The early version of me was fucking insufferable.
Certain about things I had no business being certain about. Loud in exactly the rooms where listening would have served (everybody) better. Carrying the particular arrogance that comes from getting enough things right early that you mistake luck and aptitude for wisdom, and then getting rewarded for the arrogance, again and again and again, which is the part nobody warns you about. Basically, insecurity with better posture.
I know when it all came crashing down on my end. Roughly. And it's all around the Call of Duty 4: Modern Warfare Xbox Beta debacle and a gentleman by the name of Tim Bergeron at Activision.
I had maneuvered my way into the enviable position of Director of Technology for an interactive agency who had scored the contract to handle the web presence for distributing Xbox Live tokens for the COD4 Xbox beta. The agency was paid a fixed rate for the project and I was hell bent on getting a profit while consistently being warned about how bad failure would be. Downtime wasn't an option. So I had a budget and a mandate. I, repeatedly, didn't listen to Tim when he offered to let us host on the Activision network. Which, when all things were done, ended up with me (personally) taking down Yahoo! (of all things) as collateral damage along with the hopes of millions of Xbox gamers of getting Beta tokens at the promised time.
So, yeah, sorry 'bout that.
Tim was a smart guy. A sharp guy. I just didn't listen to what he had to say, in front of people whose opinions I cared about. That's a specific kind of quiet. You do not argue in that moment. When the smoke clears, you sit there doing arithmetic on every other time you'd been that sure.
It happened enough times that the bravado stopped being sustainable. Humility was a conclusion I got argued into by circumstance, repeatedly, over about a decade. Nobody chooses it. It gets fucking installed.
These days I'm the person who makes themselves the punchline, and the world cooperates enthusiastically.
Someone at a conference assumes I'm there as a vendor. A client in an early meeting talks past me to the guy in the better jacket, addressing his answers to a person who will later ask me what the answers meant. A stranger at a networking event gives me the polite-exit smile before I've said anything worth remembering, already scanning past my shoulder for a more promising conversation.
I've never felt much need to correct any of it. The work does that, eventually, and the correction lands harder when it arrives on its own instead of being announced. An expert who introduces himself as an expert and then performs accordingly has confirmed what you were already told; you file it and move on. Someone who seemed unremarkable and then wasn't, that sticks. Surprise outlasts expectation. It's not a strategy so much as something I noticed I'd been doing for years and then decided to keep doing on purpose.
Professionally, I'm certain now for almost the opposite reasons I used to be. When there's an architecture decision on the table and the room is split, something settles rather than rises. I had that feeling recently while designing AdAstra's content model. I kept rearranging the design because every version looked cleaner from one angle than another. Eventually every experiment collapsed back to the same shape. The certainty used to be a thing I generated; now it's a thing that shows up or doesn't, and I've learned to notice which.
Outside of work I present the other way entirely. I downplay. I let other people have the floor. I play the lovable idiot when the situation calls for it, and the situation calls for it more often than you'd think. Most people read that as insecurity, which used to bother me and stopped bothering me somewhere around forty.
The distinction is between what you know and what you need. I don't need people to know what I know.
That's the tidy version, anyway. I believed it completely until the thing I actually want to talk about.
A dozen years ago, I built a company that spanned seven years with people I'd have called my closest friends, and I'd have said it without hesitating. And I'd have been right at the time.
We built a company called VITY together. Before it was a business it was just friends with an idea, stealing evenings and weekends because building something together sounded more exciting than resting. We celebrated releases at two in the morning, argued over features we'd swear were existential until someone hung up in exhaustion, and slowly accumulated the kind of shared history you mistake for permanence. Before long, I stopped thinking of VITY as something we owned and started thinking of it as proof we'd always be in each other's lives.
It ended the way those things end, which is to say slowly and then all at once and then permanently. VITY died, abruptly, overnight, but it was a death long in the making. We just didn't want to face it but, I believe, we all made our peace with it. What I had not made peace with in advance was that the friendships went with it, on the same schedule, as though they'd been line items on the cap table.
I no longer talk to 90% of those that were within VITY.
There's a decade of closeness back there and a silence sitting on top of it, and the silence has now lasted long enough that breaking it would itself be an event. I think about it more than I think about any deal I've lost.
Then there's a friend who runs a cleaning company, whom I wouldn't hire.
Nothing to do with her work. Her work is fine; by every account her work is better than fine. I just no longer mix money and friends. I've held that position long enough that it stopped being a preference and became a principle.
She heard something else. She heard that I'd looked at her business and passed.
I still think the policy is correct. That's what makes it sit badly. There's no version of the conversation I can replay where I say the true thing and it doesn't land as the other thing, and the reasoning being sound turns out to be almost entirely beside the point. The conversation left a residue that the argument didn't dissolve.
Here's what I noticed, turning all of that over at two in the morning, which is when the sorting happens: none of the things that keep me up are things where somebody underestimated me.
Not the client who talked past me. Not the conference vendor assumption. Not the room where I was the least impressive person in it right up until I wasn't. Those don't linger. They resolve or they don't, and either way I'm fine by Thursday.
I don't mind people thinking I'm less capable than I am. I hate people thinking I'm less kind than I am.
The work eventually shows what it is. The person revises their assessment, or they don't and you go work with someone else, and in neither case are you carrying anything. Whether they understood you is their project. You are, in no way shape or form, required to help with it.
The other kind doesn't work that way, because it isn't about perception at all. Nobody is wrong to be hurt by being hurt. That's not a misunderstanding you clear up with evidence, and there's no eventual correction where the accumulated body of work makes it right. You can be entirely correct and still be the reason someone feels smaller. My friend with the cleaning company is not mistaken about how that conversation felt.
So the confidence isn't what I thought it was. It's not that I think highly of my abilities and have gracefully declined to advertise them. It's that the abilities are the least interesting thing I'd want anyone to think highly of. The competence is there or it isn't, and twenty years of work will settle that question without my participation. What I'd actually like people to think well of is the kindness, the reliability, whether I showed up when it counted. None of which is demonstrable through a portfolio, and all of which I'm considerably less sure about.
Someone who had this figured out would land it cleaner. More resolution, a lesson learned, a bow. What I've got is an observation and no particular idea what to do with it: being underestimated professionally has almost never cost me anything, and falling short as a person, even in small ways, has cost me more than I would have guessed.
I've never needed people to think highly of my abilities. I've only ever hoped they'd think well of me.
I'm still working on the second one.