How My Hidden Motivations Drove Me To Reevaluate My Life

April 3rd, 2018 by Vlad Giverts

As I look back at my job at Clara Lending, I remember starting off with a powerful energy. I was proud of my accomplishments in my first six months and I think others there would agree. But just a year later I walked away disillusioned and demotivated with mutual frustration between me and my boss, Jeff–the CEO.

I’ve had a lot of shame and guilt about my private thoughts and behavior at Clara. It’s been painful for me to honestly reflect on what happened for me. It’s part of larger process of taking a step back from my ego that started a number of years ago and culminated with my quitting not just Clara, but whole the corporate world and Silicon Valley in general. This is the story of what my real motivations were going into Clara and how they played into my big shift in life.

My Motivations Going into Clara

So what motivated me before I joined Clara? I’ve tried to reconstruct and organize my “motivators” from back then and they fall into roughly these buckets: mastery, purpose, relationships, autonomy, and lifestyle.

Mastery of Management

Prior to Clara, I was a Director of Software at Workday leading more than 50 people. I felt like I leader, but I didn’t feel like a manager. For various reasons, I had delegated my formal responsibility of day-to-day management to my friend, Barzel. He was my only report, and as far as I could tell, he was doing a great job. People on our team were generally happy and those he worked closely with admired him and appreciated his support in their development. A part of me was envious. I told myself and others that the two of us were co-managing the team and I convinced myself that I was doing a good job of it. But the circumstances were murky and I wasn’t sure if I was fooling myself to placate my ego. So about a year into this arrangement, I resolved to manage a team without Barzel so I could develop and demonstrate my own mastery of engineering management. I had a vision of what kind of “enlightened” manager I wanted to be. And part of that vision involved leading a multi-hundred person organization, well beyond the size we achieved at Workday. Fortunately, Clara was going after a massive market (mortgages in the US) and the team had claimed to have it all figured out. If what they were saying was mostly true, it was possible that in three to four years time they could making huge revenues and would need their team to scale up in a big way.

Purpose in Developing Others

I loved helping others develop themselves as far back as high school when I was skipping some of my classes to tutor other kids for the Advanced Placement Computer Science test. Back then a lot of my positive feelings about myself came from being useful to others and therefore having value in the world. It helped paper over the gaping holes I had in my self-worth. As I matured I became content to simply create and hold space for others to grow. For individual engineers, that meant letting people take on technical challenges that were just beyond their level of competence and allowing them to struggle or even fail. As my teams got bigger, it meant inspiring my managers rather than “managing” them.

In my last year and a half at Workday, Barzel started bringing more systematic coaching to the management of our team and introduced me and our senior managers to the world of adult development, the process that adults go through as they mature and develop a more complex and well-adjusted way of being in the world. I had seen Barzel develop himself over the previous few years and I was completely bought into this way of living life. I wanted to take his work to the next level and make ongoing adult development an everyday part of how our team operated. I was so excited about the idea that limiting it to just my team felt like too small of an impact. I wanted to bring this kind of growth to as many people as I could possibly reach. I decided my best forward was to join an early-stage company to seed their culture with these ideas and nurture its growth so I could eventually touch thousands of people.

Relationships and Autonomy

Ever since high school (hmm, sounds a pattern) I’ve struggled with authority. It was around that time that I decided that I “knew better” and became skeptical of authority figures. The short of it was that I was emotionally repressed. I was out of touch with the experiences of others, yet I was smart and creative enough to come up with convincing stories that would rationalize my rightness and thus reinforce others’ wrongness. I had learned enough from people’s reactions to my arrogance not to be openly disrespectful, but my arrogance still leaked out regularly. The worst of it came out in my adult life while I was at Workday and started clashing with my boss. We were both trying to avoid interpersonal conflict all while thinking that the other person was in the wrong. It was frustrating and anxiety provoking for me and I imagine my boss wasn’t thrilled either. The pain trigged a difficult year of reflection for me. I realized how important it was to develop relationships with people, particularly with my boss, where we could be open with each other and have difficult conversations when we found ourselves in conflict. I also knew I’d need enough autonomy in my relationship with any future boss so I could make my own decisions and mistakes and continue to grow from them.

I had known Jeff, my soon-to-be boss at Clara, for about three years at that point. He connected with me two years before he founded Clara to get my advice on product and technology. We met every month or two for almost a year and occasionally thereafter. I was impressed with how each time we met, his ideas for the business had evolved into something that sounded increasingly plausible to me. My ego got a nice boost from the thought that my feedback had helped in some way. He seemed open to what to what I had to say and made of point of letting me know how much he appreciated my input. For my part, I tried to be thoughtful and deliberate in all our interactions. This was unusual for me as I was uncomfortable not having an “answer” right away and tended to spew out whatever came to mind first for me. I liked our dynamic and it was a deciding factor for me.

