I had an interesting conversation with a friend last weekend about how realistic it is to merge what you do for a living with what you do for fun. We both agreed, whatever path is chosen, it’s important to not be of a divided mind about it and not harbor feelings of guilt or being a “sell out” if you do work that’s not also your hobby.

Everyone has different preferences. I personally have always placed a higher value on doing work that’s really interesting to me than I have on doing work that’s highly lucrative or allows a lot of free time. Sure, I’ve had jobs at golf courses and grocery stores and construction sites that weren’t my passion, but I always viewed those as transitional while I moved closer and closer to work that expressed what I’m all about. I’m very happy with my choices, but I do know people who’ve pursued their passion and never made enough money for a decent life. They do work they love, but they’re a little bitter about their relative poverty.

I have friends who chose a different route – getting highly remunerative work that they could tolerate but don’t love so they could spend more time/money on what they do. Some have succeeded marvelously and have nice lake houses and recording studios and do a lot of traveling and cooking fancy meals. They don’t like work much, but they work so they won’t have to work much. I also know some who’ve taken this path and never done well enough to pursue what they love, and they are probably the most bitter of all, feeling both like sellouts and serfs at the same time.

The point is, I can’t tell you what’s the best approach for you. No one can but you. But it will benefit you to examine your preferences. What do you love doing most of all? Would that be better or worse if it was also how you earned your living? (I probably love playing music more than anything, but I think I would like it a lot less if I had to earn a living doing it). Why do you work? To create free space to do other things, or because it’s what you want to be doing?

Whatever you decide, be at peace with it. Be conscious of the trade-offs and why you chose what you did. The worst is to just sort of float downstream and end up doing something by happenstance, never feeling like you made a choice, and always bitter that you aren’t doing something else, or aren’t making more money, etc.

If you have a high tolerance for failure, stints of poverty, hard work, and rejection, why not go for what you love? If these things tend to be catastrophic for you, you should probably take a more staid path. Either way, the key is always to be honest with yourself about your own true preferences, and don’t feel bad about them. You don’t have to do what you love. You don’t have to do the sensible, practical thing either. But you do have to live with yourself, whichever you choose. Make it a conscious, unapologetic choice.

This isn’t a one time decision. It’s something to be thinking and rethinking throughout your life.