Redefining Success: What I’ve Learned After Building a Life Off the Beaten Path
- Jennifer Rackliff
- Jul 4
- 2 min read
I used to think success was a straight line—climb the ladder, hit the milestones, check the boxes. You know the story: stable job, good salary, homeownership, two weeks off a year, a packed schedule that meant you were “important.”
But stepping off that path taught me something far more valuable: success isn’t a one-size-fits-all destination. It’s personal. It's evolving. And for me, it’s been about reclaiming freedom.
Success to Me Now: Freedom and Choice
Today, success looks like freedom.
Freedom to choose how I live—like homeschooling my daughter on our own terms.
Freedom to choose what I do—like working only with aligned clients and creating work that feels meaningful.
Freedom to choose when I do it—like weaving world exploration into business trips or taking a random Tuesday completely off.

This isn’t about working less. It’s about working deliberately—with intention, joy, and alignment.
New Metrics: Money, Mission, and Ease
Let’s be real—money still matters.
I’m in a season of growth, building toward more financial freedom because money creates freedom: more options, more generosity, more capacity to rest.
But my metrics have shifted. Now I also measure success by how I feel in my life:
Am I calm and centered?
Do I feel spacious and in flow?
Is this easeful—not effortless, but aligned?
I want to feel in harmony. Not burned out, not bracing for the next thing—just rooted in joy and growing from there.
Risk, Identity, and Being Seen Differently
Here’s the honest part: as much as I talk about freedom, showing up fully still feels vulnerable.
When I was younger, I shared everything. I lived my life out loud on social media. I didn’t think twice about visibility.
Now, I move with more intention. Not because I’m hiding—but because I understand the weight of my work, my words, and my presence.
I still crave impact. I want to be significant. I want to do big things.But I no longer chase visibility for its own sake. I move slower, more purposefully—and that often feels scarier than being seen ever did before.
For You: What Does Your Success Look Like?
In the past, success was packaged neatly: a good job, a white picket fence, 2.5 children, a pension plan. Does that dream still hold up?
For some, it does—and that’s beautiful. For others, success might mean:
Becoming a NYT bestselling author
Running a remote business from the beach
Raising kids while making art in a cabin
Traveling the world with a backpack and a mission
There’s no right way to live your dream. But there is your way.
So here’s your invitation: Take some time to reflect on what success really means to you. Not the filtered version. Not the inherited version. The real one. And then start moving—gently, courageously—in that direction.
Because the only path that matters is the one you choose.