Time Freedom Introduction
Enjoy Life’s Journey
It’s better to look back on life and say, ‘I can’t believe I did that,’ than to look back and say, ‘I wish I had done that.
—Unknown
It’s a Thursday afternoon in August. I’m sitting on the dock, looking out on a beautifully calm lake in the pine tree-filled part of Wisconsin we call “Up North.” My family spends our summers here.
The neighbors cruise by on paddleboards. They have two boys; one is thirteen, like our son Theo. The family moved to Lake Seventeen (it’s strange, but with so many lakes up here, there just aren’t enough names) five years ago for the lake’s “water-ski culture.” I smile because I know my wife’s family shaped this culture. For over eighty years, long before Claire was born, this lake has been central to her family’s story.
Our cabin is perfect, though nothing fancy. For Claire and me, it’s all about the lake and this idyllic setting we get to enjoy. Lake Seventeen has become a defining presence in our family’s story.
Water-skiing is important to Claire. A former show skier, she has performed in front of crowds, the biggest always on the Fourth of July, Independence Day. Skiing through the show course atop a three-level pyramid with flags flying and everyone cheering is a rush Claire misses, so she made a deal with Theo years ago that whenever he wanted to go skiing, she’d take him.
He has stubbornly resisted. “No, Mom,” he’s said, seemingly forever.
“Okay,” Claire has smiled back, simply wanting for him the fun she knows he’d have.
But this summer is different.
From the shore, I see Claire in the boat and Theo floating behind it. She hits the throttle, accelerating forward and pulling Theo out of the water on one ski. He’s up. He’s really doing it.
Theo’s finally skiing—and doing pretty well at it, because Claire makes good on her promises. I’ll bet she’s logged a hundred hours behind the wheel already this summer, and I know she loves it. I’m so happy Claire is able to give him the experience.
And I’m here to witness the big event. Theo will have some great stories to tell when he goes back to school in the fall.
I’ll be back to work then, too.
***
When I tell people I get to spend entire summers at the lake, they always ask, “Are you retired?”
I say, “No.”
Then they ask, “How do you do it?”
I’m not independently wealthy. I have no trust fund. I definitely didn’t sell a business for millions of dollars.
The answer is that I’ve achieved time freedom.
It wasn’t always this way. For twenty years, I felt trapped in traditional, corporate jobs. I was fortunate not to be living paycheck to paycheck, but even so, I felt stuck, held back from pursuing my dreams. I yearned for a life of choice and flexibility. Instead, I found myself commuting three hours to and from work each day to climb a ladder I didn’t want to climb and make more money than I needed. I had little time to be there for my family, make a bigger impact in my community, or simply rest.
You may feel the same way.
And when we do, we create the clarity and capacity to move forward with intention in our work, our relationships, and our lives. Sometimes the realization is sudden, while at other times it forms gradually; either way, we sense the possibility of something better.
Everyone has the right to find work that lights them up. Often, this means creating your own job through self-employment, a major part of what this book is about. But that doesn’t have to be the case. The only prerequisite for this journey is that you value freedom and autonomy and feel you could use more of both in your life.
So, what is time freedom?
Time freedom is not work-life balance.
Work-life balance focuses on splitting time between competing demands, trying to juggle work, family, and personal interests without letting anything fall—often forcing you to compromise along the way. It’s lived hour by hour, day by day, week by week. The focus is on managing your calendar and squeezing in moments of living where you can.
Time freedom plays out over months, years, and even decades. It’s much bigger than work-life balance; it’s about shaping how your time unfolds on your terms, not constantly negotiating between the push and pull of work and life as if they were separate forces.
Instead of asking how you’ll survive each day or week, time freedom asks a bigger, bolder question: How do you want to live this month, this year, this lifetime? You won’t find talk of work-life balance in these pages. We’re after something far more expansive, something you can feel all year, not just on weekends and holidays.
Time freedom is not financial freedom, either.
You don’t need to be rich, retired, or independently wealthy to start living with more choice and flexibility. Time freedom begins long before you hit any “magic number” or level of savings.
Of course, financial freedom is a worthy goal. and I absolutely want to help you get there. There’s nothing wrong with wanting complete financial independence; it's powerful to know you never have to work again if you don't want to.
But for most people, getting there is a long journey. It can take decades. And for those who choose to get there quickly, the path often requires intense sacrifice, a stripping away of much that makes life joyful and meaningful in the moment. Pursuing financial freedom alone can mean missing the chance to actually live while you’re earning.