Family Lifestyle

My family and I had a certain San Francisco lifestyle–eating out a few times a week, private schools for the kids, expensive condo in The Mission, etc. I didn’t want to make my family sacrifice for my ambitions so I was strongly motivated not to compromise on any of it. There were just two factors that applied to any potential job: money and time. I had had to make enough to cover our ongoing expenses or at least come close. And I had to work reasonable hours, which for me meant 8-hour days with only occasional exceptions. The compensation part was easy as that gets explicitly talked about in every new job. The time part was harder. I was afraid that if I came out with my desire for 8-hour days, I wasn’t going to get it. It ran against the ethos of Silicon Valley™. Either I wouldn’t get the job or my prospective employer would insist on longer hours. So instead I decided to keep this bit to myself with the hope and confidence that I would achieve enough in the time I had allocated to satisfy my boss and that my time spent in the office wouldn’t be an issue.

Timing: Travel & FU Money

All of the above were short-term desires that I was excited about. I also had two medium-term ones. For the past few years, my wife and I had been talking about living in Europe and traveling the world with our kids. We heard from other parents that teenage kids have a much harder time with big life changes like that so wanted to do this before our older daughter went to high school. She was seven years old and in second grade at the time, so that gave us around six or seven years to find a stable place. We decided we were willing to give up roughly half that time for my next gig, with an upper-bound of four years. That’s a short time for a startup to grow up and go big, so I knew I’d be making a risky bet. On top of the travel, I was mourning the impending loss of my Workday compensation. I was making over a million dollars a year as my stock options were vesting. So wherever I would choose to go, I wanted the chance to get it all back with a big multiple for all the risk I’d be taking. During my interview process, Jeff had articulated a plausible path to a billion dollar valuation and my chunk of it would have been enough for a modest retirement in Europe.

My Motivation in Practice

In my first few months at Clara, I found a comfortable rapport with all of the engineers and felt a sense of mutual respect. I facilitated several changes that I felt proud off and I believed made a meaningful impact on product development there.

Early Achievements

First I focused on transitioning the larger product and engineering team to a flavor of the Scrum process, including PMs and designers that didn’t report to me. Once it got going, it helped us plan more effectively and provided stakeholders better visibility into our progress. We were much better at predicting when we’d deliver our work without being off by a multiple of two or three or having to work nights and weekends to meet commitments.

I also led the revamping of our hiring process to be based on specific competencies that we could consistently interview for. I’m not sure if this increased the quality of engineering hires, but it made our hiring process so much easier to run. Everyone knew what we were looking for and it was now possible to evaluate candidates against a criteria that everyone was bought into.

And for the first time in my management career, I started systematically coaching my engineering leads, not just managing them. Over the course of several months, they started to buy-into the idea of being coaches themselves for their team members. They were actually taking responsibility for the growth and development of the people on their teams. My vision for creating a developmentally-focused culture was sprouting shoots!

To top it all off, I was able to come home at reasonable hours. I still felt compelled to get some more work done in the evenings, partly out of excitement and partly to show off how hard I was working. But even that started to taper off after the first couple of months.


Things were looking pretty good as far as my motivators went except for my relationships, which were a mixed bag. Within a couple weeks I had learned everyone’s name, about 45 people, which was a big deal for me as I historically was terrible with names. I regularly had friendly interactions with everyone I came across. But I also managed to get into an argument with our new head recruiter, where I said some unfairly harsh things. The co-founder/Head of Product, felt roughly handled from how hard I pushed Scrum onto the team and felt left out of the process. And I was struggling to make a personal connection with one of my three engineering leads. Almost immediately I found myself tip-toeing in meetings where he was present to avoid conflict and had to resort to mutually unsatisfying compromise.

Things were a mixed with my boss, Jeff, too. I sensed he genuinely cared about helping me be more successful at Clara and I appreciated his intentions. I tried especially hard to be intellectually honest with myself whenever we interacted. Neither of us avoided uncomfortable topics and I stayed open whenever he had critical feedback for me. It felt like the most open relationship that I had ever had with a boss and I was committed to making it work. But boy did it hurt. Every time Jeff gave me feedback I felt wounded, unseen, and abused. I don’t think he meant to hurt me. But I had never kept myself so open and vulnerable in the face of direct feedback before. And my ego identities such as “good leader” and “competent manager” were deeply tied up in whatever topics Jeff was likely to touch on. It was nearly impossible for Jeff to bring up those topics directly without my very being feeling like I was in imminent danger and triggering a fight-or-flight response. And trigger me he did. Once or twice a month I got hit so hard that I felt demoralized for a week. I was slowly growing resentful and disillusioned with him.

