Stepping off the treadmill

ABC 148: On my biggest fears going out on my own

Six weeks ago I quit my job at IDEO, a job I loved for nearly four years. I had known I was going to leave for months. I drafted the company-wide goodbye email weeks before my last day. But the second I hit send, I felt a pang of doubt. 

Had I made the wrong choice? Should I have stayed six more months to vie for my next promotion? Who leaves a good job with nothing lined up on the other side?

I’ve heard these voices before. Truth is, I’ve always been a doubter. Whether it’s a life decision or sandwich order, I often have to unpack some combination of buyer’s remorse, Jewish guilt, and millennial fomo before I develop the nerve to make up my mind. 

In the weeks since I left full-time employment, I’ve interrogated the source of those voices in my head and compiled them into a rather personal essay. Leaving a great job is scary! I hope the essay is relatable to anyone who has considered working for themselves or chosen to zag when it would have been easier to zig.

Here’s the piece: Dealing with Doubt on the Pathless Path

Warmly,
Simo

P.S. The song of the week is some desert rock that’s perfect for a long drive.
P.P.S. Have a friend that would dig the ABC? Send ‘em here.