December 1st, 2025

Hello! 

You are receiving this email (on the BCC line) because you’re someone I’ve spoken to about my recent job search and I thought you might want to receive an update about how that’s going. I’ve spoken to too many of you over the past month to write each of you a bespoke version of this. Hence, the quasi-newsletter format.

My last day at The Ready was October 31st so it has been basically one month of looking for my next thing full-time. By the numbers, that has looked like approximately 67 conversations with folks like you, 40+ applications sent into the void, 6 outright rejections, 1 interview process kicked off, and a handful of interesting “wildcard” opportunities that could feasibly turn into something, but aren’t particularly close to being real.

Honestly, the last month has gone better than I could have hoped (other than a magical job just kind of appearing in my lap, which of course I hoped for but have to admit was unlikely to happen).

All of these conversations have helped me continue to refine what I’m looking for. From my LinkedIn post earlier today, here’s how I’m thinking about the potential paths forward right now:

1. I’m still most intrigued by an “org design-y” Chief of Staff role. Every now and then one sounds tailor-made for me, but breaking through the noise has been tough so far. My resume is devoid of Chief of Staff experience, which makes it tough to get through the application screen, but I have a very strong hunch my experience at The Ready would make me a great fit — especially for the version that has a bit more of an org design focus.

2. I jump on roles in “internal innovation,” “ways of working,” “internal org design,” and the more compelling corners of org effectiveness/development whenever I see one posted. They’re rare but often perfect fits for what I'm good at and what I want to do.

3. The wildcard stuff is the best—anything that lets me mix some combo of org design, personal development, writing, research, future of work, entrepreneurship, philosophy into something weird and wonderful.

4. I’m becoming more open to the idea that my next gig could still be in consulting. I have a hypothesis that my experience at The Ready (a beautiful collection of self-managing weirdos) has made me somewhat inscrutable to traditional orgs, whereas consulting firms seem to “get” me. I shouldn't close the door on this path just because 10 years of working with clients had kinda burned me out.

Receiving this email is proof you've already done more than enough to help me with this search. But to the extent anything I wrote above triggers any ideas or potential introductions you’d be willing to make, I’m all ears. 

Otherwise, I just wanted to thank you for already helping me find my next thing and if there’s ever anything I can do to help you, please don’t hesitate to reach out.

Your currently unemployed, but hopefully soon-not-to-be, friend,

Sam

P.S. I’m only intending to send this “newsletter” periodically (once every 6 weeks?) or until I land my next gig, but please let me know if you want me to take you off the distribution list. No hard feelings, I promise.