When to Quit – Lessons from World-Class Entrepreneurs, Investors, Authors, and More (#254)

Loved the new format. Long time listener. My 2 cents. Keep up the good work.

PHENOMENAL!! This format is the perfect complement to the regular podcast episodes and is exactly the kind of approach I had been hoping we’d get with Tools of Titans. It exemplifies two things Tim does best: find good questions, and ask them of the most qualified people, in order to build a repertoire of the best and most refined thought processes on the planet. In Tim’s regular interviews, we get to be inspired by the stories and personalities of the podcast guests, which is great and highly engaging. But, while inspiring, when it comes to actionable results, it requires more sifting through in order to find the applicable elements you can use in your daily life, and they aren’t always easy to track down in the right context when you need them. In contrast, this format takes one big, pressing question and gives us several angles of approach that feel really tactical and useful to solving problems. This one episode just helped me to answer several questions I’ve been struggling with when it comes to my personal, professional, and humanitarian endeavors. I can foresee a wonderful library of questions that would be an incredible powerhouse to refer to when we find ourselves stuck in any particular rut. PLEASE DO MORE!

Here are my favorite points and questions that each guest offered to address the question:

Scott Belsky

— Is the difficulty you’re running into causing you to question your core assumptions about the project?

— Knowing all you know now, would you pursue this over again? Or knowing all you know now, would you do something different?

— Are the sunk costs all that’s keeping you from quitting, because of what you’ve invested?

Seth Godin

— It’s a waste of time to repeatedly start things and then quit them in “the dip” (the hard part that makes it worthwhile).

— It’s important to differentiate between a dip and a cul-de-sac (dead end). Is there forward progress? Are you building assets? If so, it’s more likely to be a dip.

— Commit to not stopping in the dip and to practice differentiating from dead ends.

James Altucher

— Everything has a half-life; if you’ve passed the peak, it may be time to let a project go rather than wait until it ends out of necessity.

— You may want to quit when things are going OK: For example on a project where nothing is “wrong,” but where it isn’t getting better in proportion to expectations of the market.

— When you feel you’ve learned everything you can learn can be a good indicator of when to move on.

— Alternatively, sometimes you’re at the top of a learning curve where every incremental improvement is difficult, but it’s the appreciation of the subtleties that makes it worthwhile in spite of the slowdown.

Debbie Millman

— If you feel that you are not capable of achieving your dreams, is it because you are really not capable of achieving them, or because you’re really afraid to put your whole heart in and try?

— What scares you more: heartbreak, or rejection? What scares you more: resentment, or rejection? What scares you more: regret, or rejection?

— This is the thing about resistance: If you’re doing what you think you should be doing rather than what you want to do with your whole heart, you are not persisting, you are resisting the truth about who and what you are.

— If you are doing what it takes to make your heart sing, never, ever give up. Remember, it’s not a failure until you accept defeat.

Adam Robinson

— If you don’t get what you want, it’s a sign that either you didn’t want it enough, or you tried to bargain over the price.

— Obstacles are what you see when you take your eye off the goal.

— Connect your dream to a mission that is larger than yourself and it can give you the perspective not to quit too soon.

— Sometimes there are grey areas: You may not need to quit entirely, but you may need to pivot your focus.

Chase Jarvis

— Intuition: We are recording billions of data points moment to moment creating an archive of those, which our unconscious mind is drawing upon when we encounter questions to which we don’t have all the answers ready in our working memory.

— Two questions to ask yourself: 1. Is it working / am I making progress? 2. Do I believe deeply in the mission/vision?

— Knowing that what we’re working on is the right thing when we are all limited by time is a massive advantage.

Rhonda Patrick

— Impact as a criteria: Do you have multiple options to achieve the same goal with different levels of impact? For example, if you value teaching, professorship provides it. But a moderately successful video can reach far more people than a large classroom.

— Having data to be able to assess the proportionate impact of divergent paths before actually having to make the decision is extremely helpful.

I’m French People and I really like to learn with your blog. It is very interesting and inspiring ! Thank you so much for this !

