Confessions of a serial career switcher

I’ve shared before that I am passionate about mentorship. New grads and young professionals often reach out to learn how I found my path. Even experienced professionals have sought my advice as a career switcher (though I think I've finally found my niche!).

Frankly, I always feel a bit self-conscious discussing my path. I don’t have a “bootstraps” mentality . I know that bad things happen to hard-working people, while others seem to stumble into success. Any success I’ve had is only partly earned and partly due to incredible luck. How can a story like mine inspire anyone when it feels so random and unrepeatable?

With that said, usually after conversations where I share my path, what I hear time and again is “WOW! You have to get your story out there!” When someone says you have something wonderful to offer the world: believe them. Today I hope to share my path with you all.

I grew up in the East Bay Area, and was a first generation college student at UC Berkeley. I didn’t even consider applying to any private schools, much less Ivy Leagues- no one I knew had ever gone to one. I heard internships were unpaid, so I worked through college as a barista and eventually as the resident wine expert at Whole Foods.?

After graduating, I started my career in social work as a mental health counselor for high schoolers in a therapeutic classroom. It was some of the most rewarding yet challenging work I’ve ever done. Ultimately, I left because I couldn’t afford to live on the low hourly wage. I was developing from "young adult" into just an adult, and I realized I wanted to provide stability not just for myself, but also for my family. I needed more, and different, work experience.

But what a time to attempt switching careers. The economy was terrible, and my most impressive skill was stopping teenagers from harming themselves and others—not exactly a sought-after corporate skill. I ended up talking my way into a position at UC Berkeley Extension. After a form rejection for a job I nailed the interview for, I sent a sincere but brief message highlighting the interview’s positives and the alignment of our values and ideas. I ended by humbly requesting they let me know if they considered my skills a better match elsewhere in the organization. I got a call back within ten minutes, and two weeks later I was in my new cubicle.

I left my cubicle for a tech-adjacent role at a nonprofit, managing a fellowship program for Black and Latinx computer science students. It was demanding work with few resources, but I excelled. As my first workshop was in full swing I had a horrifying realization… I hated event planning. OOF. It was an enormous percentage of my job responsibility. I learned for the first time that the circles of "things you are good at" and "things you enjoy doing" do not necessarily perfectly overlap. During one of the final workshops I led, a speaker said to the students: “Please know that just by being black or latinx in tech and doing well for yourself, you ARE changing the world. You are changing the world for all the kids of color watching.” As a Latina woman, I listened. I began searching for my next move, still unsure of where I wanted to end up.

I applied for a position at Asana because I loved the product and thought it would buy me time to figure out my next steps. I started in 2017 doing administrative backfill work and quickly became bored… until Asana hired a new CPO who needed an executive assistant. I was initially asked to assist him temporarily, but he didn’t hesitate to invest in me and we ended up working together for three years, sharing innumerable laughs and frustrations, building out the product org together, and seeing hundreds of product feature reviews at every stage.

When I joined Asana I had no idea what Product Management was, and I didn’t think of myself as a “tech person”. Once I came to deeply understand what product management was, I had a few realizations that shocked me:?

• “This ‘product management’ thing is actually pretty awesome”
• “I think I could actually be a product manager”?
• “I actually want to be a product manager”

I had the opportunity to make the switch and haven’t looked back.?

I still reflect on my path with wonder. How did I get so lucky? Why did the hiring manager who rejected me at UC Berkeley Extension find my email response intriguing rather than obnoxious? Why did the CPO invest in ME when I could have just as easily been relegated back to fetching coffee? Most importantly, what if any advice can I offer about all these career switches that MIGHT be repeatable?

Here is what I suggest:

1. Be Authentic: The reason my reply to that hiring manager worked was because my excitement and openness were 100% real. I genuinely enjoyed meeting the team, had ideas I was excited about, and wanted to know how I might fit into the organization. If this tactic hadn’t worked, at least I was rejected for being my true self, not a facade.
2. Have Courage: Mark Twain said, “Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did.” Bet on yourself. Be willing to be the oldest associate product manager in your organization's history. Let others see you struggle so you have the chance to improve. Admit to yourself and other when you’ve made a wrong choice, figure out your next move will be, and take the leap.
3. Seize Opportunities: Opportunities often come from unexpected places. Be open to roles that may not seem like a perfect fit but offer growth. My administrative role at Asana led me to a life-changing opportunity with the CPO. In my time working with him, he presented countless opportunities for me to fail where he gave me the chance to say no. Instead I said, "I haven't done that yet; I would like to try". Start somewhere and keep your eyes open for chances to surprise yourself and others with what you can do.
4. Build Relationships: No one is 100% responsible for their own success. Build genuine relationships with colleagues and mentors. Get to know your peers, ask for guidance, and support each other. Relationships are about more than just opening doors, they are enriching and gratifying for their own sake.?Stop thinking of networking as transactional and helping you meet your goals. Connect with people without guile and for its own sake and great things will happen.

Thanks for sticking with me. For better or worse, I'm an open book- I hope you gain something by reading!