Moment of truth:

When I quit my “cool” job in an app development company and startup incubator, it was for two main reasons:

  • To have the freedom to do what I want when I want.
  • To make more money.

Pretty sure I’ve got that “make more money” thing down pat. (We won’t talk about how little I was paid so that even my lowest months right now are about 5x my former salary.)

But the freedom thing?

Yeah, I’ve let that slide at little.

I mean, I totally lived it up at first: backpacking around India for six months, doing a Yoga Teacher Training in Rishikesh, taking a two-week vacation in Thailand with my friends just because I felt like it. Then moving to Brazil to learn Portuguese, start an official business, and visit the Amazon Rain Forest.

But now?

Now I’ve been “stable” for almost three years.

Yeah, I’ve taken some trips… but not many.

For the most part, I’ve been living in the same city, sitting at a desk 5-8 hours per day, and living for the weekend.

It’s not a bad life, because I do genuinely love the work I do, I can sleep in whenever I want, and I NEVER have an annoying boss breathing down my neck.

I make my own hours, and if I want to take a weekday off, I hardly even think twice about it.

But I haven’t traveled much.

I’ve taken some trips to see family, took myself on a non-working vacation to London, and went to Portland, OR twice to go to the World Domination Summit.

And beyond some weekend trips with friends to other parts of North Carolina or Tennessee, that’s basically been it.

Which is so lame that 4-years-ago Chelsea would probably scold me for it. 🤷🏼‍♀️

And I don’t know just how much I’ll be changing up my schedule to accommodate more travel after this upcoming experiment, but I *do* know that this is a VERY worthwhile experiment…. and it’ll definitely demonstrate the “digital nomad-ness” of my business.

In my heart of hearts, I feel like I’m going to be pleasantly surprised at how much I can “unplug” from my need to have a set routine and schedule every day… but there’s always that fear that taking time off and not “hustling” all the time is going to make our businesses crash, isn’t there?

So here’s what the experiment is all about:


In four days, in the wee hours of the morning of September 15th, I’m going to get on a flight to San Francisco to start a road trip.

It’ll be a two-week road trip, from San Francisco to Seattle, stopping at all the national parks along the way.

My travel buddy also has an online business, so I think our (rough) plan is to wake up at the ass-crack of dawn (about 5 am), work from a coffee shop for 5 hours (until 10 am), drive for 4-5 hours, and then have the rest of the day to do what we want.

Obviously, save some days to explore different locations.

It’s going to be a total experiment in van life (though without the van and with a Subaru instead), sleeping wherever, and hunting for wifi.

It’s going to require trust in the power of the internet and the automation tools I’ve got set up…. and my ability to be productive in the early-ass hours of the morning. (I normally don’t even start work until after 10 am, so we’ll see how this goes.)

But I know I’ll learn A LOT, and I think I’ll come away with a newfound appreciation for my business and ideas on ways to grow it, automate it, and scale it that I’ve never thought of before.

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Where You Come Into This Experiment

Basically, I decided to make this experiment public and document it, because I LOVE the power of solopreneur businesses to give us all the freedom we desire.

Whether it’s freedom to immerse yourself full-on into van life…. or to just not have to deal with annoying, outdated HR rules anymore.

I also think that THIS is the reason so many of us become self-employed, but the moment we have full-fledged companies, we become too afraid to actually do it. So hopefully by watching me do it, you’ll get some inspiration or ideas to claim more freedom for yourself… whatever that looks like for you.

So I’ll be talking about it publicly on my Instagram profile, and inviting you to ask me questions as the trip progresses or send me advice if I find myself needing it. (And I might.)

So follow me on Instagram to see how it goes!

Most likely, there will be a follow-up blog post on all the things I learned, and how you can apply those lessons to make your business better & support your freedom too.

Wish me luck!


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