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Finding Your Swagger


This is a longer post than usual. I'll start with the punchline so casual readers can get the gist. But the rest will be a long winding path into the details of one of the most difficult professional experiences I've had, all the emotions I felt, and how they eventually led to the following lesson.

I have never been a particularly confident person. I'm not necessarily unconfident, but it takes an unusual amount of effort to build up my confidence. I don't think I'm alone in this.

Thus, I never quite realized the importance of swagger. What is swagger? For me, it's knowing what you're good at and acting accordingly — earned confidence. But it's not arrogance. Your behavior and ability are in lock step.

When you lose your swagger, you lose your self. When you lose your self, you need to spend time alone. When you spend time alone, you are left with nothing but yourself. And only from there can you find yourself, and your swagger, again.

Time for the long and winding part.

This is a story about a time I lost my swagger.

I joined a fast growing startup in 2015. I got the job by cold emailing the head of product. They brought me in for a day of interviews — all typical stuff. Until the end. My last conversation was with two of the co-founders — CEO and COO. They asked what kind of person I was. We talked for an hour. I thought they would thank me for coming in and get back to me in a couple days. They offered the job on the spot [1]. The COO left the room, printed the offer letter, and came back with a pen. I was stunned, but exhilarated. I would be the second product hire and hundredth employee.

My first six months were a whirlwind. The company was growing fast. And it showed. Sales had ambitious quotas. Engineering had more bugs than they could fix. Customers had more feature requests than we could track. I felt right at home.

I jumped in and got my hands dirty. The first problem to tackle was process. We needed a better way to prioritize work. I asked around, got input from all departments, made some changes, and communicated them out to the company. Bugs started going down. Development velocity went up. But we still didn't have a long term roadmap.

Next was focusing on my favorite thing — customer discovery. We set up a research program, combed through customer feedback over the past year (e.g. notes in Salesforce, customer support tickets, interview notes), and aligned on the areas we needed to invest over the next year [2].

Everything seems pretty great, right?

We split the engineering team into two squads. One would focus on the existing product (which was responsible for all our revenue) while another would build a new product to take us to the next level [3].

Then I had a surge of responsibility and attention. The Content team started (temporarily) reporting to me. I was presenting at the weekly all hands. And I was invited to the executive leadership meetings.

They were usually held in the CEO's office. There were two couches arranged in an L-shape, an Eames lounge chair in one corner, and his desk chair in the other . I chose to sit on the air conditioning unit by the window behind the couches [4]. During the first meeting I attended, the CEO asked for my opinion in the middle of a debate. He liked it, and pointed to my answer as an exemplar of critical thinking. It felt good. But little did I know it put a target on my back. The direction I was nudging the company did not align with others.

As the months went by, I started noticing a change. I stopped being invited to those meetings. Instead I would be told the outcome and what to do as a result of them. As a product manager, I didn't see it as my place to question those decisions (even if I disagreed with them). So I went along.

This was the first step in losing my swagger. I lost the ability to question a decision. I let my title, rather than my beliefs, dictate my actions.

Slowly, more and more product decisions were being made behind closed doors. At first they seemed innocent. Over time they became more substantial, diverging from what I was hearing from customers. But instead of challenging them, I stayed silent. Until one blew up in our faces.

I wrote a lengthy email to the CEO laying out my thoughts on the situation. He called me that evening at my personal number and asked why the hell I didn't say something earlier. I described how I was feeling (left out) and he cut right to the core of it.

You lost yourself. What happened to the Kevin I hired? To the spunky kid I took a bet on? You need to get that back, and fast. Or you're not gonna make it man.

I was so confused. How could he say that to me when he was the one who excluded me from those meetings?

Notice how my instinct was to blame him (someone else) instead of asking what I might have done to get into this situation. That sort of mentality means you're already working from a defensive position.

But this was a pivotal moment. I could choose to hear his words, re-center myself, and start solving problems. Or let the gravitational pull of my downward spiral take over. Despite my best efforts, the latter happened [5].

All of a sudden, I started spending a lot of time with the COO. He told me he wanted to get more involved with product. I thought it was great. Then one day, I stayed late to whiteboard some new features with him. I needed to get home but he said how exciting this was and insisted I give a complete download of everything I was thinking. Since I hadn't been performing recently, this made it feel like things were turning around, so I obliged.

Warning, it's about to get real sappy in here. I won't blame you for stopping at this point.

The next day I got to the office early because I was so energized from that interaction. I went to put my stuff down at my desk, and the COO called me into his office. I walked in with a big smile on my face. He cut straight to the point.

Kevin, effective immediately, you are no longer an employee at this company.

I'm pretty sure he said more, but my brain completely shut off at that point. I just sat there, motionless, with tears rolling down my face. I didn't actually feel an emotion. No anger. No sadness. Just a pure physiological reaction.

You know those movie scenes where things get blurry and the sound muddles out? Yeah, that happened. Plus tears.

Once he was finished, my legs carried me back to my desk, I said goodbye to my teammates who had since arrived, packed my stuff in a box, and left. I exited the building onto the corner of 34th and Park Ave, and just started walking. I didn't know what to do. But I knew I had to get away from that physical location.

