Awareness / Intention

Hanging Out with Tim Ferriss: The Thought Exercise He Was Curious About

Tim Ferriss(Estimated Reading Time: 11 min)

I recently found myself in an exciting scenario… While I was visiting family near Washington, DC, Tim Ferriss happened to be in town hosting a live event to promote his (kick-ass) latest book, Tribe of Mentors. As good as the full backstory is, I’ll save that for another day. Let’s drop right into the juicy part.

I eagerly jumped out of the uber and Olympic power-walked to the bar. I went straight to the bartender, ordered a beer, and walked over to where Tim Ferriss and a group of 7 others were sitting.

“Vancouver!” Tim said, recognizing me from earlier in the night when I gifted him a frisbee and asked him to come visit the Vancouver, BC Tools of Titans group.

I pulled up a chair, sat down, and began to tune into the conversation. Tim was answering questions, sharing stories, and listening to ideas others had to expand his work.

The “10-Year Plan” Exercise

About 15 minutes later, Tim was talking about some loose future plans regarding the next book he might write. Curious about how much Tim has thought about the future, I asked if he’d done Debbie Milman’s “10-Year Plan” exercise.

Debbie has been one of my favourite guests on Tim’s podcast – she seemed to have the perfect combo of wisdom and articulation. Every word she spoke had me hanging for the next. In episode 214, Debbie explains the “10-year plan” exercise:

So let say it is Winter 2027. 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 2027, 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 the 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.

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

It’s magic. (1)

Tim responded to my question: “No, I haven’t done it, but funny thing, I have the exercise in my backpack to do.”

Tim redirected the question to me. I told him I hadn’t done a 10-year plan, but recently did another form of this type of exercise.

The “If I Knew I’d Die…” Exercise

A month ago, after a weekend-long silent meditation retreat, I hunkered down in a beautiful cabin on a lake and completed a thought exercise I’d been considering for a while.

The exercise is fairly simple – to think about what I would do if I knew I’d die in 1 year, 5 years, 10 years, and 40 years.  It was an eye-opening activity, especially because I’ve never framed my thinking on a 1-year death sentence, nor with 40 years of life on the horizon.

Tim became immensely curious about this and started asking a series of thought-provoking questions – Which part of the exercise did you get the most from? What was your biggest take-away? What real impact will this have in your life?…

This took me by surprise, I must say. Suddenly it felt like I was ON the Tim Ferriss show…

We got into an interesting and deep discussion, but I felt somewhat unequipped to succinctly answer Tim’s questions. Partly because of the unique moment I found myself in – the fanboy in me was thinking ‘WOOOAAAA This is so cool”, but more so because since doing the “If I knew I’d die…” exercise, I haven’t fully processed it.

So, I’m writing this post for me to gain clarity, for Tim to satisfy his curiosity, and for you to experiment with this exercise yourself to see what you discover.

A weekend meditation retreat is not necessary pre-work, but I’m not sure I would have had the same results otherwise. Doing it after a long meditation period helped prime my mind into a space of clarity and raw emotion, instead of at the usual level of clutter and noise. Therefore, I’d recommend doing some sort of priming for this exercise – like a meditation of 20+ minutes, a long journaling session where you write 3+ pages of whatever is on your mind (aka “morning pages”), or scheduling this towards the end of a retreat.

Here’s a deeper dive of how the “If I knew I’d die” exercise works, along with some of my insights:

1)  Start by asking yourself: If I knew I’d die in one year, what would I do?

I’m not going to lie, this is a HEAVY exercise. It involves putting your mind and body into a deeply scary and sad place. Buzz kill, I know. BUT, it also cuts through a ton of BS and helps you get clear on the things you would want to do or say, projects you’d rush to start or finish, and who you’d prioritize spending your time with.

Go there. Be there. Feel the pain. Face the fear. Curl into the fetal position and whimper if you need (not required).  Write everything down.

2) Next, ask yourself: If I knew I’d die in 5 years, what would I do?

All of sudden, 5 years feels like you’ve got some runway. Go ahead and uncurl from that fetal position, we’ve got work to do! Now, there isn’t as much of an “I’m going to hyperventilate because I’m dying” panic as you rush to figure out how to complete everything you possibly can. However, despite feeling this relief, you’ll be reminded that 5 years isn’t very long. There’s still a sense of urgency, so we better develop a strategy.

I thought: How would I stretch out the 1-year list to be more thorough on certain projects? Now that I have more time, what order would I do things? What would I do differently in my relationships? What can I build for the first 4 years to complete in the 5th and final year?

Come up with more of your own questions, and once again, write everything down.

3) Then the question: If I knew I’d die in 10 years, what would I do?

