The Myths and Realities of ‘Doing What You Love'

One issue that you’ll see constantly debated in books and articles about choosing a career is the idea of “doing what you love.” Should a person “follow their passion” as a primary guiding light for their career? Or does it make more sense to choose a career based on income and aptitude?

There are pros and cons behind each path. Following your passion means that you’re going to usually end up spending a significant part of your workday doing something you deeply enjoy. However, jobs like those often have a low average wage (though there are often high-end rewards for high performers).

On the other hand, choosing a career based on average income and your personal aptitude will lead you to a job with a strong income level and a career path you’re naturally suited for, but you may not end up enjoying your job or your career at all.

My own life has been full of the push-and-pull between these two paths.

When I first went to college, I studied something I’ve been passionate about my entire life: biology. There were three classes I deeply enjoyed in high school – math, English, and biology – and I felt that the jobs I could end up doing with a biology degree would be incredibly enjoyable. I didn’t really worry about the pay too much.

As I actually progressed toward my degree, I found a great mentor who encouraged me to pair my passion for biology with computer science, which somewhat tapped into my interest for math.

This ended up leading straight into a job after graduation that I deeply enjoyed, one that I would still be working at if it still existed. I was charged with the task of organizing data for a group of researchers so that researchers in similar disciplines could easily share data with one another. It was incredibly enjoyable work, one I found deeply rewarding. The pay was good but not great, but I enjoyed the work so much that I didn’t mind. I was solving interesting problems every single day and I felt like my work was actually helping others solve interesting problems, too.

Unfortunately, the contract for that original job ended, but I had some advance notice of the job ending so I spent some time preparing for my next career step by building some skills and certifications that would be appropriate. I didn’t enjoy that quite as much, but I had visions of continuing the work that I love.

I got a long-term, full-time job at that point that paid very well and was, on the surface, very similar to what I was doing before. Great, right? Well, it turned out that the job actually involved a lot of bureaucracy and maintenance and spinning your wheels and not actually solving any interesting problems.

In short, it turned from something I loved to something I dreaded.

At that point, I started spending my free time dabbling in my other big passion – writing. Remember when I mentioned that English was one of my favorite classes in high school? I started investing my spare time in writing. I started several blogs. I wrote rough drafts of several novels, including one called Rings of Saturn that I actually sent to publishers and received some positive feedback on (it was a story about two highly competitive brothers during an era shortly in the future when we were starting to mine different parts of the solar system for resources).

What happened? One of the blogs took off – in fact, you’re reading the successor to that very website right now. The Simple Dollar started as an exercise in writing about my own experiences trying to turn our financial ship around and it eventually grew into a website with a million visitors a month and traffic and moderation demands far beyond my personal capacity to manage in my spare time.

So I jumped on board full time. Eventually, I started hiring out the moderation and server management tasks in an effort to continue focusing on what I loved (the writing), but over time that became more than I wanted to manage, so I sold ownership of the site and signed on to do just the part I loved – the writing.

Today, you could very easily say that I “do what I love” writing for The Simple Dollar. I get to write almost every day, which I enjoy. I get to have great conversations with readers – I get lots of Facebook messages with great questions and ideas every single day. I have a flexible schedule that allows me to work from home and be there when my kids get home from school each day. I make a reasonably good living (perhaps aided by the fact that my tastes are pretty simple). It’s not exactly what I always dreamed of doing – I always had visions of “writers” going to writing conferences and writing novels and such – but it’s a pretty nice way to do what I love to do.

Having been through both sides of the issue, I can say without a doubt that there are big advantages to doing what you love as well as big advantages to focusing on salary and skills. There are also a lot of myths out there about both avenues as well. Here are seven truths I’ve found about this question through my own experiences over the years that I want to share with anyone trying to figure out whether to follow their passion or follow their money.

Truth #1: You CAN do what you love and make a decent living at it.

Never, ever, ever let someone tell you that you can’t possibly do what you love to do and make a decent living. You can; I’ve done it, as have many other people.

So why doesn’t everyone do it?

The big reason is that it’s not a guaranteed path at all. The jobs that allow you to do things that you love and pay well usually have a very high skill threshold and there usually aren’t many such positions. Often, you have to end up “making your own job” via entrepreneurship or self-employment to do the thing you love, and that means figuring out how to get someone to pay you for what you want to do, which is tricky in all situations and very tricky when your area of interest isn’t widely profitable or popular.

When you go into a high-paying career path, there’s usually a ton of jobs available. It’s much easier to find work that puts money in your pocket with just a little bit of footwork.

Another reason is that it requires “grit” and work ethic. A person might deeply love writing about personal finance, but how about writing about personal finance several hours a day, every single day, for years? Even assuming you still love it after all of that (which is an issue we’ll discuss in a bit), do you have the work ethic to really stick with it so that you stand out enough to earn a decent living? Many people do not.

Many people have personal passions, but they don’t have the internal “grit” necessary to do it every single day until they hone their skills and personal assets to perfection. Many, many people start following their passion, but don’t have the “grit” to follow through with it until they can earn a decent living at it, which is rarely an immediate thing and usually involves many hours of commitment for low wages.

