The First Cohort

Earlier this year, Jean and I ran the first cohort of DRI Your Career — a course we’d spent the better part of a year building together. We had high hopes. But the first time you do something — you can believe in it, but you can only really hope. I am so happy with how it went, though. Here are some highlights.

Jean and I agonized and iterated over the format. We both find a lot of professional development exhausting — the live sessions you have to show up for at set times, the group dynamics, the performing-engagement-in-a-Zoom-call energy. As a result, we wanted to build something introvert-friendly and timezone-friendly: async, self-paced, with the depth happening in writing rather than on camera. We weren’t sure how that would land. Turns out it resonated — we had participants from APAC, Europe, and the US, and the engagement with the exercises was great. The submissions were genuinely thoughtful. People showed up more honestly, I think, because they had space to.

What I didn’t expect was how much it would feel like coaching. Reading people’s exercises became my morning ritual. You’d watch someone’s thinking shift in real time — letting go of the things that capitalism had installed within them, or getting that light bulb moment from taking the time to think deeply and express it. We went into this with the idea that we wanted to make the impact of 1:1 coaching available to people at a more accessible price point, and it was so exciting to see that play out.

The ideas in this course are in my personal operating system (and also my book). I believe in them deeply, and strive to practice them. But between building the course and launching it, I left the company where I had spent the past five and a half years to have more time for projects like this one and have taken on a fractional CTO role. The same ideas that helped me stay for so long, and get promoted twice, helped me trust and build a plan around my feeling that it was time to do something else.

This is what I want for everyone. Not “you should quit” and not “you should stay.” Having enough clarity that you can tell the difference. Being at choice — making decisions for yourself and owning them.

The course covers four modules: challenging the default narratives capitalism installs in your career, figuring out what you actually want, making feedback work for you, and understanding what you’re moving towards. We read and comment on every exercise submission.

The next DRI Your Career cohort starts in April. If you’ve been thinking about it, the early bird ends very soon. You can find out more and sign up at driyourcareer.com.

If you’re an engineering manager navigating a post-ZIRP world — fewer resources, higher expectations, less margin for error — we also built the Engineering Manager Survival Guide. The course we wished existed when we became EMs and even more when we started managing them! Same format, different focus. First cohort starts March 13th.