Untethered Is About Intention And Fucking Going For It

This newsletter is about you — the wanderlust-fueled digital nomad, active or aspiring. It’s about what you can expect when transitioning from being a corporate 9-to-5er to a t-shirt-and-jeans wearing, cold brew drinking freelancer.

Untethered Is About Intention And Fucking Going For It


I was fired on a Friday. The morning wasn't cold, nor was it particularly warm. There were no clouds in the sky. There was no sky. There wasn’t any weather at all that I can remember remembering. The 3rd floor of the parking garage I stood in, box of belongings in hand, didn’t feel empty. It didn’t feel full. It didn't feel distant or unfamiliar. There was no looking around with new eyes. As I scanned the side of the building to my office window, there were no feelings of bitterness toward the brutalist-style architecture that I had disliked so much the day before. I did not want to cry. I did not want to laugh. I did not wish to defiantly sling the tie off my neck and let out a big ” go fuck yourselves”! Any desire for a cathartic release in any form was absent in me. I was utterly numb to the outside world and would stay that way for the next year.

Here is where I’m supposed to tell you that being fired was the “best thing to ever happen to me”! Let me be clear — No the fuck it wasn’t. Sure, getting canned gave me a push to start my business, Pixel Riot. But was it the push I needed? I'm not so sure.

Why start a newsletter?

At the ripe old age of 39, I've learned that intention is rarely monolithic, but instead a complex orchestra of motivations. The ability to isolate individual sounds from each instrument is a skill, not an instinct.

Knowing this, I've grown comfortable sitting in my anxiety, not always fully or immediately understanding all that drives my motivation to do something, like starting a newsletter.

Conversely, twenty-nine-year-old Jason always had a quick and definitive response for why he did anything. He’d quickly compose an answer that was pleasing to his ears. He’d belt out melodies that filled up a room, leaving little space to hear his self-doubt. That sounds harsh, and it is, but such blind confidence can also be an asset. Young adulthood is a time for risk-taking and creation. A pompous attitude and naïve vigor harmonize well with ambitious goals. As I write this, struggling to explain to you why it is I'm starting a newsletter, I wish I had younger Jason as my maestro.

What To Expect

This newsletter is about you — the wanderlust-fueled digital nomad, active or aspiring. It’s about what you can expect when transitioning from being a corporate 9-to-5er to a t-shirt-and-jeans wearing, cold brew drinking freelancer. It’s about you leveraging your newfound freedom to travel and create new experiences. It’s about us — exploring together all the exciting and unexpected ways these unique aspects of our lives will intersect.

You can divide Untethered into three categories — Travel, Freelance, and Technology. These are the three practical and overlapping aspects of living a life untethered. The third category (Technology) helps to maintain the first (Travel) and second (Freelance). The second category works to fund the first and third. The first opens new opportunities for the second, and in some ways, possibly creates less dependency on the third (I’ll have to get back to you on that one).

Of course, there is more to an untethered life than just travel, freelance, and technology. For instance, I would argue that mental health is more important to your longevity than finding the best WiFi hotspot hardware (hint: it's your phone). However, I will not presume to advise you on how to improve your mental health in any official capacity other than this right here, right now — stay hydrated, practice your version of meditation or prayer, and find yourself a therapist you're comfortable with... possibly one willing to FaceTime with you.

Fucking Going For It

“If you don’t deal with your shit, your shit deals with you” — Sarah Silverman

I have a theory that everyone has an expiration date for working in a high-stress environment like your typical American corporate office. It’s about five years. Anything over a half-decade and you start to seriously degrade your mental health. Okay, that's not a particularly provocative theory. I think you would likely agree with it, yes? But, just because we know there’s an expiration date for this kind of work doesn’t mean we listen to ourselves when the alarms start to ring around year four.

My ten-year corporate career can be split into two halves. I spent the first six years in Gainesville, FL. I worked my way up from a regional marketing manager to the Vice President of Strategic Initiatives (whatever that means). By then, I was deeply unhappy with my career, though I could not fully articulate why. I was officially the youngest VP in the company. I had an actual corner office with big windows, two doors down from the founder of the company.

I somehow convinced the CEO to allow me to quit, start my own business, and then let me consult for her. And just like that Velocity Genius — a consulting firm that helped private, off-campus student housing companies understand their leasing and traffic trends — was born. Not knowing why I was unhappy didn’t stop me from trusting my gut and making a run at entrepreneurship. I had unflinching confidence in my new business idea. I knew it would succeed.

