Some Thoughts on Scalable Careers, Your Job, and “Side Hustles”

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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.

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.

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31 thoughts on “Some Thoughts on Scalable Careers, Your Job, and “Side Hustles”

  1. Scalable Career I really like the sound of that. I’m seeing that I can actually start to focus on some of my entrepreneurial spirit while at the same time working a day job. Perhaps one day I can move full time to my Scalable Career or perhaps not. Either way doing what you love counts for so much.

  2. Good post! I also do this (stable career and write fiction on the side). One caveat on choosing a stable career: make sure it’s not one that sucks all of your time and/or energy. Otherwise, you won’t have anything left to give to the scalable career. Plus, there won’t be time for other important things, like relationships, exercise, and down time.

  3. Just what I needed Trent! A good kick in the pants to just do it. I’m going to start getting back into my writing while doing my daily 8-5 grind at the “stable job.” It doesn’t need to be groundbreaking, New York Times Bestselling List worthy work as long as I’m enjoying my passion, right? Great site by the way. I can relate to your writing style and I love the variety of topics. Well done!

  4. I also want to push my child towards their passions and talents, not just a formal education.

    I know several educated people that are broke and have no guidance in other areas. I rather my kids bbe educated in other areas as well, not just a ccareer

  5. Nice post. I think you hit the nail on the head as far as treating your ‘scalable career/hobby’ as a journey and not a final destination. This is great for two reasons. First, it pushes always to try to be better. Second, it allows you to, at the same time, be satisfied with where you are currently at. That is, don’t worry about how well known you may be.

    It is a delusion of the highest order to think that you will be remembered for any length of time after you are dead. Do this experiment. Consider your professional field, whatever it may be.

    1) Think of all the people you can name that are currently working in your field. Now consider how many people are currently in your field. This is your chance of being famous.

    2) Think of all the people that you can name that used to work in your field and are still alive vs. the number of such people. This is your odds of being really famous.

    3) Now do the same for the poeple that have died in the last 10 years.

    4) Last 100 years

    5) All of history

    By the time that you get to number 5, you will probably be able to think of 0-100 people out of the millions that have probably done what you do.

    This really drives home that, in the end, you WILL NOT be remembered. This is not meant to be depressing. Quite the opposite, really. It should encourage people to pursue their passions for themselves, rather than for others. Realizing that your actions matter for you and those people that you immediately interact with really should be quite freeing.

  6. Like you, I never thought about it in terms of stable versus scalable careers.

    In my case, I think I always knew I would be in a scalable career (an independent organizational psychologist, as it turns out) but needed to spend some years in a more stable career building the skills and experiences I would need to make it on my own.

    So in addition to pursuing both concurrently (as you detail in the post), or doing them serially (as you did), there’s also the possibility of having a strategic interplay between them until it’s time to take the leap.

  7. It’s also possible that your “windmill we’d love to chase with our inner Don Quixote” is easily done within a stable career. I love to program. I do it in my free time, I read books about it, and I just happen to get paid a salary to do a job I love. Of course my company and field have a lot to do with that, I wouldn’t be as thrilled doing accounting software, or being a nameless cog in some larger machine. My sister has a similar relationship with accounting, she actually seeks out people with interesting tax situations so she can do their taxes for FUN. You don’t have to want to be a world-famous athlete or artist, you can be happy doing something that other people are not jealous of.

  8. To comment #3: That exact line of thinking is what gave me the courage to write my first book a few years ago.

    Nobody gets famous and ridiculed for writing a terrible book. Most terrible books just go unnoticed and unmentioned.

    It seems to me that most creative fields function the same way–there’s no harm in taking what you’ve got inside you, putting it down on paper (or some other medium) and sending it out into the world to see what others think. :)

  9. You left out some extremely lucrative scalable careers: doctor, lawyer, psychologist… in short , highly trained professional who have the option of hanging out a shingle and making their own hours. Most of my doctors work office hours 2 days a week, and one day at the hospital. My dentist works just 3 days out of her office- attached to her home. Psychologists- even more leighway. Yes, each of these has “on-call” situations, but each also has the opportunity for partnerships where each partner covers for the other.

  10. Trent this is AWESOME advice and you’ve got some lucky kids. A lot of the time our dreams are so creative/off-the-beaten path that parents don”t even know how to encourage their children to follow their heart, and default to “not everyone can be Hemingway/Magic Johnson/President of the USA”.

    It’s so important to keep talking about these issues the way you are, to encourage other parents who maybe don’t have the same open mind as you do to realize that the best thing they can do is let their child pursue the things that move them. People who spend any considerable time and effort doing what moves them deeply – even if it never scales up into a “career” – are happier, more balanced, and more likely to make positive contributions to their communities.

  11. @Jerry

    people with stable careers are just as likely to make positive contributions to their communities. if no one worked in the power plant/utilities/sewer etc i think we would all be a lot unhappier than if everyone was a writer or a musician or whatever their creative passion is.

  12. Nice post. My wife’s former “side hustle” is now supporting our family (photography).

    If you have a passion, follow it.

  13. Great post Trent!
    Finding a passion is really the first step. Passion looks different for everyone and sometimes it’s hard for people to come to grips with what is their true fashion as it might not be something someone might typically think of as a passion (ex: filing tax returns for people might be a passion).

    Sometimes we need to overcome social boundaries and embrace our passions not matter what our peers may think.

  14. Kristie,

    I am an attorney, and was thinking exactly what you wrote, and was going to comment similarly. But then it hit me, you are partially wrong lol.

    Those of us, who are in careers/jobs that are required to produce billable hours, or sit in an office 60 hours a week.

    I think it is the person rather than the position which defines where you fall on Trent’s “scale”

  15. The few people I know who are successful entrepreneurs held regular jobs and then started with something small on the side. In time that scaled up and then didn’t need to worry about the day job any longer.

