A break from doing the tech to working in tech….

I’m me. People who actually know me, know me. I’m nowhere near perfect. I have a ton of flaws, and over the years I’ve tried (sometimes hard, sometimes not hard enough) to become a better version of myself. Sometimes it’s two steps forward and ten steps back. Sometimes I catch myself mid-mistake and think, “Why the hell did I just do that?” and I’m genuinely pissed at myself for it.

The reality is I push. I’ve always pushed. As a kid I tested every limit, and as an adult I still do. Other people seem to have learned the softer edges of that impulse. I know the edges exist. I just… don’t always stop at them. It’s not ignorance. It’s wiring.

I’m driven to do big things. I get a lot of FOMO. I’m not a university or college grad, and that fact has sat in the back of my head for decades like a quiet countdown timer. The fear that at any minute the career could end and I’d be back doing whatever random job I could find. When I screw up, that specific fear hits hardest. I still wake up some mornings thinking “I’m getting fired tomorrow.” People say “You’d get hired anywhere.” Ever actually tried that in a competitive space when the narrative isn’t clean? It’s not the soft landing people imagine.

At my core, the thing that cuts both ways is authenticity. Wearing my emotions on my sleeve. Being exactly who I am in the moment. That same authenticity is what gets me in trouble sometimes, and it’s the thing I worry will one day burn the whole thing to the ground.

We live in a world where one mistake, one slip, one sentence said out loud or typed too fast can’t be taken back. The permanent record is real now. Even writing this I’m sitting here asking myself “Should I really put this out there?” or “Maybe I should just keep quiet.” – I have colleagues who made one mistake too far, and an angry mob turned friend to foe, and did everything they could to burn that person career and life to the ground. I have seen some ugly ugly things done by angry internet mobs against people who made a bad mistake. Humans make mistakes, it doesn’t make some of what I have seen in the past ok.

Pick any of the thousand diagnoses floating around. I’m sure I have a little bit of all of them. I just think it’s the human condition. The drive, the FOMO, the self-doubt, the occasional emotional overshoot — they’re not unique. Research keeps showing that something like 70% of professionals deal with imposter feelings at some point. Even people who look like they have it completely figured out still hear the same voice.

Brené Brown has spent years studying this exact tension. She describes authenticity as “a collection of choices that we have to make every day. It’s about the choice to show up and be real.” She also warns that trading authenticity for safety often exacts its own cost — anxiety, resentment, a kind of quiet grief. Vulnerability is the birthplace of the good stuff: connection, courage, creativity. But she never pretends it’s risk-free. I feel this to my very core.

I’ve been a people leader for about 15 years now, and the one thing I keep learning is that leaders never stop learning how to be better leaders. Two people I keep coming back to are Brené Brown and Marcus Buckingham. They come at it from different angles, but they both point at the same hard truth.

If you want authenticity and vulnerability on your team, you have an obligation to respect it, honour it, even cherish it. And if you’re going to do that, you also have an obligation to be prepared to pull the chute when someone goes over the line — and to do it in a respectful, leadership way that helps them rein it in. The key is not kicking them when they’re down. Being too safe, as Brené talks about, creates its own problems. We want our people to be vulnerable, which means we have to show them it’s actually okay to be. That requires creating the conditions where they can drop the armor without getting punished for it.

There’s another version of this that doesn’t look like punishment but still wears people down. Someone once called it “toxic coaching” — the leader who is constantly pushing people to be better, even when something is already good. If you catch yourself saying “that’s great, but…” all the time, that might not actually be great. Sometimes good things need to just be good things. Constant developmental pressure, even when well-intentioned, can feel like the armor never gets to come off. People stop bringing their real selves because they know the next sentence is always going to be the improvement note.

Marcus Buckingham has always pushed the idea that great managers don’t treat everyone the same. They see the individual. They focus on what people do best and help them lean into it. Authenticity isn’t some soft luxury — it’s the only sustainable way to get real contribution. People can smell when you’re faking it. As he puts it, if you’re faking your beliefs, they can smell it, and they don’t want to follow it. The same applies upward. I want to be authentic because being fake is exhausting. It’s like a six-year-old’s lie that just keeps compounding until you can’t even remember the first one, and now you’re in real trouble.

But authenticity only works if the people above you have enough humility and compassion to meet it. If you want vulnerability from your people, you have to lead with compassion. You can’t constantly brow-beat them — or constantly coach them — and then act surprised when they put the armor back on. Who we are is how we lead. If the environment only rewards the polished, controlled, or perpetually improving version, that’s the version you’ll get — and you’ll lose the real contribution that comes with the unfiltered one. This will require real cultural change in organizations to achieve.

So what do you do with that?

I don’t have a clean system. All I really have is the same imperfect loop most of us run: notice it, feel the regret, try to do better next time. Name the pattern when it shows up. Lean harder on the people who already know the full version of you — the ones who can say “Hey man, I get it, you’re upset, that’s okay” without making it a referendum on your character. My best friend does that for me. He knows me better than almost anyone, and I suspect it’s because he’s wired the same way. He is my 1000% safe space, he’s the one I can call 24×7, who will drop whatever and listen to me. Now don’t get me wrong, he won’t sugar coat, or tell me it’s ok if I did something wrong – but as he says “Let’s do the floor work”. He knows who he is, and I cherish him like no other human on earth for being my friend.

And yes — sometimes when things get frustrating or the pile gets too high, I catch myself thinking “Can’t I just get someone else to do this?” because I’ve had enough. That’s human too. The work is learning when that thought is a legitimate signal to rest or ask for help, and when it’s just the old escape hatch. Adulting is hard.

If you’ve had a bad interaction with someone — personal or professional — try giving them a little grace. You don’t know the full weight they’re carrying that day. Most of us are doing the best we can with the wiring we were given, and the scoreboard rarely looks as clean from the inside as it does from the outside.

I’m still trying. That’s all I’ve got.