Defining Your Best Life

Defining Your Best Life

Every year I review a handful of concepts, books, articles, and talks as part of my yearly goal-setting and planning practice. These pieces, and this practice, serve as periodic checkpoints to ensure I don’t stray far from the path I’ve set for myself on the way to being the best person I can be. In some cases, they’re great reminders for living a better and happier life. In other cases, cues for the causes and principles I want to always have front and center in my mind.

Revisiting these concepts on a regular basis is my way of systematizing the inherently disorganized process of adopting and integrating concepts, techniques, processes, and values into my day to day life.

Over the next few weeks, I’d like to share some of those articles and talks here.

If these pieces resonate with you, I encourage you to bookmark them under a folder on your web browser titled “annual/quarterly reads.” Add to the list as you see fit to. Set calendar reminders quarterly, biannually, or annually to take a look.


The fourth of my annual reads is the document I wrote using Debbie Millman’s “My Remarkable Life” exercise. You should write out one for yourself and review it at least once a year.

Bottom line: if you don’t know where you’re going any road will take you there. This prompt, the thought process required to respond to it, and periodic reviews will help you to know what the end goal looks like.

Most of us live in the uncomfortable reality of wanting to live a meaningful and rich life while not really having a complete understanding of what that means to us. I’ve been there.

I was fresh out of the Navy and getting ready to start graduate school when it occurred to me that I had only the vaguest idea of why I was there and what I wanted to get out of it. What’s more is that I really had no idea of the direction I ultimately wanted my life to take. Should I look for the highest paying gigs? Should I start a business? What about my personal life? Do I want to have kids at some point? What does that mean to me right now?

In short, I didn’t know what I needed to do in the short term because I had no idea what I wanted from life down the line.

Right about the time I was locked in this glass cage of emotion, I heard about Debbie Millman’s “Ten years to a remarkable life” exercise on the Tim Ferriss podcast. I put a few hours aside to do it and it changed my life.

For the first time, I deliberately thought through what I wanted my life to look like. I weighed options and made choices. I defined my destination – in concrete terms. I said “no” to the things that would not take me to that destination.

I review my “remarkable life” doc at least once a year, often more frequently. In the few years since I wrote this, big decisions have gotten easier and the small decisions seem to have unconsciously pointed in the direction of my longer term goals.

I highly recommend you take this project on and add it to your annual reading list.

Here’s how:

10 Years to a Remarkable Life

Envision the life you could have if you pursued everything that you wanted, with certainty that you would succeed. Imagine your ideal day ten years from now in excruciating detail and write about it. More is better.

So let say it is Winter 2033. What does your life look like? What are you doing? Where are you living? Who are you living with? Do you have pets? What kind of house are you in? Is it an apartment are you in the city are you in the country? What does your furniture look like? What is your bed like? What are your sheets like? What kind of clothes do you wear? What kind of hair do you have?

Tell me about your pets, tell me about your significant other, do you have children? Do you have a car? Do you have a boat? Talk about your career. What do you want? What are you reading? What are you making? What excites you? What is your health like?

Write out this day, this one day ten years from now. So one day in the winter of 2033, what does your whole day look like? Start from the minute you wake up, brush your teeth, have your coffee or tea, all the way through until minute you tuck yourself in at night. What is that day like for you?

Dream big, dreams without any fear. Write it all down. You don’t have to share it with anyone other than yourself. Put your whole heart into it. And write like there is no tomorrow; write like your life depends on it because it does.

Do not edit yourself.

And then read it, once a year, and see what happens.

It’s magic.