Keeping the Stack Tidy
On chair dancing, red cards, and practicing how to ignore “should”
Over a decade ago I sat on a too-soft couch in a renovated century home with a woven jute rug under my shoes and a Starbucks cooling in my hand. The coffee table was just far enough away to be annoying, and too heavy to drag closer without making a scene. My therapist looked at me and said, “Don’t should on yourself.” I remember almost smiling at the pun. At the time I was obsessing over how a good husband should behave, and it wasn’t helping.
The Voice Softens
Therapy helped. We were able to rebuild our marriage, and the habit of reflexive self-censoring softened. I later learned the phrase is usually attributed to Albert Ellis, the American psychologist who founded rational emotive behaviour therapy. Smart guy.
The voice doesn’t fully disappear, but it loses authority.
I still believe the core truth of Ellis’s advice. The word should can tighten a life quickly - tying you up like a straight jacket. But now, when I feel it popping up, I can usually hear the texture.
In one-on-one conversations, it’s faint. Almost polite. In small groups, it clears its throat. In larger rooms, I catch myself editing in real time. On social media, it still spikes. Every sentence lines up for inspection before it goes out.
The pattern is consistent. The less control I have over how I might be interpreted, the louder it gets.
The difference now is that it sometimes makes me chuckle. I can see it forming. And that gives me the chance to decide whether I want to listen to it.
Templates
A mentor once explained this to me when I was raising money for my first startup. He told me, almost casually, that being male, mixed white and Asian, and wearing glasses would probably work in my favour. I laughed at the time. Years later, after time in tech and HR and reading I wish I’d done earlier, it stopped being funny.
Senior decisions are rarely as objective as we hope or pretend. Whether it’s hiring, investing, or promotions, most of it is pattern-matching. People carry a template in their heads of what “works.” Every deviation from that template is a small red card. One is fine. Two is interesting. Stack enough of them and the deal dies without anyone saying why.
When you’re the one being evaluated, minimizing red cards feels rational. For a lot of high-performers, “should” becomes a strategy. Don’t wear that. Don’t say that. Don’t post that. Keep the stack tidy.
The successful get very good at self-editing.
Loud Socks
Originally, stretching myself didn’t look dramatic. It looked like socks.
I was raised on lines like “look respectable” and “dress for the job you want.” Twenty years ago my rebellion was bright, slightly ridiculous socks under an otherwise standard tech uniform: dress shirt, jeans, safe shoes. If anyone asked, I’d say they gave me something to smile about during the day. The rest of me stayed within the lines.
Later the shirts got louder with more colour. More comments followed, but nothing catastrophic.
Five years ago I gave a conference talk on AI and left the collared shirts at home. Black t‑shirt. Armband tattoo visible. I didn’t think much of it.
Afterward, someone came up to connect. “The moment you walked out in a t‑shirt and tattoo,” he said, “I knew you’d be cool and worth talking to.”
It struck me as slightly absurd. A shirt and some ink were enough to signal deviation. Enough to count as cards.
Holding the Stack
When I’m the one investing or hiring, I notice how easy it is to add cards without meaning to.
I’ve sat through interviews where, afterward, someone leans forward and says, “I’m not sure they’re a culture fit.“ Years ago, I might have nodded and moved on, especially if I already had other doubts. The sentence sounds reasonable. Mature, even.
Now I tend to pause and ask, “What would they add?“
I’ve watched the same dynamic play out with boards recruiting directors, conference planners choosing speakers, even small community groups organizing camping trips. Without something deliberate in place, it’s remarkably easy to drift back to the template.
At our most recent company, that question became part of the hiring process. We built a “culture add” interview instead of another fit check. It wasn’t even my idea. Someone else noticed the pattern we were sliding toward and codified the counterweight. The result wasn’t dramatic. Just a team that looked less like a template and felt more at ease.
I strive to remind myself that power shifts the responsibility. When you hold the stack, you don’t just manage red cards for yourself. You influence how many cards other people feel they have to carry.
