Lesson Eight: It is hard to know when to say goodbye
Parting is sometimes just sorrow, nothing sweet about it
The hardest part of a glorious ride is admitting to yourself that it is someone else’s ride to take going forward. There are times when things are obvious. When I had to leave my home at Pac-West Telecomm, it wasn’t as much of a choice as a conspiracy of circumstance. I remember that my last discussion with my boss at Pac-West he shared a nugget of wisdom.
“Jeff, Silicon Valley will not be like it is here. Your rise through the ranks will require you to move from company to company to achieve something similar.”
Boy howdy, was he right! Silicon Valley has a natural ebb and flow of talent between companies. I believe it is mostly driven by four year vesting cycles. Almost always, employees get their biggest chunk of stock compensation when they first come to the company. It is not uncommon to get refresher grants on an annual basis, but the volume and value of those shares pales in comparison to the first, big chunk. I have always referred to this as “graduating.”
It is a lot like college from this perspective, only you get paid a lot to go through school. You show up on day one and everyone is all excited that they got in the door. You meet with a guide in a group setting on day one, watch the “welcome to big tech company” presentation for the day and you might get your company branded t-shirt when they hand out the laptops. The first year unfolds at a breakneck pace and you hit your vesting date. When that date arrives it occurs that you didn’t realize you were paying that much attention to your vesting date.
The second year starts and you watch as the company changes around you and you gain new perspectives on life and doing business. You start to care about the company like it is your fraternity pledge and you are it’s big brother. You have experienced the growth. You were part of making decisions that helped it grow! You feel real ownership for not only your daily tasks but the success, or lack thereof, that waits in the future.
The third year is tough. After a couple of years you felt like you had the lay of the land but then you get thrown into upper division courses and they really kick your ass. If it is a high growth startup like Facebook, Square and Dropbox you start to notice that you are moving beyond always solving for speed. You are learning to care about what happens in six months as much as you are caring about the next six minutes.
Next thing you know your coworkers are all with you at a bar celebrating the end of your time together. Not exactly a commencement ceremony, it is really a commencement for just one team member, but something close to it. You secretly are glad that it is over and time to try something new. If you have done it right, you are not entirely burned out but you can feel the strain. You take a minute at your going away party and just look around the room, these people that are there mean a lot to you and you will never see some of them again.
Some advice! If you are at the Old Pro in Palo Alto, do not engage in the shotski with whoever is leaving. The next morning will humble you and it will hurt. It will be doubly bad if you get on the electronic bull.
Oddly, I can remember the moment I knew it was time to move on from each of the companies that gave me the experiences I am so proud of. At Yahoo! it was right after a meeting in the legendary NSC which I talked about in the last lesson.
At Facebook, I describe the personal circumstances in an earlier chapter. I will describe the professional challenges in detail later in this series, but for now let us just say it was right after I sat in a meeting and learned my job that had broad reach was about to get smaller. I learned later that this is just how it goes at a hyperscaling company, but at the time I wasn’t enthused about specializing in a geographic region or a smaller set of technologies.
Square was the one company I left when I probably should have held out a little longer in hindsight. We really were just starting to hit our stride when we went public. I left because I wanted to get back to building big infrastructure again and Square didn’t really need that. I looked around in the company to see if I could find another area that I could learn and grow within but nothing really materialized. I felt in stasis with no plan for how to grow my career. I didn’t want to burn bridges with people I truly cared about. Many of whom had suffered through the worst part of my life with me and had given me the strength to escape some of my worst habits. I could feel that I was already getting angry at teammates for no reason other than I was bored. I will always feel like I ran away from Square.
We had a much more muted going away party. It was just three friends and a bucket of pasta at Buca di Beppo with Rachel and the girls. It is my favorite going away party yet, because I didn’t end up drunk and in severe pain the next morning. But the Monday after that Friday pasta dinner I started at Dropbox and this company would gift me many experiences and memorable moments. Not the least among them is the most vivid example of knowing my time was done and in spectacular fashion.
