I keep meeting lawyers who are great at their jobs but dream of something different (my last lawyer and I bonded over video games). They usually think they're alone in this. That's why Jan DAlessandro's story was such a delight.
Back in '97, she was on track to make partner at her firm when AOL came calling. What followed wasn't just a job change - it was the start of a much bigger transformation. Jan realized being good at legal work wasn't the same as loving it.
"I got to a point where I thought, I don't really care about the indemnity clause," she told us, laughing. "And then I realized - you can't do this job anymore because somebody needs to care about that. And it wasn't me."
Today Jan leads Pledge One Percent's equity initiative, working with tech companies to direct billions toward social impact. She's found a way to use her deal-making skills for something that genuinely excites her and uses the skills she naturally gravitates towards. While she still negotiates plenty of terms, these days it's about creating partnerships that serve a bigger purpose.
Her advice for other lawyers feeling stuck? Look at what you actually enjoy doing. The stuff that doesn't feel like work. There's probably a career there - even if it's not obvious yet.
We covered a lot more ground in our conversation, from AOL's early days to the future of corporate philanthropy. Give it a listen - especially if you've ever wondered whether being good at something is reason enough to keep doing it.
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