On Playing the Long Game

Play for the long term. Choose jobs working on technology that will still be relevant a decade hence. Choose jobs that build on your strengths but significantly stretch beyond them. Always say “yes” to requests to do more or take on more. Each is an opportunity. Choose jobs working with the best in the industry. Working with the best is the quickest way to learn. Never let go of the details even as you take on broader roles. Don’t worry about money, job title, or recognition. It’ll all come and never leave if you get these four goals right. Short term decisions often yield little and what they do offer doesn’t last. Play the long game.

More advicing in the comments …

One recommendation I should have added to my short list was curiosity. I’m interested in absolutely all forms of technology and will grab every chance I can to learn the details from another field or to see how other types of systems are manufactured. It’s amazing how frequently I learn something that can be applied to problems we are working on in infrastructure. The more solutions one sees, the more likely some of these ideas are to fall together in a new way to solve a problem in infrastructure. I’m interested in all forms technology and many of the best ideas lie in new applications of technology from other disciplines. …

Source: Advice to Someone Just Entering Our Industry, James Hamilton


Shifu On Reaching - Dreamworks


Where are the gaps in what I’m able so see? Are they there because I don’t want to see or am ignorant, or … ?

Being open to new information, and alternate view points is a start towards defending against mistakes caused by this.



At critical moments in time, you can raise the aspirations of other people significantly, especially when they are relatively young, simply by suggesting they do something better or more ambitious than what they might have in mind. It costs you relatively little to do this, but the benefit to them, and to the broader world, may be enormous. - Tyler Cowen


Starting a movement

Building momentum is hard. How do you avoid fast failure with forces that would avoid change? Status quo is a hard hill to climb : “But I really need to get my stuff done. I don’t have time to try this new thing!”

On writing specs

If you want to build something and need the help of others, communicate the need and outcomes you’re after with a spec. Be sure to include these four things:

  1. What is the problem to be solved?
  2. How are we going to solve it?
  3. How can we test that the thing we built matches what we set out to build?
  4. How will we know if it’s working?

While there are only four steps, the specificity of each step is essential. The spec for a 787 jet, for example, leaves very little room for argument about what’s being created. On the other hand, “I’ll know it when I see it,” isn’t at all helpful.

If you’re not spending at least 5% of your project budget on the spec, you might be doing it wrong.

Time horizons, iterations, small batches

Jason Fried has some timely advice for me today. Namely the benefits to working in small batches can have psychological impacts in addition to business, workflow ones:

long projects

Peak energy for long duration projects high at kickoff, then tapers off

short projects

Peak energy for projects delivered iteratively renews every cycle



I will start my own first 1:1 guide for new hires with Lara Hogan’s. I love every part of it. I’m sure it’ll evolve along with me as I follow my own path but for now I think it’s great and gets at important learnings about people.


  • What makes you grumpy?
    • How will I know when you’re grumpy?
    • How can I help you when you’re grumpy?

Feedback and recognition

  • How do you like to receive feedback? (chat, in person, email)
    • In 1:1s or right when it happens? (Delayed or real time?)
    • How do you prefer to receive recognition? (public or private)

Goals and support

  • What are your goals for this year? The next 3 months?
  • What do you need from me?
  • What do you need from your team?
  • What do you need from your peers outside the team?

The wordy question

  • Human learning requires 4 things: new challenges (but not too hard or too easy), low ego (acceptance of failure, and that there are many things you don’t know!), time and space to reflect, plus timely and clear feedback. How are these 4 going for ya?

This doesn’t feel like a first 1:1 questions to me. But a great one for somebody who’s been around longer …

Lara’s most important

  • What is your favourite baked good?

Because you never know when you’ll need a pastry …


Books I’ve enjoyed reading about teamwork and helping to make collaborative spaces

  • Creativity Inc
  • The Coaching Habit
  • Radical Candor
  • High Output Management
  • Co-active Leadership
  • The Making of a Manager


“High agency means you are able to find a way to get what you want without perfect conditions. Push through, or reverse / change obstacles”

  • Fixed vs growth mindset
  • Go getters, Game Changers, Fruststrated geniuses ++ The 2 former can see a system they don’t understand or that has obstacles and will work around / through them. The latter could be a high performer but ultimately accepts the system as it is and becomes demotivated


agency 2