The Worst Case

November 22, 2011 - Seattle, WA

So I’m sitting here in SeaTac Airport for the second time in as many weeks, on my way home for the holidays, and I can’t help but be be think of a saying my friend [Haris] ( and I have been using recently: “Just go and do it. The worst case is your life stays exactly the same.” This is something that has been my on mind frequently over the last couple months as I try to figure out the next steps for my life.

Two weeks ago I was hanging out with Haris in San Francisco. Ostensibly, I was in the Valley for an interview (more on that later), but I was taking the opportunity to hang out with an old friend. Before going out bar hoping on Saturday night with some of Haris’s friends we made a pact to each talk to five girls that night. Not for any sketchy reason, not trying to ‘hook-up’ with some random girl, but honestly just trying to get better at it as a general life skill.

Did I reach my goal? Honestly, I have no idea. I didn’t keep a strict count and we hadn’t working out splitting odd numbered groups. But here is what did happen: I had an amazing night, talked to some cool people, found a couple new bars, and danced like crazy. It was a great night and all because I wasn’t afraid to go out there and just say, “Hi, I’m Jesse”. And do you know why I wasn’t afraid? Because the worst that could happen would be a conversation that goes nowhere and my life stays exactly the same. Its important to note that I had such a good time specifically because I realized I wanted to change the way my life is now, in hopes that it can get better. It was easy, because the downside was that my life goes on - exactly the way it was before I tried. So the question becomes, why not?

I’m told you that annecdote because it is a nice, easy example of my point. However, that kind of situation is really just a small piece of the idea (nothing “nice” and “easy” ever really tells the whole story). How about a more indepth example? (You get it already? Well, smarty pants, skip on down to the end for the punchline).

Going back to the real reason I was in San Francisco - I was there on a job interview. Why was I looking for a new job? I realized that my life needed to change. Say I took that next job and it was terrible? Well, in the worst case I could always go back to my last company and the way my life was before. No harm, no foul (it doesn’t always work out that way, but I’m a little lucky in that regard).

So what is the more likely ‘failure’ scenario? In the interim I would be doing something pretty cool, meeting new people, growing as a person, in a much better position for other opportunities and learning a ton along the way. Are you kidding me??? Sign me up!

But how did I realize I needed that change? We need a little bit of back story, a bit of perspective to understand my movtivations.

I was born, raised, went to school, and got my first job in Maryland. However, I somehow became really outdoorsy and a technologist (not as uncommon as you would think). I had to get the heck of Maryland. At the time, I was fortunate enough to be at a company that allowed me to move to Seattle and still have a job. A little bit of cushion for the transition to the west coast and still generally working on things I found interesting. So I sold or threw out most of my furniture, packed the rest of my stuff in my car and drove across the country. I was on my way.

At this point, I was starting to lean over the rabbit whole, looking to see how far down it really went.

Shortly after moving to Seattle, I did a couple things. I got involved in the the vibrant Hadoop/cloud community and jumped in the startup community. The former I had been involved with in MD, so that was an easy choice. The latter was just out of curiosity and a growing entrepreneurial streak. Quickly, I came up with an idea for a company and started working at it part-time (evenings, weekends). That idea didn’t prove out, but it gave me access to a really exciting community. Thats not to say doing all of that was easy - my head spinning like a top. Between working two jobs, contributing to open source projects (HBase and Accumulo), trying to stay in shape/train for a marathon, and getting out to meet new people in a new city was a pretty crazy couple of months.

I was starting down the rabbit whole. Along the way my sleep schedule got completely messed up (not being able to sleep and coding to 6 am on multiple occasions), I put on a good 10-15 lbs (not the good kind) and was stressed like crazy. But man, I was having fun.

Still at this point, I was basically doing the same thing I always had - look at whatever I have in front of me and trying to pick the thing that sounds the best, most fun, etc. However, I quickly came to realize that I was having way more fun doing the stuff in the ‘spare time’ than I was at work. In fact, orders of magnitude more fun. So yeah, I could keep doing what i was doing, busy like crazy and probably headed for a heart attack by 25, or I could cut out the things that I really didn’t love in favor of trying to optimize happiness. And what was the worst? The 40hrs a week I spent at my job. Yeah, I was doing kinda interesting stuff at work, but the hours dragged by and I looked forward more to my side projects than coming into the office.