I’d estimate that I spent several thousand hours trying to earn money from my writing before earning more than a pittance. I tried writing carefully edited and carefully constructed fiction and nonfiction of all kinds. I tried writing memoirs and train of thought pieces, too. What I ended up realizing I had a knack for was a particular flavor of half-memoir half-advice articles that I could write quickly and relatively well – the kind of stuff you’re reading right now. Is the writing great, the kind you’d find in The New Yorker? Nope, and I don’t claim that it is. Is it earnest and clear and helpful and always there with new topics and thoughts? That’s what I’m striving for. It took a long time to find that niche and a long time to figure out how to do it well, and it didn’t pay much of anything during that process.

You can do what you love. It just doesn’t offer easy entry points like many other career paths offer.

Truth #2: There is no job that’s 100% ‘doing what you love”!

I love my work right now. I get to spend much of my day reading, researching, and writing, all of which I enjoy. I get to spend time with my children with a lot of flexibility. It’s great.

That doesn’t mean it’s all perfect. I sometimes find myself really stressing out about deadlines. Before I travel, I need to have all of my writing done before I leave. I have to do media interviews, some of which I enjoy, some of which end up going in awkward political or social directions that make me want to hang up and pretend it never happened. I sometimes have to meet word count restrictions, though I do have almost unlimited freedom in terms of topics and the ideas I express. I read a LOT of emails, many of which I enjoy but many of which are either upsetting or frustrating. Taxes for self-employed people is … frustrating at times, to say the least. Writer’s block can be an utter nightmare.

There is no job that’s 100% “doing what you love.”

Let me repeat that.

There is no job that’s 100% “doing what you love.”

The most famous novelist in the world still deals with agents and publishers and the like. Models and film stars often can’t leave their homes without being accosted by photographers and media and overzealous fans. Jobs and self-employment and microbusinesses have taxes and paperwork and conference calls and negotiations.

When you choose to “do what you love,” what you’re actually saying is that you’re choosing a job where some of your time – ideally, a significant portion of your time – is spent on something you love to do. You’ll never find a job that’s purely what you love to do and if you hang onto that as a goal, you will always be disappointed.

What I “love to do” is write without deadlines or pressure so that if I’m facing writer’s block or my muse just isn’t there, it’s not a big deal. Such a job really doesn’t exist unless you’ve already achieved financial independence or have some other source of income, at which point it’s almost more of a hobby than a “job.”

No matter what you do, there are tasks that you won’t enjoy. There are pressures that will bear down on you. There are deadlines and contractual obligations.

So, what’s the point? I tend to view those “un-fun” things as my actual job. During those times when writing is fun and loose, I’d do it for free. I get paid for the times when it’s hard or when I’m doing interviews or paperwork or documentation or other things that aren’t enjoyable.

In the end, the ideal job is the one that pays reasonably well with the least amount of time spent doing things you don’t want to do. The “job that you love” almost always comes with strings.

Truth #3: The best way to start doing what you love is with a side gig, not with a full life commitment.

The two jobs I’ve loved the most in my entire life started as part-time side gigs.

When I was in college, I worked for a professor addressing the kinds of problems that I ended up solving at my first “real” job. It was a side gig to my studies, not my full time focus, but I worked so long and so hard at that job that the professor ended up strongly recommended me for a “real” job doing similar things upon graduation

My full time commitment was my studies at that time, which were honestly preparing me for a different career. My side gig was working for that professor. It turned out I loved the side gig work and then I wound up doing it full time for years.

Later in my professional life, I spent my spare time writing and building The Simple Dollar. It was a side gig to my full time job that I discussed above, not my full time focus, but I worked so long and so hard on The Simple Dollar that it ended up becoming a pretty nice success, enough so that it became my full time work.

My full-time commitment as The Simple Dollar grew was a completely different job, but I loved (and still love) writing for The Simple Dollar.

In both of those cases, I spent my full-time effort on one thing and devoted some of my spare time on a “side gig.” The “side gig” in both cases was the thing I was most passionate about – solving some very interesting problems in the first case and writing in the second case. My full-time effort was centered around something that either earned me a solid income or put me on the path to doing so, but they weren’t as engaging to me as the side gigs were.

Together, these two cases taught me something very valuable: It makes a lot of sense to pursue a passion as a “side gig.” There are two big reasons for that.

Truth #4: You will probably fail badly at first, which is why it is smart for it to be a “side gig.”

When I was in college, I tried out a bunch of “side gigs” – part-time jobs in various areas. Some were obviously pure part-time jobs just to earn a buck, but some of them were work-study jobs with professors that were in areas that interested me. I worked in a plant pathology lab. I worked as an understudy of sorts for an IT specialist. I did tech support for a convention. Those things were interesting, but none of them really “clicked” with me in a deep way – and in at least a couple of those things, I didn’t do well at all. It wasn’t until I started working for that professor mentioned earlier that I really found something that “clicked.”

