Change of Plans

Some thoughts on navigating extreme uncertainty, and a little career update.

The Remarkables Mountain Range, New Zealand

We had big plans, and in February, we set them into motion. I accepted my offer to London Business School and informed my manager and my team that I would be leaving Workday to pursue my MBA. My wife began searching for UK-based roles, and we bought our one-way flights from Seattle.

By August, everything had changed. The pandemic began and worsened. Right in the middle of it, we were thrilled to learn we are expecting our first baby. After months of deliberating and monitoring the fast-changing conditions, and evaluating how starting a family could fit into our plans, we finally decided to postpone our UK move, and instead relocated to southern California to be closer to family. I deferred my MBA and co-founded a startup.

We are lucky to be healthy with good choices available in the midst of the pandemic and an uncertain economy — but I definitely earned some new gray hairs over the past six months juggling major life decisions.

So I thought I would share a few things we learned about navigating our extreme uncertainty, and preview what I’m working on next.

But first, a quick story.

In 2008, I went heli-biking near Queenstown, New Zealand. The helicopter deposited our group high on a cold mountaintop where we would begin our descent along steep cliffs and hillsides down the through the sheep stations and back to town. We started in a rock field covered in a layer of snow — very difficult conditions for riding. To get through it, our leader instructed us to stand on the pedals out of our seats and loosely grip the handlebars.

Now, with your eyes glued to the horizon, begin pedaling at a steady pace and just let your bicycle move around beneath you, like it’s dancing.

It was a funny feeling. The bike slid in the snow and bounced over rocks, but when I kept looking ahead focused on my balance, letting the bike lurch and sway, I stayed upright and pedaled through.

Trying to plan an international move for graduate school during the pandemic was like riding a mountain bike through the snow. When we rigidly clung to our plans as conditions dramatically transformed, we fell down. When we recognized what was changing and considered how to adapt, we could think creatively and move forward, eyes ahead.

The hard part is identifying the horizon you stay glued to, versus the plans that dance beneath you — realizing what is most important, and what can flex.

My top priority seemed like it was moving to London to get an MBA, but really that was a means to an end: transitioning from corporate management to entrepreneurship. The first line in my grad school application essay reads, “I want to start a software company.”

But there were many secondary goals that seemed just as important. I wanted to return to the classroom and be a student again. I wanted to earn a graduate degree. My wife and I wanted to experience living internationally in London. We wanted to travel through Europe on the weekends, and meet lots of new people.

It took me a long time to recognize that even though studying and traveling internationally would be historically difficult in 2020, my primary goal of starting a software company was still viable. In fact, this could actually be a better time to do it.

Recognizing the difference between my true objective and my plan to get there helped me see possibility, even while it felt like everything was crashing down. It’s hard to reset after so much effort and preparation. But once I accepted what had changed, I became excited about what could happen next.

Back in June, after we finished packing up our house, and after we watched the sun set over the Olympics one more time from Sunset Hill Park, my wife and I got in the car, played “Into the Unknown” from Frozen 2, and sang along as we drove away, ready for our adventure overseas.

Little did we know that, if London was the unknown, then we were headed into the unknown unknown! In the next few weeks, from the sleeper sofa in my wife’s family’s house in Orange County, we would rethink everything we had planned for so long and start from scratch. Instead of living out what would essentially be the epic international finale of our late 20s / early 30s lifestyle, we are turning the page and accelerating our dream to start a family and my ambition to start a company.

Sometimes incremental plays make sense — methodically prepare and advance your readiness, increase the odds of success. And sometimes you should jump into the unknown unknown — trust your instincts, seize the opportunity, and go for it. But when should you take an incremental step versus jump?

My favorite thing I’ve seen on this issue is the regret minimization framework from Jeff Bezos. He says to imagine yourself at 80 years old, looking back on your life with as few regrets as possible. From this perspective, you can see beyond the short-term noise and better grasp what really matters. Choose the path you will least regret at the end of your life. From our recent experience, I think it also comes down to gut feel and summoning your courage.

A few other thoughts on navigating the past six months:

The best of times, the worst of times. This is an incredibly difficult year for many people in our family, our friends, and the world. We were sad to change plans, but we recognize we are fundamentally choosing between good things. We’ve tried to keep perspective — support people who need help, and store strength from the happiness.

Design for the present, nothing is permanent. This year, we are expecting a baby, and there’s a global pandemic. Right now, it just makes sense for us to be on the same continent as our family. And as for grad school, we were already planning for change — so I’ll go to the School of Hard Knocks instead.

We’re in this together. My wife and I make all of our important decisions together. I believe that pursuing self-actualization is in fact a community effort; my family shares the risks I take, and the resultant failures and successes. I am lucky to have a brilliant wife who supports and encourages me. As we leap into the unknown unknown, we have each other.

Mechanical time, body time. From Alan Lightman’s wonderful book, Einstein’s Dreams, sometimes we are on mechanical time, when we closely follow our routines and arrive precisely on schedule. And sometimes we are on body time, when we listen to our heartbeats and follow the rhythms of our desires wherever they may lead. 2020 is sort of a body time year, and I was lucky to be reminded of that by good friends this summer.

I left Workday and co-founded a startup. I believe that Workday is a great company filled with good people working hard and kicking ass. I am rooting for them!

I am also cheering for my fellow admits who did decide to begin their degree at London Business School this fall. This is arguably the hardest time in 75 years to move internationally for graduate school. Good luck, and I hope we get the chance to meet someday!

We are incredibly excited to be building a product that we believe will make the world a little better. I hope I can bring what I have learned from a decade in HR to drive needed change in an important area of everyone’s working life. We are busy building and will share more soon!

For everyone whose plans changed this year, keep your eyes on the horizon and let the bicycle dance beneath you.

Co-founder & CEO, Compa | ex-Workday, Juniper, Mercer