Serendipity in Career Planning

At the end of each How I Built This podcast episode, Guy Raz asks his guests, all of whom are entrepreneurs talking about their path to success, a simple question: “How much of your success do you think is due to skill and hard work versus luck?” In nearly all of the episodes I’ve listened to, guests, who range from people like AirBNB’s Joe Gebbia to Patagonia’s Yvon Chouinard, claim that a high percentage of their success is due to serendipity. I’ve noticed this in my career as well. Some of my best career moves were to jobs that just happened to come along at the right time and place.

But, are there things that you can do to increase the chances that serendipity will strike? I say yes! Luck really does favor the prepared. Even if you don’t know what you’re preparing for, there are things you can do to intentionally set yourself up for success when serendipity strikes.

Serendipity & Place

When Apple built its new headquarters in 2017, Steve Jobs had a unique goal in mind: create a building that fosters innovation and allows for serendipity. Meeting spaces that force people from different backgrounds to interact, he believed, would increase the chances that new ideas would develop via chance conversations.

Innovation doesn’t typically erupt from a vacuum. In many cases, people are working on unrelated problems, only to have a chance conversation with a colleague or friend that shows them how their work can be a solution to a different problem. Post-it note glue famously came about because Dr. Silver was trying to create an incredibly strong glue, and ended up with a weak one instead.

Mixing ideas from different industries is an important part of innovation and serendipity. The best way to do this is to regularly have conversations with new and different people. I love going to new networking events or conferences as I always meet interesting people. Some of these conversations have led to me using new processes, finding jobs, and even writing new chapters in my book. One way to prepare for serendipity is to find ways to bump into new people.

Be Prepared in General

I didn’t know that working hard as an engineer would lead to me spending two months living in Tanzania and working with the African Wildlife Foundation. When I was a few years into my career at IBM, they started a new program called the Corporate Service Corps (CSC). Modeled after the Peace Corps, IBM sent teams of its employees to emerging countries who needed our technical and business skills. It was very tough to get into the program. The first year they did it, 2008, 5,000 applicants applied and 110 were accepted into the program. It was harder to get into the Corporate Service Corps than Harvard. I was lucky enough to be chosen to go to Tanzania that year.

Had I also gone to Harvard? Was I a genius with tons of money and connections? Nope! I was a 25-year-old barely starting my career after a successful stint at the University of Wisconsin-Madison. I simply worked hard at whatever I set my mind to. The year before I was accepted into the Corporate Service Corps, I got a very high rating on my performance review at IBM. My secret was focusing on tasks that were of high value to my team and the company. Do performance review ratings really matter? I don’t think so, I’d rather be judged on how well I improve the world around me. But being successful can and does open doors. You may not know where you’re going next. You may not know what opportunities will open up, but being prepared by having a good track record never hurts.

Do What Sounds Fun

I’ve never had a grand career plan for myself. I wish I could say that I’ve been very intentional every step of the way. Instead, I typically take on activities that sound fun to me and give me a sense of purpose. For example, I took on a leadership role in IBM’s New Hire Connect group. We were basically the party-planning committee for all of IBM’s new employees in Rochester, MN. I certainly didn’t take on that role expecting it to help my career, but that leadership position helped me get chosen for the Corporate Service Corps in Tanzania. Tanzania led me to realize how important it was for me to work in the environmental space. I eventually took a job at National Geographic.

I also double-majored in Spanish (as well as Computer Science) in college. This wasn’t a career move, I just thought it would be cool to be fluent in a second language. So, I spent a semester abroad in Seville, Spain, traveling and learning Spanish. That experience, too, helped me get accepted into the CSC and that eventually changed the course of my entire career.

I can’t help but feel that some opportunities are custom-made for you. They require experience from a wide variety of fields and you just happen to have those experiences because you’ve been doing a variety of things you love for years. You couldn’t have planned it better if you tried. But you kind of did try! Just being uniquely you and following what excites you can and will lead to opportunities. So, keep doing those things that light you up.

When You Feel Stuck

Sometimes we all feel stuck. You’re dragging at work. You’re not challenged and you’re not learning. This is the time to intentionally do something that excites you. Go to a new event. Try a new gym. Pick-up a new hobby. Go volunteer. Maybe even take a career break and do something you’ve always wanted to do. Your actions may not directly lead to getting you unstuck, but the new experiences can at least take your mind off of the drudgery. If you do enough new things, they will lead to what’s next – even if it’s in a round-about way.

Embrace the Pivot

It’s good to have goals and plans to reach those goals, but don’t be so focused on them that you miss opportunities right in front of you. There have been a few times in my life where I’ve heard about opportunities (i.e. jobs) and I immediately notice that I feel really excited about them. When that happens to you, go do that thing.

A few years ago I got that feeling about an alumni happy hour at UW-Madison for the school of Computer Science. I had just moved back to Madison and wanted to reconnect with UW anyway, so I made the space in my calendar and went. That night, I ended up speaking with our new Computer Science Chairperson, Remzi Arpaci-Dusseau, asking him about what they’re doing to teach students about agile software development. That kicked off a series of conversations that led to me teaching the Computer Science Capstone course at UW-Madison, a side-job that I find incredibly fulfilling and worthwhile.

It’s incredible what will happen to you if you take the time to meet new people and have broad experiences! And it’s not just me experiencing this phenomenon. A few of my friends / colleagues and I have often talked about the role that serendipity plays in career planning. We even applied to give at talk at Grace Hopper one year about this subject. Maybe it’s time to pull that talk together again?

Is it time for you to go try something new?