For weeks I had felt the tension oozing. In 1:1’s with well meaning leaders I was brusque and ungracious. There were people trying to coach me into something that made sense to them and they really had no idea what I did. We had infighting all over the company as we were struggling to find out what came next. I was caught between our Legal Team and our Infrastructure Team over expansion plans. I was spending a lot of time building proposals for deployments that I knew would never happen. I was spending a lot of time spinning my wheels on projects in general and not seeing much in the way of support from the folks who wanted me to help them. I was very frustrated.
I can remember it like it was yesterday. I was walking down Third Street in San Francisco on my way to the Dropbox HQ on Brannan Street at about 8:30 AM. I was deep in thought, frustrated about something specific but I couldn’t tell you what it was at this point. I was crossing the street at S. Park Street when a driver pulled into the crosswalk. I looked at the guy behind the wheel with an extremely unpleasant look on my face.
Everything up to this point of this story is pretty normal in San Francisco. Things started to go sideways when the driver rolled his window down and said, menacingly, “What are you looking at?”
Normally I would just keep walking, but I was already in a bad mood so I shot back, “I am looking at you.”
The driver kept his eyes on me in an attempt to intimidate me and started to roll through the crosswalk without looking away. I saw a disaster taking shape as another pedestrian had entered the crosswalk. He was a short guy, a little more than 5 feet tall and I instinctively shouted. The driver slammed on the brakes and jumped out of his car, he was taller than I was but he was also pretty thin and wispy. I braced for the coming ugliness but was in no mood for stepping away.
The driver took a look at me, saw that I meant business and turned to look at the shorter guy in the crosswalk. I saw him calculating outcomes in his head as he alternated glances between the shorter guy and me. After a couple of glances he turned and walked toward the shorter fellow jawing at him the whole time. He got very close to the short guy and I felt my head fill with blood and rage.
I shouted loudly and the driver turned to face me. The rage that I felt only intensified when I saw that the driver had a similarly angry look on his face and I shouted even louder. I can remember exactly what I said because my Nene, my maternal grandmother, had said something similar to me when I was an idiot teenager.
“Come get your lesson!”
The driver stood there and I saw his anger turning into something else. We stood staring at each other for a few more seconds. I broke the silence, pointing right at the ground in front of me.
“Come get your lesson or get your ass back in your car and get the Hell out of here.”
There was a moment of tension and I was running through the wrestling moves I learned as a High School wrestler. I had a plan in my mind. I’d grab his arm and enact what is called a head and arm throw, hoping to drive him into the asphalt and end the fight quickly.
He looked back at the smaller guy. He turned and looked at me. He looked around and saw that there were now about 7-10 people watching from around the general area. He got in his car and drove away. I didn’t even say a word to the smaller guy, I just turned and walked to my office, went upstairs to our cafe and sat down to eat breakfast.
At first, I felt like a real badass. I wrote a Facebook status sharing the situation for all to hear. I told my coworkers about it, braggadociously. I felt great about it right up until I called my wife and told her about it. She wasn’t as impressed.
“What if that guy had a knife?”
With one question my frail facade of bravado was shattered. She was absolutely right. What if he had a knife? Or a gun? Or was a trained martial artist? There were literally hundreds of ways that this interaction could have resulted in an irreversibly horrible outcome. For me. For the driver. For the smaller guy. I had let my anger put me in a potentially dangerous situation and it was all because I was obsessing about some perceived slight that I can’t even recall just a few years later.
I knew right then and there that it was time to figure out where I was headed next.
This is an extreme example to be sure. But even in the extreme, I couldn’t really see what was going on in my own head. There is a thin line between a frustration that builds because you care deeply about doing a good job and a frustration that takes over your actions to the point where it impacts your relationships and becomes toxic. It is doubly hard to see through the fog of this frustration and understand that it could be a sign that it is time to move on when you don’t see the opportunity cost of the future and that your time spent trying to build something great is a sunk cost.
So, in summary, make sure that when you leave a company to which you have given your blood, sweat and tears that you are not running away. Make sure that you understand there is an opportunity cost that is hard to quantify if you stick around too long, there are other great things you could be doing. All the anguish and struggles are now a sunk cost. You spent that emotion, you can’t get it back. And if you find yourself challenging a guy on the street to come get a lesson, think about where that impulse came from and make the right move. When it is time, it is time.