In WC Porter's recent article, Do What You Love: Idealistic Nonsense or Good Advice?, you will find an inspirational video and loose analysis of what it takes to do what you love and earn money doing it.

But nay saying commenters call the video speaker a huckster, and others challenge the concept that it’s even possible to do what you love (and get paid for it, and still love it).

As somebody who is technically doing what I love, I find this fascinating. I travel full-time in a financially sustainable manner, paid for by a writing career that is fulfilling. I do what I love (ie: travel and writing), and I make enough money at it to get by.

But even my situation isn’t as black & white as that. In further examining the intricacies of love and money, here are some concepts that further deepen the debate.

Doing what you love isn’t always a bowl of cherries

Just because you do what you love doesn’t mean you love everything about what you do. The speaker suggested that there are certain aspects of his job that he full-on hates. I concur: there are times when I want to stab myself in the eye if I have to spend one more hour at my computer when the weather is nice and an exotic unknown destination beckons from just outside my window.

But without my writing, there wouldn’t be an exotic destination outside my window at all; I’d still be cooped up in an office somewhere working at a career I was equally marvelous and miserable at.

I also make a number of frugal lifestyle choices in order to get by with the money I make on the road. For some people it wouldn’t be ideal, and for others it would be unacceptable; it is a very personal choice.

But for me, the benefits of my writing career (and the accompanying travel lifestyle) far outweigh the costs. But there is still a cost. No dream is THAT dreamy.

Early career choices (and life partners for that matter) are like shots in the dark

Choosing any career is like choosing a life partner. How do we know once we have just escaped the throes of adolescence what career will make us happy every day for the rest of our life?

Similarly, how do we know (at any age) if we will be happy waking up next to our partner every morning for the rest of our life — happy enough to get married?

Guess what? Most people don’t know.

And because we are required to decide on our post-secondary education (and the range of careers it lends us) at such a young age (arguably before we really know ourselves), many of us end up studying for careers we ultimately won’t be happy in.

But what do we do after we have gotten our degree and are now working our way up a career ladder in order to:

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  1. pay off our debts
  2. plan an upcoming wedding
  3. buy a house
  4. prepare for child-related expenses
  5. enjoy our next vacation
  6. etc?

What do we do when faced with inevitable bills and financial goals? That’s right. Put on the blinders, keep our head down, and work. We may not be thrilled with our job, but we justify it as a means to an end (the various "ends" being listed above). We keep company with other people who also don’t particularly like what they do, and — since most people are in this boat — commiserating becomes natural.

This is how being somewhat unhappy with a career becomes an acceptable way of life. It is much easier and safer to go with what we know (despite the fact that it may not be entirely what we want) than to uproot our routine or balance to explore a new avenue.

Other people, however, see life as too long to get stuck doing something (or being with someone) that is not fulfilling. These people forgive themselves for not making the right life-enduring decision, and search for ways to improve. Ways could include changing careers, starting businesses on the side, taking up new hobbies, and finding new partners.

The bigger these people dream, the bigger the changes they make are. And who are the big dreamers? I believe that some of the world’s biggest dreamers are also some of the most entrepreneurial.

Entrepreneurs vs. Employees

I am wondering if the core root of the matter (and where each of us fits in the spectrum) boils down to how entrepreneurial — or not — we are.

Entrepreneurs don’t mind working hard for what they want, and they look for creative ways to get there. If strictly doing what they love has obscure career prospects, they find a different spin on it that makes it more lucrative.

It is likely that only the entrepreneurial souls understood the vision the speaker had when he spoke of working a full-time job, then coming home and working another seven hours on his business for the first five years. Most of us would crunch the numbers and say he’s crazy. But he had a vision for a niche idea that took five years to develop, and develop it he did.

Although that sort of lifestyle may sound unbalanced (and it is), if we are doing what we love, we don’t tend to mind doing it so much. When we do what we love, we don’t mind the sacrifices and compromises we may have to make. Why? Because if we are really doing what we love, we simply wouldn’t have it any other way.