Preparing for Location Independence: 5 Lessons Learned

Why I Don't Travel Solo
The Best of Slovenia with Roundabout Tours [Review]

Once you dip your toe into the waters of location independence it can be hard to resist its current. There are so many stories flitting around the internet, so many blogs of successful nomads who have made their dream a reality, and so many courses, ebooks, webinars, and mastermind groups offering you the solution.


I have a slightly obsessive personality, and I’ll freely admit that the lure of digital nomadism hit me hard. For several years now, I’ve been toying with the idea, slowly easing my roots up inch by inch in preparation to take flight.

But I’m not the sort of person who can just drop everything and go, despite the hundreds (possibly thousands) of bloggers who will tell you that it’s easy to quit your job and travel the world just like that.

I’m more methodical than that. I like to have a plan.

I’m the sort of person who obsessively writes to-do lists, creates elaborate budget spreadsheets, and blocks out my day by the hour (all color-coded, of course).

I am not the sort of person who just throws caution to the wind and hopes for the best.

That said, I do want the freedom that comes with location independence — and that freedom goes far beyond mere travel.

The appeal of location independence is really the independence, and the implied freedom that goes along with it.

The freedom to stay, or go, without having to tie up a bunch of loose ends. The freedom to turn on a dime and change everything. The freedom to settle down if I want to, in a place of my choosing, not the place of my employment.

And you know what? Slow and steady as I may be, I’m doing it. This reality is only a few months off for me, and the final plans are in place.

Ready. Set. Freedom.
Ready. Set. Freedom.

As I begin packing up my few remaining belongings, I’ve been reflecting on what it took to make this happen for me, methodical, logical planner that I am.

There are certainly a few things that have been necessary to my success, and there are definitely more lessons waiting for me.

As I sit on the horizon of a new start, I thought it worth sharing what I’ve discovered so far while preparing for location independence. Perhaps it will help you decide whether you’re willing to make the leap.

1. Prepare to make sacrifices

There is nothing gained without something lost, and this is as true for the preparation to become location independent as anything else. In the past nine months I have donated, sold, or trashed the vast majority of my personal possessions, keeping only what was significant or necessary.

While downsizing has taught me the joy of minimalism, it was not without challenges. I’m a nostalgic person, and I’ve kept everything from birthday cards to movie tickets dating back to the late 1990s.

Additionally, my five years of teaching produced an absolute behemoth of professional development material. My closets were jam packed with outfits suited to Ohio winters, Houston summers, and everything in between. Some of the articles of clothing hadn’t been worn in years.

Sifting through everything was a massive undertaking. Yes, I felt better when it was done, but I won’t pretend that it was easy. There is something deeply humbling about watching your life reduced to physical objects, carried away by strangers who haggled it down to a dollar.


2. No amount of planning will be enough

I can’t count the number of lists I’ve made, or how many times I’ve revised my plan of attack come September. Despite my need for order my grand plans seem to change daily.

Planning is good. Planning gives you something to aim for, a way to move forward. Without a plan I would be completely overwhelmed right now. But there is such a thing as over-planning. At some point, you just have to trust that when things go wrong (and let’s face it, something will probably go wrong at some point) you’ll be able to tackle it.

The best way to plan for location independence is to prepare for the unexpected. Ensure you have good health insurance, save up a rainy day fund, and make sure that your loved ones know your plans. Beyond that, try to loosen that iron grip over your future. It will still be there when you let go.

No matter how much you plan, sometimes you're faced with the unexpected.
No matter how much you plan, sometimes you’re faced with the unexpected.

3. You need money

There’s no way around it. You may not need a lot of money, but you will need money. If you’re lucky, maybe you have some savings. This can be a good short-term solution, but if you’re planning on location independence as a way of life, you need a more long-term plan.

Pick your poison. You're gonna need some of it.
Pick your poison. You’re gonna need some of it.