Velocity Genius lasted eight months before I ran out of money. I found another job, moved to Atlanta, Georgia, and continued my life in the corporate world. “This time will be different!” I told myself. “I’ll set boundaries. I’ll balance my work life and my personal life better”! Hell, I even got the ridiculous salary I asked for when negotiating my terms for hire. Here’s the thing that HR doesn’t tell you when you receive your offer letter — That salary staring back at you, that magic figure that will fix all your problems and make you happy, that number owns you. That number expects you to sacrifice everything for it. It expects you to answer important emails at 11 pm. It expects you, every last bit. Dave Chappelle knew it when he walked away from The Chappelle Show, and we all called him crazy for it.

At the beginning of the second half of my career, my expiration date almost immediately began to show at work. I was combative. I was likely bitter and most definitely jaded. Those boundaries I tried to set? Ignored. Brushed aside by an executive team that worked 18 hours a day and expected the same from the rookie. But I didn't want that anymore. I didn't want my entire waking life dedicated to making someone else rich.

So, if I wasn’t happy, why not just leave, as I did in Gainesville? Why not quietly save money and when the time was right, quit my job and take another shot at starting my own business? Why? I didn’t trust myself.

As my corporate career unknowingly began to wind down, I would look back at the guy who quit his job to start a business as a fool. I saw him as irresponsible and compulsive. I didn’t like that Jason. I was older now, and I wanted to do what someone in his 30’s did. Even though everything in me told me to try again, I didn’t. I abandoned younger Jason for a more responsible, reasonable version of myself. A better Jason. One who worked for a salary, contributed to his 401k, and bought new dress shirts at the Macy’s Labor Day Sale. As you now know, it didn’t work out that way.

That Friday morning, on my drive home, I called my brother and asked him to design a logo for me. I sketched out a business plan in my head and then typed it up when I got home, something I had neglected to do before with my first business. Still unsure of myself and oblivious that I had already been applying the lessons learned from creating Velocity Genius, I began creating Pixel Riot. I quickly decided that I couldn’t look for another job; the corporate world had already thrown me out like old milk past its expiration.

What I lacked in confidence, I made up for in revenge. I would start the biggest marketing firm in the world! I would get rich and one day run into the CFO in my brand new sports car. I even had fantasies of buying out the company that let me go and throwing everyone out on their asses. None of that came to pass. I do have a great company with a strong team that makes me so very proud. I have no desire to make Pixel Riot so big that it consumes me whole, however. I’m not rich, but I do okay. I don't have a Lamborghini, but my car does have seat warmers, which is pretty neat. And now I use that car to drive around the country and work remotely.

The first year trying to get Pixel Riot off the ground was rough. Aside from all the everyday stresses that come with starting a business, I was also going through the most significant depressive episode of my life. I went through a break-up, I had to move in with my father, and I faced many old traumas in new, scary ways. I remember down to the hour the first time I felt something that wasn't sadness or the feeling of nothing. It was around 11 am on a warm Atlanta summer day. I would often go out to do my laundry when I lived with my dad. He has a washer and dryer. I just used the opportunity to get out of the house and maybe even shower. On this particular laundry day, I brought my headphones with me, something I hadn’t done for a long while. The song was “Who’s Lovin’ You” by the Jackson 5.

It hit me hard. I could hear the bass guitar. I listened to the tambourine. Clearer than I ever have, I heard young Michael’s voice belt through the speakers of my headphones, through my head, down my body, and into my feet. I could listen to each instrument, in concert and individually. Don't get me wrong, I’m not suggesting that Michael, Tito, and Jermaine cured me of my depression right there in that laundromat in Dallas, Georgia. But it did mark a milestone in me trusting myself again. I’m proud of my growth since then.

Twenty-nine-year-old Jason was flawed, but I’ve since learned to look back at him with kinder eyes. He had something that I’ve grown to value — unflinching confidence and intention. The day I was fired, I felt nothing towards the outside world, but I did feel anger towards myself. Whether I could express it back then or not, I was mad because I let that younger Jason down. I questioned my intention for leaving my cushy corporate gig and brushed it off as impulsive behavior. I questioned if I had what it took to be on my own, to be untethered truly.

Why am I starting a newsletter? I can say with certainty that part of my motivation is the feeling I get when I have helped someone achieve their goals. Part of it is wanting to share my journey with like-minded people like you. And, at least a small part of my intention is to pay back younger Jason. A man, despite all his flaws and missteps, believed in me.

So, know I mean this when I tell you — I believe in you. You should too. You owe it to yourself.


Buy me a coffee on Venmo: @jasondotgov


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Are you starting your journey as a freelancer? I want to hear from you. Hit me up anytime. @secludedplacesjason