Why Your “Obstacles” Mostly Aren’t

By Garrett

Oct 18, 2016

For you recent subscribers, I just finished up a two month road trip around the western US, which is what this newsletter is referencing. For some context you can read about why I wanted to do the trip in the first place here.”

When the idea of a road trip first magically popped into my head I got really, really excited. Giddy like a schoolgirl is probably the most apt description. Because c’mon, how freaking cool would it be to travel around this (already great) country for two months?!

But nary a second after that grand vision revealed itself, I started to think of all the obstacles that stood in the way. And there were many.

“Ummm, how do you think you’ll be able to balance work and travel?”
“Bro, you don’t even own a car”

“So you’d need to pay for gas. And lodging. And probably renting a car…”


For the next two months I let these obstacles (aka fears) keep the road trip as “something I wish I could do” rather than “something I will do.” I knew it would be one hell of an experience, but I couldn’t commit to doing it before I knew how these obstacles would be overcome.

Yet after two months of waffling I realized something – I wasn’t going to figure that out until I actually committed to making the trip happen. It was the chicken or the egg problem…I “couldn’t” commit because I didn’t know how to overcome those obstacles, but I  wasn’t going to get creative about tackling them until I committed.

After making that realization I just decided “screw it, I’m doing it.” And once I started telling people “I AM doing this road trip” rather than “I am THINKING of doing this road trip” a funny thing happened – the obstacles started melting away one by one.

Within two weeks of committing, a friend offered up her car for me to put thousands of miles on. Seriously, Becca Lucas – you are a saint.

I took a hard look at my work schedule and discovered that if I only did the most important things, I could get by with doing 20 to 25 hours a week.

I got someone to sublet my apartment for more than I was paying, meaning I actually made money.

Friends started offering their places along the way to stay for free, meaning I could put that sublet income towards other things like gas, an occasional nice restaurant and thank you gifts for people’s generosity.

Does this mean everything went off without a hitch? Absolutely not! But when a challenge came up I got creative about how to solve it, ultimately knowing I didn’t have a choice. I’d committed to doing the trip so it was going to happen, no matter what.

Remember how money was supposed to be the biggest obstacle to taking this adventure? After reviewing my trip expenses this week I discovered something awesome. It turns out that while on the road I spent nearly $400 less per month than I do living in New York, for a total savings of almost $1k. Biggest obstacle my ass.

Yes, it took me sleeping in semi-illegal places, occasionally waking up next to cows or greeting the morning with frost covering my pillow and face. But I not only survived those experiences, I learned from them and can honestly call them some of the more memorable ones along my journey.

So next time you want to do something but are coming up with all of the reasons why you can’t, stop. Instead, ask yourself if this thing you say you want is truly important to you, and if you really are committed to making it happen. If both are a vehement “Yaassss queen!!” then decide you are going to make it happen and commit. You will quickly be surprised at how things start falling into place and the Universe begins conspiring to make your vision happen.

Courtyard Garriott

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