Finding a Job That Fit My Life

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This time a year I ago I was in Athlone, Ireland, slightly miserable and trying to figure out why (because it probably wasn’t just the weather).

When I had planned the trip it seemed like I was going to be living the dream, being paid well to spend time in Europe, yet somehow that isn’t quite how it worked out. As a result I spent a lot of time thinking about where I wanted my life to go and what might actually make me happy.

When it came down to it, I realized that because I love my work I had been letting what I did dictate the rest of my life, rather than just contributing to it. I would like to share some of my process and results with the humble hope that someone out there might learn and benefit from my experiences.


I was here.

How did I end up in Ireland anyway?

Here is the whirlwind version. After college I was lucky enough to land a job at a small DVD by mail company called Netflix. I spent the next seven years working on amazing things like launching a streaming service and moving a large scale business to the cloud, while interacting with and learning from great people in an awesome environment.

As a Bay Area native I then decided it was time to explore the land of startups and proceeded to work at a couple of those and then start my own. I left the most recent one with a couple of colleagues to do some consulting and start our own thing because we really wanted to build something that was ours.

As we were leaving I was also offered an opportunity to consult for a large company in Ireland, which seemed like a great way to get some money in the bank and visit some friends.

Three lessons I learned about myself

My last day was a Friday, and Saturday morning I hopped on a plane to Dublin. And this taught me lesson #1; going straight from one job to another is a high stress, high energy operation and therefore has an enormous cost.

This leads me to lesson #2: it’s great to be excited, but if you get too caught up in your work, the rest of your life can suffer without you realizing it at the time.

Finally, lesson #3; After an amazing SF summer and a trip to Bali it became really clear to me that warmth and sunshine really do make me happier.

Figuring out what I needed

I spent months doing just that, both at home and abroad, getting feedback from my friends and mentors. I had decided that the next time around I would do things differently and select a job that went with my life rather than being my life.

In the end I made a list of what was important for my balance and happiness:
* Time for introspection
* Spending time outside
* Flexibility, in both what I work on and where
* Doing new things

Once I had these core needs, I decided there were a few parameters I could use to help me select a company that would support them. One of them was company size: are they big enough that I wouldn’t have to live on the other end of the batphone?

I love to firefight and had done it for years, but it just wasn’t conducive to a good work/life balance for me. Size also gave a sense of whether the company could support a cross-functional role, which is where I am at my best and most engaged, but just isn’t appropriate until a bit later in a company’s life.


This is not what I was looking for.

Finding the right culture

Finally, it was really important that the company have a culture that would support me in my desire to live a healthier lifestyle.

One thing I found useful was asking the most senior people I could talk to (founders, CEOs, etc.) how they balanced their own lives. What kind of hours do they work? How much vacation do they take?

One of the best answers came from Kyle at Keen: “When it’s sunny out, I will take part of the day to go for a bike ride” (this was reinforced by spandex and FiveFingers for an impending bike ride) “and I will probably take 8 weeks of vacation this year.”

He also said, “I would never expect someone to do something they have done before if they don’t want to. That just sounds boring!”

These were the kinds of things that made me feel like people were practicing what they preached and not just telling me what I want to hear.


Kyle in the wild

What about compensation?

After narrowing the field I was still faced with an interesting conundrum of how to evaluate compensation from the companies I liked most. This is always a challenge because the mix of cash and equity can be notoriously hard to value.

But then there was the added dimension of how to value what my life would look like at each company. If a company pays a bit more but might be more stressful, how does that fit into the equation? What about future career growth? Some companies have clearer tracks than others.

In the end I chose to make the monetary and career aspects secondary and select first for what would best support the life I wanted to have. This was made a bit easier by the fact that in the end they were all going to pay more than enough to have a comfortable life. (#firstworldproblems)

So what’s the moral of the story?

For me it was just how valuable it was to have some time away from work to think about what I really wanted to have come next, and the best way to go about achieving that.

It’s easy to get caught up in the excitement of new things and experiences, but the result was that I lost sight of the bigger picture. So I would encourage everyone to be patient and thoughtful before you jump into the next big thing.

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