/careers
Taking inspiration from grocery bagging, pizza delivery, and the art of letting go
✍️ Tuesday, June 12
Whole Foods: What if I could bag groceries? My dad did that when he was growing up, and I’ve always loved his stories of entertaining people as he helped carry bags to their cars, channeling Zorba the Greek to find joy in anything, no matter how seemingly mundane, a lesson he has passed on to me many times. I do love the Tetris-like packing challenges of assembling items just so, and it might be interesting to meet new people every day. But minimum wage wouldn’t make sense if I could invest that time more wisely into my own business-building activities.
Administrative Business Partner (Executive Assistant): What if I could support an executive back at my corporate alma mater? I’ve always thought I would do well in a Chief of Staff-type role, helping another person optimize and organize. Then again, I would be terrible at the frantic nature of last-minute requests, always feeling on call and at someone else’s whims.
Notion’s Director of Community: I am passionate about their product, and it would be fascinating to help something I love grow from an inside, front-row seat. Alas, “You love building and scaling teams,” the description said. Doh. That’s the antithesis of what I love, and I have stated publicly many times on my podcast how little I like managing people. Strike three.
If I can’t figure out something soon, The Responsible Thing™️ would be to move out of the city and/or get a full-time job.
Alternatively, with my liquid cash reserves zapped from already leaning so heavily on them in the last few years, I could start draining my 401(k). But I didn’t build very high in the first place after just five years of contributing to it. As is, there’s not nearly enough to retire on.
It would be irresponsible of me not to at least browse company.com/careers pages, alongside Street Easy and Zillow real estate listings in other less expensive cities.
This SNL skit isn’t far off, especially if you map the “hope porn” vibes over to self-employment crises of confidence (see also
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