Have you ever had a phrase stuck in your head for years? For me, it was this one: Escape the Predictable Life.
Long before I ever made a bold change, those words rattled around in the back of my mind. At the time, I didn’t fully understand them. But as my career and life unfolded, I realized they were guiding me toward something bigger: a life outside of expectations, a life of reinvention.
In this post, I want to share the story behind that phrase, how it shaped my journey from law to travel to entrepreneurship, and what it might mean for you.
The Linear Path I Was Expected to Follow
I grew up believing in a linear path:
- Study hard.
- Get a degree.
- Land a prestigious job.
- Climb the ladder.
And that’s exactly what I did—at least for a while.
I started working young. By 14, I was juggling jobs at diners, flea markets, and eventually just about every mall in New Jersey. I waited tables, bartended, managed restaurants, and even spent time at Lone Star Steakhouse, where I was forced to line dance (yes, really).
I wasn’t afraid of hard work. That work ethic carried me into law school, where I clerked for the U.S. Tax Court in Washington, D.C., while earning an advanced law degree. And from there, I became a corporate tax attorney at one of the largest law firms in the world.
On paper, everything looked perfect. Success. Security. Prestige.
But the truth? My life was entirely predictable.
Predictability Can Feel Suffocating
In that world, I knew exactly what the next year, five years, even ten years would look like.
- More hours.
- More pressure.
- More money.
- Less life.
I saw older partners burning out, having heart attacks, or losing marriages to the strain of the career. It was like watching a preview of my own future, and I didn’t like what I saw.
That phrase—Escape the Predictable Life—wasn’t fully formed in my brain yet, but I could feel it growing inside me. It was the whisper telling me there had to be something more than this.
Quitting the Law
In my late 30s, I did the unthinkable. Just 30 days before making partner, I walked away.
To my colleagues, it was shocking. To me, it was survival.
Eric and I had already taken a one-year sabbatical to travel, and when we came back to the U.S., we promised ourselves we’d stay put for at least five years. Instead, we lasted just two and a half.
We sold everything, packed backpacks, and hit the road. No clear plan. No guarantees. Just faith that we could figure it out.
And we did.
Building a New Kind of Life
At first, I started a small travel blog just to keep friends and family updated. But when I learned that blogging could actually earn money, we leaned in.
We launched With Husband in Tow, later expanded into Food and Drink Destinations, and over time built businesses that supported a life of full-time travel. Along the way, we experimented—Amazon businesses (some successful, some not), consulting work, even yoga teacher training.
We kept our minds open, said yes to opportunities, and figured out how to make it work.
The result?
- Over 70 countries visited
- Years living in Bali, Bangkok, Spain, and Ireland
- A thriving business built from laptops and curiosity
To many, it looked like a dream. To us, it was our way of escaping predictability and embracing the unknown.
The Reality of Freedom
But let me be clear—freedom isn’t always glamorous.
There were months we made only $500. There were long hours, constant hustling, and the stress of not knowing what came next.
And yet, that unpredictability held possibility. Every day felt alive, every choice opened a new path.
For me, Escape the Predictable Life stopped being a phrase. It became a way of living.
Escaping Predictability Doesn’t Look the Same for Everyone
Now, I’m not saying everyone should sell everything and travel the world. Escaping predictability doesn’t have to mean becoming a digital nomad.
For you, it might mean:
- Starting a side hustle
- Changing industries
- Finally launching the business you’ve dreamed about
- Choosing a path that feels more fulfilling, even if it’s less conventional
I once spoke with a fellow tax lawyer who confided he was unhappy. He missed milestones with his kids and dreamed of becoming a teacher—sharing civics or history in a classroom. But he couldn’t see a way out. Today, a decade later, he’s still at that firm.
I don’t judge him—life circumstances are different for everyone. But I hope one day he takes that leap, because predictability may feel safe, but it can also be suffocating.
What It Means for Me Today
For me, escaping predictability meant leaving law behind, saying yes to travel and entrepreneurship, and living abroad for over a decade.
Now, in what I call the third quarter of my life, it means building businesses in the U.S. while also creating a space for storytelling, creativity, and connection—right here on YouTube.
This channel is my latest reinvention, a reminder that change isn’t just for your 20s or 30s. It’s lifelong.
What It Could Mean for You
If you’ve ever felt that whisper—that voice saying “Isn’t there more to life than this?”—listen to it.
You don’t have to leap across the globe, but you do have to acknowledge that desire for something more.
And the good news? It’s never too late to rewrite your story.
Join Me on This Journey
This blog and YouTube channel are about more than my story. They’re about yours too.
If you’ve ever craved reinvention, if you’re navigating a midlife crossroads, or if you’re simply ready to embrace more freedom, you’re in the right place.
Here’s what you’ll find here:
- Stories about career pivots and entrepreneurship
- Lessons from years of travel and business building
- Honest conversations about freedom, reinvention, and growth at any age
- Inspiration to help you take your own leap—big or small
Because escaping predictability doesn’t have an age limit.
Final Thoughts
For me, Escape the Predictable Life started as a phrase that wouldn’t leave my head. Today, it’s the lens through which I’ve built my life—and the message I’m here to share with you.
If any part of this story resonates with you, I invite you to join me.
👉 Subscribe to my YouTube channel so you don’t miss new videos. I’ll be sharing more about my journey, the lessons I’ve learned, and the strategies you can use to reinvent your own life—whether you’re in your 40s, 50s, or beyond.
Because predictability may feel safe, but it’s not where growth happens. And if you’re brave enough to take the leap, you might just discover that the best part of your story is still ahead.
✨ Thanks for being here for this second post and video. In the next episode, I’ll share what I call the quarters of my adult life—the lawyer, the traveler, the entrepreneur, and where I see the fourth quarter heading.
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