Designing Your Life

2 May, 2020 | Book Notes, Career

This book applies design thinking to your career.

Using design techniques such as brainstorming and prototypes, the authors describe practical ways you can think about reinventing your situation. They reframe common problems people face throughout and give practical tasks to keep things actionable. I also like the approach of passion discovery, rather than starting with the assumption you already know your passion.

Rating - 7.5/10.

View here: Designing Your Life

You may also want to view my other book notes.



First, let’s dispel some common myths:

  1. What you study will become your career - Nope. Only a small % of people actually do something closely related.
  2. Success makes you happy - Nope. Even successful people need to design a life they will enjoy.
  3. It’s too late to change - Nope. It’s not.

This book is about design thinking, applied to your life. It’s not an engineering problem with a single solution. Rather it’s a process that you iterate on. A set of steps that nudge towards an evolving goal.

We start with empathy. We need to ask questions about the right problem. Then we can reframe the problem if we need to. Some things to remember:

  • This is personal, so you need to do the work yourself
  • There are many selfs that may want different things at different times, so acknowledge these contradictions
  • Prototypes are key; not just thinking, but doing

5 mindsets for life design

  1. Be curious - Explore and play, think of everything as an opportunity.
  2. Bias for action - Try things and test them for real.
  3. Reframing - Helps make sure we are asking the right question (and will get better answers).
  4. Be aware of the process - It won’t work straight away, so be prepared to change and try again.
  5. Collaborate - Use friends and mentors for suggestions.

No one knows their passion. You need to try stuff and see how you respond.

What is a well designed life? When who you are, what you believe and what you do align.

Ken Robinson would probably agree with idea of alignment. You want to be your most authentic self. Similarly, the emphasis on trying things out remind me of Cal Newport's taking small bets.

Start Where You Are

This is a book about finding problems and designing solutions. You want to make sure you are working on the right problem, whether thats adding something new (e.g. a job) or removing something (e.g. a person).

You need to maintain a beginners mind and be open to new routes. Also, avoid “gravity problems” - problems you can’t change. For example, the market for journalists is crashing. Yes, but you can’t change that. Instead, focus on what you can change, like pivoting into a copy writer for digital brands.

First, we need to assess where we are in our life. Some key buckets:

  • Health (physical, mental, emotional)
  • Work
  • Play (joy)
  • Love (relationships)

You want to rate each one, which will give you an indication of a potential problem worth working on. There is no wrong or right, it’s personal. But you’ll have a sense of what is missing. It’s very likely it will change over time.

Work isn’t just your job. But should include everything you do and put time into.

Is 4 buckets enough? Or would I rather separate them out more? All of this requires a growth mindset. You need to believe you can change and improve in those areas. This process reminds me of Ray Dalio's idea of day-to-day activity vs stepping back and looking at the machine. You need to step above yourself and see how the whole machine is operating.

Building a Compass

Now you have a sense of where you are, you need to build a sense of where you are headed. You’ll need to build opinions about you:

  1. Workview - what does work mean to you? Why do you do it?
  2. Lifeview - what is life? How is it good?

Then you want to build a coherency between:

  • Who you are
  • What you believe
  • What you do

You’ll have to acknowledge trade-offs. There will always be tensions, so don’t expect perfect alignment. But you want to be aware if anything is majorly out of whack.

an arrow between who your are, what you beleive and what you do


This isn’t as easy as what you do now. Rather, why do you work? For all your vocations. Why do you do them? Why are they important? Does it connect to others?


What is the purpose? What do you find valuable?

Then compare them. Where do they align? Where are they different?


A way of travelling with no destination, just a general direction. We can do this with our careers by listening to two key cues.

Engagement - Is when you are focused, excited. Optimal engagement is flow - this is how you want work to feel. Disengagement - is when you feel restless, impatient or unhappy.

Energy - Does this give your energy? or take it away? It’s different to engagement in two main ways. First, often they come together, but sometimes they don’t. Second, this can actually be negative.

Life design isn’t just about completely changing your life. It can also be more subtle, what changes can you make to get more out of your existing life?