The Brick Wall

Six months in, if you had asked me how I felt about my life at Clara, I would have given you a resounding “great!”. The business was still a big question mark, but it was starting to show promise. If the early trends continued, we’d be on track for a nice fundraising come summer-time. Then November of 2016 happened. Mr. Trump became President Trump and a dark cloud rolled over the office. People were upset, Jeff and myself included. But what really hit me and everyone else over the next few weeks was the sudden deterioration of the mortgage markets. Interest rates went up and our sales volume went down. I didn’t consciously realize it yet, but our strategy was broken. Jeff had articulated a vision of what it would take for us to have a successful fundraising the next year, and there was no way it was going to happen. Not even close.

In this new reality, we couldn’t–and shouldn’t–responsibly hire people for the foreseeable future. I was sold on the potential of Clara earning tens of millions within a year or two of my joining and being the one to scaling the team to hundreds of people on the back of that success. At best, this was now pushed out by a year. At worst, we weren’t even going to survive another year. My dreams of managing a large team were now on indefinite hold. In my mind, and probably Jeff’s too, it didn’t make business sense anymore for me to spend my limited strategic bandwidth developing my people if the company might not survive long enough to get a return on its investment. My motivations around mastery, purpose, and timing were broken.

Then I had the conversation with Jeff. Actually, a series of them over the course of a month or so. My recollection of them is muddled as they were emotionally charged for both of us. What I can tell you is how I felt and my overall sense of the situation. The gist was that Jeff felt I wasn’t contributing to Clara as much as he believed I could and should. Specifically, he said he needed more of me. We weren’t exactly on the best footing with each other at this point and that request took me for a loop.

Over the prior six months, I often saw Jeff praise people’s individual contributions, which I saw as his way of motivating people. But he didn’t say much about the softer aspects of management and leadership. He was a first-time leader and manager, so I wasn’t surprised by that. I had hoped–and expected–he would defer to my experience and let me do my thing even when his own intuition told him I was in the wrong. He actually did that for a while. He practiced self-reflection and at times he could see the limits of his both his knowledge and world view. But as his anxiety ramped up, he couldn’t contain his inner-critic anymore. I started to sense that he was judging me harshly in his mind whenever we interacted and I was feeling increasingly insecure about my position. So when Jeff finally came out and asked for more, I read that as a not-so-subtle code that translated to:

Do activities that are easily observable and create an impact that is easily measurable.

And, of course, that meant working longer hours in the office, which were the easiest of all to observe. So much for my sense of autonomy and the family lifestyle that I was going for.

Wow was I triggered.

Management doesn’t work that way! Productivity doesn’t work that way! What the hell does he know? The business is falling short by an order of magnitude from what he originally promised me! What right does he have to make these demands of me?

I only said reprocessed bits of these thoughts out loud, but my mind was screaming. I was afraid of having to work long hours and being away from my wife and two little girls. I was afraid of losing my job, not for the money, but for the relationships that I had built with my team. And I was afraid that I had walked away from a million a year at Workday for nothing. I blamed Jeff for all of it.

My Self Deception

In my story I was the victim. I did everything right and Jeff was abusing his authority. But was that the reality? I wasn’t sure even then. One reason I reacted so strongly was that a part of me felt weak and exposed. I was judging myself as being selfish for holding on to my ideals of cultivating an environment where people could flourish and grow when the company was in a dire situation. The needs of the many were on the line and I was ashamed for not tending to them as best as I could. I didn’t want to believe that about myself and part of my reaction was a defense from having to feel those feelings.

Jeff was doing the best he could from the life philosophy that he held, which was different from mine. As our tensions grew, I tried to contort myself to be more palatable to his world view. I sensed he was doing the same for me. Feeling fake was the most uncomfortable part of it all. I remember playing the same game with my previous boss when I was at Workday. In both cases, I got to the point where I was constantly anxious and dreading every interaction.

But something changed for me at Clara. I couldn’t bear constantly holding back and not being my true self anymore. My year there was the last straw and my proverbial back was broken. Something in me was shifting in a big way. In April 2017, I decided to quit not just Clara, but also the corporate world and the whole of Silicon Valley. The whole culture had become an emotional trigger for me and I needed to be free of it. So a few months after leaving Clara, I put up my SF condo for rent and moved with my wife and two little girls to The Netherlands. I’m now living a simple life in a quiet mid-sized city working as a coach for a handful of people, who themselves are leaders in the SF tech industry like I used to be.

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