Boss. Friend. Boss Again. Reality Check. Unpaid Therapist. Whatever This Is.

Honestly, after 11 years, I think I have given up trying to define this relationship.

I met him in 2015. He was my first boss.

And you know how people say your first boss can either make or break your career? Well, mine gave me something much better. He gave me the space to decide what kind of professional, and eventually what kind of person, I wanted to become.

I worked with him for years, and it was probably one of the easiest relationships I have ever had.

Not because the work was easy. God, no!! But because the relationship was.

There were no mind games. No second-guessing. No trying to read between the lines. No wondering whether an honest conversation today would become a problem tomorrow.

There was trust. There was discipline. There was space!! (Aaah the space!)

I was treated like an adult. (Revolutionary concept, I know.)

He gave me opportunities I probably had no business getting at that stage of my career. And instead of hovering over my shoulder, he trusted me to figure things out.

Sometimes I did. Sometimes I made a complete mess of things.

Either way, we talked, we figured it out, and we moved on.

But that’s the professional part of this relationship. And honestly, that’s only half the story.

Because somewhere between the work, the few arguments, the ridiculous conversations, and the occasional moments of questioning our collective sanity, something much more valuable happened.

I stopped feeling the need to be anything other than myself.

Now, anyone who knows me knows that I like to have things under control. My work, my decisions, my emotions, my life. Even when everything is falling apart, I would much rather appear like I have a very detailed plan for how it’s all going to fall apart.

Vulnerability? Not exactly my favourite recreational activity 😅😂

But with him, I never had to do any of that.

I could say, “I am a mess right now.”

And there would just be silence.

Not the uncomfortable kind. Not the kind where someone is waiting for you to explain yourself or justify why you are feeling a certain way.

Just the kind where you know the other person gets it.

No fixing. No judgement. No sudden life-coaching session.

I didn’t have to be the smart one. The strong one. The one who always had an answer.

I could be confused, unreasonable, emotional, completely wrong, or just plain exhausted.

And none of it changed anything.

I think we spend so much of our lives looking for that kind of ease in relationships. Where you don’t have to rehearse a conversation in your head before having it. Where honesty doesn’t come with consequences. Where you can disagree without damaging anything.

Where you don’t have to constantly prove that you deserve your place in someone’s life.

And somehow, I found that in my first boss.

Who would have thought? 😂

The funny thing is, our relationship was never particularly sentimental.

We weren’t sitting around having deep conversations about how much we meant to each other.

Absolutely not. That would have been very uncomfortable for both of us.

Instead, we had conversations. Hundreds of them.

Some serious. Some ridiculous. Some brutally honest. Some that went absolutely nowhere.

And that was perfectly fine.

We could challenge each other, call each other out, say things that other people might take personally, and still have a perfectly normal conversation five minutes later.

There was never any emotional debt to settle.

And over time, he became that person I could go to when I needed someone to tell me what I needed to hear, rather than what I wanted to hear.

Even now, I know exactly when to call him.

Usually after I have overthought everything, explored every possible dramatic interpretation, had my moment, possibly several moments, and finally decided that perhaps it’s time to behave like a rational adult.

That’s when he gets the call.

Poor man 🥲

And the best part? We don’t even need to stay in touch.

We could go two, three, four years without speaking, and I know that when I call, nothing will have changed.

No explanations needed. No guilt trips. No “you forgot about me.”

Just, “So, what’s happening?”

And off we go.

Another conversation. Another perspective. Another little reality check.

Sometimes nothing gets resolved. And that’s okay too.

Because not every conversation needs to end with a solution. Sometimes you just need someone who knows you well enough to let you think out loud.

No performance. No optics. No expectations. Just the comfort of being known.

I don’t think I have ever properly told him what this relationship has meant to me. Mostly because that would require me to be openly emotional, and I have a reputation to maintain and he can puke in awkwardness and say “happy birthday to you too” 😂

But when I look back at the person I was in 2015 and the person I have become today, I know how much of that journey was shaped by the freedom I had around him.

The freedom to try. To fail. To disagree. To grow. To be wrong. To be ambitious. To be an absolute mess sometimes.

And still be taken seriously.

As a leader, he taught me something I carry into my own work today: you don’t have to control people to help them grow. Sometimes you just have to trust them enough to let them find their own way.

But as a friend, he gave me something I value even more.

A relationship that has never asked me to explain, defend, impress, or perform.

Just to show up as I am.

And in a world where so many relationships come with conditions, expectations, and an exhausting amount of maintenance, that kind of peace is rare.

So what is he to me?

My first boss. My mentor. My friend. My reality check. The person who has heard more of my nonsense than anyone should legally be required to.

And someone I know I can call after years of silence and still feel exactly the same ease I felt all those years ago.

Some people teach you how to work. Some teach you how to think. And a very rare few make you feel safe enough to become yourself.

He did all three.

And unfortunately for him, he IS stuck with me now.