Success & Failures

Embracing the unknown

I kept saying, "Yes," to things or to experimenting. And slowly but surely, things came together.

When I was younger, I broke my ankle in multiple places, and I could no longer dance. Dance had been my plan. After my plan fell apart, I asked myself, “What am I going to do?” And I decided to not make a plan. Either I was too afraid to make a new plan for fear it would fall apart or that I would fail.

Things kept coming together, though. I kept saying “yes” to things or to experimenting. And slowly but surely, things came together. Seeing that pattern helped me realize that I don’t have to have it all figured out.

“There have been times when I wish I would have done things differently.

For example, I didn’t know what product management was when I was younger, so I could have never planned to be a product manager. I had no idea I would ever live in San Francisco. And back when I first visited, I didn’t like it at all. But I kept an open mind, and I love San Francisco now.


There have been times when I wish I would have done something differently or something didn’t work and I had to pivot. But I try not to think about those moments as failures necessarily.

For example, in one job, I was so invested in the company that I felt like I had lost my own identity. Yet I was holding on so hard that it ended up being really hurtful and harmful to me and my development. As I look back now, parting ways with that company was actually the best thing I could have done for myself.

By the time I was even able to see how unhappy I was in that situation, it made it really hard because I had all these self-limiting doubts: What if I can’t get another job? What if I’m the reason why this isn’t working? What if this hurts my reputation in the future if I can’t make this work or I can’t figure it out with my manager?

Then, I had to ask: What actually makes me happy in a role, and what do I need to be successful?

I examined the situation, and had an honest conversation with myself, my manager and others, asking, “Are these things realistic? Can I do these things? Can you do these things? Can you support me in this way? And if you can’t, what does that mean? What is my exit plan? And then what do I want to do next?”

Those are big, scary conversations.

Afterward, I decided to take a sabbatical. I wrote down a list, being really specific about every single thing I wanted. Within a month, my current company reached out — and it literally included every single one of those things.

It’s been a year and a half, and I’m in such a different place in my life, personally and professionally. I have asked myself, “Why did I stay at my previous company so long? If I would have left earlier, what would my life look like now?” But moving forward, I know how I need to structure and reflect. I know how to be my own best advocate as a result of this experience.

It can be really easy to fall into this trap of thinking about success and failure as a binary. But every time we “fail,” we learn something new that can inform the direction or what we decide to value in our day-to-day lives.