Adam Keys is Thinking

🌶️ Hot-take: if you’re a manager and find you¹ miss building…then build²!

• On your time: mornings, weekends, national holidays.
• Whatever you want: tools for yourself, something frivolous, something practical.
• However you want: in an esoteric technology, in a boring technology, in a domain you’ve always wanted to explore, with LLM copilots, building every piece from scratch, without using conditionals, whatever!

Avoid:

• Swooping into your team’s current projects³.
• Imposing your discoveries/ideas on unrelated code reviews.
• Inventing projects and putting yourself on the critical path.
• Building and handing off a proof-of-concept to an unsuspecting teammate to finish.
• Thinking the grass is greener on the hands-on/IC side.

Don’t react to the bad parts of your previous role. It’s increasingly tricky to ride the pendulum between IC and leadership roles. You may only get to pull that lever once. Maybe building something for yourself will temper the temptation to go back to an IC role.

Instead, see if you can scratch whatever hands-on building/coding/designing itch you have in your time. You’ll necessarily have to scale it down. Honestly, that’s a great constraint! If you tried to build something big, you’d have to lead and manage it and, if you recall, that’s what we’re taking time away from in the first place here.

Follow your curiosity. The very best part about building on your time as a manager is you don’t have to make great decisions. Whatever is of interest, go with it.

Want to build a compiler, but you work in web apps? Go for it. Want to build a game, but you work in compilers? Go for it. Want to build an asset tracking web app in a really particular way, but you work in games? Go for it. Want to write in Haskell, but you work in Ruby? Go for it.⁴

Go for it.

A couple of lessons on leadership in ​Herbert’s Dune​:

“Give as few orders as possible,” his father had told him…once…long ago. “Once you’ve given orders on a subject, you must always give orders on that subject.”

Avoid, whenever possible, making decisions for people and teams. It may end up discouraging or preventing them from making any decisions for themselves in the future.

Frequent top-down decisions are the autonomy-killer, they might say. 🤓

Hawat arose, glancing around the room as though seeking support. He turned away, led the procession out of the room. The others moved hurriedly, scraping their chairs on the floor, balling up in little knots of confusion. It ended up in confusion, Paul thought, staring at the backs of the last men to leave. Always before, Staff had ended on an incisive air. This meeting had just seemed to trickle out, worn down by its own inadequacies, and with an argument to top it off.

This is what bad meetings feel like; they deflate like a balloon. Worse than indecision, they bring confusion about how to proceed, where efforts really stand, or if the current approach is the right approach. Not necessarily because of debate or disagreement. But, the lack of consensus or direction certainly doesn’t help.

Reader, I want to (once again) talk to you about the life-changing power of making a list and putting it in order.

Ambiguity of like, “what are we gonna build?” or “how are we supposed to build this?” Or was it supposed to be A or B or why did we make this decision? So having the checklist of “this is the thing,” it is a very, very cheap way to eliminate most of the ambiguity.

– Kristján Pétursson, Human Skills 018 — Creating Clarity From Ambiguity

Tasks lists are great for capturing and organizing what you want/need to do. They are sometimes good for thinking through how to execute on those tasks and projects.

Ordinarily, I’m too focused on all those incomplete items The empty check boxes, the lines that aren’t crossed through. So much potential. It’s exciting and overwhelming!

I rarely use my task list to reflect upon what I’ve done. To retrospect on how much I accomplished any given day or capture a post-hoc note or two on follow-ups, what worked, or to merely pat myself on the back for a day of honest work.

So I’m trying this right now! But, applications could stand to add more affordances for looking back in time too. This goes for applications like Things as much as it goes for Jira, etc. It’s probably our work and hustle culture. 🤷‍♂️ Always looking forward and rarely slowing down to say “hey, I did this, let’s get excited about that!”

One of the nice things about Kanban boards is you eventually end up with a giant pile of things that were done, and that’s a nice way to feel the momentum building that a bunch of stuff got done. Let’s get more of that.

