guide, not a crutch.
That’s true freedom. And that’s the definition of success I’ve come to believe in.
You should enjoy what you’ve built but not let it need you. You should still choose to be part of it but not be trapped by it. It’s comforting to know that you can pivot, pause, or press forward, and the thing you built will keep moving.
That’s what I wish more entrepreneurs and leaders would chase — not just growth, not just scale, but the ability to choose. Because when you have that, everything changes. You’re no longer operating from fear. You’re not scrambling to fix fires you created by being the center of everything. You’re leading from strength and focused on impact. You’re finally able to take a breath and ask: What do I want next?
That’s the kind of “retirement” I believe in. Not the one where you stop but the one where you get to decide. And for me, I’ve decided to keep doing what I enjoy — helping others achieve the same freedom. I want to use the experience I’ve gained not as a badge of the past but as a tool for the present.
So, maybe I’m bad at retirement, but I didn’t fail. I’ve just redefined it. In the end, what I really want for every company leader isn’t a moment when they walk away. It’s a moment when they realize that they’re no longer needed. They still can be a guiding force if they desire, but they get to choose what happens next.
That’s freedom. That’s fulfillment. And whether you own the business or lead within one, that’s the clearest definition of success I’ve found: building something strong enough to set you free.
Pat Alacqua is a business growth strategist and founder of the Entrepreneur to Enterprise Program. His book, “Obstacles to Opportunity: Transforming Business Challenges into Triumphs“, explores what it takes to build real value through leadership, structure, and clarity. Learn more at PatAlacqua.com/book.