Re-designing Your Life in 20 Minutes

I’m currently paused in the middle of listening to a delicious interview with Tim Ferriss and Debbie Millman. If you’re not familiar with Debbie Millman, she’s well known for being the host of the award winning podcast, Design Matters.

The episode title is, “How to Design a Life,” and if you’re anything like me, you are immediately intrigued and interested.

Overall it was a great episode! But the juiciest part was definitely at the very end of the podcast where she shares the very questions that she answered in order to realize all of her wildest dreams.

Note: This isn’t necessarily a *breakthrough* concept. In fact, I do this kind of thing on a whim in my journal pretty often. But sometimes you just gotta put down your DIY projects and make way for the experts.

This magical exercise (her words, not mine) was first given to her by one of her most influential mentors, Milton Glaser, one of the most celebrated graphic designers of our time. Over the course of a couple years, she modified the exercise and now gives it to her students as an essay prompt titled, “Your Ten-Year Plan for a Remarkable Life.”

Before starting the exercise, Milton Glaser instructs “us” to “envision the life that you could have if you pursued everything that you wanted with the certainty that whatever it is that you wanted, you would succeed.” (quoted by Debbie Millman)

He asked us to dream big, and not to edit and said that it had a bit of a magical quality that he experienced with his students over and over so, to be careful what we wished for.

Debbie Millman, Tim Ferriss Show #214

Oof. I’m getting all the feels now and am eager to get started! I only have 20 minutes to spare today, but I encourage you to spend as little or as long as you’d like!

Here’s the prompt below. (It’s probably best if you skim the whole thing before you get started.)

“So, let’s say it is winter, [2029]. 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? And write this day, this one day ten years from now.

So, one day in the winter of [2029]; 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 when you tuck yourself in at night. What is that day like for you?

Dream big. Dream 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’s no tomorrow. Write like your life depends on it because it does. And then, read it once a year and see what happens. It’s magic. It’s magic, Tim.”

Debbie Millman

P.S. check out my current favorite writing soundtrack.