“Dunbar’s number is a suggested cognitive limit to the number of people with whom one can maintain stable social relationships—relationships in which an individual knows who each person is and how each person relates to every other person”.

Corollary: any group size approaching 150 people (Dunbar’s number) includes at least one person who knows about Dunbar’s number.

To paraphrase a classic joke, “How do you know if someone knows about Dunbar’s number? They’ll tell you!” I’m telling you, right now, I know about Dunbar’s number. 🙃

Practically, I think this implies:

• If you’re designing an organization close to but not exceeding Dunbar’s number, you can hand-wave the details of when it grows to exceed Dunbar’s number. Someone will enthusiastically let you know that the organization has exceeded Dunbar’s number and might need reconsideration. 🥸
• For organizations as small as 10% of Dunbar’s number (15), there’s a pretty dang good chance that someone knows about Dunbar’s number. For organizations any multiple of that size, you don’t need to go around telling everyone about Dunbar’s number. Chance are, someone is telling everyone about Dunbar’s number. 😆

My experience in (software) teams is there are breakpoints far smaller than Dunbar’s number that matter even more.

FWIW, these are all folk rules. I haven’t seen rigorous work that backs any of this up!

Permit me to throw shade at the Emmy Awards for a moment.

Reservation Dogs is a better kinda-comedy than The Bear. Dogs is consistently funny and finds ways to explore the lives, relationships, and histories of the characters in rewarding ways.

The Bear is equal parts endearing and yelling. Once or twice a season, it speaks to craft and intensity. Those are my favorite episodes. The Fak family is the only undeniably comedic element of The Bear. Give us a spin-off of that and let it legitimately win all comedy awards.

The Bear belongs in the drama category, but isn’t the length of a drama because no one could sustain watching an episode of that show for that long. 🙃

By kinda-comedy, I mean “22-minute shows that are eligible for comedy awards at the Emmy’s”. The real solution here is for the Emmy’s to fix their categories in two ways:

• Don’t call “dramatic” shows that are shorter than 44 minutes comedies. This is absurd and an easy fix.
• Unrelated to The Bear, currently: create separate categories for “returning shows” and “ending shows”. Emmy voters have a tendency to award shows in their last season disproportionate to their competition.

In short: Reservation Dogs was the comedy that Emmy voters think The Bear is. 🌶️

The function key, on iOS and possibly Mac keyboards, is bound¹ to show the emoji picker.

Apple has chosen to bind a whole key, no modifiers or anything, to “convey an emotion”. A (cartoonish) picture is worth a thousand words.

🧠 Smart!

(I could go on for at least five minutes about Apple’s recent design advantage is in introducing big features without making them shout-y in the UI. Granted, the marketing is very shout-y.)

As I write this, it’s late-2024 and the job market is tough for jobseekers. If one finds a job within three months, they’re considered lucky. Some folks go 2–3 times longer in-between jobs. If you’re on this boat, break a leg!🫠

If you’re not actively seeking a job, here’s a thing that helped me go from “well this market sucks” to “welp, job seeking is my full-time job now, the only way out is through”:

I started warming up my professional network when things got spooky at my current job.

Caveat, I could have done even more than I did¹. Despite not taking more steps, the simple act of thinking through “what would I do if the worst happened and my job disappeared?” put me one step ahead, and I was a little more calm after my job did disappear.

1. The network is the work²

A strong, active professional network is the most important tool in this scenario. This is true whether the job market favors job-seekers or employers.

Especially when seeking a job without one in-hand, people are happy to respond and help out³. Fifteen minutes of writing and responding to messages could kick-start the process for your next job.

Some helpful questions I asked myself in contemplating how to warm my network back up:

• Who would I work with (again)? If former colleagues were especially easy, awesome, or delightful to work with one, a second outing is worth pursuing.
• What kinds of places would I like to work at? I find myself particularly interested in finance-adjacent endeavors.⁴ Tooling is also of interest, anything that makes people’s work lives better resonates with me.
• Why not aim for the bleachers in my next role?⁵ If I could work anywhere or hold any kind of role, where would it be? Perhaps there’s a role out there with all the upsides I’m looking for and very few trade-offs on the downside. Who could connect me to those roles?

