My Digital Nomad Year

There is no known cause of growing pains, but there is certainly evidence that it is a real phenomenon. Discomfort and growth are intertwined. The last year has been a time of growth, learning, and some discomfort for me. It is scary to write this article reflecting on my journey of entrepreneurship because it forces me to look at my own shortcomings, but I have learned that discomfort can be a good thing. Pain means you are growing.

This year I lived as location independent digital nomad. I wanted to travel with my wife since she has a remote-eligible sabbatical year, and I knew being in a different timezone each month would make normal work (even remote work) difficult, so I figured it was as good a time as any to try working for myself. Sometimes you need a push, and this was it for me.

My journey this year was funded by my savings from years of working for other people, and it has been part "pretirement", part indie hacker marathon. I worked a ton, and had a hell of a lot of fun. I visited Elvis' home in Memphis, spent a week at Disney World in Florida, and had a beer at the Beatles' favourite pub in Liverpool. I also built my first solo product and even found some people to buy it.

Freedom vs. Uncertainty

I began the year by giving myself permission to not work a "traditional" job. I wanted to build something that people could buy and that would scale in a way that selling my time never could - to put in some sweat equity to make something that I fully own. I know most small businesses fail, and I told myself that was a risk worth taking. I thought that if I could find a way to make money without an employer, that would feel great. I had enough to live on for the year, but was still scared enough to work hard every day.

I registered a company and a domain, and I focussed initially on writing. Writing scales well - you can write a book once and sell it many times. I built a small but not insignificant community of readers. I made tutorials and learned a lot. I read at least two or three books a month and like to start each day with reading. I wrote code every day. I worked on blog posts every day. I learned all about the newest tech - mostly large language models and AI. I made tutorials and book reviews about nearly everything I learned to give value back and build a community around myself. That is something that no one can take away.

The funny thing about books on entrepreneurship is that everyone has different opinions on the right approach. Every author (at least the good ones) writes their story after they have seen success. Some say it's okay to find a working model and copy it, others insist that you focus on original ideas. Some say you should give things away, some warn that free trials are the easiest way for a company to die. Some say you should solve a real problem for others, some tell you to build something you want to exist in the world. The one thing I have taken away from all of these books is that entrepreneurship is hard work so you better enjoy what you are doing or you won't last long enough. The real winners keep going until they succeed.

I had big dreams for this year of freedom - part of me thought that if I just built something useful and wrote about it along the way that I could finish the year with a revenue stream, a horde of dedicated followers, and that I may never return to traditional work. Spoiler alert – it takes longer than a year to get there. Business is a slow burn and working every day without a guaranteed paycheque can be emotionally draining. As an entrepreneur, you need to stare uncertainty in the face every morning and push on.

Part of the allure of working for oneself is the chance to own your time more fully. I did this by living a dream year with my wife - travelling around the world and staying in different cities for about a month at a time. We both worked full days during the week and took weekend trips and the occasional evening hike to see the local wildlife.

Lessons From The Road - Underdogs and Second Cities

I left Calgary, Alberta in January and have been on the road since then. The first place I stopped for an extended period of time was Tucson, Arizona. I stayed in a guest house in a small community among the cactuses. It was winter there, but felt very much like summer to me. The community had a hot tub that none of the locals were interested in because it was "so cold out". Tucson is a kind of second city to Phoenix. You can feel the chip on their shoulder from being compared to the larger city close by. This is clear in every entrepreneurship and technology meetup that I attended. Coming from Calgary, I can relate to this feeling. In both places, the tech scene is growing, but smaller than the one next door. Tucson is to Phoenix as Calgary is to Toronto.

Many of the cities I stayed in throughout the year had this character. I spent a month just outside of Manchester (in England). It likes to compare itself to London. A famous guidebook describes it as the "belly and guts of the nation." It is historically industrial, and the people have a distinctive "Manc twang" that posh elites snub their nose at. There is a toughness to Mancunians (as the residents are known) but also a real sincerity. The city mascot is the bee - hard working and industrious. The city has produced academics like Alan Turing, and famous bands like The Hollys and Oasis. Today, it's a real breeding ground for great companies. I attended an annual tech conference there and people are building exciting stuff. Poetry, academic theories and entrepreneurs all seem to thrive in places of struggle.

Edinburgh has a similar story, though it takes place hundreds of years before. When Scotland was united with England in the 1700s, many of the wealthiest people living there moved en masse to London. The middle class of intellectuals, scientists and doctors (professions that weren't as respected at the time) who remained were the architects of an enlightenment period that produced some of the world's greatest thinkers. The philosopher David Hume, economist Adam Smith and poet Robbie Burns all came out of this time. Hume is commemorated with a large statue that sits across from an iconic gothic church - a nod to his constant disagreements with them. They say he developed a lot of his most important theories during lectures he gave in pubs. Our tour guide recited part of Robbie Burns poetry to us with a passion that I don't think you would find on a tour of a big city like London.

I'm truly sorry man's dominion,
Has broken nature's social union,
An' justifies that ill opinion,
Which makes thee startle
At me, thy poor, earth-born companion,
An' fellow-mortal! - Robbie Burns (To a Mouse)

These small towns are filled with a hunger and drive that big cities and corporations can't replicate. Tucson has been willing itself into a reputation as a "City of Food" and there are startups and meetup groups talking about it. They received a recognition as a UNESCO City of Gastronomy through sheer willpower - it's difficult to grow grapes for wine there, but the arid environment gives them a unique flavour. In the small town of Florence, Alabama I rented a desk in co-working space and the office was filled with remote workers. These people are impacting businesses around the country despite the market for tech being tiny locally. We drank sweet tea and talked about growth strategies. There is something powerful to be found in underdogs.

