Imagine that you were lucky enough to find a job at a large, powerful organization that:
- Has great pay and benefits
- Has a great boss who actively helps you get better and wants you to succeed
- Is extremely stable
- Is challenging and rewarding
- Would allow you to do many of the things you love to do including building and leading an awesome team of smart developers
Now imagine that you decided to leave that job after investing 6 years of hard work even though the greatest opportunities for success were yet to come. And, the reason why you are leaving this high-profile job at a big organization is to work at a 3-person, 2-year-old startup that is still working toward profitability. Why in the world would anyone in the right mind do that? It’s sort of like if Gene Hackman’s character in Hoosiers decided to quit the team right before the state championship so that he could coach a local middle school. How does that make any sense?
Well, it turns out quite a bit. Let me explain.
I made $970,000 last year. How much’d you make? You see pal, that’s who I am, and you’re nothing. Nice guy? I don’t give a sh*t. Good father? F!@k you! Go home and play with your kids. You wanna work here – close! You think this is abuse? You think this is abuse, you $#@#$%? You can’t take this, how can you take the abuse you get on a sit? You don’t like it, leave.
Many of the most successful software developers have the ability to cut out all the distractions, overhead, misdirection and general “noise” that exists in any software development effort and cut right to the heart of the core issue to get stuff done. In other words, closing.
As a software developer, nothing feels better than after you deploy code changes, validate that everything works correctly, do your fist pump and proclaim victory. The bigger the challenge, the bigger the thrill there is when you are done. The developers that can cut out distractions and deliver more frequently and on more complex tasks experience even greater highs. To some developers, it can even be like a drug where the only thing you can think about is getting your next hit and anyone that gets in your way is an impediment to be ignored or removed. For the most intense developers, there could even be almost overwhelming fear of losing your edge if you relax even a little bit.
Now, contrast the idea of a super-intense software development “Closer” to the concept of the Family Man. To be quite honest, I did not understand what it meant to be a Family Man until I had my first child. In my mind, being a Family Man means that you structure your life around your family. In other words, when you are thinking about your day or planning your week, you first think about the various to-dos with your wife or children and then you see how your work can fit in. Before Mady was born, I more often did the opposite where I figured out what was needed for work and then I filled in the gaps with family stuff. When you have a child, though, you realize that nothing is as important as your family. Sure, you knew that before the baby was born on some level, but there is a different level of intensity in that feeling when you hold your children in your arms for the first time and then start to see them grow up.
So, the question is how to rectify the mindset of a Closer with a Family Man? At times it can be like two sides of an epic battle. The Closer views family as an impediment while the Family Man views anything other than family as secondary. Working with many different developers over the years, I have actually seen this collision of unstoppable force vs. immovable object play out in a number of ways. On one end of the spectrum I have seen developers voluntarily take lesser roles at work or move to a less intense environment so they can spend more time with their family. On the other side, I have also unfortunately seen times where developers end up ignoring their families and eventually get divorced. The hardest thing to do is to try to find a middle ground and achieve some sort of balance where you are able to spend time with your family and maintain a high level of productivity at work. It is something that I have struggled with my entire life and has tortured me in ways that are hard for me to explain. I want more than anything to be the best father and husband in the world, but I also have an unquenchable thirst to reach greater and greater heights at work. Achieving balance is something much easier said than done.
Last summer when my wife and I talked about having a second child, I knew it was time to do some soul-searching. I would love to tell you that I found the ultimate answer of how to achieve balance (I did not), but I was able to figure out one very important thing: we needed to move back to Boston. We moved from Boston to Southern California in 2003, but many of our family members, including our parents, still live in the Northeast. My wife understands I will always more than likely get up at 4am and work at times late into the night. The issue with our work-life balance wasn’t as much of a number of hours, but rather making sure we make those hours count. In other works quality, not necessarily quantity (though Carolyn certainly wouldn’t complain with more of both). In the past when we discussed moving back to Boston, I had always pushed it off because of some variation of an excuse centered around being too busy at work. No more. Even though I really had no idea what I would do for work, we made a firm decision that we would be back in Boston before the end of 2011.
OK, so that certainly explains why I moved from Southern California to Boston, but it doesn’t really explain why I left Wells Fargo or why I joined a startup. Once I decided we were moving, however, it forced me to reflect on my life and career in ways that I had been avoid for a long time. Like many software developers, I was acting like one of the hedgehogs in Jim Collin’s book, Good to Great, that identify their goals and move relentlessly, unceasingly toward those goals. The problem is that many developers don’t take the time to take a step back and ask the two most important questions for a hedgehog:
- What are you the best in the world at?
- What motivates you?
Like I had done throughout my career, I was working relentlessly toward something…but what? Sure, I had plenty that motivated me at Wells Fargo, but did I truly understand what specifically motivated me? What truly am I the best in the world at? Simple questions, but I guarantee that a vast majority of developers would have a hard time providing good answers.
So, I hired a career coach. I found Gail Liebhaber through some online searches and she was awesome. She didn’t really tell me much I didn’t already know, but she forced me to take that step back and think about questions like these ones. The biggest thing I discovered is that as much as I truly loved my current job, I wanted more. By more I don’t mean raising the ranks within Wells Fargo. I wanted something…different.
As crazy as things were at Wells Fargo and at home, in 2007 I tried to bootstrap several side businesses. They were nothing special, but it gave me the opportunity to satisfy a thirst that I could not quench at Wells Fargo. Namely, having complete control over the fate of a business and innovate in new and different ways. I do truly believe that you can be an entrepreneur and innovator within large organizations and I think I did manage to accomplish just that for the past 5 years, but it is not the same thing as truly running your own business. When Gail first asked me what my career aspirations were, I was not sure. She suggested that start talking to old colleagues and searching around online to try and find someone in the world that exemplifies everything that I wanted to become.
