10 Learnings In 10 Days – Thoughts From The Road

By Garrett

Aug 9, 2016

And we’re live! I’m currently writing from Seattle, WA where I’m a week and a half into this crazy western US road trip. The sun and clouds are currently going back and forth for who can claim supremacy of the sky, but the forecasted rain is a no show so I’m a happy camper.

The first 10 days of the trip have come and gone, and with them a host of fantastic experiences, friends and many learnings. Some are more specific to this trip, but most are informing how I want to build and live my life moving forward. My hope is these discoveries and experiences help you, even if just in the smallest of ways, point your compass more in the direction of what your most Awesome life looks like.

So without further ado, and in no particular order, here they are!


1. I’m making this harder than it needs to be

I have not been a good boss to myself these first 10 days. My schedule can literally be whatever I want it to be, and yet I’m scheduling calls at 8am to “get the day started early”, planning things until late at night, then getting up at 6:30am the next morning to do it all again. Full days aren’t bad days, but I’m not giving myself enough quiet space to relax, reflect and recharge. I want this to become a priority over the following 10, and so will actively do a better job of respecting myself and what I need.

2. If I ask, the Universe will provide

It’s incredible how generous and awesome people have been so far – offering places to stay, showing me around town and letting me drop in on their lives. Putting requests to stay with people on Facebook (what if no-one answers?) and the overall act of asking for help still feels foreign at times. But it’s amazing what happens when I get over it and allow others to help me.

3. Say yes to what feels right

The first day of the trip I said yes to visiting an old neighbor who I’d never actually had a one-on-one conversation with. It was unclear what we would talk about, or whether we’d really have much to connect on, but a part of me felt it was the right thing so I said yes anyway. Those two hours turned out to be the most interesting, personal, vulnerable and enlightening conversation I’ve had in quite some time. Going into things without expectation or the need to have there be a “logical” reason for doing them is opening up places and people I never would have experienced otherwise.

4. My unfortunate is still incredibly fortunate

I’ve slept on the side of the road a few times, once underneath a loudly humming power station. My car battery died the first day because I’m a genius and left the lights on. I wasn’t able to get cell service one morning and missed a meeting without being able to apologize. In the moment these frustrations seemed like a big deal, but in hindsight they teach me two things. If that’s the worst I’m going to experience this trip then my life is pretty damn good. And the fact that I’m even able to do this trip and sleep under the stars and have a free car to travel around in and take meetings from (almost) anywhere in the US is ridiculously fortunate! Between having a location independent business and white-hetero-upper-middleclass-male-privilege, I’ve got nothing to complain about.

5. Nature is wonderful and I want more of it

It’s weird…I come to forget how fantastic Nature is until I’m back in the thick of it. It has only been 10 days but I already know I need more of it in my life. 99% of the time I was hiking in Yosemite and swimming in Crater Lake I had this giant smile plastered on my face, and that’s the version of myself I want more often. So short term this means doing day hiking trips or weekend upstate excursions I’m back in NYC. Longer term it means moving to a place where Nature is more accessible. It just recharges the soul, and I need that in my life.

6. Same goes for exercise

I’m not talking about the going to the gym type of exercise. I’m talking hiking, swimming, sand volleyball, rock climbing… some things I can do easily in NYC and some I can’t. Whenever I’m in action I’m a smile-ier, happier, better person, and that’s something both myself and the world deserves more of.

7. Environment matters

This trip is able to happen because of the fact that I can work from anywhere. However, not all work is created equal. When I was plugging away in Yosemite Valley with no internet, phone or distractions (besides looking up at El Capitan), I got more work done in 3 hours than I usually do in a few days. Traditionally I’ve thought getting lots of work done is about focus and willpower. But I’m discovering it’s also about the environment I put myself in to do the work. I need to unplug from the internet on my computer/phone to limit distractions when I’m doing “deep work” – bouncing from one task to another is my kryptonite. And while that’s one fix I think larger structural changes are needed, such as choosing the right city, culture and surroundings that empower me to do my best work and be my best self.

8. Living on the road is cheaper than living in NYC

It’s true! I was able to sublet my place out which was necessary for that to be the case. Still – that’s pretty awesome! Sure, it’s meant eating cold chicken/quinoa a few nights in my car and eating turkey sandwiches often for lunch. But those small “sacrifices” have allowed me to splurge on nice dinners with friends when it really means something. So for anyone who says “I could never do that!” there’s one less excuse for you 🙂

9. Beginning relationships online is good, but solidifying them offline is crucial

From a business standpoint this has been my most important takeaway. I’d emailed with various financial planners the past few months before starting this journey and planted the seeds of a relationship. Yet after meeting several in person, those relationships are now 10x stronger than they were over email + phone. There’s an additional level of trust and connection that gets built when sitting down face-to-face. I’m already planning an east coast trip later this year to visit other planners I’ve connected with. Yes it will take some investment to rent a car, take a bus and perhaps pay for an Airbnb or two, however that will be grossly outweighed by the benefit of stronger relationships over the long term.

10. Progress, not perfection

How is this something I’ve “just learned” when it’s a saying I’ve used in previous newsletters and espoused frequently to clients? Well, even though I know it to be true, I don’t always keep it top of mind. So far I’ve struggled to keep my schedule flexible and not book myself solid. I’ve let non urgent to-dos steal my focus at the expense of taking full advantage of the cities I’m in or people I’m with. It’s been frustrating seeing myself do things poorly, but I also accept that this is the first time I’m doing a lot of this. I’m supposed to be mediocre at it. If nothing else at least I’m becoming aware of these things, and that’s the firs step toward making any kind of change.

Here’s to being challenged and hopefully learning as much over the following 10 days! And if any of you are in Portland, Idaho or Montana (hey, it’s worth a shot) over the next week or two let me know! I’d love to adventure with you.

P.S. you can keep up to date with pictures and thoughts on my adventures via the Be Awesome Not Broke Facebook page!

Aloe Gare-a

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