Twenty-five years ago, I landed one of my favorite clients. In the past two weeks, I signed two more just like it. That’s not a typo, and it’s not a humble brag about longevity in this business; it’s the whole point of this article. If you’re doing work you love, with people you respect, “retirement” starts to look less like a finish line and more like a moving target you’re not in any hurry to hit.
I get asked about retirement a lot these days. Partly it’s my age (nearly 30 years into a marketing career will do that), and partly it’s because people assume that once you’ve built and sold a few agencies, you’re counting down the days until you can disappear to a beach somewhere. So let me tell you what retirement means to me, and how I’m planning for it, because I suspect my definition looks different from the one most of us grew up with.
Redefining Retirement
The traditional version of retirement is simple: you exit the 9-to-5 grind, along with all the responsibilities that come with it, and you do something else (or nothing at all). Entrepreneurship, if you ask me, is just a shortcut to that same destination. When you own your schedule, you’ve already retired from someone else’s version of work.
But I’d argue the real definition of retirement has nothing to do with a last day at the office. It’s about financial freedom: the ability to decide what you do, when you do it, and who you do it with. That’s it. That’s the whole definition. No W-2 required. Retirement, done right, is a shift. It involves turning time that once generated value for other people into time that generates value for yourself and the people you love. It’s trading billable hours for memorable experiences, the kind that enriches your life and the lives of the people around you, rather than just padding a client’s KPI dashboard.
Purpose Doesn’t Retire
So, it may come as no surprise that I have no intention of fully stopping. My mission has always been to connect, educate, and entertain, and I plan to keep living that mission for as long as I’m capable of playing to my strengths. If you’re doing work that lines up with your purpose, and you’re good at it, it stops feeling like work in the first place.
That’s why I’ll keep “working,” and I put that word in quotes deliberately, for as long as people and businesses find value in my knowledge, experience, and network. Tutoring the next generation of marketers and entrepreneurs isn’t a retirement hobby for me; it’s a continuation of the same purpose that’s driven my entire career. My goal isn’t to stop generating income. It’s to avoid tapping retirement savings for as long as I possibly can, so that money keeps compounding quietly in the background while I keep doing what I love.
The Real Prep Work
None of this happens by accident, though. If there’s one piece of advice I’d pass along to anyone younger than me, it’s to start saving early and never stop. Make your money work as hard as you do. Compound interest is the only truly dependable business partner I’ve ever had; it never calls in sick, and it never negotiates its fee down. Financial freedom, in practical terms, means being able to generate income as needed, not because you must, but because you choose to. It means having enough control over your schedule that you can do what you want, when you want to do it, without first asking anyone’s permission.
What “Retired” Actually Looks Like for Me
So, what does this all add up to, practically speaking? For me, it’s the opportunity to get fit, eat well, travel, learn new skills, meet new people, and spend real, unhurried time with friends and family. I think of it as curating experiences rather than just accumulating things.
One item at the top of my list: touring around North America in a pickup with a camper, on my own schedule, stopping wherever looks interesting for as long as I want to stay. No itinerary handed down by an HR department, no PTO request to file. But here’s the catch that a lot of people miss when they picture retirement: you still need a schedule. You still need something to pull you out of bed in the morning. Freedom without structure just turns into drift, and drift isn’t the same thing as fulfillment. The goal isn’t to eliminate purpose from your days; it’s to fill your days entirely with purpose, on your own terms.
Start Now: Reverse-Engineer It
If there’s one piece of homework I’d leave you with, it’s this: start by visualizing what your version of retirement looks like, in detail, and then reverse-engineer your way there. Don’t wait for a milestone birthday or a retirement party to start living the life you’re picturing. That includes your bucket list. Why wait? If there’s a trip, a skill, a relationship, or an experience you’ve been saving for “someday,” ask yourself honestly what’s stopping you from starting now, in some smaller form. Most of the time, the honest answer is nothing other than habit, fear, or the assumption that permission must come from somewhere else. Twenty-five years from now, I hope I’m still signing clients I love working with, still mentoring people who are earlier in their journey than I am, and still pulling into a new campground with my camper. That’s my retirement. It might not look like yours, and it shouldn’t have to. But the exercise of defining it, on paper, in detail, is where the real planning begins.