So yes, by all means, pursue financial freedom, but don’t wait to live a free and flexible lifestyle. Together, we’ll create a solution where you can experience time freedom while still earning income. The secret is making that income stream as flexible, fulfilling, and sustainable as possible.
Time freedom is a new life path.
Your North Star is time, but it doesn’t stop there. Real time freedom requires a full, honest look at how you live, the money you have (and need), and the work you choose to do. When you bring all those pieces together—life, money, and work—you can build a flexible life.
This book is your invitation to join a community of time freedom enthusiasts I call “freetimers.” Freetimers are people who have reclaimed control over their time. We work when we choose, live by design—not by default—and believe freedom isn’t something we wait for but something we build. We are a diverse group of smart, hardworking, thoughtful professionals who have shifted our focus and traded in maximum wealth for faster freedom. It’s a movement to redefine how we work, rising up out of day-to-day stress to live the well-intentioned lives we want long before we turn sixty-five.
As freetimers, we intentionally design our lives to maximize time freedom and work flexibility. We’re not idle. Freedom requires hard work, planning, and discipline. To the outside world, a freetimer might appear to be at leisure—and at times, we are. But we also pursue big goals, build strong relationships, and invest in deep personal growth, often achieving more than those who follow a more traditional life path. We’re a testament to what’s possible when we reclaim our time and use it wisely.
The conventional and the freetimer’s life paths both begin the same way. We spend about twenty-five years in “early life,” the time when we are being raised and educated. But after that, the paths diverge.
Figure 1: Conventional and Freetimer Life Paths
The default, conventional path transitions into two long life stages: work and retirement. I’ve placed retirement at age sixty-five, though many people work longer to meet their financial goals. This retirement stage may look long because I’m assuming a lifespan of one hundred years. Of course, if you die earlier, you miss out on more of your non-working years.
The freetimer’s path takes a different turn. After school, we ideally spend about ten years building skills and professional networks. Beginning as early as age thirty-five, we enter a single, blended stage of work and play, made up of a series of different, multiyear “work adventures.” Each year combines periods of focused, sometimes intense but meaningful work with extended periods of personal time off. We create work we love and do it as long as we choose, possibly into our nineties.
***
I’m so glad you picked up Time Freedom. In it, I have distilled everything I know about crafting a rich, free life, plus all the frameworks and tools I teach as a financial advisor and business coach. I’ve built a unique collection of knowledge over the years, from making my first stock investments as a senior in high school to earning an advanced degree in finance and founding three still-thriving businesses.
Our journey together has stages. First, we’ll shift your perspective on building wealth for retirement and uncover your money strengths. Then we’ll dive deep into the three drivers of time freedom: lifestyle, money, and work. Finally, we’ll forecast your path to freedom, back it with simple financial projections, and show you how to create months of time off each year.
You’ll find three key activities in these pages, and I urge you to spend time on them; they’ll make Time Freedom’s ideas real for you. Be sure to collect your financial numbers (Chapter 3), design your ideal life (Chapter 6), and project your financial future (Chapter 12).
Life isn’t a simple progression of years. It is periods of stability separated by big life changes or “life inflection points.” Some are planned; some, like death, divorce, job loss, or illness, are not. Even these shocks don’t have to derail our dreams, though. A flexible life allows us to feel the impacts, reassess, and chart a new course. This book will give you the confidence to work with whatever life has in store for you.
I experienced one such inflection point in 2016, when I was demoted from a corporate director position. Though it was devastating at the time, it set me on the path to becoming what I am now: a money expert, entrepreneur, and coach. Now, I work because I want to, not because I have to. I take mini breaks and longer sabbaticals at will. I pursue interesting projects and take larger bets on myself. As a freetimer, I can work half-time by choice and with confidence.
If you want a free and flexible lifestyle fast, you’re in the right place. We’ll look at how to recalibrate your savings (or get you some) and rethink work. If you’re stuck in a conventional career that’s draining you, I can help you break free. Time freedom is a better way to live, but I had to learn how to gain it the hard way. I want an easier path for you. Ultimately, true wealth is measured in time, not money.
This shift in perspective changed everything for me. It’s what makes moments like watching Theo learn to water-ski, with Claire at the wheel, possible. Moments like this are priceless. My dreams are summers off, three months a year of slow travel, and long visits with family and friends.
What are yours?
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