Searls of Wisdom for June 2024

June was a busy month. Because Becky's business is in a sort of limbo until I finish and because I'm giving a talk at Rails World about how easy it was to finish, I am extremely heads-down finishing my work on her Better with Becky app. I can see the light at the end of the tunnel, though. I think.

This moment in every project reminds me of one of my favorite tongue-in-cheek "laws" of computing:

The first 90 percent of the code accounts for the first 90 percent of the development time. The remaining 10 percent of the code accounts for the other 90 percent of the development time.

One thing I will say is, while the ninety-ninety rule has rung true to me for nearly every team project I've been a part of in a corporate context, it doesn't resonate at all when it comes to my solo work. Maybe it's the acceleration one can build when the full context of the code resides entirely in one's own head. Maybe it's my particular "measure twice, cut once" ethos as applied to planning and testing. More likely, it's that when the person planning the work is the same person that's doing the work, scope creep becomes emotionally untenable once they reach the point of exhaustion. Reminds me of that quote often misattributed to Leonardo Da Vinci, "a work of art is never finished, merely abandoned."

Anyway, because I've been so busy building that app, I haven't gotten out much. Of course, I say that in Orlando-adjusted terms, as I did manage to find time to meet a beloved character actor from Raiders of the Lost Ark, attend a preview event to ride a new theme park attraction, and see the new neighborhood drone show in between pomodoro timers.

Today, we're going to talk about pressure.

As someone who struggles with the topic of convincing myself and others to do things or to not do things, I've been fortunate to have so many people in my life teach me better ways to think about motivation:

• My wife Becky was a professional educator and is a natural-born teacher, and early on she introduced me to Alfie Kohn's Punished by Rewards, which challenged my assumptions on the effectiveness of extrinsic motivation
• My business partner Todd was an engineering manager and is doggedly committed to improving at it, so before we founded Test Double he encouraged me to read Daniel Pink's Drive, which distilled academic work (like Kohn's) into a 3-part formula to foster intrinsic motivation: autonomy, mastery, and purpose
• My mentor Daryl was a preternaturally insightful consultant and advocate of systems thinking, and after watching me flail through two stressful engagements he encouraged me to read about Deming's life and work, which helped me grasp the folly of narrowly explaining people's behavior as a matter of individual motivation, divorced from the broader environment they were operating within

These resources, the conversations they inspired, and (most importantly) my experiences trying to put them into practice did a lot to shape the trajectory of my career. They equipped me with a repeatable system for answering, "why is that person doing the things they're doing?" It wasn't long at all before I found myself able to spend a day at a new client—observing their teams and interviewing their people—and, by the end of the afternoon, draw up a pretty good list of the top five things their leadership should focus on.

It's not that I'm some sort of management consulting genius. It's because, like so many things in life, the solutions to our most persistent problems are simple but hard. Most people already know the right answers to the questions that dog them, but will—if put under sufficient pressure—revert to their baser instincts. Doling out rewards and punishments to change others' behavior. Telling someone how to do their job without explaining why it matters. Calling underperforming colleagues "lazy" while ignoring the systemic factors that incentivize them to keep their heads down.

There I go. "Under sufficient pressure." I can't last two paragraphs in a discussion about motivation before bringing up pressure. The two are hopelessly entangled in my mind.

What is pressure's role in whether people feel driven or demotivated? Is it inherently good or bad? Does it matter whether the source is intrinsic or extrinsic? To what extent do the effects of pressure vary from person to person?

I can't pretend to have the answer to any of these questions, but I can share a bit of my own experience.

Running in zero gravity

Anyone who has experienced intense, debilitating pressure to perform will understandably yearn for relief from it. I was pretty burned out when I read Andy Hunt's Pragmatic Thinking & Learning, and I found myself clinging to his phrase "pressure kills cognition" for dear life. If only I could get the chance to write software with zero pressure, then I would finally be able to do my best work!

As fate would have it, I soon had exactly that opportunity. I landed a project with a clearly-identified problem but no preordained solution—unfettered autonomy to build the right thing. I was working solo, so others' expectations were a non-factor. No deadline in sight. Zero pressure.

It didn't go great.

I started sleeping in late and clocking out early. I oscillated between half a dozen approaches, switching gears the instant the work became challenging. I lowered the bar for "good enough" from "good enough to solve the problem," to "good enough to get away with it." After all, in the absence of any pressure, what was the point in making myself uncomfortable?

It is somewhat inconvenient when you become so radicalized as to stake out an absolutist position ("pressure is the problem!"), only for reality to slap you upside the head and remind you that life is rarely so simple. Clearly, environments lacking any pressure whatsoever also also less-than-conducive to drawing out my best work.