Good-time Journal

  • Activity log (daily) - Log of your activities, with a score for energy and engagement
  • Reflections (weekly) - Record any insights and observations relating to the above

From these, develop actions:

  • Try to remove or delegate low energy/low engagement items. Or try to change them, what about them specifically makes them low engagement?
  • If they are still crucial and can only be done by you, put them at a time of day/week that you have the energy for.


For optimal reflections, you’ll want high detail logs: A - Activity - What were you doing? Was it active or passive? E - Environment - What kind of environment? How did it make you feel? I - Interactions - Was it new or familiar? O - Objects - Any objects? Alcohol? Phone? U - Users - How did people add or detract form your experience? Who where they? Anyone standout? How many?

e.g. I went to dinner with work friends (activity). Tim stories where hilarious (users) but I was anxious around so many people (users/environment).

You can also do this thinking back about big milestones or times in your life. What made them so great?

How does building your skills fit into this? Everything feels more fun when you're good at it. So is there some element of just getting through that first stage?

Getting Unstuck

People get stuck in jobs. They know they are unhappy, but they don’t know what to change.

Reframe: I’m stuck → I’m never stuck, because I can generate new ideas. Reframe: I need one correct solution → I need many ideas to try and test.

Designers often get stuck. But they also know how to generate new ideas to test. To know what you might want to do you first need to generate lots of options. Realise that there are many great versions of your life, not one specific version, so feel open and liberated by that.


Focus on quantity. More ideas eventually leads to better ideas. So come up with as any as possible and reserve judgement until the end. Why?

  1. We choose better from many options?
  2. Our first idea is never the best, but our brain tried to convince us it is because its lazy.


  1. Write a thing you like
  2. Write 5 connected things
  3. Then 5 more form the second ring
  4. Connect ideas between

You can come up with a lot of ideas this way. You’ll realise some also make your existing job better, not just coming up with completely new jobs. It’s good to also have crazy ideas though.

Anchor Problems

If you get attached to the first solution too much, it can weigh you down. Don’t get fixated on a solution. Remain open and prepared to iterate. Anchor problems are not the same as gravity problems. Anchor problems you can reframe, whereas gravity problems you can’t do anything about.

Reminds me of Rob Walling's speed bumps vs road blocks.

Design You Lives

We have multiple lives within us, not just one.

Reframe: Plan one perfect life → accept that life is a constantly evolving mix of decisions.

So we’ll come up with alternatives. Not just ideas, but actual possible plans. And they should be separate and different.

  1. What you do (current view).
  2. What would you do if not 1.
  3. What would you do if money wasn’t a consideration.

For each bucket, make a plan, which includes:

  • Visual Timelines - With specific milestones (not just work, but life events too).
  • Tag line - 6 words.
  • Questions - 3 questions about the plan.
  • Gauge - On resources, likability, confidence and coherence. You might also consider geography, who you’ll meet, what you’ll learn and impact for future.

Ideally, share these with someone close to you. Get them to reflect and amplify what they think makes sense and is good.


When finding a new career, the best way is to make small nudges towards it, testing its the right fit along the way.

Cal Newport would agree - take small bets and edge your way over time.

Reframe: You don’t need data on all options → You need a small selection of real life experience to inform your decision-making.

Why prototype? We can’t get lot’s of abstract data on many life decisions. Instead, prototyping enables us to:

  • Ask the right questions
  • Reveal our own biases
  • Understand the problem better
  • Build momentum
  • Isolate part of a career idea and test it with real experience
  • “Creep up on the future”

Rushing into things without having tested it is also a bad idea. You may realise it’s not what you actually expected.

How to prototype?

  1. Conversations - Easiest one. Interview people in your chosen career path. See what they like and dislike. If they are similar to you, maybe you’ll feel the same.
  2. Experiences - More important, higher fidelity. e.g. Day at friends work, week long project, internship. Actually do it yourself.

Mom Test - up to you to ask good questions. People might be tempted to just say their job is great, because they feel they have to, so ask about their real experiences. It's sort of like a career MVP. Lean Startup of career building.

