Rounding up and winding down
Identity traps, meaning matrices, and the entrepreneurial casino
Hello! I’ve been too sick this week to write anything new, but I’ve still been absorbing a bunch of stuff from others, so this week is a round-up of my recent favourites as this year winds down.
Worth reading
On careers & winding paths
All three parts of On Wise Agency by Paul Millerd is the best series I’ve read all year. I’ve already fallen into the “identity trap” of wanting to grab a new work identity before even fully leaving another behind (or knowing if I actually want to). It’s something I constantly struggle with (who do I want to be, a tech lead who podcasts? a “creator”? something else?). It’s a reminder that I need to be comfortable being lost for a while, which I also struggle with a lot.
Dare to abandon the 5-year plan - I loved this post by Melissa Clements on her journey as an artist. Consider it a wholehearted nudge to ditch the plan and bet on momentum. Sometimes cluelessness is a feature, not a bug.
Mentorship, sending scary emails, and making cool connections from Carly Valancy and Sasha Chapin landed in my inbox at the perfect time, as I’ve been thinking a lot about mentorship outside traditional structures (and finding one myself). If you have any experiences with mentorship, good or bad, please send me a message, as I’d love to do a deep dive into this very topic!
Stick or Twist: Should You Quit Your Job? - A great, practical way of thinking about what I suspect is the perennial question for many who read this newsletter, from Alex McCann.
Positioning for portfolio careers from Brie Abramowicz is a straightforward guide on how to position yourself as someone who does multiple things. The biggest takeaway for me is not to feel forced to treat every platform the same. Definitely will be attempting to apply this advice to my own profiles.
The year I published my novel - An honest look behind the scenes from Emily J. Smith on launching her first book and going from full time tech to author. I feel like life as an author always seems a bit vague and mystical so it’s nice to see a glimpse of what that really looks like, especially from someone who has pivoted from the 9-5.
On meaning
Aliveness and where to find it - I’m a sucker for a good graph, and the “meaning matrix” here is excellent. Ben James breaks meaning into four quadrants, and it made me realise how much I default to just one or two of them. Quadrant 4 (“creating together”) is the one I neglect most. The big takeaway: meaning is created, not discovered. You have to actively build it across multiple areas, or you can end up hollow even when you’re “productive.”
I thought about that a lot is a wonderful collection of 24 essays by 24 contributors. This year I particularly enjoyed the things I want to say to my boss (a good reminder of what it takes to lead people & maybe even yourself) as well as finding the space to belong (“I used to think belonging meant being surrounded by people who spoke your language. Now I think it’s about being understood without apologising for who you are.”)
On AI & creativity
I’m an AI-assisted author. You’ll get over it - Chad Rye writes from the heart about his author journey and using AI. AI-use often feels like a weird witch hunt these days, and I partly get it. There’s so much slop around that it’s Merriam-Webster’s word of the year. It’s absolutely something to be cautious of, and yet I absolutely hate gatekeepers telling you what counts as “real” creativity and who counts as a “real” writer.
Two things have proven consistently true for me: (1) AI can become a crutch that stops you from learning your craft - whether that’s writing, coding, or anything else. Be very cautious of this. (2) The result is ultimately what matters. Obvious and lazy AI usage is obvious, but for those using it really well, you probably don’t even notice. Spending your energy trying to figure out if something is AI-assisted already feels pointless.
Books I’m loving
Consider This: Moments in My Writing Life After Which Everything Was Different - Chuck Palahniuk. Recently finished and absolutely loved this. I’ve been writing more and more fiction lately so this was a well timed pick-up. A lot of actionable writing advice wrapped in memorable stories, making the book itself feel like a “show don’t tell” lesson on how to write well.
Leaving the Casino from Jessica Lackey - I’m about halfway through and it’s been a good reality check. The ‘casino’ is treating your work like a slot machine and hoping for a jackpot instead of building something sustainable, backed by your values. As I’m trying to build something of my own, it’s helping me to ask: am I actually building with intention or gambling?
Worth doing
Reflect: There’s a lot of “end-of-year reflection” stuff online right now, and way too many apps brute-forcing a “wrapped” campaign (no LinkedIn, I absolutely don’t need you to summarise my year on your platform). That said, I’ve done written reflections for the past few years, and I do find them a great way to stop and remember all the stuff I’ve actually done in the last 12 months.
If you’re feeling that urge to take stock, here’s how to do it:
Year Compass - My favourite. Print off a copy and do it on paper. All you have to do is follow the booklet. It’s free and available in a bunch of languages.
Reflect on your year in 90 minutes - A great method outlined by Kel Rakowski which is actually pretty similar to the Year Compass in method, but even more straight forward and easy to get started with.
Reflecting Forwards by Jonny Miller - Uses archetypes and comes in two modes: first-timer (light) or deep dive. Also includes a collection of other yearly review templates if you want more inspiration to roll your own.
And a random tip: At the end of the year I try to clean all my email subs. I recently learnt that if you’re a gmail user this is incredibly easy, as going to this URL gives you a clean list of all your subscriptions with a one-click unsubscribe button for each. It’s even sorted by frequency: https://mail.google.com/mail/u/0/#sub
This is the last newsletter until the new year. I’m going to rest, recover, and do my own reflecting. Thanks for being here! Whether you’ve been reading for months or this is your first one.
If you’ve sent me a message this year, opted in for a paid subscription, or even just opened these emails every now and then, it means a lot to me. It’s crazy to think I’ve only been sending these regularly again since May, but I’ve made so many awesome connections that I’m very grateful for.
See you in January!
— Mike
Thank you for compiling the wonderful resources Michael!
So glad you’re enjoying the book!