Dream Job or Day Job?
Most people I know have a frustrated passion. There's something they'd rather do a lot more of, but making a living gets in the way. Some people simply accept that their passion will get short shrift, while other people make great efforts to arrange their life so they can follow their passion. For the latter folks, I'm familiar with three general strategies: dream job, day job, and early retirement.
The dream job, of course, is making a living by following your passion. However small the fraction of writers, artists, actors, dancers, musicians, and athletes actually making a living at their art, you know it's at least possible — you can see people actually doing so any time you turn on the TV. With some hard work, a little luck, and the talent you were born with, maybe you could be one of them.
Of course, not everyone's dream job is in the arts. There are plenty of people who dream of jobs in engineering, science, politics, teaching, business, medicine, and so on. Contrariwise, many passions offer no hope of a dream job — raising your kids being an obvious example. WC Porter just had a good post on doing what you love and trying to make money at it, and it's good to keep all your options in mind — if you can't find your dream job, maybe you can create it. (Still, it's worth trying to find work worth doing and then trying to land a job doing it. Certainly, it's better than doing work you hate.)
It's easy for a dream job to become a nightmare. Sometimes your passion isn't quite as much fun when you have to perform on schedule. Sometimes your dream job turns out to include less following your passion and more filling out status reports, soothing customers, and running everything past legal. And, more than just sometimes, you find yourself competing with people who'll do the work for free, because it's their passion too.
Still, none of that is to say that you should give up on your dream job. Just be realistic about it and go into it with your eyes open. One part of keeping your eyes open is considering the other two possibilities: day job and early retirement.
If you want to follow your passion, but also have to earn a living, one practical option is a day job. There are whole categories of day jobs that are popular with people whose passion makes demands on their time. Aspiring actors and dancers, for example, often end up working as waiters — because it's a job that lets them schedule around casting calls, auditions, and rehearsals.
The main criterion for a day job (aside from paying enough to support you) is that it doesn't drain you of whatever you need to follow your passion. A day job that leaves you exhausted might make it impossible to pursue your passion for music with late-night gigs. Working as a software engineer, I found that certain kinds of work seemed to use up whatever it was that let me write fiction. It was just certain tasks, so generally I could work at the day job all day and then come home and write in the evening. If that hadn't been true, I might have needed to find a new day job.
The best sort of day job for someone with a passion is one where you put in your hours and then you're done. Any kind of hourly work is good. Salaried work is less good — you're expected to get the job done no matter how long it takes. Worst is the sort of high-stress job where you're spending your nights worrying about your bosses, clients, customers, processes, or deliverables, and find that you can't focus on your passion. Because of that, a lot of people who go with the day job end up working what would otherwise be considered a low-end job, because it's one that leaves them with time and energy to follow their passion.
Even so, resist the temptation to settle for a job that's bad — in particular, for a job where either they don't respect you or where you don't respect the work. There is so much work that's worth doing, it's just stupid to flush your life away doing work that's worthless — even if it pays a little more. The downside of the "day job" strategy is that you're spending forty hours a week doing something other than your passion. Don't compound that by spending those hours doing something that you don't respect.
You can retire early if you combine a high-paying day job with a certain amount of frugality. The more frugality, the earlier you can retire. (Higher pay lets you retire earlier too, but if you work out the math, it doesn't help as much as you'd think. Between taxes, the almost inevitable higher standard of living, and the extra work that the higher-pay jobs tend to require, it turns out that frugality is the adjustment that ends up making the big difference.)
I covered the "retire early" scenario just a few days ago in my post on buying your way out of the rat race.
The main thing I'd caution against is the tendency to defer following your passion.
It's one thing to have to fit your passion into the spaces left around a job, a family, and all the other things you have to do. That's normal. It's fine. It's even good. Unless your passion is an odd one, the connections that grow out of living your life will feed into your passion.
But it's altogether different to put your passion aside until some future when you'll have enough time. That's almost always the wrong choice. Follow your passion right along. That's how it grows. That's how you remember why you're putting in the time and effort. That's what keeps your soul together.
As long as you don't put off following your passion, any of these strategies can work.