2. Take a stroll down accomplishments lane

Another easy thing to do⁶ is get (back) in the resumé writing mindset. That is, the self-promotion mindset where you’re talking about all the things you’ve done, how great they were, putting numbers to how much they improved customer outcomes, and generally putting maximum shine on your work.

This is the point where I wish I had kept a good brag doc.

In lieu of a record kept in the moment, I took out some stickies and wrote out what I’d done in each of the last 6+ years at work. The goal here was to shake the dust from my brain and remember all the cool projects we shipped, excellent people I’d worked with, and improvements I’d made across the board. Keep in mind, no feat is too small and the sequence of projects doesn’t matter much! I’m only getting in the groove here. The two-ish page limit on practical resumés is forces compressing this list later.

Don’t feel bad about taking time to do this. At any high-functioning organization with a performance management cycle, what you’re doing here looks exactly like what you’d do for your regular performance review ceremony.⁷ Two birds, one stone!

2a. There must be 50 ways to write your resumé

An updated resumé is a pre-requisite. I’m not (yet!) so internet-famous that I can get by without one. I didn’t start rewriting my resumé right off the bat. Instead, I dusted it off and considered how I’d change it when the time came that I needed it.

Writing about oneself is challenging. It feels awkward, like something one is supposed to avoid. A few insights helped me here:

• My resumé is the marketing/advertising that will yield the job I hold for several years of my life. Multiplied out by annual pay, this document is a tool I’m using to generate the next several hundred thousand dollars that fund my life. Basically, any time I spend on it is worthwhile.
• Ergo, it’s worth spending days, all day, iterating, improving, and trying new things. It was this iteration that helped me get over the cringe of writing about myself.
• Cover letters seem to have fallen entirely out of fashion.⁸ Your resumé now has to do even more work. All the more reason to keep at iterating and customizing it.
• If it helps, write your resumé like you’ve already landed the hiring manager interview.⁹ Convince the reader that they were right to pull your resumé out of the stack. Tell them about all the great stuff you’ve done. This is where you want to refer to all your accomplishments, emphasizing the most recent and those most relevant to the kind of role you’re seeking.

3. One job is plenty

Looking for a new job is an exhausting endeavor. Iterating on resumés, tweaking LinkedIn profiles, and updating online presence consumes a lot of time and emotional energy. That’s not to mention actually finding promising jobs, customizing your resumé to suit the job descriptions, filling in application tracking system forms, responding to leads, and scheduling of interviews. Phew!

If you can avoid it, don’t seek a new job whilst trying to hold down another one. Especially one that has “gone spooky”. Granted, there’s a lot of luck and privilege wrapped up in that advice!

If your luck affords it, make the search for one’s next full-time job a full-time job. That is, give yourself a few month sabbatical to recharge and focus on the job search. Granted, don’t take this route in a market that heavily favors employers and make sure your savings are topped off in case of surprises.

All this said, preparing for seeking a job is not the same as seeking a job. It took me longer than I’d have liked to realize this. Actively seeking a job, for me, looks more like marketing and sales than building or leading. It’s playing a “numbers game”: the more people you network with and the more jobs you apply for, the better. Thinking through how I would execute that helped!

But there was a hump I had to get over, entirely in my head, about actively/explicitly putting myself out there. Some social barriers I had to let go of, like not “reaching out” to folks via email or LinkedIn. Doing sales-y things, it’s a big growth area for me. 🙃

Finally, a thing I’m learning about this most-difficult job search of my career: every step on the job search is one step closer to finding that job.¹⁰

If you find yourself actively seeking a job, or merely feeling the spider-sense tingle about your current role, good luck! I hope this helped.