I only met Dharmesh briefly in person at a conference and really I don’t know much about him personally, but I found him to be the closest thing to what I want to be. Besides running the smart, innovative, marketing company, Hubspot, Dharmesh is viewed as an expert on startups and provides guidance and angel investment to many small businesses through his blog, OnStartups.com. He is viewed as an industry expert and is often invited to speak at conferences. He also continues to actively code on a number of projects including the Hubspot Grader.com tool. Even though he runs so much at a high level, he is very involved at a low-level as well.
The reality is that you just can’t do that at an organization the size of Wells Fargo. There is nothing necessarily wrong with it and it is not something I could or would even change if I ran such a big company myself. It is more just how things are. When you are big, you need the people in charge to manage the “bigness”. It is almost laughable to think that my CIO, Reza Lealli, would spend one minute writing code. It just wouldn’t make any sense. There are so many big organizational decisions that need to be made and Reza does a great job at that. When given the choice side-by-side, however, as much as I love Reza, I want to be Dharmesh.
Conclusion
I have no doubt that if I stayed at Wells I would continue to have success and enjoy my job. But, there would always be something missing. The things I love about Wells Fargo include the opportunity to build a great team and working toward some really big goals. That is great, but it is just one aspect of what I want to do. That is why I said I need more. I truly believe that my team at Wells Fargo Dealer Services is one of the best places for most developers to learn and grow. There is a world of opportunity there and they are set up for success. My future path, however, will be in a different direction as I continue to try and achieve work-life balance while also chasing my dreams.
Up Next…
Not too much here about my new company, Mesh01, but I will save that for the next blog. In the meantime you can check out Jason Robert’s Techzing podcast where he talks a little bit about my move to Mesh01.









Jan 09, 2012 @ 04:33:04
I definitely don’t deserve this level of admiration, but thanks for the kind words.
Wish you success in your journey. And, to answer your question: Nobody in their right mind would do a startup. That’s one of the things that make those that take the leap, special. We’re not of right mind.
Cheers.
Jan 09, 2012 @ 11:00:42
Thanks for the comment and the re-tweet. You set the bar pretty high, so I have some work to do.
Sep 07, 2012 @ 12:47:33
Essentially you have to decide between a cushy job in a large organization, naturally dominated by factors such as politics, moving mighty and steadily but slow, OR being creative moving things fast, dominated by your own ability but also contrained by scale and resources. In my current company, I started when we were 600. We are now 12k. Things defintely have changed and sometimes I am wishing the old days back when a bunch of highly motivated geeks set together in a conference room designing how the Internet looks in a couple of years, instead of talking of slow incremental progress where innovation becomes a process. Today, I can now play with millions in gear but you trade that for agility and creativity. I might follow you…
Sep 07, 2012 @ 13:41:40
I was serious that innovation can happen within large companies, but it is just different. Actually, idea that I like from Guy Kawasaki is to create a completely separate group within an organization that acts just like a smaller company and innovates without many of the constraints of the larger corporation. Of course, that type of thing is easier said than done, but if I was ever lucky enough to build my startup into something much larger it is something that I would at least try out.
Sep 07, 2012 @ 14:10:47
The problem I have seen in my consulting practice is when organizations grow and career management replaces organically grown leaders. Those guys often do not have any technical background and perhaps are political appointees. I observed in quiet a few instances where those new leaders took credit for work they had no part in. Once such things are observed, the motivation to innovate within the organization goes down: why should I go the extra mile when in the end I get nothing, or worse get fired, and somebody else who had nothing to do with it gets a promotion or bonus? As a consultant you are used to people taking credit for your work – but at least you are getting paid handsomely. But in an internal organization such behavior creates a toxic environment and most often can never be fixed again, even if ineffective management is removed. In reverse, if leadership messes up, innovators keep quiet because they do not want to become scapegoats or attached to failure. So people pretend things are all cool when in reality the ship is sinking. As a consultant you often tasked to fix such situation in secrecy, but it often paralyzes large organizations. Smaller organizations do not have those issues. You swim or drown and it becomes quiet apparent what the contribution if each individual is.
Sep 07, 2012 @ 14:25:31
Unfortunately, I think a lot of what you say is true for a majority of larger companies. However, I still think (or perhaps just hold out hope?) that this is not universally true. Its funny, though, because when you live through those situations (I have both been a consultant in the situations you describe as well as an employee of a large company) you see some of this stuff go on and you almost think, “Is this a Dilbert cartoon? Did that guy really just claim credit for this right in front of me?”. The people I know that are innovative in large companies understand that this type of stuff exists and they almost view it as part of the game. They don’t let the large company shenanigans affect them emotionally or mentally. I used to tell my team at Wells Fargo to not care about all the “noise”. In fact, they need to almost expect that other people will be difficult to deal with at times and just come up with a strategy that works around them if need be.
Your last comment is kind of interesting (i.e. You swim or drown and it becomes quiet apparent what the contribution if each individual is.) because I have seen even really talented developers become complacent at larger companies simply because their work gets muddled along with everyone else’s and they aren’t held accountable as often as they should be. There seems to be a common mistaken thought that as long as I “work hard” that is all that matters. And, since it difficult for even them to realize what work they actually did, almost everyone believes they have “worked hard”. At a small company, however, “working hard” is expected and it is more about the actual output. If you worked 100 hours and didn’t get that job done then it will be obvious and you won’t look good. If you get the job done regardless of the number of hours you will be recognized and rewarded.