I knew I should call my wife immediately but couldn't bring myself to do it. She was 7 months pregnant with our first daughter and I was too scared to face that reality [6].

Instead, I walked the Highline for the first time. Despite working in the city for over 2 years, I had never taken the time to visit. I reached the southern end and saw an Ample Hills Creamery. I grabbed myself a cup of Ooey Gooey Buttercake ice cream and sat on a park bench eating it by myself — unemployed with dried tears on my face [7].

You can't make this stuff up people.

I decided to call my parents. They did the natural thing parents do — tell you it's going to be okay, it's their loss, you'll find something better, everything happens for a reason. I heard all the words but none of it mattered. I felt like a complete failure.

Then I finally called my wife. She told me to meet her at the train station so we could go home together. Once we got home, she knew exactly what to say. It just so happened to be exactly what the CEO told me a few months prior (but in her own words).

You lost yourself. And you need to spend the time to find yourself before you look for a new job. What did they first see in you? What are your inherent strengths? What are you better at than anyone else? Why are those valuable to a company? Where did you succeed? What created doubt? How can you protect yourself from those?

I wish I could say I went through a day of rigorous reflection and found myself on the other end. The truth is I really struggled. It required a lot of uncomfortable conversations (mostly with myself). And ultimately came down to writing...a lot [8].

I thought about my best moments. I thought about my worst moments. I derived the behaviors and attributes that led to each. I wrote a list of personal values [9]. I described the best version of myself (professionally) in narrative form. Typically I wouldn't share something like this — and I won't be sharing the full version — but I always find it useful to see real artifacts. So I'm including an excerpt of that narrative here in hopes it resonates with someone and helps them perform a similar exercise.

Start pushing. Live into that dream. Be the one that gets people excited. Be the one that can give the feedback that needs to be given, no matter who they are in the company. Be the one that aligns the company. Be the one that thinks more strategically than anyone else in the company, regardless of titles — they aren't important. Be the one that the company knows in its bones is responsible for the direction of the company. Be the navigation system for the company.

The CEO sets the destination. You get the company there.

You plan a route and know the next two directions by memory. You are reassessing the plan every minute to see if you need to re-route.

Be assertive and opinionated even when you aren't as sure. Go back to having strong beliefs. Know your beliefs. Hold onto them. Especially when it *feels* right. Especially when you can point to historical events. No one should be able to shake you of your beliefs. No one in the company is above you for ensuring the success of the product. Don’t be an asshole about it, but push for what you need and don’t give in to every request.

It is critically important to remember that the above was written by me, for me — not you. You need to write your own version. You need to learn enough about yourself to write it. Then and only then can you live into it. Then and only then will you know how to find your swagger.

If this resonated with you or you ever feel like you lost your swagger and could use someone to talk to, my inbox is always open.


[1] I felt an incredible pressure. It was a powerful move. It felt like an exploding offer. It felt like I had to take it. While I don't regret accepting the offer, I do wish I would have been more thoughtful in evaluating it. Let this be a cautionary note for anyone looking to join a startup.

[2] I'm oversimplifying what happened. It was way more winding. The executive team did not agree on where we should invest. It took a lot of effort to get partial alignment. And even more effort to retain that amount of alignment over time.

[3] Dividing your engineering team this way isn't an inherently bad choice. But the way we did was. You can't put two engineers oncall 24/7 to maintain the existing product while everyone else works on something new. It misplaced the risk tolerance the company could afford from several dimensions. This was a clear showing of my lack of experience (and understanding of the current engineering team).

[4] This is a weird but recurring behavior of mine. When sitting with a (professional) group for the first time, I will always put myself at the edge. It's not because I'm avoiding the "power position" or anything. It's that I prefer to observe everyone first. And the best place to do that, is from the edge.

[5] There are many stories I could tell at this point. But they would be very one-sided and unfair. The truth is, I don't really know what happened behind closed doors. So I've chosen to focus on my own actions. Suffice to say, startups can be a coliseum.

[6] Fortunately, the company agreed to provide COBRA which would cover our insurance costs for the delivery. This was a massive relief (more than I even realized in the moment). For anyone who ever has to fire someone who is expecting, please consider COBRA. It makes a difference.

[7] I went back to that Ample Hills Creamery exactly two years after that day. I had launched a new product at my dream job. I took the day off to explore the city with my now 2-year-old daughter. We walked the Highline together. We got Ooey Gooey Buttercake ice cream. And it tasted so damn good.

[8] It was all handwritten. I don't know if it made a difference. But I couldn't bring myself to sit at a computer. It felt like work. I still have all the pages of rambling thoughts. I didn't try to be very eloquent. It was all about getting things out. It didn't matter how they came out, just that they got out. Then I could sit with the words — like literally sit with the pages around me — and come to terms with them.

[9] I have shared this list with people before, so it's not like some secret. But it felt odd to post it here. My concern is that people would treat it like a new productivity app — something they could quickly adopt that would solve their problems. But that's not how it works. Values are very personal. And need to be built up over time. I started with 3 and have added to that list each year. If you don't have a list of values yet, start small. Start with something you know in your bones about yourself. Then revisit it over time.