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Finding Your Swagger

2021-11-06

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.


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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.



NOTES

[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.