Career Advice I Wish I’d Received at Age 20

It’s possible to have a career without really thinking about it. Nothing wrong with that. I’ve had at least three-and-a-half accidental careers so far.

• I started doing computer support and database design right out of college, just a few hours a week, at my dad’s friend’s company, learning as I went. Ten years later I was the Senior Database Administrator for the San Francisco Symphony, and I still do freelance db work to this day as my main source of income. But none of my friends ever remember this, because it’s so boring that I never talk about it.
• My record label business partner wanted to start a weekly happy hour at an art gallery. I thought it was a terrible idea. The ayahuasca-snorting gentleman he initially partnered with to throw the event got a little squirrelly and they parted ways. I reluctantly stepped in, and under our management we had a decade-plus run as one of the biggest dance music events in San Francisco, lines around the block, written up in international guide books, DJs from around the world eager to play to our crowd.
• I had no interest in DJing. But we needed to promote our album. So I learned to DJ at my own party, trainwrecking mix after mix. Spesh put me through DJ bootcamp and I got a little better. Soon we were headlining the biggest dance clubs in San Francisco, voted among SF’s Top DJs in the Nitevibe poll, on the cover of The SF Weekly, and touring in Europe. But eventually I quit because I don’t like travelling, or listening to hundreds of promo tracks to find the few good ones.
• I started a blog in 2009. I can’t remember why. Probably to practice writing, to express myself, to share my ideas. Eventually some of my health posts (about sleep and artificial light, about the paleo diet) got popular. The blog hit a million views. CNN interviewed me. A TV show The Doctors flew me to Hollywood to be a guest. I experimented with advertising. Then I wrote a post about how I regrew some of my hair by intensively massaging my head, and things went crazy. Views through the roof, readers begging me to make instructional videos, asking for personalized advice. Should I take up hair regrowth coaching? I thought about it. Maybe I could help Tim Ferriss regrow his hair, or Prince William. But I’m not patient enough to be a coach, and I didn’t want to be the hair guy. Or another paleo guy. So I made it clear to my readers that though while I would still write the occasional health post, the content of this blog was much broader (systems for living well, self-experimentation, the creative life).

One career — producing electronic dance music — I started on purpose. I wanted to be like Moby or The Prodigy or The KLF. I saved up money from part-time jobs while in college and bought myself a Roland D-70 keyboard, wired it up to my MacPlus. The contraption sat there unused while I tried to decipher the manual poorly translated from Japanese. My roommates thought I was crazy, felt a little sorry for me for wasting all that money on gear. They were surprised when I signed my first record deal. Since then I’ve released hundreds of tracks on over 40 labels, started my own label with Spesh, licensed music to TV shows like CSI, games including Dance Dance Revolution, and written a few tracks that are considered to be dance music classics.

But what I’ve really wanted to do, since I was a kid, is write science fiction. I wrote my first sci-fi stories in the 3rd grade. I took a few writing courses in college but I got distracted by life. Instead of writing I traveled the world, fell in love, trained dolphins, studied martial arts, started some careers, fell in love again, got married, wrote some bad screenplays, had a kid. Finally in 2013 I decided to commit, to write more days than not, to really give it a go for at least five years. While it’s a twistier, steeper road than I expected, I’m making some progress. Slowly, more of my stories are making it out of the slush pile to get read (and usually rejected) by the actual editors. I recently sold a story to Strange Horizons, a professional SFWA-qualifying market. I’ve got a nearly-finished novel I’m eager to shop as soon as I’m eligible to join the SFWA as a voting member (my first major writing career goal).

The most exciting thing about starting a new career is the feeling of growth. Even though I’m starting at the bottom, I’m improving and feeling excited about the work. And more than any other possible career I can imagine, it’s a good fit.

But enough about me. Have I turned any of the above experiences into actionable guidelines? Following is the advice I wished I’d received when I was twenty.

Six Questions to Ask About Your Career or Potential Career

Does the work match your values? (D&D alignment matching)

How many people get into banking or law, but then oh-shit-my-soul? They have to quit and start over (the right choice), or stay and feel trapped and drink themselves to death.

Rule of thumb: Don’t take a job more than one Dungeons & Dragons alignment away from your own. If you’re Neutral Good (like me), then you can do Chaotic Good work, or Lawful Good work, or True Neutral work, but not Lawful Evil or Chaotic Evil work.

What value can you offer that few others can?

Even though there are plenty of people writing science fiction and making dance music, there aren’t many people who can write the kinds of stories and music that I write. And I try to remember that, to go deep into my quirks and interests, and not try to write broadly appealing material. Do the kind of weird that only you can do.

If you have a knack or deep interest in something, see how far you can take it. This is better advice than “follow your passion.” You won’t always feel passionate about your work, because work (all work) sometimes gets hard and gritty and tedious. But if you’re doing something that few others can, you’ll feel compelled to keep going, to keep serving because you in particular are needed.

How will you be compensated?

Get real about the money. I don’t expect to make much money selling music because I’ve seen what a Spotify royalty statement looks like (even with millions of streams, you’re not gonna pay rent). I don’t even expect to pay the bills selling short fiction either (a “pro” rate is only 6 cents a word). Fortunately I have other income sources.

Do the research. Find out how people get paid in that career, and how much, and if that’s going to work for you.

What will your lifestyle look like, and does that appeal to you?

Every job has hard bits that are part of it. Club DJ’s have to stay up late and hustle for gigs. Writers get most of their work rejected and get judged by their potential publishers on how many Twitter followers they have. Fitness teachers have to get up super early to teach that 6am pre-work class. MMA fighters get paid poorly unless they’re in the top 1%, and are guaranteed to get injured and maybe killed.

Look at the hard bits closely before you commit. Can you eat that kind of pain for breakfast and still smile?

What are your top 5 career goals? (and ignore the rest)

This is a great focusing exercise from Warren Buffett. I learned about it from this post. Make a list of your top 25 career goals. Decide which 5 are the most important, and commit to pursuing those. Now look at the bottom 20. Resolve to do absolutely nothing about those bottom 20. For now, forget about them. You can revisit those once you cross off the first five.

I did this exercise recently and was blown away by how freeing it was to backburner so many of my vague ambitions. For those of us with minds that reach too far and too broad, this is a must-do exercise.

I also found it useful because in the past I have over-focused. For a long time I tried to pursue only a single goal at a time. But this is too limiting. Life is wild and woolly and opportunities present themselves in weird ways and we always need to be ready to pivot, to be opportunistic. I still have a #1 goal (to become SFWA qualified), but that doesn’t mean I shouldn’t be researching agents or pursuing other writing-related goals simultaneously.

Generally, systems trump goals. It’s more important to establish beneficial daily habits than achieving some artificial milestone. But goals are great too, because they point you in a specific direction, and give you something concrete to works towards. Don’t buy the bullshit that setting goals will make you feel inferior or “less than” because you haven’t achieved them yet — that’s only true if you don’t have an abiding sense of gratitude in your life.

What’s next in your career?

If you’re not moving forward, you’re moving backwards. As succinctly explained by Casey Neistat below, and in more detail here. You never make it. Your life and career are always a work in progress.

Always think about what’s next. What’s the next big thing? Even if things are going great, if you’re not thinking and planning at least 1-2 years down the road, you’re failing. Comfort is decline. If you’re cruising, you’re losing.

I got complacent about my music career, and lost momentum. For many years I wanted to write but didn’t commit to the practice. I regret both things. My life is great, so I’m not complaining. But moving forward, will I keep the pedal to the medal if I get something going with fiction writing?

Yes I will.