If You Could Not Fail...

Do you ever listen to The Tim Ferriss Show? It is one of my very favorite podcasts of all time. Tim gets interesting thinkers on his show and interviews them in a way that makes them open up and talk frankly about themselves and their craft and the big questions in life. I loved the episode with Maria Popova as well as the one with Alain de Botton.

A few days ago, I was looking for something to listen to while cleaning. (I don't know if this happens to you, but I have the hardest time getting started when the house is a disaster and I don't know where to begin. For some reason, putting in my ear buds with a good podcast always makes a gargantuan mindless task easier. I'm transformed into a cleaning machine!) So I did a bit of browsing and after starting - and abandoning - three other podcasts within the first few minutes, I came across Tim's episode How to Design a Life with Debbie Millman.

I had never heard of Debbie, but the title grabbed me right away. As we get closer and closer to the end of J's program and still don't have a set plan in place for next year, I get more and more anxious. I feel like I don't know what I really want in life, but then at the same time, I do. Does that make sense? It felt like serendipity that I happened upon that particular podcast episode right then. I have been thinking about it ever since.

I absolutely encourage you to give it a listen in full, but the one main action item that comes out of it is an exercise that Debbie does with her students, and had done as a student when she studied with Milton Glaser (he designed the I heart NY logo. You're welcome.) The exercise goes like this...

What would your life be like, what would you pursue and go after - if you had absolute certainty that you would not fail?

I've seen this sentiment before on a square magnet on someone's fridge and it seemed really inspiring, but vapid. Debbie's exercise goes deeper. Rather than stopping there, she asks you to write, in prose, a long-form essay of your life TEN YEARS from now. "It's a January day in 2027," she starts, "what kind of bed do you wake up in? What kind of sheets are you sleeping in?  Where do you live? What do you do? Who do you see? From start to finish, write out your day. Write it out in extreme detail from the moment you wake up until you go to sleep at night." Once you're done, you simply put it away, although Debbie did extract a bullet list from her own, and then you pull it out and read it once a year.

She says that she gets emails and messages from students all the time who are so startled, a decade later, at how much of theirs has come to fruition. She warns that "it's spooky!" and you have to be very careful and deliberate in what you include and put into it because it will probably come true. I was utterly fascinated and dumbstruck. It's so simple, and so obvious a way to design one's own life. Why hadn't I thought of that?!

Imagining a winter's day in 2027 is a lot scarier than I expected it to be. I sat down to give it a go and was so broadsided by the thought of Coco being 15 and Theo being 12 that that was enough for one day. But that is all the more reason to sit down and write it all out in detail. If the next ten years slip away like that last ten years have, it would be easy to miss out on a lot. I heard somewhere that we're the busiest in life between 35 and 55 and I believe it. It's kind of the filet mignon of life and I want to savor every bit of it.

So while I haven't gotten to the exercise yet myself, I just had to share this with you. Download the episode and get cleaning, or go for a long walk, or let it capture your imagination on a long drive or commute. It is one of the greatest things I've listened to in a long time. It might even change your life.

(Photo via Pop Sugar)


  1. Thank you SO MUCH for sharing this exercise! I immediately listened to the podcast and I'm so inspired. I'm writing my "essay" today and I'm so thrilled to have found some focus!

    1. You're welcome, Emma! Glad it came at a good time. xoxo


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