Brainstorm experiences

  • Lots of ideas
  • Defer judgement
  • Have other focused brainstormers with you who know you

General technique

  1. Frame a good question (not leading, some constraints, not too vague)
  2. Warm up activity (playful mood)
  3. Brainstorm itself:

    • Facilitators (frame question, record ideas)
    • Quantity > quality
    • No judgement
    • Build off each others ideas
    • Wild ideas are encourages (stretch the idea space)
    • Name and frame outcomes - group them, vote on them, develop associations

How to Not Get a Job

Don’t start with the internet. It rarely shows all the available jobs. Descriptions are always bad.

But if you do:

  • Use the words they use
  • Highlight only the skills they are after

Reframe: Focus on your needs in the job → Focus on the hiring managers needs.

Designing Your Dream Job

Reframe: There is no one dream job → There are lots of decent jobs out there and you can co-create into a better job.

What about The Element? Is there a thing where our talents and our passions align?

Luckily, one of the best ways to get a hidden job is the same way as prototyping - having conversations. Sometimes they’ll offer you a job.


Reframe: Networking is about hustling → Network is about asking for directions, people like to help.

The internet is not great for finding jobs, but it is good for finding people. So its a useful tool for networking.

Offers > Jobs

Reframe: Get lots of jobs → Get plenty of options for us to review

Why the distinction? Job descriptions are often so bad that we’ll need to find out more information through the interview process. Likelihood is you can even shape the job a bit. So be curious and have an open mindset.

Choosing Happiness

Happiness is about choosing, rather than the choice.

Reframe: Don’t choose one perfect life → You learn to choose well.

Life designers have a process to choose:

  1. Gather and create options - Know yourself, know the world and the options, generate lots of ideas.
  2. Narrow down - Can’t have too many options, so cut it down to flesh out fully.
  3. Choose - Use all your decision-making faculty. Not just your logical brain, but also your emotions. Learn to quiet other things (and people) and build your intuition.
  4. Let go and move forward - We get unhappy when we feel we’ve left options on the table. So move on so you can invest and enjoy your new route.

They reference mediation as a way to build better intuition.

Reframe: Happiness is not having it all → It’s letting go of what you don’t need.

Failure Immunity

We can’t stop failing, but we can prevent some of the negative feelings. Failure often means new learnings, so we can reframe it as growth.

Reframe: Life isn’t about the outcome → It’s about the process

Life is an infinite game. We can continually play. Which means we can learn and build on that in the next stage.

Be > Do > Become

When you try new things, it will shape who you are. There is a cycle. You want to build a skill for learning from failure and reframing them as a useful way to shape who you are.

idea, do, fail, learn in a loop

How to build failure immunity?

  1. Track your failures
  2. Categorise them

    • Screwups - just forget these (you’d normally get them right)
    • Weaknesses - you regularly get these wrong, but unlikely to change much
    • Growth opps - somewhere you think you can make improvements
  3. Act on the growth opportunities.

Failure immunity is building a process that lets you react emotionally to failure and improve and grow as a result.

Pain + Reflection = Progress → Failure Immunity. How can I build a failure log + reflection into my regular process?

Build a Team

Value of collaboration.

Reframe: It’s your life → But others can help you design it.

Design Team

  • Supporters - They support you and show encouragement.
  • Players - Active participants in your process, design, prototypes.
  • Intimates - Best friends and family. Most effected by your decisions.
  • The team - 3-5 most active people who know all the details and you trust them.

Roles - There should be one facilitator (normally you) who organises the meets but then its just conversation between friends. Focus on: respectful, generative conversation.


  • Counsel vs advice - Advice is when people tell you what they’d do. But they aren’t you. Counsel is when they help you figure out your own mind. They ask more questions. They listen and reflect back to you. They reframe your answers.
  • Discernment - They can help you notice what seems most important to you.
  • Long term vs local - Some mentors will be for specific periods (job change) or area of your life (finance, career). Be a good mentee by steering the conversation.


  • Purpose - some shared thing that brings you together
  • Meet regularly - consistency is important
  • Shared ground - in terms of goals and values


Humans go through seasons. We are always changing. Life design must therefore be a continual process.

Continue to employ the 5 mindsets of life design throughout. Use some of the tools as and when you need. Feel like things are getting away from you? Start your good time journal again. Feel lost at work? Come back to your compass. Develop good habits that clear your direction (e.g. meditation, journaling).

You may also want to view my other book notes.

© 2022,