The Real Truth about Facing Risk

On avoiding, mitigating, and learning to embrace risk

Leaving Comfort for Growth

I didn’t realize how unhappy I was with my first full-time job for a while. I left campus bright-eyed, optimistic, and naive. I was a PM at Microsoft, a cushy big tech job. I still felt grateful given my own struggle during college. I knew this was just the beginning, and I wanted to make my mark.

For the first few months, I was happy to be learning and absorbing all the hard skills around product management. I didn’t mind the 1 hr+ commute each way on Caltrain. I felt privileged to be at a company like Microsoft. I was hungry to grow and better myself. And I had a great manager who believed in me. I even earned a quick promotion with their support.

Yet I could sense something was wrong, beyond the typical post-college disillusionment transition. I wanted to do product to solve real problems with software. I wanted to collaborate with teams in a dynamic environment. I wanted to learn more about innovation, the design process, and how great teams build great products. The reality was I wasn’t getting this experience. I never worked with a designer. I was on a late stage API product, with a yearly release cadence (!) Eng leadership in our org largely set the priorities, with a CVP in Redmond chiming in now and then.

I decided to pay attention to my gut. Though I was learning things about building software, I wasn’t growing in the way I wanted to. I couldn’t shake the feeling—I needed to get back on the right path. So shortly after I got my first promotion, I left Microsoft.

I did everything you’re not supposed to do when navigating a career switch. I didn’t get multiple offers for leverage, I didn’t weigh my financial opportunity cost, I didn’t think about how to brand myself. I was just in a hurry to get out.

I listened to my gut. I knew I cared the most about my growth. And I believed the best way I’d grow was if I followed my curiosity about technology. So I ended up as a PM at Vevo, the music video company. I’d always loved music, and though it’d be interesting to explore how software could help musicians connect with fans and express their artistic creativity. I liked that all the people at Vevo were passionate about this mission too. In retrospect, this should have felt like a risky decision. One that needed careful deliberation, given how it’d shape my life path. But in the moment, it didn’t feel that risky. And I’ve often wondered why.

Quitting my first full-time job wasn’t the only hard decision I’ve made that felt intuitive to navigate. There’s been many more. Being a PM for 10 years and working closely with founders has made me reflect on how I face risk and get comfortable with it. But in the last year or so, I’ve spent more time unpacking what goes into the decision-making instinct and how to strengthen the muscle. It boils down to 3 questions and 1 truth that I internalize whenever I’m facing a “risky” decision.

My Risk Framework

Whenever I face a decision that feels high stakes, I ask myself these 3 questions:

1. What’s the worst thing that can happen?

2. How likely is it to happen?

3. If that happens, what can I do about it?

Let’s break down why each matters.

Question #1: Worst case: we often worry about what can go wrong. We let our minds escape into imagining how bad things can get if we mess up the decision. And this only heightens our anxiety around getting the decision right.

If you (or someone you love) dying is the worst objective thing that can happen… well, it turns out, most decisions we make are not life or death. Answering literally “what happens if I mess this up” will make you realize the stakes are not that high. And there is power in convincing yourself most decisions you make don’t really matter.

Question #2: Likelihood: okay, let’s say something bad may happen. And this decision does matter. The next thing to examine is: will it really happen? I once heard “worrying means you suffer twice”. The monkey brain in all of us can’t be present, because we’re worrying about things that may happen in the future. In the process, we suffer more than we need to. Ask yourself objectively if there is a high likelihood of the bad thing happening. More often than not, the odds are not that high.

Question #3: Mitigation: if both the outcome is bad and the likelihood of it happening is high, then I start thinking…I should probably do something about it. Can I avoid it altogether? Can I be better prepared to react to it? Are there things that I can control to minimize the negative outcome? This thought process starts making me feel more comfortable about the risk I’m taking on by examining the agency I still have.

It’s not that you need to ask these questions in exact order or even think through them consciously. But it is important to control the mind when facing risk. I’ve learned that so much of the anxiety we feel when making tough decisions comes from the discomfort we feel about future uncertainty. But these questions orient around focusing on what you can control. And that tricks the mind into feeling more at ease with uncertainty.

Accepting & Reframing Risk’s True Nature

So let’s go back to when I decided to leave Microsoft. I didn’t have the formal 3 question framework at the time. I was 22 years old. But my instinct was roughly telling me to quit Microsoft & join Vevo:

1. Worst thing that could happen? I hate the job at Vevo and I have to find another one a few months later. Is it really that bad? I know I’m already unhappy with my current job.

2. Likelihood of that happening? I’d be building software for musicians and music fans. I’d be thinking about music videos and streaming. I’d be collaborating with a design team and learning a new way of building. I don’t know, sounds pretty fun. Not sure how I’d hate it.

3. What could I do if that happens? If I really did end up hating the job, I could still interview and find something else. There’s always options.

Sweet, risk avoided! Ehhh…except that’s not how life works.

The reality was my ride at Vevo ended with another worst case scenario I didn’t anticipate. The entire tech org imploded a year after I joined. I jumped ship and narrowly avoided sweeping layoffs. I failed to identify a bigger worst case than hating a job: that the business itself might shut down and I’d be forced out of a job.

Now did I make the wrong decision at a critical moment in my life? Maybe there’s one narrative that would say yes. But I reject that narrative and embrace another one. I celebrate the experience and find reasons to be grateful for its role in my journey so far. This is because I’ve internalized something else: the hard truth about risk is that it’s unavoidable.

We can do mental gymnastics to identify it, quantify it, mitigate it…but the risk always exists. Every decision we make can be risk-minimized, but never risk-free. This is because we can only control our decisions, not the outcomes.

I’m reminded of this truth over and over again. As much as I use my 3 question framework to better face risk, this truth is what comforts me the most. After I’ve exhausted what I can in action, the rest of what I can control is in my head.

We obsess over trying to get major life decisions right. But the unintuitive reality of these decisions is that there is no right or wrong. There is only the decision you make, and the reality that unfolds accordingly. How you choose to write the narrative about what happened, even in scenarios where something bad happened, is the only reality that matters. These decisions may be uncertain, but they are never final. They lead us to new chapters, new risks, and new truths. In embracing this, I’ve learned that it isn’t about avoiding risk but about writing the narrative that makes the risk worth taking.