“Can I make a living and have a life doing something I really care about?”
I remember the moment 20 years ago when I first asked myself this question. I was just starting my career. It was 1996, and I had moved from Austin, Texas, to Washington, D.C. in a pickup truck with my future wife, our dog “Lucky,” no job, and a ton of debt.

My future wife, my dog, and my pickup truck.
What more could a person want?

I landed a job at a small non-profit organization dedicated to drug policy reform – at a time when that issue was very controversial. My salary was less than $20,000 a year. I worked a second, retail job at night to make ends meet.
One day while I was hanging out with a colleague during his smoke break, our conversation turned to whether one of us could ever make more than $100,000 a year, which seemed like an astronomical sum. We concluded that it wasn’t possible. We had no idea how we could ever reach that point, especially since we both had wildly unconventional career aspirations.
Actually, that’s an understatement. We both wanted to change the world. My friend wanted to legalize marijuana. And I wanted to be at the forefront of promoting classical liberal ideas – freedom, writ large. Neither of us had any idea how we would get from where we were then to where we wanted to be. But we were both idealists, believing it was possible.
We were right.
Today, my friend runs the first-ever medical marijuana dispensary in Washington, D.C. (within eyesight of Congress). And I run a national organization that works with college students and professors to study and advance the ideas of a free and open society. We both have meaningful, purposeful careers, and we’re both doing well enough to provide for our families and lead comfortable, happy lives.
This seemed impossible to me not that long ago.
I’m telling this story because I believe almost everyone, at some point, finds themselves wondering the same thing I wondered on that smoke break. I realize this anew every time I speak to a group of students. When we’re young, many of us have impractical – sometimes crazy – ideas about what we want to do with our lives. We want to make a difference somehow. We want to tread a new path and challenge the status quo. And we know, deep down, a conventional career won’t provide us the meaning and fulfillment we desire.
Despite this, too many people eventually settle for something practical. Our youthful idealism fades, replaced by the growing sense that an ideal career is hopelessly naive.
What do I mean by “ideal career”? I define it as career that: (1) gives you a deep sense of meaning and purpose, (2) provides a comfortable income, and (3) can be pursued in balance with other key elements of a happy life – strong relationships and good health.
This sort of career seems impractical to most, especially when we’re young. But what if there’s a practical way to pursue the impractical?
There is.
I’ve spent the past few years reflecting on my own experience and the experiences of others who have somehow found the career that once seemed intangible. If I’ve learned anything, it’s this:

You have to be impractical about what you
can achieve, but deeply practical about how
you achieve it.

Put another way, it’s not enough to “follow your dreams” or any of the other cliché, feel-good phrases. You need a practical approach to discover what your ideal career is and to pursue it.
Over the next several weeks, I’ll share with you my thoughts on how to practically pursue the impractical. I’ll lay out the “toolkit,” as it were, that I’ve refined to help others identify a career path that is meaningful to them and then pursue it intelligently.
You won’t find this useful if you want a safe or conventional career that pays the bills but doesn’t satisfy your soul. Nor is this for anyone whose main goal is to get rich, become famous, or gain power. Those are all conventional goals, and there are plenty of conventional careers where you can pursue them.
What I’m interested in – and what I believe you’re interested in – is the unconventional career, the seemingly unachievable career, the ideal career. Such a career exists for all of us, and it has never been easier to abandon practicality in pursuit of something more.
The downside risk of pursuing an impractical career might seem large now, but it isn’t in the scheme of things. The upside potential, however, is infinite.
This piece was originally published at LinkedIn.