Lesson Fourteen: Sometimes moving forward means stepping back
Growth mean change and it doesn't have to be a bad thing
I could have made a lot more money if I stayed at Facebook for longer than I did. I could have made a lot more money if I stayed at Square for longer than I did. It doesn’t even matter how long I stayed there, these statements are absolutely true. The longer you are at a game changing company, the more refresher stocks you get and eventually they begin to pay people market rate salaries. At the periods when I was at these companies, we mostly took salaries below market rate in exchange for Stock Option Grant, or Restricted Stock Unit, upside.
These are not profound statements but rather statements that should drive some introspection for all of us. I don’t spend much time at all looking back and trying to change things, but I do look back and try and understand why I left. Why did I leave when there was more to do and experience? Why did I leave when there was more money to be made?
For me personally these two questions are diametrically opposed. I care about the answer to one way more than I care about the answer to the other. I have craved action and experience, and this has guided my career choices. Money is secondary as a motivation and I learned early in my career when I took a job that didn’t align well with my interests that money as a primary motivating factor is most likely always wrong. I care about it obviously, but it can’t be the reason I am doing something in and of itself or I will be extremely unsatisfied.
At Facebook, we were growing so fast that things were changing in ways that I thought I was uncomfortable with. When I first arrived my job was to support our Network Engineering team for every product line (for Services, my partner Sarah managed the Hardware category) across the entire globe. This meant that if we were going to build a new purpose built data center in the middle of North Carolina, it was my job to find the right Network Service Provider to build fiber into the middle of North Carolina in conjunction with the Network Engineering team.
It also meant it was my job to find the right colocation market to use as our egress points, again in conjunction with our Network Engineers. Once that market was identified it was my job to identify the most efficient solution for deploying our hardware in that market. Did we need to access a specific Peering Exchange (IX for short) to interconnect with the largest networks in the region? Could we deploy our gear down the street from the building with the best IX and get a better overall price and experience?
If we followed this path, and we were deploying in two buildings, how would we manage redundancy? Were there multiple Dark Fiber providers in the market that we could use to negotiate the best price? Was the distance between the two facilities going to have an impact on the hardware Bill of Materials that we would need to order?
For me the best part of working at Facebook was working with my Network Engineering brothers and sisters to find the right questions to ask and then pushing to seek the right solution for the specific challenge. There were many like this that don’t even fit into the questions above and my job felt like I was always asking cool questions and collaborating with people I admired to get to the right answer. I loved it, my job felt important and I got to use my brain a lot.
I was working on all Network Services around the entire planet. So the challenges I was allowed to confront went beyond the middle of nowhere in North Carolina. I was working with folks in Brazil and Argentina. We had just cracked the code and our Asia Pacific user growth was starting to look like the rest of the world. I had projects in Europe, Australia and we were starting to think about building our own network from the ground up. All of this was exciting and would require a great deal of work.
But with growth comes change. I found myself sitting in a conference room with two senior leaders, a new teammate with six months time at Facebook and another with two months time at Facebook talking about how to carve up my job into three pieces. We talked about doing things regionally. We talked about splitting my job into different categories and continuing to do things globally. We talked about making the new guys leads in different categories.
I had already taken a new employee under my wing and taught her everything I knew about sourcing Network Services for our Corporate Network. This was a much different animal than the Production Network and I really didn’t mind giving it up. She was also new to the discipline and it felt awesome to help someone grow into a new thing and see her take off and do well. I felt like I had displayed that I could mentor teammates and there really shouldn’t be a discussion about who was going to be the lead, I had earned the opportunity.
Because of this meeting and the fact that my role was going to get smaller and there were questions about my ability to lead the growing team before it even really became a team, I stewed. I was already in the midst of a lot of other personal challenges and this meeting felt like the stress I had gone through to try and help build a world changing company was not really appreciated. My boss had only been at Facebook for about eight months and he had no experience with the specific field in which I was an expert. He was in the meeting talking like he had been involved for years.
All of this was the wrong way to be thinking about things. Clearly I was cracking under the pressure coming from multiple fronts and I wasn’t being very honest with myself. I could have taken it as a message that I had to grow a little bit to get where I wanted to be but my ego wouldn’t let me see it that way. I wasn’t quite ready to look at myself in the mirror and be honest.
My wife had already asked me to find a new job because she blamed the pace at which I was working for the problems in our marriage. I called a friend who had left the company recently just to catch up and run some things by him. When I told him about the things that were bothering me he told me that he had experienced some similar things and that they were the reason he left. I took that as validation and dove deeper into the wrong thoughts. I was weaving my own web of dissatisfaction by picking only the negative aspects of my current work situation to focus on. I was making a classic mistake that is responsible for a whole bunch of the Earth’s biggest problems, I was starting with an answer and seeking information to support that answer rather than seeking facts and formulating an answer.
I had already been talking to a recruiter at Square after seeing their product in the wild and being enamored so I went full bore after that opportunity. About a month later I was shaking hands with Jack Dorsey on my first day as a Square. I felt a bit like the sheep with the golden fleece, how lucky I was to go from one juggernaut to a company that had every opportunity to be another one. But I mistook that luck for something else and my ego grew.
When I interviewed at Square there were some very specific questions asked that allowed me to expand upon the things I had learned at Facebook and Yahoo! For one question I was given a scenario of “If you were going to plan and lead a deployment in Japan, what would you do?”