You can lead a horse to the office

So, if some amount of pressure is useful, what kind and how much? Where is the line between a healthy sense of urgency and undue duress?

This is where I've landed: good leaders can set the right tone and good teams can promote psychological safety, but how people deal with the expectations of others ultimately depends on the individual. An organization can do its best to foster an environment that promotes healthy, productive stress responses in people, but it can't control them directly. The best manager in the world can't successfully reassure every single unnecessarily-worried employee to chill the fuck out and get back to work. There exists no vision so inspiring and work environment so perfectly designed that it will successfully achieve a 100% aligned and intrinsically-driven workforce.

You can lead a horse to water, but you can't make it excited about working towards its Q3 OKRs.

Even the best managers and policies and compensation packages will fail to maintain the perfect pressure-motivation mix in the hearts and minds of every worker. So, what's that say about all the less-than-perfect workplaces out there? It says that you can't rely on your employer to motivate you.

Be your own pressure cooker

To talk about pressure is to talk about expectations.

When trading your time for money, you can't escape the fact that someone will place expectations on you. You can't control how (or even whether) those expectations will be communicated. And even if you do everything absolutely perfectly, there's no guarantee you'll satisfy those expectations, either.

Expectations are the invisible truth flowing between people in organizations, and pressure is a manifestation of how those expectations are perceived. If expectations are the message, then pressure is the tone, volume, context, and hand gestures by which others' expectations are conveyed. Reasonable expectations communicated with a threatening shout can be debilitating. Impossible expectations dressed up as fantastical adventure can be exhilarating.

Once you realize your motivation relies on the right amount of pressure for you individually, it makes sense to seek out an employer who will strike the balance you need. And maybe you'll succeed! Maybe by carefully identifying the best places to apply to work or maybe by sheer coincidence, one manager on one project will strike the perfect chord and maybe that will spur you on to greatness. But that's a lot of maybes. That's capturing lightning in a bottle. You can't plan your life around that. I know too many people whose careers took off because of one magical moment in which their individual needs and their work environment happened to be perfectly aligned, but who subsequently wasted years of their life bouncing between jobs in a futile attempt to recapture that magic.

Don't do that.

I was fortunate to experience that kind of cosmic alignment for myself on a few occasions—where my bosses' expectations were fair and reasonable, my clients' deadlines were grounded in real-world constraints, and my colleagues pushed me to do better work. But I saw those projects for what they were: a lucky draw. Who's to say my next manager will be so understanding? Or my next client's demands won't be hopelessly unrealistic? Or that future colleagues' feedback won't make me feel stupid and small?

Once I had experienced that perfect balance of pressure at work, I knew I couldn't rely on others to pressure me just so in order to perform well. I knew that whatever I needed had to come from within. I needed an intrinsic pressure that could reliably unlock intrinsic motivation, regardless what was going on around me. I spent years knowing this intellectually and craving it emotionally, but exactly how I would increase or decrease the amount of pressure I felt always eluded me. And so my motivation tended to ebb and flow at the mercy of the whims of others.

One time, a CTO screamed at me about missed deadlines until he was red in the face. Another time, I watched a product manager break down and express worry my team was so far off the mark that he'd be fired for it. And I'll never forget when a group of colleagues confronted me to say I was representing them poorly in public. I knew in each of those moments that it was nobody's (primary) objective to make me feel like shit. They didn't want me to melt into a puddle of anxious goo. They wanted me to meet their expectations. But what I didn't know was how—as a puddle of anxious goo—to do anything but shrink away and escape through the nearest air vent. In each case, I could only think of the impact others' words were having on me, as opposed to what was actually being said or why. In each case, I failed to meet the moment.

It didn't take many experiences like those for me to grow desperate to make a change. To claim some semblance of ownership over the pressure I felt at work.

Rather than live or die based solely on whether I was living up to others' expectations, I began striving to simply understand what others wanted while claiming responsibility for setting my own expectations for myself. By gradually decoupling my own sense of urgency and stakes from the way in which others communicated their needs to me, I discovered a freedom of movement that empowered me not only to thrive in otherwise unhealthy situations, but to meaningfully improve the environments that create them. It's been a years-long project, and I still struggle at times, but I can honestly say that I've wrested back control of whatever knob governs my internal pressure valve, and I've learned how to adjust it to gather the motivation I need to do great work.

I don't know where you're at or what you need, but perhaps there's something in my telling of it that will encourage you to revisit your relationship with the pressure you feel in your own life.

No pressure. 🫀