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Searls of Wisdom for November 2023

I finished Starfield last month, which included this unsettling scene of my own avatar giving me some free advice:

Justin in a spacesuit saying: "That's good. You'll need that clarity later"

Having a receding hairline is generally miserable, but the frustration is especially acute when futzing with a video game's character creator. As much as I'd love to grant my digital analog the curly mop of hair I shed long ago in my early 20s, I can never bring myself to so brazenly signal my dissatisfaction with my own appearance. I will admit, though, I usually consider selecting the hair I wish I had… before inevitably choosing whichever of the three balding scalps matches mine best.

Lower your expectations

All this hairline talk is a great segue to this month's topic: expectations management.

If you know me well, you may have gathered that I have impossibly high expectations. Of everything. I'm tough on myself, for sure, but my default wiring is to hold others to a standard that reflects my hypothetical all-time best performance, 24/7, and with no regard for their experience or circumstance. Oh, also, I should mention I rarely bother to convey what that standard even is, which results in my routinely feeling let down by others for failing to meet my unspoken expectations.

(Yes, Becky is a saint for putting up with me. And for pushing back on me.)

The nice thing about struggling with unrealistic standards, however, is that they rarely survive prolonged exposure to reality—one can only have their hopes dashed so many times before the dam breaks. As a result, I find that I've developed an unusually detached, fluid relationship with the expectations I place on myself and others—both in terms of awareness of what's driving them and of the ability to dial them up and down as the situation warrants.

So today, I want to share a few brief vignettes about expectation management from my career, as food for thought about your approach to managing expectations in your own world.

"You just stole a fortune from Big Oil!"

The first story is a lesson in the importance of defining appropriate boundaries around our expectations, especially when we derive meaning from them.

During one of my first experiences playing an account management role in which another consultant would be doing the work, I learned that a lot of programmers have a particularly strong expectation that their work be used in the real world and by as many people as possible. This may sound like a rather obvious goal, but for me—as someone who spent the first four years of my career shipping product after product that was killed somewhere between my creating it and its public release—it nevertheless struck me as bizarre and foreign.

Anyway, the client was in the oil & gas extraction business and the consultant (understandably) had ethical reservations about working for them. Unfortunately, our company was still young and we didn't have any other sales opportunities at the time. It was this or nothing, and we couldn't afford to pay a salary for nothing. I did my best to convince him it'd be fine—reminding him that most projects fail, so it was exceedingly unlikely his work would succeed in destroying the planet.

Fast forward 6 months, and that same consultant was having an absolutely fantastic time working on this project. He was developing close friendships on the team, building truly innovative user interfaces, and helping his team repair longstanding communication breakdowns with other areas of the business.

One day, out of the blue, the consultant called me, audibly upset and deeply frustrated. "They cancelled the project! It's never going into production!" I paused to remember that this is something most people care about, then responded to point out the friends he'd made along the way, the things he'd learned and taught others, and the healing he'd facilitated that would outlast his direct involvement on the team. He had nailed the execution of everything that was in his direct control, but still found himself wanting to hang his hat on the one thing he had zero influence over: what a massive corporation would do with his work after he handed it off.

When I had finished consoling the consultant by exhorting him—"don't let someone else control how you feel about your work"—I reminded him of where he was six months ago, not even wanting to take the engagement in the first place. I said, "think about it, they just paid half a million dollars for you and this team to have a phenomenal experience and then decided to flush that money down the drain—you just pulled off a heist! You're Robin Hood!"

That reframing instantly lifted his mood. Pinning his expectations on the fate of the overall project, his work was an undeniable failure. But benchmarking himself against how he showed up and the things he actually did, everyone's expectations (including the client's) were wildly exceeded.

"It's totally going to work this time!"

The second anecdote is an example of why it's better to embrace failure than to expect success.

On a particularly long-running engagement, I spent a lot of time (six months, maybe?) paired up with the same client developer. The system we were working in had ample test coverage, but those tests were very slow for a combination of necessary and unnecessary reasons (this project is what inspired one of my best conference talks). He and I became fast friends… when 6 hours of your workday is spent staring at green dots and red 'F's appear in a terminal window at glacial pace, you have lot of time to get to know someone.

The tests were so slow that after writing a line of code, figuring out whether it worked or not was an ordeal. It took so long to get feedback from the computer that I would read and re-read our changes before running the command. I found myself holding my breath while refactoring and girding my loins while waiting for test results.

