Scalable Careers, Your Job, and “Side Hustles”

Recently, a friend suggested to me that there are two distinct types of careers – and it left me thinking quite a bit about my own career choices.

A Look at Different Career Paths

First, there are stable careers. You’re an hourly employee or a salaried employee with small bonuses (or none). You work hard to try to get ahead, but getting ahead usually just means a 10% raise in a few years or possibly a small promotion. No matter what you do within the course of this career, you will never increase your earnings by an order of magnitude. However, your income is quite stable – and it’s often plenty to live comfortably on.

On the other hand, there are scalable careers. Scalable careers often revolve around self-employment and often offer opportunities for enormous growth in income and prestige. Examples: writers, professional athletes, actors, entrepreneurs, small business owners, and musicians. However, in these careers, there are often just a handful that get the lion’s share of the attention and the earnings, while the others subsist on little – often significantly less than those in stable careers earn – and try to make their way up there.

Which career path are you on?

workers and activists making their point.  Photo by Old Sarge.
workers and activists making their point. Photo by Old Sarge.

The Big Choice

Most career advice encourages people to avoid scalable careers and to focus on stable careers – and for good reasons. Stable careers enable you to live a comfortable life. Stable careers have comparatively less risk, too.

Yet, quite often, the big dreams people have are all about scalable careers. When I was very young, I dreamed of being a professional baseball player. Later on, my dream shifted to being a writer. Some of my friends had similar dreams: a sculptor, a painter, a professional golfer, and several more writers.

For those folks, quite often the stable career becomes the choice because it is the safer choice. They’re walking through life without a safety net – if they fall, they can’t just land in the safe arms of a parent or into a strong financial net. Talented people often sit down, do a realistic risk assessment of their life, and conclude that a stable career is the way to go, regardless of their talents or passions.

I found myself in this very position early in my college career. I was drawn to writing – and thus choosing a career in English – but I recognized that there were limited career opportunities down that path. So, I put away training for a scalable career and chose training for a stable career – I majored in computer science and biology, figuring I would find work as a programmer or a research assistant (which I wound up doing).

Scalable Careers as “Side Hustles”

Many people who really dream of a scalable career but settle into a stable career hold onto that dream through a “side hustle” of some sort. They attempt to practice it on the side while spending much of their time working at their stable career.

One friend of mine, Jon, did this quite well. He’s passionate about bluegrass music and plays it all the time on the side, often making a few bucks from small gigs, but his “stable career” is in science.

Another friend, Ron, is a gifted sculptor. His “stable career” is teaching, but he fills his summers with sculpting and plying his trade at art fairs and other venues.

I actually have many friends doing this – one friend does office work and spends the weekends writing. Another friend does system administration and spends the weekends being a DJ.

I did this myself for many years. I spent my weeks working in a research lab. On the weekends, I wrote – short stories, essays, and all kinds of other things. I sent them off and got all sorts of rejections. It took many years of failure before I saw even a bit of success – and it was in an area where I didn’t expect it (personal finance writing).

Why this compromise? To put it simply, it lets people follow the scalable career they’re passionate about on their own terms while still earning a stable income. As I said above, many, many talented people do not have the financial safety net to give a scalable career a try.

Musician.  Photo by flat luxe.
Musician. Photo by fiat luxe.

Starting Your Scalable Career on the Side

The way it really worked for me – and for many of the people I mentioned above – is that I just viewed my “scalable career” as a time-consuming hobby. Quite simply, I really enjoyed doing it, so I just took it on as a hobby.

To many people, writing short stories, sending them off, and getting rejection letters doesn’t sound like a popping good time on a weekend. Yet, inside almost all of us, there is some sort of windmill we’d love to chase with our inner Don Quixote. We might never conquer that imaginary giant, but the journey to get there seems like a lot of fun to us – though it might seem a fool’s errand to others.

My suggestion is simple: whatever that dream is that you have, don’t let it go. Instead, spend your free time practicing it in the way you want to. If you already have a stable income, don’t worry about what sells and what doesn’t – just do it. Practice deliberately. Have fun doing it. Don’t worry about the end product – just have fun with the process and try new things.

In other words, treat that hobby as you might treat a scalable career if you didn’t have to worry about the income at all. It actually frees you to experiment, since income is merely an unexpected bonus. Try new things, practice the details, and enjoy what you’re doing.

What happens next? You get better. You produce interesting things. And people begin to pay attention. It might take years – it might never happen – but does it really matter? You’re enjoying the process.

Eventually, things might click and opportunities fall in place and you can ride the rocket ship of a scalable career on the bloom. But, if it never happens, you’ll have fun anyway.

Encouraging Young People

A final thought: I’m a parent. Will I encourage my own children to try a stable career or a scalable career?

For me, it depends greatly on the child. If they have an obvious talent – one that’s recognized by others, not just by me as a proud parent – and they want to ride that talent and see what happens, I’ll encourage them to do just that.

However, most of us don’t have that sort of awe-inspiring talent right out of the chute. Millions of kids grow up playing basketball in the driveway, but very, very few are LeBron James. That doesn’t mean, of course, that we can’t grow that talent through practice and passion over the long haul. After all, Michael Jordan was cut from his eighth grade basketball team.

So, my plan is this: instead of pushing them towards a career, I’d rather push them towards discovering their passions and cultivating their talents. My dream is not to send my kids to an Ivy League school at age eighteen. Instead, I’d rather have a child knowing where his or her talents lie and how he or she might utilize them. In the end, all I want for them is that they’re self-sustaining, self-reliant, and happy – and if they find that in a scalable career or in a stable career, I don’t care at all what it is. Your life isn’t over if you don’t get into Yale, after all.

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.