Tim Ferriss

January 9, 2025

Tactics and Strategies for a 2025 Reboot — Essentialism and Greg McKeown (#786)

“I think all of us are prisoners to the way our mind currently works, and we’re prisoners until we become observers to it.”
— Greg McKeown

Greg McKeown (@GregoryMcKeown) is the author of two New York Times bestsellers, Essentialism: The Disciplined Pursuit of Less and Effortless: Make It Easier to Do What Matters Most. He is also a speaker, host of The Greg McKeown Podcast, and founder of The Essentialism Academy, with students from 96 countries. 200,000 people receive his weekly 1-Minute Wednesday newsletter, and he recently released The Essentialism Planner: A 90-Day Guide to Accomplishing More by Doing Less.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform. Watch the conversation on YouTube here. The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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#786: Tactics and Strategies for a 2025 Reboot — Essentialism and Greg McKeown

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Want to hear the last time Greg McKeown was on the podcast? Listen to our walk and talk conversation here where we discussed Greg’s system for effortless execution of daily tasks, poetic mysticism and matchmaking introspection, Maslow’s forgotten pinnacle of self-transcendence, why self-actualization is an insufficient foundation for meaningful relationships, the benefits of treating social media as an option rather than an obligation, blocking time for top priorities, why AI is a good servant but a poor master, and much more.

What was your favorite quote or lesson from this episode? Please let me know in the comments.

SELECTED LINKS FROM THE EPISODE

Connect with Greg McKeown:

Website | Twitter | Facebook | Instagram

SHOW NOTES

[00:05:12] Handling destabilizing events and personal turmoil.
[00:10:47] Writing as therapy and “screaming onto the page.”
[00:13:35] Using Morning Pages and AI tools for personal reflection.
[00:17:52] Carl Rogers and the power of deep listening.
[00:20:33] Reviewing the core concepts of Essentialism and Effortless.
[00:24:54] Temporal landmarks and the fresh start effect.
[00:29:25] Personal quarterly offsites and the importance of direction over speed.
[00:31:13] The three essential questions for quarterly reviews.
[00:34:16] Making essential tasks effortless — practical examples and strategies.
[00:37:03] The law of inverse prioritization — why important things don’t get done.
[00:38:45] Strategies for making tasks simpler — the microburst concept.
[00:44:37] The courage to be rubbish.
[00:47:09] Pre-mortems and anticipating obstacles.
[00:52:37] Michael Phelps’ preparation and routine.
[01:07:31] The 1-2-3 method and defining what “done” looks like.
[01:15:19] Meaning over productivity, and making vs. managing.
[01:23:14] Radical gratitude and finding meaning in suffering.
[01:36:43] Parting thoughts on deep connection and listening.

MORE GREG MCKEOWN QUOTES FROM THE INTERVIEW

“I think all of us are prisoners to the way our mind currently works, and we’re prisoners until we become observers to it.”
— Greg McKeown

“That process of screaming into the page, of letting it all out, separating ourselves from that discombobulating internal state, is extremely powerful because it helps us to go from prisoner to observer. And then from observer, I think once we start observing, we are better able to become a creator, so I think that’s the shift.”

— Greg McKeown

“Changing the ratio of consumption to creation is one self-evident shift that I think a lot of people would benefit in.”

— Greg McKeown

“Insecure overachievers can endlessly complicate any task to an infinite degree. … If you don’t know what done looks like, you cannot be done.”

— Greg McKeown

“Radical gratitude is expressing thanks for things you’re not thankful for, because that’s what gratitude actually is.”

— Greg McKeown

“Essentialism, in one word, would be ‘focus.’ Effortless, in one word, would be ‘simplification.’”

— Greg McKeown

“Essentialism is figuring out what the right thing is to do, and Effortless is to do it in the right way.”

— Greg McKeown

“One of the principles in Effortless is the courage to be rubbish and doing it in a shorter period of time.”

— Greg McKeown

“I think most addictions really are, at the core, to avoid the experience of being alive. And that’s because it’s so painful to be alive.”