Holy smokes, now we’ve really got time! Going from 5 to 10 years is a much bigger relief. At the same time, I found it really hard to think 10 years out. Unlike Debbie Milman’s exercise, I didn’t get granular. I avoided the details of who was with me, where I lived and what pets I had… Instead, I opted for larger vision ideas and bigger brush strokes. For example, how would I springboard from the 5-year ambitions and continue to evolve down the path I’d already be on?

The content, projects and even to some extent the people I’m surrounded with became fuzzier in this time frame, because there are many variables I can’t anticipate. I found myself reverting to core values – What would I want to be remembered for? How and for who can I be a role model? What long range goals can I now tackle?

This ended up being my shortest section with only 6 bullet points. I wondered about trying this again with the mindset of Debbie Milman’s 10-year plan, but I don’t think it’d be effective since it’s much different imagining you’re dying in 10 years, as opposed to being in the middle of the life you dream of. (Nevertheless, in the spirit of experimentation, I’ll try Debbie’s exercise separately soon.)

4) Finally, the question: If I knew I’d die in 40 years, what would I do?

First off, WOW. I have never thought with this sort of horizon in mind. And after the 1, 5 and 10-year exercise, I felt a flood of gratitude. “I’M NOT DYING!!!”… Massive relief!! I felt a bit silly about the whole fetal position not too long before, but who cares, what a privilege it would be to live until I’m 75!

Thinking of actual projects, achievements and decisions was really challenging for me here. On the other hand, the expanse of possible opportunities was exhilarating. What I wrote down focused on vision, wisdom and character traits. It was impossible to imagine who would still be around and how life would actually play out. I’ve experienced enough loss to know that life doesn’t always work out the way we expect it to. However, I could imagine the kind of person I wanted to be, and the ways I wish I could be of service to others. This gave me a model for who I wanted to become.

Tying it all together

After doing all this, the missing piece was how it all tied together… The perfectionist in me likes a nicely bundled conclusion. But, to be honest, I haven’t fully fleshed this out and I’m not sure I ever will. Right now, here’s what I can report:

I have more of a compass for the future than I did before, along with a better sense of what to focus on now. I also have a framework for what to do if suddenly the floor falls out from under me and I’m faced with the worst-case scenario.

A lot of my thinking was framed around: What can I create or leave behind that will have an impact on others? For example: experiences and conversations with family and friends; work, projects or contributions that would continue beyond my existence.

As for my personal revelations, Tim was very curious about this, so you probably will be too:

  • I have a lot I’d like to write… dozens of blog posts planned and hundreds of ideas for others. If I knew I’d die in one year, writing a book would be a top priority because it’s the most effective way for content to endure. Since next year will be quite full and I don’t expect to die, writing a book has become a 2-5 year priority. Worst-case scenario someone could publish this collection of blog posts into a book. What’s most important now is to get content out into the world. When I do decide to write a book, I’ll go all in and it’ll be my #1 priority (advice I’ve heard from Tim on his podcast – “Don’t write a mediocre book”).
  • Meditation is a top priority across all time frames because it’s the best way I’ve discovered to be connected with myself, others, nature, and most importantly – the impermanence of life. If I knew I’d die in 1 year, I’d do 10-20 days of silent meditation (with a top meditation teacher). Looking to 2018 and assuming I won’t die, prioritizing a 10 day retreat is challenging. However, I can do 3-4 weekend retreats of 1-2 days each. Over the next 5 years I’ll do a 10-day and then likely a 1 month retreat.
  • I’m 35 years old, so the decision to have kids or not is one I’m starting to feel from all directions. This is a hard decision, but no matter which way I go, I’m looking forward to the next phase of life where I build relationships with kids and become a role model. I’m comforted knowing that there’s no right decision here, which means I can’t make a wrong decision.
  • Having the experiences of being gay and working as an organizer for 10 years in the world of ultimate frisbee puts me in a unique position to help shape this amazing and nascent sport to be more inclusive as it grows. There’s work I’m contributing to now, such as transgender inclusivity, but I’m not entirely sure what the best path forward is so I’ll keep exploring opportunities.
  • No matter what, I’ll voraciously continue to seek: learning, generosity, wisdom, compassion and love
  • Mornings have become my rock and foundation. I’ll keep spreading the good word of creating good mornings through this blog. (Shameless plug – subscribers get content not published here AND entry into monthly book give-aways. The book giveaway for January 2018 is a SIGNED COPY of Tim Ferriss’ latest book – Tribe of Mentors! Plus, I’m giving away 2 BIG prizes for 2018 – a premium ticket to the World Domination Summit and to Tribe Conference – Sign up via this link!)
  • What a privilege living 40 more years would be! Whether that happens or not, I’m super grateful to even have a shot.

Why do this exercise?

We don’t know how long our journey of life will be, but we know it will be unpredictable, constantly changing, and then come to an end at some point, probably before we’d like it to. We may as well pack as many tools as we can to be prepared for the twists and turns, highs and lows, angels and demons. We’ve all had them. We’ll all have more of them.

