What’s Your 5-year Plan? *Uncontrollable Laughter Ensues*

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People like to ask today’s knowledge workers what their 5-year plan is. Unless you happen to be a professor in a University, it’s unlikely that your 5-year plan will be something you can imagine. More than that, it’s generally seen as undesirable to have a 5-year plan you stick to. We needn’t look far to see this sentiment echoed.

  • Marc Andreessen has written that “career planning = career limiting”.
  • Marisa Mayer has stated that had she stuck to her 5-year plan from when she was 18, all the great things that happened to her would have never occurred.

If you need evidence that hits home a little more, think back on your own life. Start from this year and go back five years three times. So, for 15 years ago, 10 years ago, and 5 years ago, assess whether you could’ve predicted where you’d end up 5 years from each point.

My Own Unpredictable Journey

I did the above thought exercise for myself and what I came up with follows.

  • In 2001, I couldn’t have imagined I would be in the Midwest going to graduate school in 2006. Even in 2005, I was declaring how I would never leave the east coast. Boy was I wrong!
  • In 2006, I couldn’t have imagined that I would end up working at MIT Lincoln Laboratory (MIT LL) in 2011. I’m not even sure I knew this was a place someone could actually work!
  • In 2011, I couldn’t have imagined that in 2016, I’d be leaving Shape Security, a Silicon Valley startup whose premise is centered on fighting (software) robots to join Google to help protect its massive user base.

How the hell could I have predicted any of that?

Why Career Paths Are Unpredictable For Knowledge Workers

If you’re out in the world accumulating knowledge in an open minded way, you’ll be affected by it. Your beliefs will change. Your understanding of the world will mature. Fortune will cause doors to open and others to close. As you go through the open doors and maybe forcibly open others, you’ll end up somewhere. But it’s unlikely you’ll end up where you predicted.

This whole experience can be a lot planning to go to a restaurant.

Planning on a Restaurant

Let’s say you were super interested in a restaurant in San Francisco. The only way you know of getting there from San Jose is 101 North. You check the news and see that there’s a ton of traffic on 101 so you think: “this is going to suck.” But in your sadness, you remember a friend mentioning an app called Waze to you. You download it and it suggests you take 280 North instead as it has much lighter traffic and will get you to the restaurant sooner. And just like that, a whole new route that you hadn’t even considered has opened up to you! Life is good.

The Plot Thickens

But then you go to the restaurant’s website and realize they actually have a location in San Jose, so you don’t even need to get onto any major highway. With this game plan in the bag, you figure you have some time to kill so you turn on the nightly news. In it, you find that tons of people in San Jose have been getting food poisoning from this very restaurant. This new bit of information was a total wet blanket. Your motivation for going out has dropped to zero. You spring for cooking your own meal at home instead. Deep down, you tell yourself, you always did want to cook more. “Maybe it was meant to be,” you tell yourself.

The Plot Gets Even Thicker

As soon as you go to grab a pot, your friend gives you a call and tells you: “Drake is at Studio 8!” Your friend has VIP access so you’ll be able to hang out with Drake in the VIP section. You drop your pot, get dressed and head out the door. A plan to go to a restaurant has unpredictably turned into what will surely be a memorable night at Studio 8.

How the hell could you predict any of that?