How To Have A Better Life

In this post, I consider the life-improvement techniques outlined in the book Designing Your Life. This post is not a summary or a review. Instead, these are my personal takeaways from reading the book. If you have any comments, feel free to reach out — my email is

There’s no shortage of self-help books out there and — as we all know — most of them are no good.

Recently though, I came across a useful self-help book called Designing Your Life. It’s useful because it’s practical and simple to implement. The book is written by two Stanford professors and is based on a class they teach. Their class has become the most popular course at Stanford.

The main idea is that in order to set up an amazing life for yourself, you should use the process and thinking that designers use.

In this post, I’ll explain how to do that. It begins with a shift in mindset.

Think Like a Designer, not an Engineer

Consider this eye-opening fact: no one really knows what he/she wants to be. The saying that you should “follow your passion” is actually nonsensical.

The truth is that most people don’t have preexisting passions. You don’t know who you love until you have a relationship. Similarly, you don’t know what you love until you try it out.

It’s even more complicated. Your “self” changes —so what you loved 5 years ago isn’t what you love today. And the world changes — what it offered 5 years ago isn’t what it offers today.

If you stop to consider all the moving pieces, it seems silly to think that life can or should be perfectly planned. It’s too hard to know enough about your future self or the future world to plan perfectly. Doing so ignores too much of what the future may bring.

Psychologically, we seek certainty. This makes sense when survival is at stake. But today, what’s at stake is not only survival but also fulfillment. As such, uncertainty can be an opportunity for discovery rather than something to fear or eradicate.

Designers don’t plan. They make serendipity more likely.

New Life Heuristics

How can you make serendipity more likely? Here are four rules of thumb:

  1. Restrain your instinct to plan multiple steps ahead. It’s hard to see how things will evolve. A focus on the end-game will keep you from trying things. Focus instead on the next step.
  2. Be actively curious. Assume that you know very little. When you come across something you don’t know (e.g. a new food, experience, person, etc.) default to active curiosity. This will force you to sample from the unknown.
  3. Don’t think your way forward, build your way forward. Speculation and analysis are bad discovery tools. The best way to know something is to experience it directly. Analyze less, build/experience more.
  4. Other people are gold. They have sampled from different corners of reality than you have. Enlisting their help or learning from their stories will make you aware of things you had never considered.

These four heuristics usher the unknown into your life. Compare them to a mindset which craves planning and control. Compare them also to a life of “lather, rinse, repeat.”

We need to wrap these heuristics into a process or system that helps us live better. We need a system because otherwise we’d be like leaves drifting in the wind, drawn to whatever commands our attention at the moment.

The key tool for our life-improvement system is prototyping. It allows us to efficiently sample a life-change without committing to it.

Prototyping: An Example

The below is a real-life example, from Chapter 6 of the book, that illustrates how to prototype life changes.

Clara is a mom with grown children. She wants an encore career but can’t identify her “passions”. She likes the idea of spending time helping women in need.

She finds a local seminar on how mediation can help battered women. After the seminar, she proactively approaches the speaker, who invites her to a mediation course. She takes the course and learns of a part-time job helping battered women. She begins work and enjoys it.

Through continued research, Clara discovers the Women’s Foundation for California (WFC). She applies for a job there and works for them for three years. While there, she gets experience writing grants and discovers many non-profits working to solve social problems.

She becomes increasingly drawn to the issue of homelessness. Through the WFC, she meets a philanthropist who asks her to join a local shelter’s board of directors. Right then she knows that she has found her encore career. Homelessness became her passion.

She arrived here through a series of small prototype experiences — attending a talk, taking a course, working a part-time job, working for a non-profit, and meeting people. Her path could not have been planned from the outset.

Failing To Prototype: A Cautionary Tale

Contrast Clara’s journey to Elise’s, which illustrates what happens when we don’t prototype.

Elise works in HR and does not like her job. She is finally ready for a big change. She loves Italian food and has always dreamed of running an Italian deli.

She takes a leap of faith and goes for it. She rents a space in town and completely renovates it. Months later her deli opens to great fanfare and is a financial success!

But Elise is miserable. It turns out that she hates running a deli.

Elise is a great cafe designer and renovation manager. But she’s not a great deli manager, and that’s what she spends most of her time doing.

She did not prototype to learn what running a deli was actually like. She could have tried catering first, which is easy to start up and shut down. She could have gotten a weekend job bussing tables. She could have interviewed three happy and three unhappy cafe owners to see which group she was more like.

Instead, she relied on her preconceptions, which caused her to over-commit to a change that did not make sense for her life.