But of course, this exercise doesn’t just end here… I’ll leave you with a few more considerations to think about:

“It’s not enough to know what you want to do. You have to do it to be what you want to be.” – Paulo Coelho

“How can you achieve your 10 year plan in the next 6 months?” – Peter Thiel

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(1) Source: From the website My Ten Year Plan

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  • Reply Ben December 13, 2017 at 11:07 am


    This is an amazing post. I want to do this exercise. Do you have any resources for guidance, or would you be willing to run a session if I can cobble some people together? One of my largest struggles is getting my limited time organized by priorities. Too much on my plate creates decision paralysis that I think this would help alleviate.

    PS I completely understand the challenge of being succinct in front of a respected icon. I am sure you did much better than your mind lets you remember.

    • Reply Craig December 14, 2017 at 1:36 pm

      Hi Ben! Yes, this would help get clear on priorities, especially the short term exercises. Other than what’s in the post here, I don’t have any guidance. I can’t remember how this idea came about, but if I got it somewhere else, I don’t remember when or where…. As for running a session, I’d consider it in 2018. Shoot me a message – craig at and we can chat it through to see what that would look like.

  • Reply Safiya Robinson December 13, 2017 at 12:38 pm

    Excellent post! I would like to do the exercise, but I have a great deal of fear around thinking about what I would do if I would die, especially since I already feel as if I am soooooooooo far away from figuring out what I want to do with life (except that I am quite certain what I am doing now is NOT it!). However, it might be just the thing I need to do to get clarity, as I feel as if I have too many ideas! I am interested to see how important a role meditation played not only before you did the exercise, but also coming out of the exercise. I agree with Ben – you might have said more than you remember. I hope you are able to create some action points out of this introspection! Best of luck

    • Reply Craig December 14, 2017 at 1:40 pm

      Safiya, it’s a hard exercise so fear makes sense… I’d say that timing and openness are crucial to make it work. You could reframe the exercise and think: what are the changes I can to make in 1 year, 5 years, 10 years and 40 years to live the full life that I desire?

  • Reply Erin H December 13, 2017 at 9:03 pm

    Cool concept Craig- I love the idea. Thanks for sharing.

  • Reply Carolina December 14, 2017 at 5:48 am

    Yikes! This exercise is Not for me. Love your blog but I am not your typical reader. I am 75 years old. Think of these questions from that age viewpoint. Yikes again! A few years ago doctors thought an illness I had would take my life within a year. I can tell you I was almost paralyzed with sadness at the thought of leaving this beautiful world — even with the promise of a more beautiful one.

    • Reply Craig December 14, 2017 at 1:47 pm

      That make sense Carolina and you bring up an interesting point – when actually faced with 1 year to live, dealing with the paralyzing emotions are unimaginable (whether one believes in an afterlife or not). This means that actually being able to do what I said I would in the thought experiment would be monstrously challenging. I’m unsure if I’d be able to get past that if facing it.

  • Reply Marta December 14, 2017 at 8:39 am

    A part of me is scared to do the exercise, because then I would see how the life I’m leading is not aligned with the life I dream of….(even though I understand that the concept is to get you closer to that dream, but I have some sort of block there)

    • Reply Craig December 14, 2017 at 1:48 pm

      Having the awareness of that block is a step in the right direction. Much like I commented to Safiya above, I wonder if reframing the exercise would work better for you.. Instead, think: what are the changes I can to make in 1 year, 5 years, 10 years and 40 years to live the full life that I desire?

  • Reply kelly December 17, 2017 at 2:07 am

    Honestly, I think I’m content to carry on as is and die at any of those times. I do not feel the need to create or leave behind anything specific, apart from the love I share with others along the way. I am glad you found the exercise useful and wish you luck with all the outputs. Thank you for sharing your work.

    • Reply Craig December 17, 2017 at 10:49 am

      I totally appreciate this Kelly. It seems like you’ve covered the most important part: “…apart from the love I share with others along the way.”

  • Reply Mark January 15, 2018 at 4:13 am

    My challenge is that I have done some of these things your pamplet mention, my problem is implementing the rest of them, or feeling anything throughout the day to move me to doing them. I’ve become so accustomed to guilt and feeling unaccomplished, that to feel good and having met my goal (even if one in a day) is still an ‘eh’ moment.

    I’ve lost my verve.

    • Reply Craig January 16, 2018 at 6:05 pm

      Hi Mark,

      I hear you, this takes continuous effort and patience. Many people quit before getting enough momentum. Keep going, and celebrate the small wins as much as you can. In terms of feeling meh about achieving small goals, that definitely happens, especially over time. I’d dig deep and question this narrative you have” “I’ve become so accustomed to guilt and feeling unaccomplished” – what would it take for you to feel accomplished? Why do you carry the guilt? What would it take you to get your verve back? (These are deeper questions I don’t expect you to answer here).

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