I’m more comfortable one‑on‑one than I am in big rooms. I’ve heard the same from others, especially in work settings where hierarchy is obvious. So I try to build from there. In meetings where I’m the more senior person, I know my reactions weigh more than I’d like them to.
A couple of years ago I had a director who also liked ridiculous shoes. I get a kick out of party shoes especially; my shoe section of our closet at home is bigger than my wife’s, and it’s not because my feet are larger. We lived across the country, so we started each video 1:1 by showing whatever ridiculous pair we were wearing and telling the story behind it. It was unnecessary, slightly absurd, and definitely outside what a one‑on‑one “should” cover.
Once we’d contrasted preferences and compared colour choices, it was easier to talk about the things that didn’t fit neatly into a quarterly plan. Doubts, experiments, and mistakes all became less threatening.
When I go first — admit I’m unsure, share something unfinished, or just show up in loud shoes — the temperature changes. The stack doesn’t disappear. But it feels lighter.
The Knee Slide
A couple of weeks ago my wife and I signed up for Valentine’s dance lessons. at the aptly named Underdog Dance Corp. She’d been taking heels classes for a while, and this time the format flipped. Magic‑Mike‑style chair dancing. We were the ones performing; our partners were the “guests” in the chair. The ads were perfectly provocative and I knew I’d be out of my depth.
I went to post about it on Instagram.
I typed something fun, read it back, and hesitated. Was posting about a chair dancing class appropriate? As a CEO? As a father? As someone who occasionally writes about responsibility and judgment?
Before I could decide, the app crashed.
The juxtaposed relief and disappointment were immediate.
I’ve met that reflex before.
I posted it later anyway. The sky didn’t fall.
What surprised me more was how the same dynamic showed up in conversations afterward. Most of my male friends admitted they’d feel uncomfortable about doing something like that. You could see them scanning the room, checking other men’s reactions. Chatting with women, though, was totally different. They loved the idea. One guy heard his partner’s reaction and suddenly he was game. What had felt like a red card turned green in real time.
For what it’s worth, I nailed the knee slide. The floor was forgiving. No permanent damage.
Ten years after a therapist’s office, five years after a black t‑shirt, I’m still noticing what I’m about to post.
The voice is quieter now.
It still tries to keep the stack tidy.
A Note on Practice
Funny thing: talking about the chair dance class has been way more uncomfortable than actually going.
The class was great. Fun music, creaky hardwood, a room full of adults pretending we weren’t self-conscious. Posting about it? Waaaay harder.
I could feel myself drafting for imaginary critics. CEOs. Investors. Friends. Whoever lives in my head that carries clipboards. When my wife shared the video clip to our family chat, the reactions were expectedly awkward. Definitely make writing more challenging.
Also kept thinking about how easily we hand “shoulds” to our kids. That’s probably its own essay, and I’m still mid-practice on that one.
If you’re local and the dance thing sounds fun, the instructor said they’d run more if there was interest. Happy to connect you. Or just follow them: https://www.instagram.com/underdogdancecorp/
Still makes me laugh that the bravest part of the whole thing was a blinking cursor.
In the Margin
Here are a few things this piece kept brushing up against. I’m sharing in case you find them interesting as well.
What I’m Reading
Recent articles I’ve enjoyed and recommend
The “culture add” idea matters more than people realize. Fit keeps things comfortable. Add makes things better. In my experience, sometimes being slightly outside the norm is what makes you more relatable. Happy Thursday Joseph!
Wow - the culture add is a huge thing. I’ve been a part of enough ‘we’re like family’ cultures to know what that really signals - they’re all alike. And if you’re gonna fit in, you need to be like them, too. I’m adding this phrase to my growing list of interview questions.
As a lifelong contrarian thinker, I’ve learned to not ‘should’ on myself. I’m aware what I bring so others can take it or leave it. I want to be somewhere that my slightly introverted self can be appreciated instead of looked down on as a non-team player. Or that my indifference to great swag isn’t a personality flaw. Or that my preference to work solo isn’t a move to silo information.
Loved this post!