Building a Real Product - My Journey to Marv

Artificial Intelligence these days can be polarizing. Some see it as force that will destroy jobs and steal intellectual property, others view it as a source of limitless opportunity that can create a utopia. I am worried about the potential risks and downsides, but ultimately I think it is just a ton of fun to work with. It is something that is so fun to build with. It brings me back to my early days learning about programming and the web and since I am my own boss this year, I decided to work on an AI project.

I can see two distinct career paths emerging in this space right now - core machine learning engineers who build the foundational models, and AI engineers who connect those models with useful apps for people to use. This second (middle) area of AI between models and consumers is a really interesting space, since the frontier models (the things that OpenAI, Google, and Anthropic are building) are making money, and therefore will continue getting better and better. In the next five to ten years a lot of people are going to work and create fortunes in that space, and I wanted to get some experience now while I have the time.

The first thing I made was a generative Choose Your Own Adventure style book. I loved those as a kid, and this just seemed like a fun project to cut my teeth on. It was a fun project to start with and is still live over here. It's not really something I expected people to pay for, but it was a good learning project.

My next build was Marv. The name comes from an example that OpenAI provides with this system prompt: "You are Marv, a chatbot that reluctantly answers questions with sarcastic responses". The first version of Marv was sarcastic. He was mean. It was fun. I wanted to make it more useful and generally palatable, so I added some skills - web search, image generation, and a specialized persona for trivia.

This is where Marv starts to look like a product - I hooked him up to a phone number so that I could text him while I was on the road. Texting Marv felt like something special, and I shared it with my wife. The first time she said "Let's just ask Marv", I thought that just maybe there is something here that people will like.

I hustled and found some close friends and acquaintances that would test out the early versions for me. People seemed to enjoy it but often said things like "I think you'll really miss out on a lot of users by charging for this" as if the goal wasn't actually to make something valuable enough that people would pay for.

Developing a product when the costs are coming directly out of your living budget is an interesting constraint. I was (and still am) paying for every message that Marv sent myself. Every decision I made was important and making the wrong one might mean I would run out of money to live on. I chose frugal hosting options, but prioritized spending money on parts that would save me time since I didn't have a team of developers to rely on. The savings that come from building something myself had to be balanced against the time I would lose by not working on other things.

Marv worked great in Canada, but the first time I tried it with an American phone number, I got no response. The laws there are more severe. In order to develop an automated text messaging service, one must be approved by a regulating body. This involves paperwork, privacy policies, and a process that took a few weeks and more than one attempt to finish. I wrote about that here. With my approvals for American distribution in hand and a couple of testers I met during my travels from south of the border, I kept pushing on.

I continued developing Marv, adding payment rails so that people could subscribe and maybe even pay me one day, a web site, some tutorials, and more features. I added vision APIs so you can send Marv images, and message scheduling so that you can request reminders and schedule messages for later. He transformed from a little robot into an anthropomorphic wolf to give him more character (I added a feature for fun where you can request Marv send you a selfie from any location), and I removed the sarcasm. I continued testing with free users and fixed bugs and tweaked features and prompts.

One user asked if I could connect Marv to their AI project and help them with distribution - a phone number you can text is a great way to onboard users. I thought that was a great idea, so I learned how to write a contract, had a meeting, made my pitch. I offered to build something out for them for a small fee and started to think that my months of learning these tools and systems might actually bring in money. They agreed and said they would sign the contract and get it back to me this week. I got a beer with my wife and celebrated. A week passed. They backed out. I was crushed.

Building any product is an immense challenge, and I think that most people don't ever push something over the finish line. I did, and I am proud of that. If nothing else, this year has taught me that this is something I can do. I now have a product that I can sell and a small (but growing!) number of people have bought in. Distribution and marketing are new challenges for me, they are difficult in ways I did not expect. People are fickle with their money. In order for anyone to even try a product you have built, it really needs to solve a problem for them.

Wisdom and Perspective

We have become accustomed to software being free. Our money is hard earned - We have traded our time and often some sanity for it. We deserve to keep as much of it as we can. The global marketplace is large, and a lot of startup software companies are perfectly fine losing money. Many food delivery services still post negative earnings despite being incredibly popular. The game they are playing is to become the biggest and then enjoy a monopoly and reap the rewards. I am not sure my little indie project fits into that category - at least not yet.

Right now, my goal is to gather a small group of paid users. The ones who are using it now are enjoying it. Marv sends scheduled messages to them every day, and I see the usage going up over time. I have a dashboard set up to monitor usage rates and stickiness and the features that are most popular are scheduled reminders and image generation. Since this is a small product, I reach out to every user and have conversations about what they like and don't. This personal approach is not something you can count on getting from a product with a larger user base.

I am proud of what I have built this year. I developed a lot of skills that I didn't have before, working for yourself means you are now a marketer, business strategist, architect, developer, writer and salesperson - sometimes all in the same day. Marv will bring in some money, but this year and my experience has given me wisdom and perspective, and I truly believe that those will prove more valuable in the long run.