The career "what if...?"
Issue 56: The decisions that impact our career are often small with big implications
“Time. Space. Reality. It’s more than a linear path. It’s a prism of endless possibility where a single choice can branch out into infinite realities, creating alternate worlds from the one you know. I am The Watcher. I am your guide through these vast new realities. Follow me and ponder the question: What if?”
These words introduce every episode of the new Marvel show “What If…?” streaming on Disney+. The show is based on a comic book series running from 1977 up until 20181. The premise starts with Uatu, an alien known as The Watcher, who overlooks earth and its alternate realities. Each story starts with the mainstream reality and goes into the divergent point, a decision or moment that changes everything in time and reality. An example is “What if Spider-Man Joined The Fantastic Four?” which stars the web crawler as the fifth member of Marvel’s iconic family.
We won’t focus on comic book nostalgia, instead reflect on those two powerful words: “what if?” It can be used to look forward and backwards. The phrase is a powerful provocation for exploring wildly new ideas, challenging people to wonder “what if we could do this?” That’s looking forward. The phrase can also be used to look back, as a way to ponder. What if I married someone else? What did I miss by not moving to my dream city earlier? What if I decided not to watch Ted Lasso like the rest of the world?
Like in the aforementioned comic book series, there are so many divergent points in our lives that can dramatically shift your trajectory; maybe that of the world. I’ll sharea “what if?” moment I remember in a Seattle parking lot nearly 20 years ago. I was sitting in my Nissan Xterra after work talking to my brother Daniel on my iPhone 3GS. He had an ungodly commute from Sacramento to Oakland at the time, which allowed a lot of time for us to kill time. I’ve spent the last two years working and creating art to apply for graduate school. At the time, my aspiration was to earn my MFA so I could teach at the university level. After talking with many programs such as the University of Notre Dame and a few upstate New York institutions, I was accepted to California College of the Arts (CCA) in San Francisco, CA. I achieved my goal, and it was the dream to live in San Francisco. The problem was I I did not receive any scholarships and little financial aid so tuition would be a lot of money. I could have made it work, but personally did not want to accrue a bunch of student loan debt. After many conversations with Daniel, I declined the offer to CCA. I was devastated. I worked so hard to build to this moment. How could I say “no” to this? Am I going to regret this years later?
Months later, I started getting connected with other opportunities and started freelancing as a user interface designer for an emerging platform called iOS. My skills from art school really transferred over because many developers were looking for someone who knew Photoshop well to create naturalistic assets to help people understand how to interact with this glass phone with a 480-by-320 pixel screen. I was really good at making realistic leather buttons so I was in. Flash forward a 10 years later, my career shifted into software design and had the opportunity to grow along with the iOS platform. I also ended up living in San Francisco when I moved to work at One Medical. It turned out not going to grad school was the best decisions I ever made.
I’ve been thinking of careers more as an odyssey instead of ladders and linear paths. To be abundantly clear, the role of career ladders serve important purposes, such as clarity on compensation bands and expectations, and it’s a crucial tool to have. Career odysseys go beyond the ladder, and the current role you’re at. One time at a Blue Bottle Coffee on Samsone in San Francisco, I met up with a designer to have a 1:1 conversation. That coffee shop along with Philz Coffee on Front St. are two of the most popular places in San Francisco where people meet and discuss job opportunities (every hiring manager knows this). This designer told me her career challenges she was facing at work. As I sat there listening and enjoying my Cortado, I asked her in the end, “Let me ask you this. Are you even sure you want to be a designer in the long run?”
“You know…I really don’t,” she responded with laughter. What gave her purpose and joy was collaborating with humans on a shared goal to make business impact. Years later, she’s now a product manager.
Pathways in careers have many divergent points. Prior to joining Webflow, I considered many different paths: being a founder of my own startup, shifting into venture capital, or becoming a Head of Product—shifting out of design completely. I mapped my career odyssey.
This visual could have included so many other nodes and divergent subsets. One common trend I realized is a lot of these decisions that propelled me into this path were not large decisions, rather a series of small decisions that led to a different path. It’s wild to think about the impact of these decisions looking back at it many years later. There is this Japanese saying, ichi-go ichi-e, which translate to “one time, one meeting.” Celinne Da Costa shared a interpretation by her friend Miyako:
Ichi-go ichi-e speaks to the idea that no one encounter can ever be recreated: each moment and each convergence of time, space, light, mood, thought, and circumstance is singular and unrepeatable. As such, every encounter should be met with one’s full, attuned senses. Some encounters plant seeds that take root over time, while others change the course of one’s life in a single moment.
One encounter. One opportunity. Every decision has its unique place in time. At the decision point of every “what if?” moment, you’ll have to make a decision that could dramatically alter your future. Annie Duke, author of Thinking in Bets, has a method called 10-10-10. It makes you reflect on the consequences of a decision in 10 minutes, 10 months, and 10 years. Like when I rejected the opportunity to go to grad school, what is important to you 10 minutes in front of you feels much different than 10 years.
The possibilities are infinite. What you think will propel you into your long-term career goals might not be what you expect. You may be facing a decision on taking a job offer or pondering a career pivot. I personally try not to think too much of all the divergent paths with any regret, instead for learning. Each decision you make will forge you into a path with no return. Give yourself a moment to reflect on the 10-10-10, and remember to ponder the questions…what if?
Someone made small paintings based on their zoom class—so cool!
Headspace is hiring a product designer for design systems
The series could still be running; not 100% sure
I know the Head of Design and CPO. They are both the best people I’ve had the chance to work with; highly recommend