— Greg McKeown

“We live in a time where it’s so easy to have what I would describe as counterfeit agility. So you’re moving fast, life feels fast, life is fast, and you’re taking messages, you’re sending messages, and you’re doing things, but actually, they don’t add up to a lot of progress toward what matters.”

— Greg McKeown

“What I have learned is this strange law of inverse prioritization. … The most important thing in our lives at any given time is the least likely thing to get done, which is really strange.”

— Greg McKeown

“Courage is a virtue, but courage always feels terrible. It is an awful feeling. It’s not like you imagine when you see other people being courageous.”

— Greg McKeown

“If you think about the future as only a perfect, best-case scenario, you are setting yourself up for really frustrating, stressful, poor execution.”

— Greg McKeown

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pablo power

11 months ago

since you love the song “syria” – i guess you gonna love this tune…
[Moderator: YouTube link to “FARHOT – YAK SHER (Official Visualizer)” redacted per YouTube embed policy.]

all the best, thanks for the bullets

Kaushal

11 months ago

Is there a transcript for this show? I don’t see it.

Todd Beacham

11 months ago

Thank you for another awesome and insightful interview! Greg is now added to my short list of favorites on my journey of self-improvement.

I have only 1 request…
Please put Rob Dyrdek on your short list for future podcast!
I discovered you and Rob almost simultaneously, when I was homeless and living in my car in Los Angeles in 2008. Both of you saved my life with your inspiring personal journeys, I would not be here to make this request without you!

Thanks again for sharing your work with me and the world, your remarkable impact cannot be measured!

Best wishes in 2025 and beyond,

_todd

Miranda

11 months ago

Hello Tim,

this podcast episode came at exactly the right time for me. Synchronicity works in wonderful ways, doesn’t it? I also have to handle an unexpected event in my personal life that concerns the well-being and care of a close family member. I know that the points raised in the episode will be a reference guide and roadmap for the coming months, not just regarding this matter but extending to the rest of my life as well.
I am currently reading a book by a psychiatrist that I wanted to recommend to you. It is called “Addiction, Reality, and our Search for Meaning”. In the spirit of Gabor Mate and Donald Hoffmann, it raises many thought-provoking points regarding our perception of reality, truth, health and illness. I think you will enjoy it.
Also, thanks for everything you are doing. Your podcast, newsletter and general outlook on life (you truly are a modern Goethe, Tim.) have been companions through the last years of my life and have shaped me in innumerable ways for the better.
Have a fantastic weekend!
All the best,
Miranda

Liepa

11 months ago

Hi Tim,

You showed interest in using Chat GPT to get out of your thought loop. Here are a few prompts that have been really helpful for me, and can help you and your readers get out of their thinking minds and take action in the midst of internal or external turmoil.

Prompt Structure: Describe the situation that is bothering you / write out your thoughts, then add one of these prompts:

Roast me – best for breaking negative thought patterns or insecurity. You can specify how honest, direct, or empathetic you want Chat GPT response to be – e.g., respond in the tone of Carl Rogers, Derek Sivers, Kevin Kelly, or even Gordon Ramsey (if you are feeling brave).
Give me perspective using provocative psychology (insight, provocation, challenge) – great for gaining a fresh perspective and actionable tools to reframe obsessive thinking.
Blend ego, Jungian shadow work, and Internal Family Systems to uncover insights about my situation that I do not see – best for a more philosophical understanding of the human psyche if you want to go down that rabbit hole.

I could write pages on how to fine-tune these and other prompts for personal growth, but I’ll spare you (and your team) the full details of my intellectual love affair with Chat GPT.

Greetings from a Lithuanian in Barcelona,
Liepa

Connie

11 months ago

Reply to Liepa

This is gold. I hadn’t realized I could do this. I was having a bad day yesterday after a whole melancholy Christmas season, so I typed out a couple of paragraphs pouring my heart out to ChatGPT and asking it to roast me in the tone of Brene Brown. I cried when I read the response. It was hard to believe that she hadn’t actually said those exact words to someone at one point. Maybe she did and that’s where ChatGPT picked it up. At any rate, it was exactly what I needed to hear, and much cheaper than an actual counseling session.

