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Navigating The Quarter Life Crisis, or Why Living Out of My Car Was the Best Thing I Ever Did

TFT_badge_150x150Something had to give.

I was living in NYC in an apartment my mother owned as part of my compensation for running a business with her.

But even though it was part of my compensation, it still felt like I was just basically living at my mom’s house.

I had begun making progress on my credit card debt, which had ballooned to over $20K. But I didn’t want to pay it off over several years — I was willing to make some big changes in my life in order to wipe it out really fast.

I was 27 years old. I’d been building a business since I was 18. I’d been in love and had my heart broken. I’d had incredible adventures in New York. But now it was time to go.

So I decided to sell the apartment, get rid of almost all of my belongings, and take off on a road trip of indefinite duration, called The Freedom Tour.

In retrospect, I think The Freedom Tour was born of my Quarter Life Crisis.

Leading up to the decision to take off on the open road, my life was pretty amazing. Yet, little bits of resentments, feelings of dullness, and an itch to make a big change that wasn’t going to be scratched by getting a new haircut had begun to bubble to the surface.

I knew I wasn’t going to live in New York City forever. I knew I didn’t want to be in debt forever. And I knew I didn’t want to live in a home my mother owned forever.

It was time to grow up.

And growing up for me meant dramatically changing pretty much everything about my life.

For some Millennials, also known as the Boomerang Generation, growing up has been a bit delayed.

Many of our parents supported us well beyond college. Many of us moved home, in one way or another. Many of us hung out in the gray area between adolescence and adulthood longer than we’d planned, than we were proud of, or than our parents had had in mind for us.

I was one of those.

But then, within 9 months of deciding to fly the nest, I wasn’t. I managed to unravel the business with my mom so we could both be set free, I doubled my income, I paid off all of my debt, and I fell in love.

Not bad for the results of a Quarter Life Crisis.

Here are some of the signs you might be going through a Quarter Life Crisis:

  1. You have no idea what you want to be “when you grow up.”
  2. You’re beginning to imagine every man you go on a date with in a “husband suit.”
  3. You’re getting over the party scene and sometimes you find it more nourishing to spend a night home alone, even if it is a Saturday.
  4. You feel lost.
  5. You’re depressed.
  6. You feel resentful.
  7. You find yourself calculating how old your parents were when they got married, bought a house, and had kids, and comparing it to how old you are currently.
  8. You realize that you thought you’d be “further along” by this time in your life.
  9. Your tendency to spend money willy nilly without thinking has caught up to you and you’re finally ready to do something about it.
  10. You have an itch to make a big change which may include leaving your job, starting a business, traveling the world, or going on an indefinite road trip.

If even a few of those signs apply to you, here’s what I recommend:

Scratch your itch to make a change sooner rather than later. Your life is waiting. (Tweet it.)

Though most of my family and friends were supportive when I embarked on The Freedom Tour, some told me I was crazy. They asked me a lot of questions, to which I simply answered, “I don’t know.”

I found liberation in the not knowing, and I went on the trip anyway.

The worst thing to do is to sit around for another 5 years feeling lost, depressed, disengaged from work, and restless.


Nothing changes unless something changes. (Tweet it.)

No matter what your age, giving your life a makeover in honor of your soul’s calling is never a bad idea.

Yes, your new business may fail. You might get Giardia while traveling the world and have to come home. You might realize that you hate the new career and have to move on to something else.

But your bag will be packed with all sorts of insights and new information about yourself and about the world that you never would have gathered sitting in your cubicle or on your mom’s couch debating whether or not to take the leap.

If you’re questioning everything about your life, celebrate it. It’s simply a sign that you’re alive and that you’re fueled by a desire to live extraordinarily.

Then turn that celebration into action. You may end up somewhere else than you thought (like I did, engaged to the “random” guy I invited on my road trip) and that will be a good thing.

If you want more inspiration for navigating the Quarter Life Crisis, my friend Christina Hassler is hosting a free online conference called The Quarter Life Upgrade: Everything You Need To Know To Rock Your 20’s & 30’s.

In my interview for the conference, I shared:

  • Tips for how to get out of debt and release the shame you have around it
  • Breaking free of credit card payment avoidance
  • Ways to increase and appreciate your abundance right now
  • How to set up your “money for me” account and make loving spending decisions
  • Tips for you if you are receiving financial support from your parents

My friends Mastin Kipp, Gabby Bernstein, Lissa Rankin, and Amanda Steinberg are also part of the event.

Get access to the entire Quarter Life Upgrade FREE Virtual Conference, which runs from July 22nd to 26th, by clicking HERE.

Over to you:

Did you experience a Quarter Life Crisis? How did you navigate it?


It’s not going to turn out the way you thought.

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