jason scared sh!tless the nomad experiment

Truth Be Told… I’m Scared Sh*tless I Have No Idea What I’m Doing…. (Dealing Big Life Changes…)

This Is A Story About Life Change And The “Oh Sh*T” Moments In Life

It’s about coming to terms with the reality that in life things get messy, times get lonely, and sometimes you’re all you’ve got. But more importantly, it’s about realizing that you have a backbone, and that you can get by with a little help from your friends, nomatter how big or small that life change may be or what your goals are. It’s about understanding that there are often many destinations to travel in your journey. You have to celebrate getting to each one while realizing that there’s likely still far to go to reach your goal.

Yes, this is me having a bit of a freak out about where I’m at right now, but with a little bit of how I got here first.

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Can My Big Life Change Freakout Help You?

I hope it helps you in your journey. It’s important to recognize that most people probably second guess their decisions, vacillate, or maybe even choose not to act at all out of fear of unknowns. And if folks try to lead you to believe that they have it all figured out, please feel free to call bullshit on them, since they’re likely full of it!

Read my story and see where there are parallels in your life, or where the change you’re considering isn’t likely as scary as you’re making it.

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One Year After Starting My “Experiments,” I Sit Here Looking Around Wondering What The Hell I’ve Gotten Myself Into!

Yep. It was just about one year ago today that about 8-9 years of pent-up “keeping up with the Joneses’”, overly-consumerist aggression caused me to snap and get rid of about 50-60% of my clothing and other household belongings in one fell swoop over the course of a weekend.

I’ve always known that my happy place was more in nature than in the city, and that I yearn to travel. I’ve studied the possibilities of living with less, van life, or just being more nomadic and able to get up and go. All of this “planning” culminated in a serious as f*ck freak-out that ended in a huge influx of donations to Goodwill and a hefty tax write-off.

And it was gloooooorious!

Small Goal: Simplify & Digitize

The freedom feeling from the weights that were lifted by getting rid of over half of my crap was amazing. I pawned my paperweight of a motorcycle, extra dressers and shelves and hundreds of books. I digitized all of my thousands of printed photos (with this nifty scanner, and yes, it was worth the coin…) and shredded all of my old bills, paperwork, etc.

It was totally worth it and continues to keep me feeling lighter and able to move more freely. Of course, a lot of that purging and digitizing took many more months to complete after my initial purge. But that was just the first phase (here’s phase two…). Kind of like getting to that first destination and enjoying it, but realizing that there were more ahead.

That only changed the complexion of the place I lay my head on the regular; the things that affect me when I’m at home in Charlotte, NC.

That’s Small Stuff. What’s The Bigger Life Change?

The reason I was doing this was for a larger life change. A life that is more about being in nature, with less of the burdens of “normal life” and the so-called Joneses’, and above all with more travel and experiences. Choices that I had the opportunity to make because of where I was at in my journey; not my mom; not my best friend; not my neighbor, or anyone else. This was about blocking everyone and everything else out and trying to figure out what change was looking for.

My Impetus for Change: Travel Goals

One of the major dictators of my life was my career, clients and the projects that I took, as I had been self-employed as a graphic designer for over eight years. I had somehow come to allow my chosen career to dictate my decisions as opposed to actually taking control and attempting to steer my life with consciousness.

Don’t get me wrong, I love design and most of my clients, many of which have become friends close to my heart, and I love signage and wayfinding. It’s OK if you don’t know WTF that is; just stick with me here. But I constantly felt that taking 2-5 year project contracts had created a stranglehold on my ability to be flexible. I wasn’t allowing myself to experience life and meet my travel goals the way that I wanted to, especially given the facts and details about my life at that moment.

The beginner traveler's guide to going nomad book by Jason A. Robinson

Tough Love, Tips & Strategies To Help You Finally Kick-Start Your Travel Life…Or Go Full Nomad!

Been wondering how the hell all those digital nomads, location-independent travelers, and remote workers, travel “full-time?” Maybe you’ve thought about living that life one day, but you’re really not sure where to start.

