My Story: Pressing Shuffle on Life
Last year I realized I wanted more from life and that it was time for something different. This is the story of that change.

Wake up call
I always used to laugh inside when people talked about specific ‘turning point’ moments in their lives. I mean, who just makes rash life choices like that? Certainly not me, a painfully rational realist. Well that changed when a bit over a year ago, I literally woke up disappointed — in my life. “How underwhelming” I thought. I had ambitions. I was going to change the world. Now I am slowly rolling out of bed wondering if I will get to work by 10am. Everything was going so well, how did I get here?
The lure of freedom through money is a cruel trap
I had slowly let myself get too comfortable. I already had all the spoils that a degree in Computer Engineering affords: pay, stability, pleasant work-environment, interesting project work, and nice coworkers. What could the next year really bring? Maybe an incremental promotion, a bit more money, a bit nicer car/house/stuff? Do I even care? Almost at once I felt silly for how much I had previously thought about those things. All I ever really wanted was to dream big and work with other dreamers. To make inspired ideas into reality. To move as fast as possible while proving the naysayers wrong. The entrepreneurial dream. How far away this reality had slipped was depressing. The lure of freedom through money is a cruel trap; one that many never get free of.
It is far more pleasant to let your mind be wrapped up in the task at hand then to dive headlong into introspection, many people seem to successfully avoid it altogether. For me this deep thinking lasted for a full week, at the end of which I decided instead of focusing on what I had done (and missed out on) I was going to make a change. I had no idea what that meant, but I was resigned to it. (I would later sum this up by simply saying I had a ‘quarter-life crisis’. )
Opportunity knocks
Out of nowhere a large reorg happened at work and it was clear to me that my current project setup was not long for the world. A bit of background is needed to understand why that was important. At that time I was working as the team lead of a small group of engineers tasked with a project best described as a startup inside a bigger company. We had freedom to make our own choices, mainly because we were working on complex stuff no one had really done before and very few took the time to understand it. Though my title was ‘Software Engineer’ I was really more of a product manager spending the majority of my time designing, planning, coordinating, and acting as an interface between engineers and upper management. I feel I did well under this unique setup. Back in college I made every effort to prepare for a career in ‘technical entrepreneurship’, always favoring big-picture problems over coding. I bet I was the only college kid in the midwest that answered ‘what do you want to be after college’ with ‘Angel Investor’ (in 2008). I primarily had taken a software engineering role to better understand the development lifecycle and to gain some engineering cred before jumping into management. In retrospect I would say it sort-of worked, but I would change things if I got a do-over.
Cue a timely email from a Google recruiter. Next thing I know I am on a plane bound for Silicon Valley to interview for Product Manager. But a funny thing happened on my way out there — a thought crept into my head: is this really what I wanted for my change? The new work and resume-building would be appreciated, but surely it would be a stepping stone and not the end game, right? I wanted to work with more freedom — not something a large firm can really offer. I remember thinking “huh, I am only 50/50 on what a year ago I would have described as my dream job”. That was an incredibly liberating realization and kept me relaxed during the interviews (probably overly-so). I made it through every round, but in the end did not get the job. And boy am I happy about that.
The eject button
Increasingly ugly politics at work and another brutal Minnesota winter looming spurred me to double down on action planning. I decided I was leaving. Where was I going? What was I going to do? I didn’t really care. I was just leaving. I started selling and donating my belongings, even things I liked. I went from a nice 2br apartment full of stuff to having everything I owned fit in the back of a pickup. This was hard work; never underestimate how easy it is for physical stuff to tie you down.
People started to wonder about me and rightfully so. It is very unusual for someone in the midwest to make radical changes, especially when life seems to be going great. “Are you doing OK?” was always the first question from friends and coworkers when they realized what I was doing. While I appreciated their sentiment, I couldn’t help but feel sorry that the only reaction to my excitement equated to ‘you must be seriously depressed’. After a while there were just too many questions I couldn’t answer. I needed a destination. As luck would have it I had a cool coworker that was a Kiwi. He was always talking up his home country and most of the time it sounded too good to be true. “OK, what is actually wrong with it?” I finally asked him; his answer: “Realistically? Pretty much nothing.” Sold!
To me, New Zealand sounded downright exotic and the fact I could get a one-year work-holiday* visa without much effort was ideal. They spoke english. It was safe. It looked amazing. What could possibly go wrong? (Plus peoples reactions were priceless when they heard the news. Answering “what’s up?” with “oh not much, just selling everything so I can move to New Zealand” never got old.)
All I had left to do was to dream up something to keep my mind stimulated while away. Mostly by accident I found myself enamored with informatics, more specifically improving how long it takes to find useful information. Hello Put Simply Inc.™(my first venture-scale startup). The more I thought about the company goals the more resigned I was to make it all happen. At the time I truly believed I could work online and see another country simultaneously. Ha.
* A work-holiday visa means that you can work — or not — as you please without sponsorship making it the best visa around.
A suitcase and a one-way ticket.
Within the month, I handed in my resignation, gave notice to my landlord, and moved my few remaining belongings to my parents basement. I booked an AirBnB for 4 nights in Auckland. I didn’t have a plan. I had done just enough research to be dangerous. I could taste the freedom. One-way in hand, I hopped aboard a Dreamliner to begin my grand adventure...

I will not go into detail of my trip here since that would take far too long. Here are a few highlights from the trip
- I bought a fun car (Scirocco 2.0t) and proceeded to solo-travel the entire country
- I hopped from one AirBnB to another for months
- I met amazing people from every corner of the world
- I moved from staying in AirBnB’s to hostels and learned so much from travelers living outside of our money-culture
- I did more adventuring in any given week than in the years before
- I picked up a camera and started snapping
- I found it really, really hard to work while traveling. (Hello dial-up speeds)
- 8 months is a long time for your first solo trip
- New Zealand is spectacular. You really should visit.
- No regrets.




1 year later…
I am now back where I started in Minneapolis. I am still living out of that same suitcase and renting a humble room. My bank account is missing many numbers. While the adventures have slowed to a trickle, I am more invigorated than ever to conquer the world’s problems. Freedom is what you make of it. Having a job is great, just don’t let that define your life. Welcome the chance to pick up a pen and write a life story you are proud of.
Have a similar story? Interested in startups? Curious about NZ? Something else? Send me a message! :)
I am trying to write more, so follow along if you are interested in stories from this trip and my thoughts on business/startups!
