How to find good opportunities

In my current job, I occasionally mentor people and one of the questions I often get is: “How do you find good opportunities?”

By which people mean cool technologies to explore, great projects to be part of, opportunities to talk at conferences, great companies to join, interesting people to meet, and so on.

Is it all luck?

Yes, it’s all mostly luck.

Looking back at my career, even life, all the defining moments that had a big impact were pure luck.

A few examples:

• When I finished school in Rome, Italy, my mother gave me a copy of “DER SPIEGEL” magazine, which had a ranking of all universities in Germany. The bottom line was that smaller is better, because it’s easier to meet professors, find lab seats, etc. So I applied for the two or three smallest ones and got accepted by Clausthal Technical University. This turned out to be the beginning of a very happy and wonderful period of my life: my years as a student. Who knows where I would have ended up if my mom hadn’t brought home that magazine? Or if one of the other two universities had answered earlier, or if any other stroke of luck has propelled me to some other university?
• During my student years, I jobbed at the university’s compute center. One day in the mid 90es, my boss (the head of the compute center himself, because, small university) showed up and asked me to check out this World-Wide-Web thing that he had heard of. That’s how I became webmaster of the whole campus, visited the 3rd international WWW conference at Fraunhofer Institute in Darmstadt (no official website available anymore, but here’s an article about W3C from TidBITS), and played with different web servers like CERN HTTPD, Spinner (remember?), and finally Apache. I was also trying out new web browser on an almost weekly basis, like the original Mosaic, Athena, or Netscape, which became the ancestor of today’s Firefox. Google didn’t exist back then, instead we used AltaVista, Yahoo! and other search engines of the time.
• The sysadmin for the institute for mineralogy at my university remembered me because I helped him install their first web server, after he moved on to become a Systems Engineer for Sun Microsystems in Germany. He emailed me about a student job they were looking to fill for a project that Sun sponsored with the German public broadcasting agency. I accepted, because Sun was my hero company, since I worked on their workstations all day (brilliant sales move, BTW: give as much discount as possible to educational customers and watch your hiring pipeline fill up with enthusiastic students). That’s how I ended up working at Sun as a student, running the ARD.de web server back then, which was a humble Sun Ultra 1 in the Sun Hamburg demo room. I ended up writing my diploma thesis about bringing web technology to TV set-top boxes and finally, after getting my diploma, I started working for real (my third career, if you will) at Sun.

Life is a game of Pachinko

These are just three episodes of the younger part of my life. You can see how much randomness is involved when choosing places to move to, technologies to specialize in, or careers to follow. In my case, the rest is history: Sun was all about workstations at the time, then came servers, microprocessors, Solaris, ZFS, the cloud, and now AWS. A myriad of opportunities to meet great people, play with cool tech, visit inspiring events and watching IT history unfold.

The point is: life is shaped by many pieces of random events, each of which can move your future into any unpredictable direction. Like a Pachinko ball, people hit random other people, events or discoveries, then either follow them or not.

Adrian Cockcroft (who I first met at Sun, then re-met multiple times while he was at eBay, Battery, Netflix, then after joining AWS) had a similar set of Pachinko moments that he wrote about on his own blog: What Adrian Did Next — Part 2 — Sun Microsystems. And there are many more examples like these.

So when people ask me: “How did you uncover all of these opportunities?”, my first, honest answer is: “I don’t know! I just followed the next cool, shiny thing that interested me!”

Luck with a side of decision-making

Looking back at these and other examples, a few patterns emerge:

• It’s always your decision. The advantage compared to the Pachinko ball: You can choose if you want to follow some new opportunity, or not. My personal strategy was simple: follow what I found most interesting. Others may have better strategies. Decisions can be influenced by random events, though: At the 3rd WWW conference, I visited the SGI demo booth. Back then, they showed early versions of the VRML standard. Boy was that shiny! In 1995, we already had the “Metaverse”, we just called it VR. SGI was one of my hero companies at the time (because, 3D-rendered dinosaurs and stuff), so I wanted to ask for a potential internship. I approached a random SGI employee, and he said the polite equivalent of “go away, I have more important people to talk to”. I guess he was prospecting or something. That turned me down a bit. Then there was this other booth showing a completely different kind of demo: A crazy web browser plugin that allowed you to run actual code within the browser! Independently of what CPU or OS that browser was running on! Shiny! Cute animated mascots waving at you from the browser included. The people there were very enthusiastic and, more importantly: They were approachable. I had great conversations and, you might have guessed it, this was when Java was introduced to the world. That episode might have steered my decision a bit more away from SGI and a bit closer to Sun, who knows? But in the end it’s always your decision which opportunity to take and why.
• Given it’s your decision which opportunity to take, the next question is: How do you decide? You could “follow your passion”, or “ask your gut” or come up with a pro and a con list and decide more rationally (famously invented by Benjamin Franklin), or whatever. I personally found that following your instincts somehow works very well. Your subconscious mind has a way of collecting a lot of data over time, then let it settle down into your gut, so it can give you quite good advice. It’s the sum of your ambitions, fears, experiences made, opportunities missed, passions, desires, painful lessons learned and what not. Even at a young age, it has a way of pretty accurately telling you where to go next. Derek Sivers famously summed it up as: Hell yeah or no.
• Missed opportunities are ok to miss. There really is no such thing as FOMO: For every opportunity that you might not have taken, many others might develop over time. You just have to wait, and keep your eyes open. History is full of great opportunities that you might have been part of, but weren’t. And that’s ok. The future will hold at least as many, if not, more opportunities for you to explore. Just keep your eyes open, and wait for that “hell yeah!” moment.

Gaming your luck at the Pachinko table

Coming back to the original question, which was: “How do you find great opportunities”, it turns out that while there’s a lot of luck involved, there are two things you can do to increase your odds at life’s Pachinko table:

1. Keep your options open. By this, I mean room to breathe, headroom to act, resources to invest, or any other thing that allows you to actually seize that opportunity once it presents itself. How are you going to invest in some fantastic investment opportunity if you don’t have any spare cash? How can you take on that career-defining project if you’re currently 100% committed to other less cool, but somehow necessary, tasks? How will you learn that new and exciting skill, technology or hobby, if you can’t come up with the necessary time? Keep an “opportunity buffer” in terms of time, money, resources, etc. that allows you to follow up on that “hell yeah!” opportunity when it comes along. An opportunity buffer also gives you opportunity (sic) to try out random stuff, look around, and actually spot those opportunities, that otherwise might have escaped your attention.
2. Increase your area of exposure. Quite literally, the bigger your exposure to the world (in terms of people met, conferences visited, conversations engaged, things tried out, books, blogs and webcasts consumed), the higher the probability that something you exposed yourself to turns out to be a great opportunity for your career or your life. If you’re the (now autonomous and path-choosing) Pachinko ball, then you want to maximize the amount of potential nails you can hit within your path until you have found that perfect opportunity to turn left or right and enjoy your own “opportunity of a lifetime”. There are many ways to expose yourself: Try out new hobbies, technologies, activities, etc. Visit conferences, meetups or discussion forums. Write blog posts, publish books, host a podcast or give a talk. Meet new people, move to a new town, change to a new team, department, or company. Start a new project. And much more.

When you keep your options open and increase your area of exposure, then new opportunities will find you.

Turning your life into a game of Pinball

So by keeping your eyes open on the many opportunities that might open up for you, a bit of reserve so you can choose to pick the ones you want, and having some strategy about which opportunities to choose, and which to let go, you can go out and maximize your exposure to opportunity, until the right “hell yeah!” one comes along. And the next one. And the next.

Even if life seems random, even unfair, like the path of a ball in a game of Pachinko, you can nudge it here and there, and encourage some more serendipity, to help luck find you. Now the game you play resembles more a game of Pinball: Still, there’s lots of randomness and luck involved, but your chances to hit that multiball jackpot are much bigger now.

I fully agree with decade-old advice by Tim Bray on tough times: branch out, contribute, network. As the world is shaken by multiple disasters at once, it becomes more important to keep your reserves available, your area of exposure to opportunities wide, and to watch out with open eyes for your next “hell yeah!” moment.

That’s it. And now, the next time someone comes into my office hours and asks me about opportunities, I have an article to point to!

What were your favorite moments of Pachinko? What ways did you discover to find your own opportunities for career, life, or else? How did you turn your career or life into a game of Pinball?