Beyond giving you the stepping stones to dive into short-term domestic and international travel, this book will show you how long-term travelers extend those tools, maximize their budgets, and turn weeks into months…or even years…of traveling the world indefinitely.

Let’s Just Go With “Thirty-Something…”

See, I’m in my (very late) 30s, fairly free of debt (but with little so far as backups or nest eggs), chronically single, and with very few other ties to hold me down. The reality of my situation is that there’s a lot of freedom if I choose to grasp it, assuming I continue to pay the bills. I’ve gotten around in the professional word and am extremely entrepreneurial. I also feel like I have my sh*t fairly together and that I can do anything I put my mind to. (I can thank my parents and grandparents for that little foundational nugget of confidence.) 

So let’s be honest, we know that change isn’t easy.

You get comfortable, and it becomes crippling to even think about giving up financial freedom or presumed comfort at only a chance that your new decisions could be a positive move or something that brings you more happiness than your current situation.

If change were that easy, we would all be much more likely to be rolling stones than gatherering moss.

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My Big Life & Job Change Moment…And Explaining It To Others

Fast forward to a month ago when I had to make a choice about my job…and life, since they go hand in hand. I had two of my major architectural clients asking me to be on their teams for at least a 3-year contract. They were actually competing against each other over the project, as well as against other firms. I could either nut up or shut up and take the chance and see what attempting to regain control of my life could bring, or choose to continue with the path I was on.

Time to nut up or shut up.


It was a Monday evening and I was working at a coworking space that I frequent when I got the return call from the partner at an architectural firm that I had worked with on nearly a dozen past and ongoing projects. I cautiously pulled off the band-aid and let him know that I wouldn’t be able to take future long-term projects, and I had to decline all of the ones on the table.

Explaining The “Why”  Of My Big Life Change

I also got into my goals and why I was making the change, as this person was someone I valued as a friend and mentor, and whom had many more life experiences that I did. It was also important for me to make sure that they were taken care of and that I would fulfill my obligations or contracts, or find a competent counterpart in the industry who could.

Understand please that this was emotional. I may be stoic to my family and friends, but trust me, deep down I’m a big old, mushy teddy bear.
I mean…I am a Pisces.

Letting anyone down, whether it be personal or professional, isn’t really an option, especially when I’ve given my word. That’s a big deal to me. But I had to make a choice here and try to balance a few things, keeping in mind that this was one of those situations where it was OK and of utmost importance for me to make sure to put myself first for my own sake.

Life Change Engaged…Now What? (Hint: It Rhymes With Schmalchohol…)

A 30+ minute conversation ended, and I went back inside to grab my bags and head home. I was in no state to be around peeps at this point. But as I left a longtime friend (of over 15 years, actually) saw that something was awry and stepped into the hall to ask what was up. He had been privy to my plans and journey for about a year-and-a-half at that point.

With water welling up and a shake in my breath I let him know what had just transpired. The gist of my part was “I just gave up more than 50% of my immediate future income, and now I have to have the same conversation with another architect tomorrow.” And his response was unequivocally, exactly what I needed in that moment:

Well, if that’s not motivation, I don’t know what is.

Touche My Friend; Touche.

Damn. Yeah, that was the first thing out of his mouth. Not “you’ll be fine”, or “you’re tough” or some other mental masturbation to get me through. It was a brass-tacks, this is what you signed up for touch of reality that was exactly right at the moment. He did go on to remind me that I have him, other friends, and loads of family that will always be there if the fan gets too shitty. Although he doubted that I would need it.

Then I went home, had a stiff drink, and lost it.

I haven’t cried that much since the last time I saw Titanic.

Next Steps For Change: Follow-Through

In the past month I’ve let most of my other clients/partners in that architectural project space know that there will be changes, and have started transitioning back to shorter-timeline print, branding, and copywriting clients, which allow me more flexibility in my life.

Truth be told, I also love those project experiences more. They get me more touchpoints and allow me to be more personal and conversational in my relationships with my clients. I’ll still work in architectural signage, but only as a consultant with shorter timelines that allow me the freedom to travel that I’m looking for. I wonder if you could find the same kind of balance and compromise if you’re struggling with your job?