Hi, my name is Jesse. I’m have a type-A personality. I am a maker. I have to build to be happy.

Once I realized that, making the leap was easy. But where did I want to go? Being in the startup community, I had a lot of options. Cloud skills on a good dev are sexy right now and I quickly found I was a hot commodity in a dev’s market. All of a sudden I had bunch of really good options doing really fun stuff. In the worst case, I could join a company (or start my own) do that for a year or two, and if those failed or I hated it, then I could always get a job at some big company or go back to the one I’m at now. Life could always go back to being comfortable.

Here is where it started to get really interesting (read: stressful). Not only did I have a lot of options, they were also varied - everything from being employee #1 at a currently 3 person startup up to getting a job at Amazon (I am in Seattle after all). So which was the best? Turns out, at the time I didn’t have a good metric to choosing. My basic criteria were: (1) doing fun cloud stuff, (2) working with smart people, (3) having leadership opportunities, and (4) making enough money to be comfortable. In short, I wanted to awesome stuff in a cool place with good people.

Well, I could do that basically anywhere. I couldn’t do anything really ‘wrong’, just potentially not as great. So close my eyes, spin around and just pick one, right? Not really an option being the type-A nerd that I am - I want some real goals and real metrics to guide my decision. Otherwise, I can just flip a coin.

Before I had a perspective on life looking to the next year and not thinking about concrete, long-term goals, but rather “I want to be THERE doing X”. That is totally ok for a twenty-something just getting out into the world. However, not thinking more deeply about what you want means you are going to be skipping from one thing to the next. And hey, that could be just fine. But for me, I need structure and goals - somewhere to be (A-type, remember?). Interestingly, having all the options for my next step actually forced me of the one-hop lookahead to instead the 3-5 year lookahead (still only two to three hops out). Its probably apparent to older folks, but recently I’ve had to take a hard look at really where I want to be in two years, in five years; 10 still feels like a ways out, so I can again label it as ‘doing awesome stuff at a cool place’.

Okay, so that took about a week of introspection to build a solid plan (solid enough - it still changes weekly, but the basic scaffolding is there). For me, I realized I wanted to start my own company doing cloud (yup, still gonna keep the idea stealthy) on the west coast. Well, once you have a longer term goal, just start splitting the time in half until you figure out where you need to be. If I want to be Z in 5 years, then in two-ish years, I need to be doing Y and then to be at Y I need to do X next, and then etc. until you find out what you need to do today to help enable that. Once I start working through the plan, a lot of the options become comparatively less attractive, until you can cut it down to a few options.

Then it becomes all about the story you want to tell with your life (well, at least next five years). It frequently doesn’t turn out the way you planned it (the plans of mice and men, right?), but it builds a consistent logic that is not only inherently elegant but also puts you in the right place, to meet the right people at the right time - serendipity. And that is how you can go out and change the world - baby steps within your bigger plan. Don’t be afraid to change the plan if conditions are right, if you are having fun, if you are really living your life, but make sure you know what you want. Otherwise, you might as well be flipping a coin.

And all that magic happens because you went out there and did something. And yeah, maybe it was uncomfortable. But know know what? Probably means its the right thing to do. The one thing I do know is this: sitting in your basement by yourself, doing the same thing you do everyday isn’t going to change anything. But if you start putting yourself out there, I bet 10:1 that people are going to come knocking.

Think about in 30-40 years, sitting around the hyper-television drinking your future-scotch, telling your kids/grandkids about your life story. You want it to be fun, exciting, and smattered with some life lessons. You do want to be cool parent, right? That means taking some risks, diving in head first when the time is right (and sometimes not) and make a dent in the world. Because you know what? If you don’t, thats going to be one heck of a boring story.

So yes, start that company. Find the job that will make you happy. Grab a beer with your friends. Talk to that cute guy/girl at the coffee shop. Write your own story. Follow your own rabbit hole.

“Just go and do it. The worst case is that your life stays exactly the same.”


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