I loved the question because I had started supporting infrastructure deployments in Japan all the way back at Yahoo! I got up to the whiteboard and drew a rough map of the United States and then an oval that was meant to be Japan because I couldn’t rough out a Japan shape from memory. I drew circles at specific points on the two “countries” I had drawn. I drew house shapes in two specific places, one meant to represent the Bay Area and the other to represent Tokyo.
I walked the interviewer through what the shapes were. As I was doing this I drew lines connecting them and labeled them with the names of potential cable systems. The circles were where there are cable landing stations. These were facts you’d have to consider in order to make sure the network never went down, or had the best chance to at least mostly be available for whatever you were serving from the data center back in the Bay Area to the Colocation facility in Tokyo.
On my first day at Square my new boss pulled me aside and said, “You remember that stuff you drew about Japan when I interviewed you? We haven’t done any of that and we are about to announce that our global expansion will start with Tokyo. How quickly can you make it happen?”
Two weeks later I was on a plane to Tokyo with two of my new coworkers. We were there for a total of 48 hours over three calendar days. Not really enough time to take in the sprawling city that is Tokyo but I loved it anyway. I was back in a role where I felt like my knowledge was important and appreciated. We made quick work of selecting a site to deploy, I got network services delivered and we were all ready to take on the world within about six weeks of me joining the company.
Ego is a helluva drug. I felt like I was unstoppable and was convincing myself that I was the reason all this awesome stuff happened rather than grasping the fact that all of this stuff took a team. I looked forward to more big awesome projects to attach my name too. I was not going to make the same mistake I made at Facebook and let someone else take over what I was building.
Square continued to grow but it was a lot different than Facebook. We did not build infrastructure at the same scale. I was able to grow my skill set and drove the planning of our physical infrastructure deployments, moving beyond Network Services and thinking about ways that we could prepare ourselves for multiple potential futures.
Were we going to need larger scale data centers? Were we going to grow in the Public Cloud? I spent a lot of time diving into all the options available and figuring out how we prepared for both because the answer really wasn’t apparent. Like a lot of debates about technology infrastructure the answer would eventually prove to be that it wasn’t really an either/or type decision. The answer became both and we had done a good job of making sure we did our core deployments in facilities that had room for us to grow our physical capacity while still being in a position to connect to whichever Cloud Service Provider made sense in the future.
It was around this time that the company started to grow headcount by a lot. I started to get territorial and wanted to see my own career grow. I was dissatisfied with the performance of my then leader but instead of handling it in a constructive way I told him he sucked at his job. Even so I was surprised when other folks were promoted before me. This wasn't like the Corporate Feudalism at Yahoo! Worthy candidates were getting promoted and part of the deciding factor for why I wasn’t was because I was being a jerk to people who could help me. I failed to recognize that and instead chose to be aggrieved.
One of the folks who got promoted was my former protege at Facebook. She joined Square about six months after I did. I wasn’t able to help her come over other than to tell folks who asked about her what I thought because I had a one year no recruiting clause in my employment agreement with Facebook. I was so excited when she came nonetheless, but a little bit confused by her promotion.
She became my boss, my fourth boss at Square. I was genuinely happy for her, but also angry for me. It had happened again. I decided to speak with a leader who was several rungs above me in the org. During the discussion, in which I was pretty selfishly focused I made a crack about how many teams used to report to him and we both laughed at how much the company had changed. Though it did not hit me appropriately at the moment, his response was something I really should have grabbed on to in that moment.
He said, “That is what growing at a startup is. Losing span of control and getting more focused on an individual area. If that didn’t happen, our company would die.”
Not long after this I had an opportunity to go work at Dropbox with a bunch of my friends from my Facebook days and I took the leap. Dropbox was a better fit for my skills at the time, they were moving infrastructure out of the Cloud and into their own computers in a couple of ways. I was coming there to help them in a very similar way to what I had done at Facebook and mentally I was drained from my experiences at Square.
In hindsight this was the wrong move to make for the wrong reason. I will get into that a little more in Lesson 16, but the reality was that after five years of a struggling marriage that included two lengthy separations, Rachel and I had found our way back to a good place, a place that has only gotten better since thankfully. Life was on the upswing and it felt like a good time for a reset.
My behavior towards my compatriots at Square had justifiably created problems for me and the business had changed to the point that my primary skill set was not as in demand. It isn’t easy to get folks to help you to find a new path when you are really having a hard time seeing the forest through the trees. I have since patched up my relationships with the people I treated worst. I am grateful that they even respond to my text messages let alone that I have had lunch and talked about the good ‘ol days with some of them.
It felt like the right time for a new beginning but I could have avoided ever needing that new beginning if I had taken the view of the VP who so clearly stated a hard truth about how change impacts roles at a startup. I should have already grasped this lesson from how things went at Facebook, I never needed to leave there and I could have grown both professionally and personally if I had stayed. Square was no different.
The lesson here is that when you work for a startup it will be a whole heck of a lot easier to improve your career standing if you understand that as the company grows, you will be faced with choices. Your career path can go in a bunch of different directions, one of those is that your role may get smaller and you might not have a lot of say in how it does. If that is the case, you can use that as an opportunity to grow your knowledge and refine your skills. Or you can do what I did, twice, and fail to see the opportunity.
I know that even though my family has done well financially from my time in Silicon Valley, I could have avoided a lot of heartache and stress by choosing to see the opportunity in every potential outcome. We also could have done better financially if I had stayed put for longer. If you find yourself in this position make sure you always see the upside in a growing company but what you may perceive to be a shrinking role. The old axiom “It is what you make it,” is entirely true.