My Honeymoon with Clara

October 18th, 2018 by Vlad Giverts

They say that when we fall madly in love, we’re not in love with a real person. We’re infatuated with our idea of that person.

If there are any qualities that we lack in ourselves (joy, self-worth, strength, etc.) we project them onto our object of affection. Somehow that other person makes us feel complete, as impossible as that might be.

For a while, we’re blind to our lover’s flaws and imperfections. Whatever part of us that tends to judge and criticize–even if it’s just secretly in our heads–stays quiet.

But after some time, we start to notice cracks in our ideal image of the other person. We might notice a habit or two that we find annoying. Perhaps we discover this person disagrees with a value that we hold dear.

And we wonder: How did I ever miss this? If only I knew!

But we couldn’t have known. We’re evolutionarily wired to fall into romantic love. Our genetic programming gives us this temporary hallucination for its own ends.

Our imaginative drive is so powerful, there’s little we can do to be fully in touch with our reality.

It turns out that this is true for other types of experiences, too. I’ve often talked of a “honeymoon period” when someone first joins a company. I’ve seen it last three to six months for most people. And I’m no different.

When I first joined my last startup, I had created an idealistic image of how wonderful the company could be. Those ideals blinded me and led me to make mistakes at my job. These mistakes contributed to the company needing to get acquired two years later because we weren’t able to succeed as an independent business.

This is the story of my honeymoon at Clara Lending.

The Bad Breakup

Before I was CTO at Clara Lending, I was a Senior Director at Workday. I was responsible for a team of 60 people, the most ever for me. It was a public company with five thousand employees and the majority knew of me or my team. I had been there two years and had five to six figures worth of stock vesting almost every month–on top of my nice tech salary.

I had status, power, and what was quickly becoming a life-changing amount of money.

I was lucky. By many people’s standards, I should have been grateful. But I was miserable.

I had a bad relationship with my boss. I didn’t respect many of my executive peers (this was on me more than them). I didn’t even respect myself.

I didn’t like who I was at this company. For some reason, I had taken on this persona of a cocky tech entrepreneur. It’s as if impressing people with my flashiness would magically make me more successful.

So when I decided to leave for Clara, it wasn’t because I couldn’t stand Workday anymore, it was because I couldn’t tolerate who I was there.

A Shining City on a Hill

I had many motivations going into Clara and I wrote about them earlier. But what energized me most was my vision of what kind of a company Clara could become–and my role in creating it.

I imagined an environment where everyone was constantly learning and growing. Where it was ok to be vulnerable, to not know, to make mistakes, because our co-workers–our friends–would be there for us. We would trust each other in our good intentions and have the support we need for our personal growth.

This was a place where we could be our full selves. Not just the professional sliver that we feel “safe” to show. Our talents, desires, and fears could all be on full display. And we could all truly be safe and fulfilled.

Managers wouldn’t run teams. Teams would run themselves. The managers would be their coaches and biggest supporters. They’d shine lights on the teams’ blind spots and support each individual through their own personal development.

Clara would be the kind of company I wished existed, but I never experienced.

I knew Clara wasn’t there yet and it would need help getting there. And that’s where I thought I would come in:

I would model the ideal manager as a sort of moral authority for others to emulate. I would be the sherpa that guides them to Utopia.

“Already There” Illusion

Clara was a year old when I joined. Our engineering team already had a tendency to build things the “right way”. This meant investing in extra work up front so things would work better and be easier to maintain later.

The problem was that we hadn’t sold anything to a real customer yet. Our future was uncertain. We didn’t know if anyone wanted what we were building or ever would.

I’ve been at enough startups to know that there’s a fine balance to investing in the future vs delivering something today. And in this case, my experience should have told me that we needed to deliver ASAP.

But that experience didn’t kick in. Instead, I believed we were on a predictable march towards a profitable business. And we would soon become a large and enlightened company. My desire to create an ideal environment was so strong, I imagined that it was already happening. I was living out my dream for Clara one day at a time.

So I continued and encouraged Clara’s engineering tendencies. I planned for the long-term and made our short-term business success secondary.

I had supported what turned out to be a two-month refactoring project that occupied almost half of our team. That was a whole man-year of engineering time right there!

We then invested in a couple of man-years into engineering and office productivity. Because, hey, everyone is happier when things “just work”. Even though the office might not be around in 24 months.

And I spent an inordinate amount of time trying to hire women engineers. Because, of course, my ideal company was egalitarian and progressive. But it was a costly use of our scarce resources.

And there were lots of other smaller examples.

This all would have made sense if our success was assured. But it wasn’t.

We spent too much time and money investing into the distant future without enough to show for it in the present. And both, the time and the money, ran out.

The Crux of Leadership

It took me half a year to snap out of my honeymoon phase and see reality clearly again. I was startled to realize that my boss and my colleagues weren’t the perfect creatures I had imagined them to be. And, that our company was just another struggling business that might not survive another year.

And, then, my disillusionment set in–like in a relationship when the initial high of the romance wears off, when we start to see our partners for the ordinary and flawed human beings that they are.

These days, I spend my time doing “inner work” trying to notice my objective reality. Or rather, I practice noticing the stories I’m telling myself that cover up my reality. Mostly I notice the everyday variety:

Why my wife and I are fighting (and why it’s all her fault).

Why I’m frustrated ay my daughter (and how she simply needs to listen).

How I’m a great coach or why I’m a terrible coach (so many reasons).

These thoughts are often implicit, below the surface of my awareness. I’m not conciously aware that I have them, but they inform my feelings and beliefs. Just like my idealistic vision for Clara shaped my decisions without me realizing it.

Our mental stories are a powerful tool. As leaders, we can use them to paint a picture of a better future and motivate ourselves and others to act on it.

The crux of leadership is to ground our stories in reality.

I like to remind myself that our stories are only possibilities. The future is always uncertain and will surprise us.

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