As Austin Kleon says, what you love and what loves you back only overlap if you’re lucky.
For most of us, we spend time in each of the sections of this diagram, but rarely in the space where they overlap. That means we’re either spending time doing what we love without being adequately compensated for it, or we’re working a job that loves us back with money, benefits, freedom, and so on, but we’re not enjoying it.
When you love doing something people don’t want
This is a hobby.
Doing something you enjoy that nobody will pay you for is not a sustainable career.
There are two ways to approach a hobby like this: either be content to keep it as a hobby and focus elsewhere for your income, or work hard on it until your skills are good enough that people will pay you for it.
Sean McCabe calls this second approach the overlap technique. By overlapping a hobby you enjoy with a separate, unrelated day job, you give your hobby room to breathe. You can spend enough time doing it to know whether you really want it to become your job or not, and you can use your day job to keep pressure off your hobby as an income stream.
Sean did this when he learned hand lettering, which he’s now best known for. While working a day job as a web designer, Sean spent his free time practicing hand lettering because he loved it. As he shared more of the lettering he was creating, he started to build up demand for his lettering services.
Eventually the demand grew to where he could leave his day job behind and turn his hobby into a full-time job.
Doing what people want when you don’t love it
The other extreme is to do something you don’t enjoy which is in demand. As a day job that supports other pursuits, this can work for a limited time. But if you’re building a career doing something you don’t like, you’re heading towards chronic stress, drain, boredom, and possible burnout.
The trouble with this situation is that it’s really hard to pull yourself out of. The “golden handcuffs” scenario puts you in a comfortable position where your bills are taken care of, maybe you have some nice benefits, you have autonomy and working for this company gives you credibility. It’s hard to give up those things. And it’s scary to walk away from security.
But the alternative often means your work drains you, rather than energizing you, and you have nothing left to give to other parts of your life. Your health, relationships, and hobbies suffer.
It’s like an introvert (someone who draws energy from spending time alone) spending the biggest part of their week surrounded by people. Or an extrovert (who draws energy from others) spending most of their week alone. At the end of each day, they’re going to be drained and bored.
I don’t know about you, but that’s not the way I want to feel after a day’s work.
Finding work you love that loves you back
We all want to be able to enjoy our work. But how do you go about finding work you enjoy that also has enough demand for you to make a living from it? Here are a few starting points.
Give it time
Another great lesson I learned from Sean McCabe is to really test whether you enjoy the process of doing something, rather than just the idea of it. Many writers have been credited with saying they don’t enjoy writing, but they enjoy having written. If you don’t enjoy the process of your work, you probably won’t want to do it day in and out for years to come.
Starting out with a day job that covers your expenses is a good way to test out other options. You can take them up as experiments or hobbies and give them time to develop. If you take up painting but you decide after a few weeks you don’t enjoy it as much as you thought, you can move on to something else.
It’s hard to understand the reality of a new type of work before you get stuck in and do it for a while.
Sean’s lettering story is a great example of finding demand for something before you try to make money from it. By sharing the work he did for the love of lettering, Sean created enough demand to eventually become a full-time lettering artist.
If you’re starting out with a new type of work, share your progress and any work you’re really proud of. This gives other people a chance to see what you do, and it lets you develop your skills in public as well as in private.
This could be in the form of a portfolio, a public showing of your work, or even case studies explaining how you develop a new piece from scratch.
Find your unique angle
What is it about your approach that’s different? What do you have to say that hasn’t been said before? What new combination of tools, styles, or techniques have you come up with?
Finding your own angle will help you carve out your own niche in terms of what you love doing, but also demand for your work.
There’s no demand for copycats—everyone’s looking for something original.
Find the gaps in existing solutions and focus on what you do that’s unique.
When you’re lucky enough to find a career that you love, which also loves you back, you’ll notice working energizes you. You’ll be refreshed after a day’s work, not exhausted, and you’ll have energy leftover to spend with friends and family, and on developing new skills and interests.