There are any number of ways that you can accomplish this, from transitional, temporary work in whatever location you choose to digital options like copywriting, web design, or tutoring. There are a ton of great places to get started, including UpworkFiverr, and

I’m lucky in that I have a writing business that I started with Marie from Ardent Camper five years ago. When we started the business we hadn’t yet decided to take the plunge into location independence, but we did know that we wanted to escape our day jobs. The business has grown from a resume service into a full-fledged copywriting firm, and will at least partially help sustain me.

Figure out the bare minimum that you need to get by. This includes food, lodging, health insurance and transportation costs, as well as any debt payments you need to make (I’m looking at you, student loans). Then, add a little extra for a buffer. Whenever you exceed your minimum, sock it into savings.

If you are planning to travel, make sure you take that into account and employ money-saving techniques. Don’t forget to consider exchange rates, travel-related taxes, and travel insurance.

4. You need support

It always helps to have a cheerleader in your corner. Not everyone is going to understand or agree with your decision, and that’s okay. Different strokes for different folks and all. But I’ve found that it’s absolutely essential to surround myself with people who are either pursuing similar dreams, or wholly supportive of me as I pursue mine.

That’s not to say that you should ignore criticism. Often times your biggest critics are speaking out of concern and love rather than disdain. If someone you care about keeps trying to poke holes in your grand plans, try not to take it personally and instead address their concerns directly. They may bring something up that you hadn’t thought about, giving you a chance to prepare.

My biggest supporter is, of course, Tara, who has assured me that I can continue to crash at her Los Angeles apartment even if I’m making pennies. Beyond that, I’ve felt the support of other bloggers, entrepreneurs, and location independent individuals.

Having trouble finding support? I highly recommend joining a community. For me, the members of Cody McKibben’s Digital Nomad Academy have been amazing, and became the source of my first mastermind. Additionally, Isabelle Rizo is a constant inspiration with her BellaVie lifestyle, and her Facebook group is full of inspiration and positive vibes.

At the end of the day, you want to feel uplifted, not pulled down.
At the end of the day, you want to feel uplifted, not pulled down.

5. You need to hold yourself accountable

On January 1, 2015 I wrote the following date on a post-it note: September 1, 2015. That post-it note went on my wall, next to my desk, and I’ve looked at it every day since.

September 1, 2015 is the day I want to be free of everything that is tying me down. Everything that I have done in the intervening months has been for that goal. Money saved, credit card bonuses earned, apartments abandoned, and business ventures started — all in the name of lifting those pesky roots.

I have a very black and white way of looking at the world sometimes, which makes it easy for me to hold myself accountable. When I set a goal for myself it becomes an inevitability, not an option.

Unfortunately, this means that when I do have to quit something it’s incredibly difficult for me. But it also means that if I set my mind to something that I truly care about, I’m usually at least moderately successful.

Set goal. Meet goal. Repeat.
Set goal. Meet goal. Repeat.

Location independence isn’t for everyone

For all I know, it might not be for me. I haven’t arrived yet, though all of the pieces are slowly falling into place. But even if it turns out that I prefer firmly laid roots, I don’t think I’ll ever begrudge myself for making an honest attempt.

You may notice, as September 1 inches closer and inevitably passes, that there are more posts about surviving the location independent life. I don’t mean just in terms of travel, either. I want to share the good, the bad, and the ugly of untethering oneself in all aspects of life, including entrepreneurship, education initiatives, and relationships.

Life is short, and I’m in the position to make this dream a reality. I have the gift of good health, marketable skills, and stubborn determination. In the end, I know I would be angrier with myself for never trying than for giving it a shot and changing my mind.

Why I Don't Travel Solo
The Best of Slovenia with Roundabout Tours [Review]
  • contented traveller

    All very astute points and serendipity on your travels will make it even more memorable.

  • Victoria@celebratetheweekend

    What an incredible post! I greatly enjoyed your writing and wish you lots of luck (that too you need) as you start on your new adventure (September 1 is a great day to start something new. Not only it is my birthday, but is the official first day of school in Russia and is celebrated as a Day of Knowledge holiday)

    • Thank you so much! I didn’t know that about Russia, but I love it! Seems perfect. 🙂