Untangling Management, Leadership, and Making Cool Stuff

How I learned to embrace (eventually) my inner leader.

For as long as I can remember, I’ve always been the person in my group of peers, colleagues, and friends avoiding any kind of management or leadership role. Managers and leaders always seem to get in the way of making cool stuff. Now, I’m beginning to realize it’s my flawed perception of management and leadership that’s getting in the way.


Photo of my first office (garage).

Leaders. Who needs ‘em?

Very early in my career I started a web design company with a good friend. I was learning about web design and business much faster than I had in college or as an employee. Within a couple of years the two of us were working with nationally recognized brands. We were busy, consistently raising our prices, and building a solid reputation.


Even ten years later, I look back on that time fondly. We were living the dream. But then everything changed.

We hired an employee. Then another… And another… Until I realized I actually had to manage people. Maybe even lead them?

Over the next few years we kept growing. We were working with more and more nationally and internationally recognized brands. Unfortunately for me, life just wasn’t the same. To the outside world it looked like rainbows and sunshine, but I was getting more and more frustrated. I didn’t realize what I was struggling with at the time, but now it seems clear.

It was managing and leading people. Or more precisely, it was being responsible for the growth, happiness, and success of someone other than me. Ain’t nobody got time for that!

I wanted peers, not employees. I wanted colleagues, not subordinates. I wanted friends, not followers. I’m obviously not cut out for this management and leadership stuff.


Photo of Performable’s (my favorite client) first office.

Startups are cool, right?

Eventually I stepped out of the company and dedicated all of my time toward consulting for startups. It was a tough couple of years. My previous reputation didn’t mean a lot in this brave new world and I wasn’t anywhere close to my previous comfort zone.


I was making things that people intensely needed at an extremely fast pace. I wasn’t following things through to the nice, polished result that I typically expected from myself. This was frustrating, but it was a different kind of frustration. It was a frustration in my lack of skill in prioritization, awareness, and seeing the larger context clearly. These things I can learn, and I was learning again. In fact, I was learning at a pace I hadn’t experienced in years.

For a while it was intoxicating. Everyone seemed to be pulling together to get things done. Supporting each other even when it was out of our comfortable skillsets. We had to help each other out of necessity, or the company just wouldn’t work. It felt just a little closer to peers, colleagues, and friends.

Eventually, clients started believing in me enough to work directly with the people building the products. Not as an outside consultant with a primary contact, but as a team member. I wanted to stay in the comfortable peer, colleague, and friend zone. I didn’t want anyone to be reliant on me or for me to be reliant to anyone other than the person writing the checks. To my horror, this was exactly where I found myself.

I’d just spent the last few years climbing a new career mountain to get away from this. What had I done?


Photo of HubSpot’s Engineering Team area.

The bigger the better?

Shortly after realizing the predicament I had put myself in, the next major opportunity on my career showed up. An offer to join a larger company in a semi-influential role. Large enough to have a noticeable hierarchy. Large enough to have several structured teams.


Instead of avoiding people, I thought it would be good to jump into the deep end and learn how to work with people. Somehow, I’d made it a decade into my career without needing to think or care about any of this. It was time to grow up. This could be the next major learning curve of my career.

I was right, I was learning again. Learning like crazy. But it was all weird…

It had never occurred to me how the desire to change something can feel surprisingly intimidating when there are layers above you. Now you have to worry about pissing people off for doing something that could overlap with another’s work. Plus, you need to accommodate all of the people who think they deserve to know what you’re doing because they’re “responsible” for you.

How can you get anything done under these dreadful conditions? Woe is me!

To grow in this environment I needed to seek out new internal and external resources without relying too heavily on my coworkers (resourcefulness). I had to learn when to let things go and when to keep pushing (awareness). I had to learn how to keep something important in progress without letting the naysayers bog me down (determination). I had to care about other people’s goals and understand how that they related to my goals (empathy).

It’s hard. It’s confusing. Only now, almost three years later, do I feel as though I’m getting the hang of it.


Photo of my dad, Buddy, and I in Idaho.

What do I know now?

I’m loving this new learning opportunity, but these challenges don’t feel like things I could learn by grabbing a few business books, going to a conference, or reading some designer blog posts. The more I search for relevant advice, the more I’ve ventured out into psychology and self-help books. The more I find myself talking to my friends and family.


People mature through different things at different speeds. Heck, I didn’t even know what a team larger than two really felt like until I was a decade into my career. We can’t reasonably expect everyone to have the same social abilities and know what a strong and effective team requires at at any given time. Those are skills that need to be developed and practiced just as aggressively as domain knowledge and tool competency.

Through these last couple of years of trial and error I’m starting to feel like I have it all backwards. I never needed to manage anyone, just contribute so the team can get things done. I never needed to be a leader to anyone, just help wherever I can. I never needed to perceive employees or coworkers differently. All I need to do is treat my team exactly like I treat my friends.

I still don’t know if I’m cut out for any of this management and leadership stuff. But now I know what management and leadership means to me.

Also, making cool stuff is fun again.
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