Tuesday, 24 November 2015

Dick Bolles: "How to decide what you'll do in five years" | Summary

How do we figure out what we'll do five years from now?

This is probably the question I hate most during job interviews, and of late it's a question I'm asking myself a lot as well.

I found a Google talk by a guy Dick Bolles who's apparently written one of the most famous guides for job-seekers - 'What colour (color?) is your parachute.' - and here he's talking about how to think about five years into your future. I watched it and then re-watched it just now because I wanted to take notes and I'm putting them up in the hopes that it helps someone else out as well.

Generally people have one of three strategies for thinking about 5 years into their future:
  1. They ignore it
    • They rely on their Luck.
    • "I'll see where I'm at in five years and see what's happening."
    • Effectively, they hope to see the next big wave and then jump on it as it happens.
  2. "I'll know it when I see it"
    • They rely on their Intuition and on being watchful.
    • This is about pattern matching and noticing what's happening.
  3. They decide to try some forethought.
    • That's fine if you're "designing" but "planning" doesn't work.
    • You cannot plan for five years from now.
    • War, natural disasters or new technologies could completely upset your calculations.
    • You can design for the future though; Like planning for a camping trip, you take things you "might" need.
    • Design is gathering together whatever you might need to deal with the future scenarios.
Each strategy has certain conditions that need to be fulfilled if it's going to work. There's no right or wrong or "best" strategy, it's about how you operate.


  1. Whether this strategy works depends on Intersections; the more people you run into, the more likely you'll have "luck"
  2. Maximize your intersections.
  3. Pay attention to meetings, getting on social media, and meetups with people in real life.
  4. For job seekers, get on Linkedin.com, jobswithfriends.com (check for companies where friends of yours work).
  5. Note: Basically it becomes a kind of numbers game.


  1. Intuition depends on what you notice and generally you notice things in relation to some kind of benchmark.
  2. Then it becomes important to properly set your benchmark so that you're then more sensitive to deviations.
  3. Think of what kinda jobs you like best:
    • data
    • people
    • things (computers and whatever)
  4. So once you decide that, you can spend the next 5 years focusing on jobs related to that specific field.
  5. That way when something truly cool turns up, it'll be a significant deviation from the norm and you'll notice it.
  6. This is just one way to prime the brain to notice things, check out the video below.

Lifestyle Design

  1. Do an inventory of yourself.
  2. You're constantly put in boxes by situations and other people: "I'm a coder", "I'm in HR", etc and then you live in that box.
    • If you want to learn, you must first unlearn. And the biggest thing to unlearn is the limiting picture we have of ourselves.
  3. The inventory should not be "I'm this" or "I'm that".
    • Instead it can be "I am a person..." and then "I am a person who..."
  4. Again, you're gathering a set of things you think might be useful in five years... 
    • When you go camping, the most important thing is a tent.
    • For job seeking, or fulfilment, the most important thing to do is rethink who you are.
    • What you do flows from who you are!
  5. (Detailed inventory thing is in his book... some "crass commercialism" here. :p)
  6. The inventory should be a set of stories about yourself. Those stories should then boil down into a set of skills.
    • Focus on skills because the more atomic you get in your understanding of yourself, the more flexibility you have.
    • If you're good at teaching, researching and writing then you could be any number of things like a speaker, a scientist, anything.
  7. Think about how you like to use your brain, and what skills you have.
  8. Nevermind what the marketplace wants initially, you can persuade someone to pay you for your skills later. 
    • It's enthusiasm that's the real secret ingredient.
  What you're doing 5 years from now will depend on who you are right now.

Further reading 

This was a super useful talk, I'm sure it'll come in handy soon. Meanwhile here's some other thoughts about work if you're interested:
  1. Your lifestyle has already been designed | Raptitude.com
  2. 3 ways your office building hates you | Cracked.com
  3. How to be creative | GapingVoid.com
  4. Job Advice | StillDrinking.com 
  5. Makers schedule vs Manager's Schedule | Paul Graham
  6. Screw finding your passion | Mark Manson

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