“I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.”
― Jack Kerouac

Introduction

Packing up my life and moving has always been one of the hardest things for me to do so it’s funny to think that I built my lifestyle around it. My parents have lived in the same house in Portland for as long as I can remember (you can still see my height marks in the hallway), but also for as long as I can remember, I’ve always had this longing of leaving and forging a new path.

Working for yourself requires overcoming your personal obstacles and persevering.

I’m really shy. I always have been. Even as a older child, I would hide behind my dad’s legs around new people and not say a word.

I was 11.

Yet at the same time, I wanted to get to know them. In middle school, I would have my mom answer the phone when a classmate would invite me to a party so that she could tell them that I was busy. So yeah, I was that shy.

One day, I started telling myself to do the thing that scared me because it made me scared. 

Finally, in high school, I started to come out of my shell and in to my own person. One day, I started telling myself to do the thing that scared me because it made me scared. Low and behold, I started making really good friends and starting getting over my fear of someone new, and this started a new pattern for my life.

When I graduated high school, I decided to go to university in San Diego, California (over 1200 miles from home) and leave behind the good group of friends that I worked so hard to make. Between my academic and athletic scholarships, it would be foolish not to go. Not much time passed before I missed home terribly and started making plans to return and go to University of Oregon.

Your fear of leaving something behind shouldn’t keep you back from doing something that you really want to do.

But by the end of my first year of university, I didn’t want to leave. The school year had ended, I returned home for the summer and had leave my good friends at college yet come back to my good friends in Portland.

Four years of this back and forth between the school year and summer taught me that no matter what, good people and good friends can be found where ever you go. Your fear of leaving something behind shouldn’t keep you back from doing something that you really want to do. For me, it was a drive to see “what else?”

Experience

Immediately after graduating, I wanted to work for myself. I graduated with a computer science degree and had done some freelance work and an internship throughout my last year of university. I thought I was ready, but in retrospect, I wasn’t even close.

Instead, I accepted a web developer position at an advertising agency back in Portland, where I developed most of my agency experience. By working in a structured environment in a company with a bigger name than my own, I was able to be challenged and work on larger projects than if I were to be on my own, as well as meet people and form relationships that are vital to my career today.

I needed to spend my time in the industry and get the experience I really needed before I just went and ventured out on my own.

After a couple years in Portland, a friend of mine moved to Denver and told me that moving there was the best decision that he has made in his life. After he convinced me to come visit, I ended up falling in love with the city, and I can now say the same. Within the span of a month, I found myself uprooting myself from Portland and moving to Denver.

My developer experience in Denver was much faster paced than when I was in Portland. This meant that I had to adhere to the specific workflows and coding styles of my employers, which in the long run ended up forming a lot of my current practices today.

At the time, I found these workflows and practices too tedious. I now know that I needed to spend my time in the industry and get the experience I really needed before I just went and ventured out on my own. My development processes are so much better than if I wasn’t forced to learn these practices in those work environments. In turn, I can get more accomplished faster and more efficiently because of it.

Actually Quitting

Throughout all these experiences, I always knew that I still wanted to work for myself. Many of my good friends were all flight attendants and the lure of free flights and freedom to work from anywhere kept tugging at me. But my dad always told me that I should build some sort of safety net.

Now that I had the experience I needed and the connections that I had, I started putting them to use. I reached out to my first boss (who never hired someone to replace me) and he had multiple consulting opportunities ready for me. I reached out to another friend who is an entrepreneur and he had a big project for me. In addition to a few different agencies reaching out to me about opportunities.

Things were lined up, but one last thing stood in front of me, fear.

Things were lined up, but one last thing stood in front of me, fear. Fear of failure and the risk that the decision held. The timing seemed perfect, but I still couldn’t get myself to do it. I reached out to my first boss because he worked for himself for five years before accepting the job at the agency. His response was simple yet telling.

“It’s always a bit of a leap of faith when you start.”

I took that statement partnered with the projects as my sign from the universe to quit my office job and take the leap of faith. I’m so happy that I did.

Now

No matter what, life is about overcoming your obstacles.

The process was by no means easy, but so worth it. I finally feel as though I’m following my calling. To be able to see the world, take time for my own personal development, and of course to not be in an office all day. Instead, I can work from:

A oceanside balcony in Puerto Vallarta,

A grassy park in Amsterdam,

A rooftop in Manhattan,

Or a café in London.

Our stories are stories about an unrelenting hunger for something and overcoming fears in order to make that thing a reality. That shy boy hiding behind his dad’s legs never imagined finding himself working from a stranger’s house in some small town in Netherlands, but that’s a reality.

But there are still more obstacles. No matter what, life is about overcoming your obstacles. Even though I have these opportunities to work anywhere, I love the life I’ve built in Denver. I have some of the greatest friends a guy could ask for, a beautiful house, sunshine nearly everyday, and seasons! Fall is beautiful! It’s hard for me to plan and make these trips when I’m always going to miss someone or something. But the call is there and the hunger must be fed. I’m sure you have one too so don’t let yourself starve.

Don’t settle for good, when you can have the best.