Well, I did it.

A mere few days after my last post, I started on an exploration for new job opportunities. In that post, I didn’t shy away with the stress I felt working at a high-risk, sales-driven company, and I felt that I could only reasonably sustain that for so long. The same mentor about whom I wrote pointed me in the direction of a very cool tech company and I felt so drawn to it that I followed up immediately.

At the time, Bloomberg Sports was going through a transaction, which culminated in the purchase of the company. If there was ever a responsible time to leave a senior leadership position, doing so with some acquisition activity sure was it. I’m glad that I stuck around for that process; I learned a lot, and it quieted my concerns about leaving the engineering staff in a critical, vulnerable position. By waiting around until the deal closed, I felt more assured that, if they wanted to stick around, the team had a foundation on which to stand.

During the acquisition’s due diligence process, however, I was conducting some due diligence of my own; I was going through the oft-frustrating interviewing experience. I was being very intentional with where I wanted to work, so I had a (very) short list of companies whom I would engage. (I do not take for granted how fortunate I am to be in the tech industry, where there is a catastrophic lack of supply. With such high demand, I had the luxury of being a little pickier, and I know not everyone is so fortunate.) In a very short amount of time, I knew where I wanted to go.

Palantir is a mission-focused company bent on solving hard problems for some of the world’s most important organizations. (Excuse me while I wipe the Kool-aid from my lips.) But, seriously, we are. We want to protect consumers from fraud, to help law enforcement crack down on crime, and to help respond to natural disasters. And so much more. Engineering is core to how business is done. Everything about this company resonates with me. I wanted in and, as it turned out, Palantir wanted me in, too.

Some can argue that this was not a risky move at all; I was looking for a new job while still employed and I tendered my resignation after all of the necessary paperwork was done. From that perspective, I’d agree. But switching to a new job was a pretty scary thing for me, despite the full amount of support that I received from Palantir. Here’s why:

• I had an established network. I knew a lot of people (and who to call when I needed something), and people knew who I was.
• I had known expectations. I knew what people expected of me and what I needed to do to do a great job. My role was pretty well defined and I knew how all of the staff fit in the picture.
• I had subject matter expertise. I knew the system, and how things worked. I could solve problems and fight fires.

Moving to a new job changed all of those things; I was starting over and I moved from a place of familiarity to a place full of unknowns. Of course, most people who make that sort of change goes through the same thing, but this was the first time I ever quit a job, so it was all brand new to me. In time, however, I certainly expect that all of the things that I “lost” to be found at Palantir.

While this was a very big move, I am not defined by my job. As I look back on what has transpired over the past year, there are other great things to briefly note (owing mostly to the length of this post already):

• I joined the Forefront Leadership Team. This is a group of volunteers who are immersed in the community, charged with providing support and guidance for the church.
• I am connecting with Generation Harvest, a fantastic organization that solves two problems at once in New York: preventing food waste and hunger. I am hoping to get more involved with this group next year since food and service are near and dear to my heart.
• I traveled a lot! With work, I had the privilege of traveling to Japan (twice!), and I took a fairly epic cycling trip to Italy and France with friends from university.

So, clearly, 2014 has been a pretty big year for me. I’m so grateful for my family and friends, all of whom have been so supportive and encouraging in my life. As the last days of the year wind down, I find myself thinking of how, next year, I can do a better job providing support and encouragement to all of those around me; I’ve spent a good chunk of time/energy on me this year, setting myself up to focus elsewhere next year. I hope we all have fantastic 2015s together!

A good friend of mine – someone who has worked with me, served as a mentor, and shaped my career- recently commented that I am afraid to take chances. In my head, I thought that it was precisely because I took chances that I allowed him to influence me the way he had; I accepted new roles and grew into management by saying yes to the challenges he laid out for me.

I responded to this friend by saying that I take chances when the circumstances are suitable for them. One has to question, however, how much of a chance something is when I’m waiting until a situation favours its outcome. (Mathematically, I am still exposing myself to risk if the outcome is not assured. Realistically, I am being fairly conservative.)

When I think about why I behave like this, the temptation is to trace it back to how I was raised. I grew up in a home where both parents were not particularly adventurous; it felt like both of them were highly methodological and intentional with what they did. While in some ways, I had great freedom as a kid (e.g. no formal curfew, limited spending limits), the big decisions were often not mine. I didn’t have much of a say when I was enrolled into Boy Scouts, nor in piano lessons, nor to the high school I attended. In some ways, then, I felt like I was deprived of some of the big opportunities to forge my own path and open myself up to failure.

Perhaps that was done for my “own good” and out of love. (I’d certainly like to believe it was.) But being able to experience, handle, and grow from failure is an essential part of life. At work, despite prevailing pressure to expand quickly and capture as much revenue as possible, I maintain that growth has to be organic and that risk has to be contained. In a business context, there’s the adage to innovate when the cost of failure is low. Not everyone sees it that way and I often get really stressed out because, at the end of the day, it’s often up to the engineers to make good on new business deals. Unless the engineering staff is scaled appropriately to the work, there is a real concern that we’ll fail our existing obligations. But maybe some failure at work is a good thing, too. I can’t always protect people against themselves, so allowing them to experience the consequences for which I think they are singing up may encourage them to reevaluate their perspective. (Does this make me a bad team player?)

The personal trainer I occasionally see often reminds me that he wants me to fail; if I always finished the prescribed number of sets and reps, it meant that I didn’t push myself hard enough (which then reduces growth potential). This all makes physiological sense but it’s still hard for me to come to grips with it. When I don’t hit the numbers, I don’t get 100%, and I feel bad about it. Maybe it’s because I was born to two somewhat stereotypical Asian parents who indoctrinated a higher-than-usual value in marks and success that pervaded the rest of my life.

Recently, I have found myself consciously letting go of some of the control I exercise over my personal life. (That means I’m still in control, right?) Inspired by a friend of mine who embarked on a “Year of Risk” last year (which saw her move from Australia to New York with her husband, get a pixie cut, throw down in rap-offs, engage more strangers, and the like), I have started to open myself up more to both uncertainty and failure. At the heart of it, I realized (again) that life on earth is finite and, by limiting myself to what I know and to what I can control, I run the real risk of missing out on joy. Debbie Millman writes: “If you take away uncertainty, you take away motivation. Wanting to exceed your grasp is the nature of the human condition. There’s no magic to getting what we already know we can get.” How great is that?

2014 is nearly half over, and this is the first post in well over half a year. But it is my hope that this is the first post of many more where I can share about how I’m continuing to grow, failure be damned.

Compromise with people, not on them.