The Remarkable Life Exercise

Write like your life depends on it, because it does.

It’s five years from today.

What are you doing? 

Where are you? 

Who are you? 

In July of 2017 I took my first attempt at answering those questions for my future self. I did this after discovering an exercise called The Remarkable Life via a Tim Ferris podcast. The podcast episode interviews Debbie Millman, a writer, designer, brand expert, teacher, and insert lots of other titles. Tim and Debbie talk about how easier things become when you know what you want. 

Without establishing a direction, you can spend all day moving and never get where you want to go.- Debbie Millman. 

Their conversation detailed a “life changing exercise” that Debbie was asked to do while enrolled in a creative writing class. In her class she was asked to ‘envision the life you would have if you pursued everything you wanted, with certainty that you would succeed.’  

Her teacher gave the class three rules:

1. Dream Big 

2. Don’t edit yourself 

3. Be careful what you wish for (because it may come true) 

Millman dove in and years later realized that nearly everything from her writing came true. She wasn’t alone, other classmates had positive outcomes. The exercise is garnished with supporting advice, including the importance of being specific and not holding back from what you really want your life to look like. You’re encouraged to squeeze out the details and explore small specifics. Things like, what you’re wearing, what your coffee cups look like, what your house is like, and how you spend your time. She encourages you to explore what a full day, five years from now, would look like. Once complete, re-read the entry every year. No exceptions. 

Listening to the podcast I could feel the magic of this exercise and immediately knew I must try it. 

So, I did. 

It was 2017. I had just returned from a seven month ‘’round the world’ adventure with Clayton after quitting our sexy Chicago startup jobs. (think WeWork style, chartered planes to Cancun company retreats, foosball and beer on tap). Another essay to come on that. 

 I was working remotely for an event company, shipping plastic cups across the country and coordinating drink specials for a tacky 90s themed bar crawl. It gave me flexibility, but I was unsure what to do next. Start my own thing? Find a remote gig and continue to travel? Settle down in another office role? What was I even good at? What did I actually know? I faced the harsh reality that my identity was wrapped up in my past jobs and past adventures. 

Five years into the future felt impossible to envision, but with my pen, my ‘never stop exploring’ journal, and my pounding heart I began to write.

July of 2017 put my future self in July of 2022. I struggled to get into it. I found myself starting over again and again, afraid to write down things too lofty or admit to myself exactly what I wanted. After a few scratched out pages, and a handwritten pep-talk to myself, “can you please stop being such a baby, enjoy this, it’s supposed to be F-U-N’, I decided I needed to really go for it. 

“I’m 33 years old. It’s sunny out. I got up early to drink black coffee, practice yoga, and enjoy quiet time before everyone else is up and moving. I’m married to Clayton. I can still fit into my size 2 Madewell jeans.’ 

I continued. Page after page detailing my future. 

The five-year time period that this exercise covered has come and gone, yet I still have moments where I exclaim, “I wrote that down!” Some specifics are different, (we don’t have two little boys), but much of the general themes have unfolded: a flexible work schedule, walls filled with travel photos, deep connections with neighbors, and actually marrying Clayton. 

This exercise has reminded me that once you say something out loud or write something down you start believing it. And once you believe it, you start subconsciously making decisions that guide you in a direction you want to go.

I’m set to do The Remarkable Life exercise again this summer. When I think about the blank pages ahead of me, I am prepared to take the next attempt at this exercise more seriously. Five years from right now, I’ll be entering into a new decade. I'll have an 8 year old and a 5 year old. I’ll still be married to Clayton (please, God), and I’m over the whole jeans fitting again thing. 

For this next exercise, I’ve got a lot of dreaming to get serious about. I’m promising myself to really get specific this time, to believe that my dreams can become realities, and mostly I’m prepared to not edit myself because as Debbie says “write like your life depends on it, because it does.” 

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Want to do The Remarkable Life exercise yourself? Below are some resources to get you started.

🎧 In true Tim Ferris style, here is the two hour Podcast with Debbie. . 

✏️ Check out this blog from Debbie and you’ll be all set to change your life. 

♠️ I didn’t know this was a thing until I searched for the Podcast. Let me know if you order these!