It was as if we were strapping a monkey into a space capsule, then scurrying to a control room to hit the big red button, only for three-fourths of the rockets to explode on the platform. It was torturous. (No actual monkeys were harmed in this engagement, only figurative ones.)

My colleague and I developed a facetious collection of verbal tics to get us through the day. One of his contributions was the motto, "it's totally gonna work this time!" which he intoned sarcastically every time he pounded the Return key. It was his way of making failure feel safe by mocking success itself.

It's been over a decade since then and I still find myself muttering, "totally gonna work this time!" when I catch myself getting frustrated by frequent failures.

It's easy to talk a big game about adopting an experimentation mindset, striving to "fail fast", or to claim failure as life's greatest teacher, but it's quite another thing to overcome the negative emotions we feel when we fail. As somebody who helped numerous teams adopt agile methodologies for which "embrace failure" was a core principle, I never once saw a manager or executive fully shed their ego when people and initiatives actually failed—the visceral emotional reactions failure evokes are too deeply entrenched for most people to overcome them.

Humor, though, has a way of bypassing this instinctual response, at least for me. Rather than suppress my fear of failure, I would jokingly reject success. In effect, I made failure my default expectation (especially for anything involving computers) as a way to blunt the negative impact of failing over and over again.

"We're going to change the world!"

The third reflection is an affirmation that unreasonably high expectations aren't all bad. There are unreasonably many things to do in the unreasonably finite time we have in this life, and high standards can help us choose where and how to invest that time. In fact, maybe this is an area where you'd do well to place higher expectations on others.

Developing the brand of a "bootstrapped", counter-cultural software consultancy during the VC-backed boom of the 2010s probably meant it was inevitable I'd develop an allergic response to the bold proclamations of ludicrously ambitious startup founders and funders. My skin crawled and never uncrawled when Doug Evans stated his goal was to "scale the unscalable" by selling a $700 juicer that was less effective than squeezing its packets of diced fruit by hand.

As someone who shipped out-of-the-box with unreasonably high expectations, unbounded ambition is the enemy of my successfully managing those expectations. If a founder were to convince me to chase an impossibly ambitious goal, I'd be at risk of working myself to death to accomplish it—even if success was literally unattainable. A lot of other programmers are wired the same way, which is how crunch culture often emerges, even in the absence of coerced overtime.

At conferences and on sales calls, I so often found myself listening to less-riduclous-than-Juicero-but-not-that-much-less-riduclous pitches from founders looking for a development partner that at times I doubted myself: were my instincts completely wrong? Was I being a cynical stick in the mud by passing on so many slam dunk opportunities to get in on the ground floor of the next unicorn that would disrupt the very idea of disruption itself?

Of course not. I always concluded it was the founders who were wrong. (Well, them and and the VCs preying on their naive ambition as grist for the fundraising mill to pump valuations from seed to A to B to C to "not my problem anymore, suckers!" to IPO to epic flameout.)

But not everyone eluded the song of the startup sirens. A lot of brilliant people got sucked in, chewed up, and spat out by it. Some saw a great payout. Most didn't. All lost a bit of themselves from the grind. The only reason I escaped was that my own impossibly high standards make me extremely dubious of people who think they are, for lack of a better term, Hot Shit™.

I was never tempted to join any of these startups, because every time I looked closely at any of these wannabe Steve Jobs types, I'd be repulsed to find their own work was drenched in mediocrity. Meandering e-mails riddled with typos. Sloppy presentations propped up by unearned bluster. Foolish, short-term thinking. No number of brilliant hires can save a leader who holds themselves to such low standards: people who tolerate their own shit work lack the drive and diligence needed to do anything other than accept shit work from others.

Anyway, when the stakes are high and the circumstances warrant it, don't be ashamed of setting a high bar for yourself and others.

Programming note

After last month's issue, which marked the formal end of my hands-on engagement on any timeline-based social media apps (I also commemorated it on the tail end of this podcast), this web site is quickly becoming my only outlet for non-code creativity. As such, I posted a lot more there than usual this month. Here's all those links in one place:

I'm not sure whether this is the new normal or not, but I am really enjoying how it feels to be reclaiming my voice in the absence of the pressure to represent anyone else. (There's no confusion whose views my web site represents—it's right there in the domain name!)

My parents (👋, hi mom and dad) are visiting us in Orlando to celebrate the holidays in a couple weeks, so—depending how that goes—expect to see many fewer or many more posts from me this month. Separately, the plans for what I intend to work on in 2024 are also firming up, and I'm really excited to share more about them.

Ok, that's it. Take it sleazy.