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

Sunday, 15 November 2015

Owning and re-writing our mental software | Summary

I personally struggle with chronic procrastination a lot (like a lot a lot) and in reading about (beating) it you come across the words "Motivation" and "Productivity" quite often. Those two words alone are multi-million dollar industries each that sell people books and seminars and individual coaching a la people like Tony Robbins, David Allen (of 'Getting Things Done' fame) and others. Not to say that these products and services aren't helpful but there's always felt like they didn't contain the complete picture...

What I've come to realize is that these myriad books and things presume that you have a good reason to want to be more productive. In other words, "Purpose" is assumed and then from there the books help you get other road-blocks out of the way. Of course it's a lot harder to talk about purpose, and harder still to find it for oneself. But in ignoring Purpose itself, the blind pursuit of increased productivity can leave you feeling drained and fatigued. From there you then think you need to start reading the Motivation books because you're so tired all the time and you just want to curl up and binge-watch Scrubs.

To break out of this cycle the thing to do is to sit and really be honest about what you really want. And none of that beauty pageant bullshit about "World Peace" if that's not true, this isn't the time for that. Write out your desires and also your aspirations for accomplishments or experiences in the future. Mostly you might find that this list will have things that you've sort of worked on in the past but for whatever reason it then fizzled out mid-way. Most likely you then blamed yourself for being "too lazy" or "not smart enough" or "not motivated enough" or whatever.

I've been in a similar state recently and in that context I came across the latest article from 'Wait, But Why?' about Elon Musk titled "The Cook and the Chef". There have been a handful of movies and books and things that've dramatically altered the course of my life thus far and this article has that feeling already, of being something momentous.

I highly recommend reading the original article but it's a bit of a mammoth read so here's my tl;dr summary to get you started:
  • Elon Musk isn't so productive because he's especially unique, he only seems that way in comparison to everyone else; with some analysis we could all be dramatically more effective.
  • Everybody has some version of mental software running in their brains that informs how they interact with the world.
  • Your mental model is a collection of "Wants", tempered by a set of "Beliefs" about what is possible in reality. In the overlap of those two are your "Goals".
  • Be aware that your software can be inherited from your parents, from culture and from society; You could be running out-of-date software and not realize it.
  • Think like a scientist, reason each component of your mental model from "first principles" and constantly re-adjust as you learn new information.

I'm really trying not to have this post be completely just fanboy-ish but I really think it's vitally important to be aware of one's own biases and mental models and see if they're really taking you where you want to go. Maybe first write out your current wants and beliefs and goals and just look at them and see if they're really yours or if you've accepted someone else's priorities for what your life should be about.

Speaking of helpful mental models, there's also this excellent video about the purpose of doing things : Use This Chart To Achieve Happiness. If you find yourself unhappy at a job, or feeling stuck in a role or whatever, maybe take a step back and see what's gone wrong and why you started doing it in the first place... The chart might help with that. Here's the link again, I'm not in the mood to embed videos right now : Use This Chart To Achieve Happiness

If you see me somewhere, I'd love to talk about how you decide to do things; how do you think about purpose for yourself and how do you choose goals from among a bunch of things that might all really cool things to work on. Or whatever, leave me a comment or send me an email or something and we'll chat. :)

25/11/2015 : It's David Allen who wrote 'Getting things done'. Confused him with Tim Allen from 'Home Improvement'. :p