  16. This is a FANTASTIC post. And the comments are almost as good as the post. Excellent reading. I don’t have time for more detailed constructive praise at the moment (got a four-year-old in need of assistance with building a train track), but I just *had* to take a moment to say thanks for all you do. I read everything you post but rarely take a moment to do that. Thank you!!

  17. In my opinion, so called ‘stable careers’ carry far more risk. You are essentially putting your livelihood in the hands of others. They may fire you, furlough you, downsize you. Their company may go out of business, their orders may decline. They may change the whole structure and lower your pay. In short, you control very little.

    In a ‘scalable career’ you are in control of everything. If you are one who finds yourself capable of handling such a pressure you will find that there is no contest when it comes to security.

    When I left my job to start a business several years ago I was told by many of my stable career co-workers what I fool I was for leaving such a stable company with health benefits and quarterly bonuses. Most of them have lost their jobs while my income has increased by 500%. If this was an aberration that would be one thing, but to me this seems the norm. Those who are smart and willing to take risk find that their level of stability is far superior to an hourly employee.

  18. My mom started sewing custom baby items in the evenings, then took them around to Macy’s and Bellini’s. Before long, she was the go-to person for interior designers, and worked out of the garage. My dad was able to quit his job, and start his own electrician company. We went from dirt poor (surplus cheese on stale bread everyday, and meat MAYBE once a week) to comfortable fairly quickly. But it did NOT create more family time, and the household became infused with deadline tension. Once my parents’ businesses started catering to the very wealthy, they had material desires that they had never had before. More stuff, but money stress was replaced with business stress. Zero-sum gain, but we ate better, and got new clothes once in a while.

  19. Just FYI Michael Jordan was cut from the varsity team when he was a sophomore in high school. He was still on the Junior Varisity team. Just thought i give a friendly reminder from a huge jordan fan.

  20. Semantics question- Third paragraph under ‘scalable careers’ you list “entrepreneur” and ‘small business owner”…what’s the difference?

  21. I have a scalable career now (as a freelance writer and educator), and I’m very aware that my husband’s choice to put his love of music into the ‘hobby’ camp and pursue a stable career as a scientist allows all of us to maintain a frugal but comfortable lifestyle while I pursue those dreams.

  22. I loved this article. I think it is very sound advice. There are a lot of people out there who are all about follow your dreams and do what you love which I agree with but there usually is a process involved in being successful doing your scalable career. Many people think that their passion will be enough but often it is not.

  23. Love the post! My website is my scalable career and it is just starting to go places! Thanks for the encouraging words within the story!

  24. Great article Trent! I am in a position where I would like to have Photography as a scalable career, however, based on the advice of people who are already professionals, to enjoy photography, I need to keep my day job :). As tempting as the income from the potential scalable career is, I think you hit the nail on the head when you repeatedly mention that the income should just be considered a potential bonus. Again, with photography however, the outflow from one’s pocket can take an exponential curve very quickly. Thanks for this wonderful post!

  25. Great post!

    My advice to my kids will be to hedge your bets. Hold a bill paying job and then develop your passion into a wealth builder.

    “Steady” jobs are dangerous and far from stable– I discuss the idea of Multipreneuring and Defensive Entrepreneurship with family, friends, and readers all the time.

  26. Great post! Unfortunately right now my “stable job” sucks up so much time it takes away from my scalable pursuits (um.. acting)

  27. This is interesting, but I think your either/or framing is somewhat misleading.

    I work for a small business (grown from 20 to 50 employees in my time there) in a position that directly relates to my major outside passion. In the past year, as a result of taking on some new responsibilities that gave us access to a couple of new business opportunities, I saw my income increase by about 50%. Not an order of magnitude, but still nothing to sneeze at.

    My whole career I’ve worked for startups and small businesses, which offer a great deal of scope for people with an entrepreneurial bent. It’s less stable than most corporate environments, but definitely mitigates many of the risks of self-employment, plus a lot of the challenges associated with running your own business in terms of managing areas far outside your expertise.

  28. You are correct about stable careers (working for an employer) having limited opportunities for a pay increase. Most places I have worked over the past 20 or so years have limited merit increases (rarely more than 5% and these days 1% – 2%) and promotions usually only get you an increase of 5%.

    The answer – at least in my line of work – is to change jobs every few years early in your career, each time getting yourself a 10% to 15% increase. Over a 30 or 40 year career this results in your income tripling or higher.

    At the later point in your career, staying with the same employer is desirable for a couple of reasons – you need to build up your service time to increase your pension – also, unfortuneatly, it is a lot harder for an older person (50+) to change jobs.

  29. Great post Trent. I really liked the use of the words “Scalable” and “Stable” – they describe the situations perfectly, and helps me think about the ‘pay the bills job’ vs the ‘if i could do anything’ job. I can really relate a lot to this same situation. One of my favorite posts Trent, thanks!

  30. Great post.

    My side-hobby, flying, is a money pit. It will likely always be a money losing thing for me, but it is extremely fun!

  31. One point I’d add is about common perceptions in regard to such disciplines as “English” and other humanities – it’s misleading to align them with “scalable” or “creative” careers. i.e., a kid doesn’t have to go into math or science etc. to get a stable career. The academic humanities themselves produce their own stable careers which are not at all necessarily linked to “creative” work. Also, so-called “creative” careers in entertainment industries, etc. might themselves take the form of stable jobs and not scalable ones.

    Overall I like the stable/scalable distinction, especially how “stable” fits somewhere in the middle. It’s good to point out how Pareto’s law works for the scalable careers (less than 20% will get 80% of the profits, reputation, attention, etc. – it might even be more like 10/90%).

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