From Idea To Prototype

If you have an idea for something you want to change in your life, prototype it before diving in.

There are many possible prototypes for an idea. So consider several prototypes before picking one. Ask friends and mentors for prototypes — fresh perspectives help. Start simple and layer in more complex prototypes later.

Coming up with a prototype is not always easy. The good news is that it’s like exercising a muscle: the more you do it, the better you get coming up with prototype experiences. The best investment you can make in yourself is to build up your skill in generating prototype experiences.

The simplest prototype is having a conversation. Say you’re considering a career switch to a new industry. Talking to someone in that industry, ideally someone who knows you, will clear up misconceptions you may have about what it’s like and whether your skills transfer. This is why the size and quality of your network matters, and why its worth the time to develop a diverse network.

Though a conversation is useful, ultimately the most informative prototypes are hands-on experiences. If you’re considering buying a house in a neighborhood, renting a house in that neighborhood is a much richer prototype experience than talking to someone about the pros and cons.

Each prototype experience expands your horizons and makes the next prototype experience that much easier to generate and execute.

Deciding What In Your Life To Improve

It’s critical to prototype ideas for life changes. But how do you come up with ideas for life changes? What in your life should you focus on improving?

The easiest way to identify improvement areas is to assess your current life. The authors recommend filling out a Health-Work-Play-Love dashboard (see the worksheet here). This entails giving a score to the major areas of your life. Low scoring areas are candidates for improvement.

So, for example, if your Play score is low (because you’re too busy to make time for play), then you can generate prototypes that answer the question “how can I get more play?” Your prototypes might be (e.g.) to join a weekly squash league or drawing class.

A second way to identify improvement areas is to start an activity journal. Each day, record your activities chronologically and rate each activity on a scale of 1–10 in terms of energy and engagement. If you do this for 2–3 weeks, you’ll start to see patterns. Generate prototypes that let you reduce time on the least engaging activities and increase time on the most engaging.

Sometimes ideas for life improvement find you, rather than the other way around. When you live by the four rules of thumb listed above, you try new things and meeting new people, which naturally brings ideas for life improvement. You’ll find people doing interesting things. Get their life stories, career stories and book recommendations, and generate prototypes to see if you’d enjoy doing what they do.

Keep in mind that most life-design work is tuning the life you’re in, not making large structural changes.

Iterating and Integrating

Once you find an enjoyable prototype experience, continue layering on top of that prototype. Clara’s started by attending a lecture. She then crafted increasingly involved prototypes (taking a course, getting a part-time job, getting a full-time job, etc.) that got her more and more informed and committed.

The ultimate purpose of prototyping is to test configurations that could improve your life. If you find something that works, continue to prototype it until you can integrate it into your life.

As you integrate new activities into your life and remove old activities, you’ll inevitably be forced to make trade-offs. A common trade-off is money versus spending time on things you love. Another is pleasure versus principles.

It pays to write down your beliefs about life and work. Articulate a short life manifesto and work manifesto (a couple of paragraphs). These are works in progress and can evolve over time. They constitute your current north star and allow you to make trade-offs in a way that is true to yourself.

The System

Let’s bring all of the above together into a compact system for life improvement:

  1. Adopt a mindset consisting of the four rules of thumb
  2. Identify areas for life improvement through current life assessment, activity journaling, and talking to new people
  3. Select the top 2–3 ideas from Step (2)
  4. Generate 2 prototypes for each idea from Step (3)
  5. Actively execute on 3 prototypes at any one time. Spend 5–10% of your time (a few hours a week) executing these prototypes.
  6. Iterate and integrate the successful prototypes. Discard the unsuccessful ones
  7. Go back to Step (2) and start the process over

This system never terminates. It has no end goal. Life becomes a process of continually improving your life. It becomes an infinite game.


Designing Your Life is a great book, one I’d easily recommend. It offers a practical, systematic procedure for building a better life. What’s more, I find that living according to the four heuristics reduces stress and makes life seem more magical.

Generating prototypes is a skill everyone should learn. Those who follow Lean Startup Methodology know to do this in business. It’s even more sensible to do this in life, where there are more moving pieces and strong cognitive biases at play.

If you enjoyed this post, please share! For future research and book takeaways, connect with me on Twitter @RasheedSabar






Hedge fund manager at Ellington, co-founder of data science firm Correlation One, advisor to several startups, lifelong learner.

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Rasheed Sabar

Rasheed Sabar

Hedge fund manager at Ellington, co-founder of data science firm Correlation One, advisor to several startups, lifelong learner.

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