The Deliberate #66: One Month In

If you’re a friend who has had a conversation with me about my job search over the past month (I know there’s more than a handful of you who subscribe to this) then this edition is likely to be quite redundant to an email you recently received from me. Feel free to skip to the end the media recommendations.

FOR THE REST OF YOU THOUGH, hi. Hello. It’s me again.

Turns out the best way to get me to write a newsletter on a cadence more frequent than the typical gestation of a human being is to be unemployed. Nothing focuses the mind and moves the fingers like impending doom a steadily decreasing savings account, apparently.

It has been a month since my last day at The Ready and a little over a month and a half since I publicly announced that I quit my job. Since then, my full-time gig has been finding (building?) my next full-time gig. Did part of me think that perhaps this job search would end before it even started with some divine being floating down from the heavens with a beautifully wrapped and glowing box that said, “Sam’s Next Dream Job” on top? Maybe. Did that happen? Sadly, somehow, it did not.

Turns out the vibe out there is much more Charlie Kelly

This is what getting in to my job cannon has looked like for the past month:

• 67 conversations with former colleagues, clients, friends, and strangers about why I left The Ready and what I want next.

• 40 job applications through various frustrating portals (still better than a decade ago).

• Of those, 6 rejections.

• 1 that’s become an official interview process (I’m two rounds in).

• 1 that had me do an assessment I passed—radio silence since.

• 4 “interesting wildcard” conversations with follow-ups scheduled.

• 2 that may turn into small projects via my fancy new LLC.

These conversations, other than just being fun and a great excuse to connect with great folks from my past and new folks I’ve never met before, are helping me clarify what I’m looking for:

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.

5. The entrepreneurship urge has not completely left me. Getting my LLC set up and other administrative hurdles handled has made this path more attractive than it originally was. More to come, possibly, on this front…

I know it’s a rough time to be looking for a job. I’ve worked with enough orgs to know that the time between American Thanksgiving and Christmas is the most dead of dead zones. Nothing happens. I’m using the time to keep planting seeds so I have something to look at once things pick up again in the first couple months of next year.

If anything you read above sparks an idea about something I should check out or an introduction you could make, I’m all ears. Otherwise, though, just subscribing to this thing and lending me your eyes periodically is more than enough. I promise to not turn this into an ongoing record of my own job search, but for now, at least, that’s what it needs to be.

I do more than just look for jobs. Here’s what has had my attention the past few weeks.

Silksong. It has been the only thing I’ve played for weeks and the game is truly a masterpiece. I love that it took forever to make. I love that you can tell it took forever to make. I love the lore and how it feels to play and how it sounds. Truly one of the best games I’ve ever played. I’m closing in on 100%-ing it and will need to set it aside in favor of something else. To be determined what that will be.

I’ve finally started Ulysses by James Joyce. It’s one of those books, you know? The scary hard ones. And, somehow, I’m actually really enjoying it and not finding it all that hard? I think it’s the rare book that actually benefits from the way I like to read. Meaning, it benefits from an approach where you don’t try to understand every last word. Because it’s constantly phasing in and out of dialogue, internal stream of consciousness, and dream-like impressions it benefits from kind of just letting it wash over you. That’s my favorite way to read so, so far, I’m really enjoying it. My full reading log can always be found on Goodreads, too.

Other recent reads that were worth the effort: Enshittification by Cory Doctorow, The Grief of Stones by Katherine Addison and Leading into the Age of Wisdom by Brian Gorman.

Emily and I really scratched one off the ol’ Are We Getting Old? bingo card by going to a Sunday 9:45 AM(!) showing of “Nuremberg” this weekend. It was pretty good. Russel Crowe did a great job. The movie struck the notes it needed to hit: the banality of evil means that Nazis were human and could be charming and friendly and that’s actually made their type of movement so disturbing as a societal force and worth thinking very deeply about today. It was a bit of a tightrope walk to see if it was going to land in a place where the current Nazis among us (I’m sad that’s a phrase that makes sense today) could point to it and say, “See?! They weren’t so bad/they were right!” I don’t think you can take that reading from the movie at all.

On the small screen, Slow Horses. Seriously, ‘nuff said. Best thing on TV nowadays.

Thanks for inviting me into your inbox and thanks for hanging around.

Until next time!