Brian’s Brain

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How's the Job?

I get this question a lot. I had a thirteen year, successful program management job at Microsoft. I helped ship six versions of Windows. Then, one day, I surprised everybody – including myself – by leaving Microsoft to do iOS development for Urbanspoon. Now, when I run into family members, or friends, or old coworkers, the first question always is, “How’s the job?”

Until recently, I didn’t have a good answer to that question. Yes, working at Urbanspoon energizes me, but every new job is bright and shiny and awesome. And the small-company experience is just so different from Microsoft that I couldn’t really compare them. It’s apples and elephants.

But now that I’m finishing my seventh month at Urbanspoon, I feel like I’m finally wrapping my head around the full scope of the change, good and bad. I can give a nuanced and long-winded answer to the question: How’s the job?

The short version: My quality of life is better than it has been in years. I’m eating better, exercising more, drinking less, and sleeping more. I feel great when I wake up in the morning and I look forward to going to work each day.

However, I also wouldn’t give up one day of my Microsoft experience. The Internet seems filled with people trying to encourage you to quit your BigCo job and enter the exciting world of startups. You don’t need another person telling you that. Instead, as someone who’s worked in both places, I’m going to tell you why you should keep and enjoy your BigCo job. (To quote Joss Wheedon: This doesn’t make me a hypocrite. It just means I have layers.)

Why you should keep your BigCo job

  1. You’ll get more practice dealing with people. Computer legends abound of the lone geniuses who, armed with just their keyboards, build projects that change the world. Every computer science grad dreams of being the next Tim Berners-Lee, or Steve Jobs, or Mark Zuckerberg. But however brilliant these people may be, they did not change technology on their own. They changed technology by getting lots of other people to believe in their vision and help them realize it. If you want to leave your mark on this world, you’ll need to master people as well as technology. Working at a big company gives you tons of experience working with people.

  2. It’s the easiest way to experience a new time horizon: years / decades. I admire the “lean” philosophy, and I like experimentation / quick iteration. But while you want your discover your bad ideas quickly to weed them out, your successful ideas will live a long time. (You do want to have a few successful projects, right? Right?) Working at a big company gives you hands-on experience with the engineering work that must happen to build something that lasts. I was just a few years out of college when I started program managing features in NTFS. That code base was about twelve years old when I started working on it. It’s now well over twenty years old, runs on over a billion computers, and is responsible for the data in probably a few trillion files. Working with NTFS (and Windows in general) taught me what it takes to engineer software that lasts.

  3. You’ll get to be part of something important and impactful. Big companies become big because they have businesses that are important and make a difference. You can’t beat the rush that comes from shipping products that improve millions of lives, even if it’s just in tiny ways.

  4. It’s the simplest way to achieve financial security for your family. God bless the founders and employees of Instagram. I’m as captivated with their story as everybody else. But please, don’t mistake a good story with the real world! If you’re a good engineer, the lowest-risk way to achieve financial security is to work at a large, successful company. My years at Microsoft didn’t make me a billionaire, but I’m still amazed and humbled I could provide for my family by doing nothing more dangerous than wiggling my fingers over a keyboard.

In short, a BigCo job will teach you success — as well as the problems of success. Yes, big companies have bureaucracies and internal politics, but that’s what happens when you have people — lots and lots of messy, imperfect people. Yes, big companies use outdated technology, but that’s what happens when you build something that’s still relevant and important after a decade. There are many problems that come with being big and successful, and if you don’t solve those problems you’ll stop being big and successful. It’s simple. But these are the problems you want to have.

How’s the job? I’m excited, energized, and learning every day with the problems I get to work on at Urbanspoon. I’m doing everything I can to make Urbanspoon succeed. And I know that when Urbanspoon succeeds, I’ll be drawing on my experience at Microsoft for ways to deal with the problems of success.