S2E03: Lucky Breaks & Opportunities Essay

I came from a high-pressure, achievement-oriented environment. Gifted schools, special programs in the summer, and a fancy college. I was not the smartest of that bunch, but I could hang, most days, most of the time.

I learned to focus, to avoid distraction, and keep moving toward the goals I set. By the time I was a teenager, I had honed this ability to focus and considered it a strength. It got me through high school and college.

When I decided to move to Los Angeles to be a rock star, I figured this same ability to stay fixed on my goals would pave the path to success and help me speed past and above the other musicians who were distracted and lacking discipline.

I was wrong.

Life isn’t school, for one thing. School is structured, with clear goals, tests, and paths forward. Real life is anything but that. Life is unpredictable and features odd, serendipitous moments.

The music business -- at least when I was in it -- didn’t really care about how much effort you put in, either. How hard you worked on your music, image, marketing plan, gigs, flyers, demos, guitar playing didn’t matter.

What mattered was whether or not enough of the right people liked what you were doing. And hard work wasn’t really going to change any of that. If anything, the entertainment business is often about making what is difficult look easy, effortless, and carefree.

I kept my eyes on what I assumed my goal was, stayed on the path of what I thought my music should be. I didn’t want to “waste time” by experimenting or taking detours or wandering down other paths.

It was a huge mistake.

Those blinders and that single-mindedness became handicaps. They kept me from building relationships with people, kept me from trying new things with my own music as well as playing with others, and kept me from realizing what I was doing just wasn’t working.

In the end, the thing I thought was a strength was a tragic flaw. My error was in thinking the solution was just more focus and hard work, and that no matter what, more intensity was the answer.

By the time I realized it, it was largely too late. My energy, money, and time were all spent, burnt up running down what turned out to be a dead end.

It was only in the last year of my time as an aspiring professional that I freed myself, and those last few months were the most satisfying of that part of my career.

Focus and hard work matter, but luck matters more. You have to know when the right opportunity comes along, then seize it and work it.

Even then, there are no guarantees. Know when to give up, know when to move on. Always say yes to opportunity, especially if it is going to take you in a direction you did not expect or anticipate.

Most success stories in the entertainment biz are about unexpected detours, fluke meetings, and surprise connections. Few are about people who laid out a plan and stuck to it as hard as they could.

There is also a kind of “going with the flow” aspect -- if you are tired from swimming against the current all the time, well, maybe you’re doing it wrong. Some success is hard-won, but sometimes it feels as easy as falling off a log.

I finally began to understand when two things happened. Someone suggested I spend a summer teaching a class to kids at Duke University. Instead of saying “no, I’m focused on my music”, I said “sure, that sounds interesting, even though I’ve never done anything like that before. Let’s see what happens”.

Not long after I returned from that life-changing experience, some of my friends called me up and said “hey, you should move to San Francisco and come work with us on this internet music idea we have”. Instead of saying “no, I’m focused on my music”, I said “Sounds interesting. I’ll give it a try and see what happens. I can always move back to L.A. if it doesn’t work out”.

Well, that particular business ultimately didn’t work out (in about 3 different ways). But more than 20 years later, I am still in San Francisco, and I am still saying “Sounds interesting. Let’s try it and see what happens”. Perhaps I have learned to at least jiggle the handles of the doors of opportunity and peek into a few that open.

You would think my time in L.A. as a professional musician would have taught me that more focus and hard work isn’t always the right answer for things not working out . Nope. For someone who occasionally describes himself as smart, I seem to be a slow learner sometimes.

My second-act career as a technology professional had a similar trajectory to my music business career. In the early days, I used to stress myself out, working crazy hard, trying to prove to everyone (and perhaps myself) that I was smart and capable. It was annoying and exhausting.

I was also disappointed with the results. Not just my own work, but in the responses from my colleagues, which were frequently less-than-enthusiastic.

At some point, perhaps from exhaustion or just my own inherent laziness, I stopped trying so hard. I started saying things I thought were obvious, rather than overthinking. When stuff wasn’t working out, rather than hitting it harder, I looked for different solutions, preferably ones that didn’t require so much effort. I learned to take breaks and walk away for a while.

That was when everything began to work out.

Bill Gates famously said he often gave the hardest problems to his laziest developers, because he knew they would find creative and efficient solutions.

I suppose the takeaways here are that you should always be trying to open new and different doors of opportunity. If the one you thought you wanted won’t open, go find a different, easier door to open. You might be pleasantly surprised at what you find. The hard work and unrewarding preset goals you set for yourself will always be there, should you wish to go back to them.

Me, I don’t.

Image: L’acte de foi, René Magritte (1960)