This week on Random Access Memories, I’m diving into my conversation with Adam Arellano, Field CTO at Harness, and genuinely one of the most interesting and thought-provoking people I know.

Adam is hard to miss. Red hair. Kilts. Occasionally heels. Very strong opinions.

But what I loved about this conversation was getting underneath all of that.

We talked about why Adam deliberately stands out, what his younger self has to do with it, why senior security leaders probably aren't as technical as they think they are, why you should actively seek out people who disagree with you, and why obsessing over success might actually make you less likely to achieve it. Let's get into it →

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You don't stand out by following the same path as everyone else.

Adam is visually impossible to miss. Red hair, kilts, occasionally heels. But his point about standing out went much deeper than appearance. Too many people follow the same well-worn career path and build roughly the same skills. Adam thinks you should work out what your particular mind brings that others don't, then lean into it.

Standing out isn't about being louder. It's about knowing what makes you different.

You probably aren't as technical as you think you are.

This one hurt. Adam's argument is that lots of senior security people still think they're technical because they once were. But the skills we had 10 or 20 years ago aren't necessarily relevant today. You can't spend your days leading teams, talking to customers and building strategy while staying immersed in technology at the same depth.

You might be technical in 2006. Unfortunately, it's not 2006.

Stop looking for people like you.

Adam's favourite working relationship was with someone almost completely opposite to him. Adam saw the big picture. His colleague lived in the technical details. Together, they effectively ran security for a 4,000-person organisation. Adam actively looks for people who fill his gaps rather than reinforce his strengths.

Don't build a team of people who think like you. Build one that sees what you can't.

Study humans like you studied technology.

As technical depth decreases, communication becomes increasingly important. Adam thinks we should learn it the same way we learned technology: read, practise, get things wrong, reflect and try again. We spend thousands of hours deliberately developing technical skills, then somehow expect leadership and communication to happen naturally.

Humans might be the most complicated technology you'll ever have to learn.

Being right isn't enough.

Adam has a painting behind him that says: "It's more noble to be effective than to be righteous." We compared it to punk. You can stay underground, preserve your purity and have nobody hear you. Or you can become Green Day, compromise a little and reach millions. Security has plenty of people who are technically right but completely ineffective.

Being right means very little if you can't convince anyone to do something about it.

Adam said something in this episode that stuck with me: "There was no language for what I was feeling."

He was talking about growing up in the 90s and not having the words or visible examples to understand his own identity. If he'd seen someone like himself today, openly weird, queer, successful and respected, maybe his younger self would have understood himself sooner.

It made me think about how often we experience something before we have the language to explain it.

Burnout. Imposter syndrome. Anxiety. Being in the wrong career. Feeling successful but unfulfilled. Or simply feeling like you don't quite fit the version of yourself everyone expects you to be.

Finding the words doesn't necessarily change the feeling.

But it gives it shape. And more importantly, it tells you that someone else has felt it too.

That's why Adam being so visibly himself is more interesting than personal branding. He described it as "talking to my past self."

He's trying to be the person he needed to see when he was younger.

I think there's something powerful in that for all of us.

As we get further into our careers, maybe our responsibility isn't to look more like the people who came before us. Maybe it's to become more visibly ourselves so the people coming behind us can see another way.

Sometimes being visibly yourself isn't about getting people to look at you. It's about making sure someone who feels alone can see you.

Adam finished the conversation with something that hit me harder than I expected.

He said the more anxiety you attach to success, the worse you're likely to perform. Do everything you can, but eventually you have to let go and accept you can't control what happens.

His words were: “The sooner you stop caring about success and start caring about yourself while participating in that process, the better off you'll be.”

My immediate response was basically: shit, I think I needed to hear that.

I turned 40 last week. You can't really prepare to turn 40. It just happens. But it inevitably makes you look backwards a little.

I've spent most of my adult life chasing something. The next role. The next company. The next speaking opportunity. The next financial target. The next marathon time. And whenever I get there, I'm remarkably good at moving the finish line again.

Meanwhile, Ollie is 12 and Izzy is 8. Those numbers don't wait for the next promotion.

Ambition isn't the problem:
I don't want to stop being competitive or chasing difficult things. That's part of who I am. But there's a difference between wanting success and needing it to feel successful.

The finish line will always move:
There's always another job, number, opportunity or goal. If happiness exists on the other side of the next achievement, you can spend your entire life nearly reaching it.

Some things can't be chased later:
I can run another marathon. Build another company. Take another job. I can't go back and have another Tuesday evening with my kids when they were 12 and 8.

Maybe turning 40 isn't about chasing less. It's about getting slightly better at noticing what I've already caught.