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This spring, I made a big career transition. I resigned from my role as Director of Product Management — giving up the compensation and stability that I worked a decade to earn — to begin a solo venture in product coaching & consulting. For this transition, there was no clear map. Instead, I forged my own path by leaning on a series of experiments to uncover opportunities and mitigate risk incrementally. Driven by my entrepreneurial spirit and armed with my project management tool of choice (#teamtrello), I became the customer in order to find out what lay on the other side of corporate life. Yes, the product manager ‘product managed’ herself. Here’s how I did it… ↗️
I spent the last 12 years climbing the career ladder as a product manager in tech. In that time, I reaped huge rewards: I launched groundbreaking B2C products while collaborating with some of the smartest brains in the industry. I experienced the perks that tech had to offer when growth felt endless. I was incredibly lucky.
But, like many others, I increasingly found the digital workplace bringing me down. Working remote over the past 3+ years, I spent more time drowning in emails, stuck on zoom calls and fielding slack messages. I had zero left in the tank at the end of each day. I sought support in a peer coaching circle and with dozens of product people online. Here’s what I learned… ↗️
Through connecting with folks I met online, I learned a lot about myself and what was possible:
- Through the peer coaching circle and mentoring I provided other product managers, I learned I loved helping other people solve their career challenges. I felt most energized empowering others to beat their blockers and gain confidence in their professional and personal lives.
- Through my interviews with dozens of product people, I discovered alternative career paths. I saw that professional fulfillment wasn’t just a far fetched millennial cliche, but a possibility so many around me were already living.
- I realized virtual networking wasn’t so hard once you got the hang of it. I made internet friends. Some internet friends became IRL friends.
Here’s where I did about it… ↗️
So I did the product thing: I created a vision, an experimentation plan and OKRs to go with it.
Those who know me say that entrepreneurship is in my blood. I’ve been ideating businesses since the ripe age of 10 (notably a travel agency, a restaurant, a clothing swap service BEFORE Rent the Runway was a thing — yes, I was a true innovator). But, I’ve never bet on myself in a real way. Though I’ve been ambitious in my own career as an employee, I remained a “shadow artist.”
So, I started coming out of the shadows. I used cheap, rapid experimentation to learn and move quickly. And just like that, I product managed myself out of the doldrums. Here’s how I tested… ↗️
Experiments I Ran
(1) The Question — Should I stay or should I go? I’ve only ever known corporate life. It wasn’t anything I ever questioned until it started bringing me down in ways that were all consuming. Because the days were a blur, I couldn’t reliably piece together how and when to step away. Product Leader Hazel Chi, inspired me to conduct a simple exercise. It involved running a quantitative experiment on myself to make sense of my qualitative emotions. 🎢
Method: For a month, I rated my days (terrible, ok, great ← super scientific, right?) If I had the energy for it, I would add details. The details identified patterns and I easily saw what energized me, what depleted me, how who I spoke to and how I spent my time had a profound impact on my rating.
Results: Using this exercise helped me quantify my struggle and paint a more accurate picture of my experience. It was a practical, reliable tool when emotions ran high. And in the end, it helped me see that a departure from corporate life wasn’t possible but necessary (for now).
(2) The Question — Should I coach other product managers? Following my participation in the peer coaching circle, I set out to learn why I liked it so much and what value I brought to others. I took my talents outside of the circle and started mentoring other product managers. 🏀
Method: I plugged into a handful of mentoring networks (Merit, ADPlist.org to name a few) and offered my support to dozens of product managers around the world. While my tactical product experience was the hook, it was my empathy and relatability that made these sessions successful.
Results: I didn’t take on mentoring to become a coach. I mentored other product people because it felt good. But once I started mentoring, I uncovered a new path. The sessions taught me where people needed help and where I was able to offer the best support. My consistency gave me clarity on my value prop. And the sessions gave me confidence to move from mentorship (free) to coaching (paid) rapidly. Without experimentation, tweaking my approach, my language, my tools, I wouldn’t have moved into coaching as quickly as I did.
(3) The Question — Should I create a website? When I was finally ready to bring on paying clients to coach, I immediately concerned myself with branding and packaging. Amid the incredible competition out there, I struggled with how to represent myself. My identity was a product manager and now, I was calling myself a coach. Imposter syndrome at its finest. 👹
The Method: It was on my networking journey in conversation with Rachel Wynn, a product leader and consultant, that I remembered to start with an MVP. Rachel reeled me in and suggested creating a google doc. Soon, others (many in The Old Girl’s Club) reinforced the concept of a 1-sheeter as the next step. So, I made a google doc with my offerings, my rates and an about me section.
The Result: It wasn’t perfect, but the 1-sheeter combined with my LinkedIn got the job done. It saved me time and got me going sooner than I would have if I focused on building a website from the start (plot twist: I eventually built a website). It was here that I harnessed one of my best friend’s mantras: a right next step. It’s tempting to figure out the big picture from the start. But the reality is, its usually wrong. Now, I reel myself in and focus less on the end goal and more on what a right next step is. Needless to say, getting things done has gotten a lot easier.
(4) The Question — How should I sell sessions? Charging people for coaching was a scary process. I’ve done my share of willingness to pay research in product roles but never for myself. Most of all, asking people to pay was straight up uncomfortable. So I tried a lot of different things. 🤑
Method: I A/B tested different packages, price points, and language. At one point, I was redoing my rate sheets on a daily basis. Through all of these tests, I learned to communicate my own value as a product coach.
Results: I learned what worked well for some worked terribly for others. I pitched too high and lost some potential clients. I lowballed when there was room to go bigger. Similar to booking travel, dynamic pricing options and models seemed to be key, especially in a rapidly changing economy when people’s elasticity is in constant flux. Similar to the website debacle, if I worried about nailing pricing from the get go, I wouldn’t have worked with as many coachees as I have today.
Though I’ve taken the leap, I’m still actively experimenting to learn more about how I can improve my approach, my offering and myself. Aside from experimentation, I lean heavily into conducting my own customer research, collecting data to continuously learn and improve. Best of all, I found using rapid experimentation wasn’t only effective, it was just straight up fun. I guess it’s what made me fall in love with product management in the first place. I look forward to experimenting even more in the future and sharing more about my results here in the coming months. And last but not least…
1) A shameless plug
Are you looking for product support? Do you know someone who might benefit from coaching? I’d love to connect! (Yes, you saw this one coming) (I also have some limited availability for product consulting!)
2) A list of related reading on experimentation
- Sprint: How to Solve Big Problems and Test New Ideas in Five Days — Jake Knapp (my experimentation bible!)
- The experimental mindset — Kelly Liu
- What Would You Do If You Had To Start a Career Coaching Business? — Michael Lin
3) A Thank You
Thank you to the long list of product people who inspired me to take this next step. Time is money and your time means everything to me. I’m looking forward to paying it forward.
And a special thank you to all my mentees. Without you, I certainly would not be on this path today.
Hey — I’m now on Substack. Subscribe to get the latest from me here.
