School Didn’t Teach Me: How to Turn a Hobby into a Career (Without Losing the Passion for It)

Alevin Chan

Alevin Chan

Last updated 10 December, 2021

Formal education may give us a leg up in life and career, but less so on managing money. School Didn’t Teach Me, a SingSaver series, is your informal education in personal finance.

Trying to have your hobby as a career isn’t as idyllic as we’ve been led to believe. It is entirely possible to be happy and thriving doing what you love; but you need to be willing to confront a few harsh truths along the way.

When I landed the job to develop and launch a travel and lifestyle blog, I was beyond thrilled. The role brings together two of my passions - travel and writing - which was just perfect. 

So you’d expect that I’d be happily feeding my office snapshots and videos of the gigantic replicas of famous landmarks from around the world I spotted in the inimitable Terminal 21 shopping mall in Pattaya, during a mid-year break I took in the carefree days before COVID-19. 

But halfway through trying to capture the iridescent glory of the four-storey high, LED-light festooned Eiffel Tower display (a brave, if foolish, task with nothing but an iPhone), a sudden thought stopped me cold: Did I really want to work while I’m on vacation? 

“Find a job you love, and you never have to work another day in your life.”

I’m sure you’ve heard of this saying, or some variation of it. It’s an appealing statement, a promise that once you find that dream job, everything will fall into place. 

The birds will sing, your hair will become lustrous and shiny, and you’ll be breezing through life like some long-lost Disney princess finally reclaimed by her Prince Charming (feel free to substitute whatever gender pronouns you’d like to fit your worldview).

This thinking manifests, then, in an understandable desire to turn your hobby into a career, in the name of following your passion. 

Understandable, but flawed. Because, as always, reality has a way of intruding onto our fantasies, and if you’re not careful, it will bring the house crashing down around you. 

Why trying to turn your hobby into a career causes the magic to fade

Let’s take a closer look at what it really means to turn your hobby into a career. 

By definition, a hobby is something that you do outside of work. It’s an activity you engage in to blow off steam, to experiment, to be creative (read: make mistakes), and you’ll have a blast even if the result isn’t superb. 

Now try doing that in the context of work, or a project a client is paying you for. Chances are, unless you’re Jackson Pollock, whatever mess you created won’t be earning you millions of dollars, and will more likely get you fired.

Therefore, we can deduce that trying to turn your hobby into a paying profession doesn’t quite work because of the following reasons.

Most recreational activities aren’t employable

The hard truth is, many hobbies or recreational activities are simply unemployable, and you’d have to be very lucky to land a job doing exactly the things you’re passionate about. But even if you do, it’s not all roses from then on - more on this later.

So that means it’s much more likely you’ll have to forge ahead on your own, as an entrepreneur or freelancer.

Sure, you have your influencers and your Twitch streamers and your e-sports professionals, and some very successful ones too. But for the vast majority, how sustainable are their careers? (Hint: not very, especially in the case of pro gamers.)

This, then, presents the first and most immediate problem: how to earn enough money to make a living from your hobby.

And by that, I don’t mean making just enough to barely clear the bills and keep yourself sheltered and fed. 

I mean earning an income that is large enough for you to meet not only your daily expenses, but also to cover your financial needs, goals and aspirations. This means things like sufficient insurance, savings for life goals like marriage, and putting aside money for retirement.

Can you make enough money from your hobby to do all that?

When hobbies become work, you get boxed in

No matter how much you love baking, or photography, or posting on social media, it becomes different when clients and money are involved. 

The couple who engaged you for their wedding photos aren’t gonna accept prints that look like they belong in a history textbook, no matter how deep you are in your Sepia Period. 

The mother who promised her four-year-old a birthday party isn’t going to be understanding when you can’t deliver the cupcakes on time, no matter how urgent the family emergency you’re facing.

The client who wants you to review their product won’t be happy about your criticisms, no matter how insightful or witty. (Even those so-called ‘honest’ reviews are moderated and negotiated behind the scenes, because what company in its right mind will willingly pay thousands of dollars only to be savaged in public?) 

When your hobby becomes work, there are deadlines and expectations to meet. These basically draw a box around you, within which you have to perform, whether you like it or not.

You’ll need to learn skills you may have no interest in

Besides just working on the stuff you’re passionate about, you’ll also need to cultivate other skills that you may have no interest in but are nevertheless important. 

I’m talking about things like learning how to create an invoice and bill your clients properly, how to develop contacts and networks from which you can get work, support and resources, how to deal with client disputes, and so on. 

Even if you land employment that fits in with your passion, you’ll need to learn how to navigate an office environment, how to negotiate a fair salary, even how to deal with being promoted. Advancing in your career might mean being moved from the shopfloor, to a supervisory position, where you have less opportunity to do the work you like. 

Just because it’s your dream career doesn't mean Agnes the office gossip won’t be a pain in the butt.

How to succeed in turning your hobby into a career

So are we all doomed to a life of wage slavery, forever spending the best parts of our days toiling away until we manage to save up enough for a meagre retirement? 

Well, not exactly. It is entirely possible to make a decent living while following your passion - thrive within the box, so to speak. Here are some tips to help make that happen.

Be willing to align yourself with your client

Pursuing your passion as a career can only succeed when you recognise that you have to align yourself with your client, and use your talents and skills to serve their needs and goals.  

Yes, that means that you’ll have to adjust your style and edit your work to a form and format that fits what your client is looking for. Even if they aren’t experienced in the field you’re dabbling in, it is your duty to advise them on what would work in a commercial sense.

It’s not about selling out, or being fake for the sake of money. Instead, think about your clients’ requests as hints on how to translate your talents or passion into something marketable.

Always seek to improve

The previous point also highlights an important principle: you need to be the expert of your own domain. 

Maybe you’re getting good at video editing, and the short clips you’ve been sharing on your TikTok have been garnering you a fanbase. You’ve even been approached by a few marketing managers who like your work, and want to engage you for a professional video to market their services. 

So you accept the commission, get the work done, put your best into it, the video launches to great success, and everyone walks away happy. What’s next? Do you stop learning new techniques? Do you give up honing your skills and sharpening your style? 

Of course not, because the next client will have different needs and higher expectations. Which means that you’ll need to continue building your skills and mastery in your field. And you may need to do so in a hurry, if you hope to keep up with the competition.

Do you see the difference? When you were doing it as a hobby, you were free to play around at the level you’re comfortable at. However, when you’re going professional, you’ll need to be more than good enough. 

To be specific, you need to be good enough to consistently get commissions, because otherwise how are you going to feed yourself? And because the market changes over time, you’ll need to improve as you go along. It’s a constant process that never stops.

Have fun with your work when you can

Going pro with your hobby is starting to sound more and more like a job, isn’t it? But that doesn't mean you can’t have any fun while you’re at it. In fact, letting yourself enjoy your work is crucial in keeping your passion alive. 

Having fun doesn’t mean doing haha-silly things that would be an awkward fit in a commercial context or professional setting. It simply means seizing opportunities to inject your own flavour. 

There is, however, a fine line between having fun and being cheeky, so when in doubt, less is more. 

Thinking of going freelance? Make sure you have your savings in order before you take the plunge.

An ex-Financial Planner with a curiosity about what makes people tick, Alevin’s mission is to help readers understand the psychology of money. He’s also on an ongoing quest to optimise happiness and enjoyment in his life.


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