5 steps to a resilient career path from engineering leader Ron Pragides

The term Black Swan was made famous by Nassim Nicholas Taleb in his book of the same name, which he describes as an event that has three attributes: (1) it is an outlier, outside the realm of regular expectations; (2) it carries an extreme impact; and (3) in spite of being at outlier, we devise an explanation for its occurrence after the fact.

The COVID-19 pandemic certainly qualifies as a Black Swan event, and 2020 demonstrated the need for resilience: we’ve all had to withstand and recover from a lot this year. With 2020 coming to a close, I want to share my thoughts on resilient career paths for engineers in my role as Executive-in-Residence at Terminal.

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My resilient career path journey

I’ve experienced three Black Swan events during my career: the 2001 Dot-Com Bubble (boom & bust), the 2008 Great Recession (the financial housing crisis), and the 2020 COVID pandemic. You never know when a Black Swan event will occur. You may encounter several Black Swans throughout your career, so it’s important to be resilient when they happen.

I’ve been in engineering individual contributor (IC) positions and engineering management roles. My career journey was not a direct, binary path to management. Between 2000 and 2004, I straddled the line between engineering IC and first-level engineering manager. Without knowing the differences between those roles, I had to try them out for myself. I had to get comfortable with my own choice in terms of what I wanted to do, where I got my energy, and what I wanted my career to be.

It’s important for engineers not to conflate career progression with becoming an engineering manager. The best companies provide parallel tracks for engineers to contribute to their team and to grow their careers. Engineers start their career on the ground floor and eventually face a choice: to progress as a technical lead, or take the path of leading as a manager. After seeing both sides, I eventually chose to focus on engineering management. Even though this was my path, it’s not the destiny of every engineer to become a manager. It’s up to each individual to plot their own career journey.

I’ve had the opportunity to work across different teams, different companies, and different business verticals. My former colleague Amit Kulkarni (CEO, Heymarket) suggests that we can think of our careers in terms of epochs. I’ve mapped my own career to four distinct epochs: 

• 1992–1998: Large Public Companies
• 1998–2004: Startups & Dot-Com Bubble
• 2004–2014: Scale-Ups & New Business Models
• 2014–2020: Platforms & Network Effects

I’ve had the privilege of joining amazing companies, some of which have grown to become iconic businesses. I’m proud of all the organizations that I’ve had the chance to help build.

Each person’s career is a combination of teams and roles, woven together into a unique tapestry of industry experience. No matter what happens, be prepared for Black Swan events that might come. And remember to be resilient in how you think of opportunities for yourself.

How to develop your own resilient career path

There are five principles that I believe will help anyone develop a resilient career:

Be a lifelong learner. Whenever a subject intrigues me, I try to learn more about it. We now have multiple ways to learn about any topic: tech-talks, meetups, conferences, news & social media, massive open online courses (MOOCs like Coursera, Udemy, etc), books, podcasts. It’s amazing to live in a time when we have Internet-connected supercomputers in our pockets. Go ahead and read some (or all) of the books that Marc Andreessen recommends. If there’s anything that you’re curious about, go learn more about it! There are few barriers to acquiring knowledge, and there’s also no penalty for stopping once you feel like you’ve had your fill.

Stop and look around. One of my favorite film characters is Ferris Bueller, famous for his mantra, “Life moves pretty fast. If you don’t stop and take a look around once in a while, you could miss it.”  I’m going to embrace and adapt that: Industry trends can move pretty fast. If you don’t stop and look around once in a while, you could miss the next one. Try to be aware of industry and technology trends as they are happening. Shifts in trends that are apparent now, in hindsight: (1) the transition from mainframes to PCs (mid-1970s to the early-1980s); (2) the emergence of the Internet for commerce & business software; (3) the ubiquity of mobile phones and their evolution into handheld Internet devices. Changing trends sneak up on you. So every once in a while, pause and reflect on what you’re seeing. Being observant can inform where you direct your career and how you focus your time.

Know where you get energy. I like to use the Japanese concept of Ikigai to guide career decisions. Ikagai means “reason for being,” and it can be found at the intersection of What The World Needs + What You Can Be Paid For + What You Are Good At + What You Love.  If you can find your Ikigai, you’ll be fulfilled, you’ll be fully engaged, you’ll be directing efforts to a worthwhile endeavor — and it won’t feel like a job, because you’ll love doing it! This is a powerful way to think about how a vocation, a mission, a profession, and a passion can all line up.

Decide for yourself. My parents immigrated to Chicago’s suburbs from the Philippines, and they would have loved for me to become a doctor. But I just couldn’t do it. I was not interested in the medical profession. I wanted to do something in the engineering realm. I knew that would bring me joy and satisfaction, and I had to make that choice for myself. There are people in your life that influence you: your parents, your spouse, your kids, and your friends. But it’s important to ultimately make the right decisions for you. Because whatever you choose, you have to live with the consequences. 

Live courageously. Trust your instinct. Trust in yourself. Trust in the ways you’ve thought about your decisions. Remember that you’re the one who is in control, and you’re the one who can put things into motion. Don’t wait for life to happen to you. Actualize your decisions.

A Black Swan will come again

2020 was a year that disrupted our career paths and made a lot of us ask ourselves where to go next. Black Swan events don’t have to define your career. No matter what path most speaks to you, you can take steps to make your own resilient career path and set yourself up for success when the next Black Swan event happens. 

Farewell to 2020: a year that tested our resilience.