Finding Your Path Between Passion & Regret

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What Do You Want to Do With Your Life?

This question sucks.

It really does! Think about all the things you’d like to do during your lifetime. Some of them seem downright impossible, some of them are probably a tad lackluster (yes, someday I would really like to finally beat Ocarina of Time). There’s an endless array of passions to chase!

The trouble is, this question does very little to help you find your “big” passion because there’s so many ways to answer it. I’ve found two different questions that I like to ask people, because it helps me understand a bit more about who they are and what their goals are. Interestingly enough, I’ve discovered those same questions can help me determine what my goals are… or should be, at least!

What Could You Do Every Day?

Question one: You are set for life, but you have to do the same thing (or type of thing) every day. There are zero educational, financial, or technological barriers – it can literally be anything. The only requirement is that it needs to be something that you can be satisfied with long after it loses it’s luster.

I’ve gotten some great answers to this question. My best friend somewhat dodged it by responding with “R&D.” But that’s true to who he is – someone who is passionate about creating something new. For others it’s adventure, or improving their community, or helping a loved one. Some don’t know, and that’s o.k., as long as it doesn’t stay that way.

The answer can change over time as you try things out, but by and large this helps you to identify what you really should be pursuing. So pursue it hard, right?

What Will You Regret?

Question two: You’ve just found out that you have a day to live. What parts of your life are unacceptable to you? Who do you wish you had spent more time with? What have you not done? Should you have parented differently? Studied more? Less?? Whatever things you’d regret, take note.

Back to reality: you’re not dying tomorrow, so change that crap before it really is too late!

Merge, Everybody Merge

If you’re playing along, you’ve probably discovered that what you’re passionate about and your regrets may be in conflict.

For example, I want to be working where faith (BTW, I’m a committed Christian), the community, and the family intersect to make life better for everyone in the little chunk of Vermont that I call home. A tiny fraction of that work is creating economic opportunity, which is where Indelible Inc. comes into play. Down the road I’d like to spend less time building websites and more time tackling even harder issues, requiring Indelible to pay me more for less of my time.

To achieve this, I work hard. Long hours, late nights, weekends, holidays, you name it. Society celebrates people like me as go-getters. But my family celebrates me as a dinner guest. If I were to die tomorrow, that would be my greatest regret, and it stands in direct opposition to the pursuit of my “career goals.” Don’t worry, change is in the works. I’m sure there’ll be a post on that soon…

What I propose is that you have to find a balance. Clarify your passions. Clarify your current and potential regrets. Now chart a course that gets you as close to your goals as possible without sacrificing the non-negotiables.

TLDR; In order to do what you love it also needs to be something you can stand doing even when you don’t want to. Once you know what it is, pursue it as hard as you can, tempered by the regrets you don’t want to have down the road.