The hobo business model

June 20, 2024

From time to time, folks will inaccurately describe me as a digital nomad. On the one hand, this description is technically valid. I work in tech and travel frequently. I have no “real” job. Digital nomad? Perhaps.

However, I prefer a much more descriptive and accurate phrasing. I say, I operate a hobo business model – updated for the 21st century.

What is a hobo?

You can read more about hobos here, but I can fill in the most important bits. Hobos were common from the late 1800s through the Great Depression. They were simply migrant workers – and often skilled workers at that. They traveled for work and worked to travel.

In the vernacular of the time – hobos were not tramps, who traveled but did not work. They certainly were not bums, who neither traveled nor worked. They were an essential compliment to farmhands – who worked but did not travel.

Applying the hobo model to the 21st century

Working as a hobo today only requires a small adjustment in thinking. A hobo is a contract worker (i.e. a 1099 contractor). A farmer is a small business owner and the farm is the business. Same exact concept – just a 100 years later.

A collaborative partnership – Hobos depended on farmers as much as farmers depended on them. The working relationship was based on trust, fairness and reciprocity. Although people claim this kind of business ethic no longer exists, those people are wrong.

It’s not for everyone – If you value independence and are confident in your skills, there is little other life to choose. It is a sword that cuts both ways. As soon as you step off the path of being an employee and begin to forge your own way, you are sentenced to walk that path for life. The good news – while a more difficult journey, being self-employed is also incredibly rewarding.

You must read the signs – In order to survive as a hobo, you must learn to cut for sign in unusual ways. You need to be able to vet and size up a potential client in minutes. You have to understand which projects are a fantastic fit and which are a nightmare waiting to happen. You begin to see the world with different eyes. You’ll quickly understand that you need a sizable skillset and it must be razor sharp.

You must be able to sell yourself – No body is showing up on that farmer’s doorstep to sell your skills for you. Not only must you be well-versed in multiple facets, and an expert in at least one – you must be an expert at sales and marketing. A thousand other hobos might pass through this valley and you need to find a way to convince the farmer you are different. Easiest choice here – be different.

You have to travel light – Hobos can carry what fits in their bindle and in their head. While this literally applies, a metaphor lurks as well. You can’t bring with you heavy frameworks, or methods that depend on a given set of expectations. You have to show up to the problem with nothing more than your wits and solve the riddle with ease. This means your techniques must be varied, vast and honed to perfection. The simplest machines do all the work, and they can easily be crafted via jigs stored in your brain.

Use your downtime wisely – A smart hobo knows that the time between jobs is not for rest; it is to sharpen the tools of your trade. You must be the epitome of sharpening the axe before cutting down the tree. I invest a tremendous amount of time and effort in research and development. This “time between jobs” is the most valuable part of my day, week, or month because it makes me able to do what I do. Hobos knew this and often learned trades from each other, during those endless hours on the road.

You must have morals – Word is bond. You cannot take advantage. You must act accordingly – or starve. This means honoring handshake agreements, and providing the pinnacle quality work.

Final thoughts

To be honest – I am probably a hobo because it runs in my veins. My grandmother was raised during the Great Depression and she was the single greatest parental figure I had. She often told me stories about how hard things were during the dust bowl. Use it up, wear it out, make it do or do without. These were the core principles I was engrained with.

Given that kind of background, it only makes sense that I gladly put a laptop in a backpack and leave town for a month. I walk into a business in any country, flash a smile and pitch my skills – regardless if I speak the local language. I am nothing more than a hobo – transported 100 years forward.

Nomad? Not exactly. I always maintain some sort of base of operations. Instead, I prefer to travel for work and work to travel. The difference is subtle and nuanced, but well-worth considering. It also shapes why I am not for hire.