DL (Deborah) Walker

11 months ago

Thank you for many pearls of wisdom from this episode—I shared several with my class today, including the ChatGPT trick (it was a hit).

On a personal note, as a recovering overachiever, I’ve been pondering what “done” means for me, processing what it looks and feels like. I wonder, how do you know when let it go and trust that it is complete?

Which got me thinking about the challenges that you shared about completing PT while traveling. What if “done” in Physical Therapy wasn’t about clinic time or exercises, but something integrated into your life—completed while you’re skiing, practicing archery, or just moving through your day. Wondering if this shift in strategy would make Physical Therapy effortless?

Denise

11 months ago

Greg’s story about Erik Newton’s wife took me straight back. Six years ago, I shared this same profound level of deep connection with a dear friend in her final weeks, and watched it unfold with her other loved ones as well. Her parting wisdom was beautifully simple: life is love. Choosing resentment, hate, frustration, etc. is simply borrowing time from our own joy.

To echo Tim’s insight about mastery, “life is love” isn’t a destination but a daily practice—acknowledging truths, honoring feelings, and actively choosing to not let anything other than love take permanent residence in my mind and heart. And yes, there’s something deeply reassuring about knowing that each day we can choose again to connect more deeply.

Marnie

11 months ago

Hi Tim,
I love your podcast. I am teacher librarian (yay good books!) and I really enjoy your interview style and the variety of people you have on your podcast. I always learn SO much! I heard you mention your back pain again. I too have struggled with chronic pain over the years and have tried a ton of different approaches(it’s exhausting). I just learned about neuroplastic pain about a month ago – have you heard about it? The pain is real (and in many cases can be worse than non-neuroplastic pain). Our hypervigilant brains misinterpret safe signals from the body and get stuck in a pain/fear habit cycle. I read Alan Gordon’s book “The Way Out” and it has been life changing – not just for my chronic pain, but also for my anxiety too. I have no affiliation with him, but figured I would share. I am also taking a neural reprocessing for pain class and learning how to re-wire my nervous system. It’s fascinating. I know it can be annoying when people tell you one more thing to try, but I figured you are curious and a lifelong learner, so why not. 🙂
Best wishes,
Marnie
PS – thank you interviewing Jake Muise – that episode inspired us to try Maui Nui venison and we not only love the products but also the work they are doing in Hawaii!

Frank Donaldson

11 months ago

Huge fan of Tim Ferriss, but this is one of his best (IMO). Key points for me:
1) Quarterly personal offset – 3 questions 1) What are the essential things we are under investing in 2) What are the non essential things we are over investing in 3) What is the most effortless way we can make this shift.
2) Pre mortems – key questions 1) where have you been 2) where are you now 3) where do you want to be 4) what is stopping us from doing this
3) Defining “done” – 3 questions – 1) what 2) so what 3) now what, which is 1,2,3 method 1 = most essential thing, 2 = essential and urgent, 3 = maintenance or laundry items
4) Radical gratitude – definition of gratitude = living with a spirit of thankfulness. Could there be meaning in suffering.

Offer

10 months ago

This is such a heartfelt and inspiring comment! It’s amazing to hear how Greg’s interview resonated with you and how both he and Rob Dyrdek played such a pivotal role in your journey during a challenging time. Your story is a testament to the power of perseverance and the impact that positive influences can have on our lives.
I completely agree—Rob Dyrdek would be an incredible guest for the podcast. His entrepreneurial spirit, creativity, and ability to turn dreams into reality align perfectly with the themes of self-improvement and personal growth. Fingers crossed that this suggestion makes it onto the list for future episodes!
Thank you for sharing your story and for being part of this community. Your gratitude and resilience are truly inspiring, and it’s comments like these that remind us of the profound impact these conversations can have. Keep shining and pushing forward—your journey is a powerful example of what’s possible!

David Hume

7 hours ago

Color coding books instead of by topics makes no sense. I’ll leave it to a psychologist to make sense of that.