Similarly, in my spare time later in my career, I tried tons of “side gigs” that seemed well in line with my passions. I started a computer consulting gig. I started a number of blogs, including a parenting blog. I played online poker (I actually did well at this, but then the legality of it came into question and I didn’t want to bank a career on it). Most of those things failed – I’d call the online poker a semi-success along with a parenting blog. However, real success didn’t strike until The Simple Dollar took off.

I have failed at countless side gigs in my life, far more than I ever succeeded at.

And that’s completely fine. I’d even call it normal.

The thing is, if I had completely thrown all caution to the wind and followed any one of those passions full time, in most of those situations, it would have become a complete failure. I would have struggled to put food on the table or keep a roof over my head. I would have perhaps stuck with half-successes, continuing to push them along in mediocrity and never really succeeding.

Leaving them as part-time side gigs gave me the ability to fail and move on to other side gigs. It gave me the chance to try different approaches and learn from failure and apply those lessons to the next side gig.

Truth #5: The best route is to train initially for a great-paying career that you can somewhat enjoy to support the ‘side gig.’

Of course, here in the real world, most of us have people to support. We need to keep food on the table and clothes on the back and a roof over the head of ourselves and likely of others, too – children, spouses, parents, and perhaps others as well. The vast majority of people don’t have income streams from parents to fall back on, either.

If you’re in that group of people, meaning that you don’t have any income or wealth to fall back on if things fall apart, it makes more sense to train for a great-paying career that you can enjoy to some extent rather than focusing solely on “doing what you love.” Leave the “do what you love” for side gigs.

The reasons for this are many. First of all, if you have a great-paying main career, you can financially support almost any side gig you might want to dabble in. For example, you might want to be a software engineer so that you can support your side gig as a romance novelist. You might want to be a lawyer so you can support your side gig as a board game designer. You might want to be an actuary to support your side gig of being a poet.

This allows you to explore that side gig without any initial need to earn money at it. Your goal solely is to build experience and learn the craft, as it doesn’t have to put food on the table for you (yet).

Better yet, you can fail over and over and over again. You can try experimental approaches and take risks and if it doesn’t work you won’t be putting you and your family out on the street. Instead, you’ll just gain valuable experience and insight for your next attempt.

If you’re smart with your income, you can actually plan ahead to retire or partially retire much earlier than the average person, which then enables you to tackle side gigs full time.
Truth #6: The thing that really clicks is usually different than what you initially envisioned.

If you had told me 15 years ago that I would spend a significant portion of my adult life writing about personal finance, I would have never, ever, ever have believed you.

I might have wanted to believe you if you simply said I was a writer, but once you added the “personal finance” part, I would have thought it was farce. Writer? Sounds cool. Personal finance writer? Me? Ha!

It’s funny how things turn out sometimes.

The same thing was true when I was in college. I wound up writing tons of computer code to solve some very interesting problems and I did that for several years professionally. If I had described all of that to myself at a younger age, I wouldn’t have believed I would do anything like that. Writing software? Possibly. Solving those kinds of problems? Not a chance.

Again, it’s funny how things turn out sometimes.

The number one key to doing what you love is to keep your horizons as open as possible and try lots of things, even if they seem completely strange or completely different than what you dreamed about.

Sometimes, you’ll find that the exact thing you always dreamed about – like, say, being a science fiction and fantasy novelist – doesn’t quite work out like you dreamed that it would. However, if you stick with the parts that you like – like, say, the routine of writing and the pleasure of touching people’s lives – and try different angles on those parts – like, say, writing about personal finance in a very human way – you can sometimes find success that you never could have dreamed of that allows you to do the things you love in a very different way.

Truth #7: You might fall out of love with the thing that you love, so keep trying new side gigs.

Even now, although I do something I love as my full-time job, I dabble in side gigs based on my various passions and interests. I do this to earn a little money and to deeply explore things that I enjoy, and I’ve found success here and there in the things that I’ve tried.

However, the real reason I keep dabbling is that there is always a risk that I will fall out of love with writing for The Simple Dollar, and when that happens, my current job will become miserable. When you spend a significant portion of your waking hours employed at something that makes you feel miserable, then your whole life is going to have an unhealthy dose of that feeling.

I still work on writing science fiction, and I dabble in fantasy as well. I’ve written mobile apps. I’ve worked on podcasts and YouTube channels. I’ve done all of those things as side gigs since starting The Simple Dollar.

Have any of them been runaway successes? No. Have they allowed me to dabble in things I’m passionate about to figure out how deep the passion goes and learn about new approaches for the future? Absolutely.

Never stop side gigging. Never stop trying new things. Even when you think you’ve found the best thing ever, never stop experimenting and digging into the areas you truly enjoy and truly excite you.

Final Thoughts

You can, in fact, “do what you love,” but betting everything on it from day one might not be the best approach. Instead, take a more measured approach – give yourself a foundation to stand on and allow you to fail without devastating consequences to your life. You can pick yourself up, learn from the failure, and move on to try new things and new approaches.

Sometimes, if things fall into place just right, you can find yourself doing what you love with financial security to boot. This is the best route I’ve found to get there

Written by Trent Hamm,  the simple dollars man.