Exploring Different Travel-Related, Location-Independent Work Opportunities

I’ve also started exploring seasonal and one-off work opportunities that will get me on the road and traveling. Mind you, I will make a fraction of what I make in my design life. But as I said to a friend this week, I’m so over the strangle-hold that making money seems to have on our way of life.

It’s really about, or at least should be about, the experiences more than the money. Many of my favorite memories are traveling to and working crazy long hours at events. Commiserating with crews of friends or coworkers, and making little or no money to show for it.

By getting rid of the extra expenses and fluff, I actually need much less money to live these days.

Letting Others Know About My Changes And Goals

I’ve had multiple highs and lows over the past few week…and year for that fact. Not only coming to terms with what I’ve done, but also with the potential of the future, and I’ve had many conversations with friends and family as a result.

This week I sat down, separately, with four old friends. I let them in on the goals I have and change that is taking place in my personal and career/job life as a result. Some of these were old clients or partners that have become friends that I hold close to my heart, but we may not have spoken in years.

The Reality Of Life…And Big Life Changes: There Are Always Highs And Lows

Over the course of a 24-hour span, I went from being at a pride-swallowing low to being back up to the height of my motivation. This was all because of the strength, interest, and positivity that those friends showed me while they were learning about what I was up to. It’s likely that none of them completely understand the levity of the change or what’s been transpiring over the past year.

Regardless, they showed true interest and heartfelt optimism that this was clearly what I need to do at this point in my life.

They told me about their lives, or of loved ones in their lives, or of other friends that have done something similar, and that it’s possible. They encouraged me by telling me that I wouldn’t be disappointed with this decision even if I woke up in a year or two and realized that I wasn’t happy on the new course.

Simply finding out whether this is right for me is monumentally better than never taking the chance and never finding out at all.

One way or another, I’ll sleep better for the rest of my life knowing I at least gave in to the universe and took this chance as opposed to wondering “what if?”

You’ll Get By With A Little Help From Your Friends

I guess the moral of this story is to never forget that you can “get by with a little help from your friends.” When you decide to throw caution to the wind and engage those big life changes you’ve been pondering, they’ll be there. Just make sure your friends are the good kinds that maintain positivity and optimism and have good in their hearts. Hopefully you’re keeping the other kind of “friends” at more than an arm’s length.

Aspire to do good and be good, and surround yourself with like-minded folks. You too can bite off the biggest chunk of “Oh Sh*t” ever and make it through to the other side. And let’s be honest. What’s the worst that can happen?

No, really, what’s the worst that can happen?

Good luck my friend. And thanks for the ear.
— Jason

The beginner traveler's guide to going nomad book by Jason A. Robinson

Tough Love, Tips & Strategies To Help You Finally Kick-Start Your Travel Life…Or Go Full Nomad!

Been wondering how the hell all those digital nomads, location-independent travelers, and remote workers, travel “full-time?” Maybe you’ve thought about living that life one day, but you’re really not sure where to start.

Beyond giving you the stepping stones to dive into short-term domestic and international travel, this book will show you how long-term travelers extend those tools, maximize their budgets, and turn weeks into months…or even years…of traveling the world indefinitely.

Travel Planning Tips

Figure out where you are going & how are you getting there…
I suggest using at least 2 to 3 different travel search sites. Start with Skyscanner or Orbitz or Booking …or whatever aggregator site you prefer. Then when you see what airlines to use, check their respective sites for better deals or rewards flights.

Figure out where you’re going to stay…
If you’re interested in hostels, search Hostelworld or Hostelling International. For longer-term or more private digs, look at Airbnb, VRBO, or you can look for hotel rooms in the links from the search engines listed above. 

Get comprehensive travel insurance, or in the least, travel medical insurance if internationally…
Especially with Covid not going anywhere, get covered. Start with an insurance aggregator like Insure My Trip, or with SafetyWing, World Nomads, or another. Then decide what is important to you; trip cancellation, baggage coverage, medical, or all of the above. And get a yearly evacuation plan, since you’ll have to get home after your emergency! 

Need more resources? Click here!

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