Photo by George Becker.
Last week, 500 pounds of paint came off the exterior of the 1920s bank building that serves as our headquarters. 500 POUNDS OF PAINT. Do you know how much paint that is? So much! Never mind that limestone is porous. Never mind that the stone needs to breathe or it erodes. Someone applied the first coat in the 80s and after that not a single person with a paint brush stopped to ask if they should. They just did. Layer after layer. Coat after coat. Year after year.
Forty years later, with the right tools, the paint comes off in big strips. From the place where the building touches the sky right on down to the ground. Just one enormous metaphor for shedding skin and putting down the things that no longer serve you. And from that place of naked truth, figuring out what happens next.
Our people are starting businesses, ending businesses, going back to school, buying first houses, moving cross-country, and doubling down on community in the cities where they live. They are choosing to feel optimistic about the world, despite little evidence to support said optimism. They are on the move both figuratively and literally. And have we mentioned that this is all happening just in time for the building to shed 500lbs of paint? Coincidence? We think not!
No fate but what we make
The neat thing about humans on the move is that many of these changes are less table-flip and more thoughtful culmination of thousands of data points. And so while the punchline sounds big, if you’ve been paying any attention at all, these moves are just a natural extension of things already in motion.
Sure your city-dwelling friend is heading to the woods, but if you’re honest with yourself, they’ve been craving more green space for a long time now. And yes, that founder just sold to PE, but when you stop to think about it, they’ve been very tired for a very long time and were struggling to raise a new round of funding. Your colleague is going back to school after surviving multiple layoffs. Well, watching the workforce steadily dwindle around them is enough to put anyone in a reflective mood. Less table flip. More 999 steps in the rearview that make the thousandth a foregone conclusion.
Humans are quite leaky. If you listen, they will talk about the 999 steps along the way. They will tell you about a graduate program that caught their eye. Or the last vacation where they felt their heart unfurl. Or the business they’d love to start…someday. This listening and paying attention to the details makes you a good friend. But the same skill set also makes you a good boss.
Your team is full of people 999 steps on their own paths. And sometimes that’ll line up quite nicely with your org and what you’re trying to get done. And sometimes those things will be totally at odds. Most bosses develop an intuition for when something’s brewing. But every so often, we meet a boss who is perpetually surprised by big changes for their reports. When we ask them to reflect, they acknowledge that things had gotten busy, their 1:1s had gotten irregular, and that the signs were probably there if only they’d bothered to notice.
If this describes your management practice right now, we need to have a word. We don’t need you to plot your people’s every move. We don’t need you to over-index on every graduate program that’s mentioned in passing. But if you haven’t been listening because the market is tight and hiring is a shit-show and sure your people might not be happy per se but they also don’t have a lot of alternatives — expect to be surprised.
That’s what the money’s for
Look, there are seasons to management, for most bosses. There are times, weeks or months or maybe even years, when every day at work is a chance to help your people grow. To put cool opportunities in front of them, to listen to their ideas because you know that one of those ideas might be the future of the business. Conversations rooted in mission, and values. Those are good days. Shoulders-down seasons, when work can actually be a site of meaning and fun, when change is an opportunity, not a threat. The managers we talk with try to live in these days as often as they can.
But there are other seasons. Seasons when money is tight, or your own boss is sitting on your head. When you’re in meetings with people who’ve been shouting a lot lately. Or meetings where they’ve been methodically making the next round of layoff lists. It’s not true that you stop caring about your team during these stretches, it’s just that caring often manifests as keeping everyone locked in. Heads down, boats not rocking, hitting targets even if they don’t make sense. Managers talk about being shit umbrellas and while that’s generally not a great model for transparent and accountable teams, we get why some seasons bring out a desire to hunker down, instead of lifting up. In those moments, the message floating in the air, whether anyone says it out loud or not, is: you’re lucky to have this job. I get that you may not love what’s going on right now, but that’s what the money’s for. Let’s just get through it.
One of the wild things about the last several years is that we have thrown entire industries, entire sectors of the economy, into shitty seasons in lockstep. This isn’t a coincidence, particularly not in the case of tech and tech-adjacent spaces, where it’s pretty clear that the major employers synchronize their efforts at labour and wage suppression. But from COVID lockdowns and layoffs, to RTO mandates, to anti-DEI backlash, to compulsory AI use followed by more layoffs — the median worker experience in an impacted org has been pretty fucking bleak. To say nothing of those looking for work.
So when we tell you that we see a pattern emerging. That people are making moves, changing up where they live, how they work, and the stories they tell about themselves. That’s noteworthy to us for three reasons. First, it’s noteworthy because it hasn’t gotten any safer to make these changes, but they’re making them anyway. Second, because change begets change. When you see other people, and other orgs, re-assess and start to tell a new story, it shakes things loose in your own storytelling, and makes your own friction points louder.
And third, because if we’re seeing it in as many places as we are already, then it’s coming for you, too.
Fresh eyes on old stories
The season is changing.
The season of “keep your head down, be happy you have a job” is running out of steam. Zuck — forever a beacon of horseshit management — has spent years leading from that place. He’s now been reduced to ordering his remaining staff to have more fun. They aren’t happy, and they aren’t keeping their heads down. We don’t have a lot of love for folks building nightmare surveillance apparatus over there, but it’s nevertheless clear that the money and the fear doesn’t buy him the compliant workforce it used to.
We know that you aren’t him (unless, Mark if you’re reading this, get wrecked!), and that you don’t run your team the way he runs his. But your team is also on the precipice of big change. And change begets change.
So the first thing to do is probably to let your shoulders down. As a boss you’re about to be called on for some flexibility and creativity, and hunkered down is not a good pose for that. Your people are changing. Each in their own way, but also sort of all at once. You don’t need to fear that.
Because, as luck would have it, your org probably has some pent-up change, too. Even if your mission and your values are the same (are they?), the way you do your work is probably different. And that means there’s an opportunity for your people to show up differently, too. If you listen — to the changes in your team, and the changes in the org — you will often find incredible opportunities hiding.
And yeah, if it helps to name it: one possibility is that they will have changed in ways that have them leave your team, or your org, or the whole industry. That might be a commentary on you, sure, but it might also be that they’ve been walking down their road for hundreds of steps while you’ve been walking yours and it’s just now clear how far those paths have diverged. In any event, if that’s where we are, it won’t help to suppress it, or avoid the conversation. Pretending away your downside will make you miss the upside.
Because some of them are ready to take on bigger roles, or to expand laterally in surprising ways. Some of them have wacky ideas they’ve been waiting to share with you until it felt like there was room for wacky ideas again. They, too, might be choosing optimism, and your team can be where that optimism flourishes. Finding a way to channel that optimism into work that the org needs is the good stuff of management. There’s not much better, as a boss, than seeing someone grow into a role they are almost ready for, and watching them utterly crush it.
— Melissa & Johnathan