It would be cool to hear an episode about “what the listeners learned”

That is, asking your listeners what they have taken away from the lessons/strategies/ideas provided by you and your guests. How listeners implemented lessons in their lives and what difference that has made.

Love everything you showcase on your podcast. I love 5 bullet Friday,also. I am I corporate sales & I love

sales & selling. My question I would like to ask you,

as an experienced sales executive 20+ yrs dealing

with executives from Fortune 500 companies, how do you motivate younger sales executives to share the

vision to success I have experienced?

Debbie’s portion was sorely needed today. It even stopped streaming for about 10 seconds at a particularly paramount part, as if the universe was demanding me to think about the preceeding sentence. I listened to it three times in a row and was in tears on the way home. Thank you, Debbie….

Thanks, not sure I like the audio format in the latest podcast as much. I personally like hearing a conversation more and I like hearing your input and questions too. But that’s just me. I do have a question. Not that you have time for my question. I get that. If I never hear from you, I understand… I’ve been writing now, for small but growing number of horse riding enthusiast. I’m a trainer/teacher and I love to write short inspirational articles. Lately I’ve been getting more people sharing my stuff. It’s great. But the not so great part is, I’m also getting more criticism from new people who either don’t like what I say or the way I say it. I get more good than bad so I feel I shouldn’t be so sensitive. But I am. How do you deal with criticism? How do you read a negative comment and then go about your day without the constant reminder that someone thinks you suck? I get over it. I’m not depressed about it, but it does carry weight for longer than I want it to. What are your or your colleague’s tricks for dealing with criticism? How do you manage comments in the social world or on your site? Do you delete them? Do you respond to them? Shit, that was more than one question. Sorry. and thanks for doing what you do.

If we are talking “world class” can we have folks from some other parts of the world and people of color; have given you the benefit of the doubt so many times but now it’s just getting old. Check out Bozoma Saint John @badassboz, I’m sure she can get give you a whole host of folks to check out. You’re getting stale, expand your horizon and get out of your comfort zone!

I noticed that the last few podcasts were recorded in MTL. I live there but was in Tokyo the past few weeks. Is there any chance you’re still kicking around the lilypad? If so, I’d love to shake your hand. If not, it’s the fault of the FHWW. Without which I may not have traveled to Japan for almost 2 months this year. I’m a comic book writer and VO actor which allows me the freedom to move about willy nilly. If meeting you is not in the cards at this time that’s cool. However, this year I traveled to France, LA, Florida, and Tokyo. I’m down to meet you anywhere you happen to be in the world. I don’t want anything, just the chance to say thanks in person. (Which as I write it sounds like I’m an assassin of some kind. Tony says “Thanks.”) Barring that, thanks for everything! Your books, shows, and podcast are a continued inspiration to me.

PS: Will be Taking the JLPT this December in TO! Again, thanks to your example.

This is easily one of the most valuable episodes I’ve listened to. Loved the format! I thought it was awesome to hear such a high-calibre group weigh in with different angles on the same question—I think it brought a level of depth to this topic that would not have been possible with just a solo guest. Possibly the coolest part was just being able to step back and reflect on all the different responses and weave together the combined, overarching message for myself. It was pretty sick, brah!

I know its a great podcast when i stop to take notes.

This was just the perfect information at just the perfect time. I was on the road to quitting (in that dip) but after hearing this podcast it’s clear that the goal is still valuable and the work is still worth doing.

Thank you very much Tim for positively affecting one humans trajectory.

I love this new format, please keep these types of questions and group responses coming!

Hi Tim!

Your podcast has had a profound, wonderfully enriching impact on my life for years. THANK YOU more than I could ever say.

I’m an artist, designer, and seamstress. If you ever need an amazing costume or something more serious it would be an honor to make you something as a gift. (Travis Brewer, ninja, can vouch for me being a real person with skills.)

I loved the Animal video in the last 5 Bullet Friday to help decompress from stress. [Moderator: link and some text removed.]

Great episode (and timing for me personally). I think my favorite quote would have to be Debbie’s: “If you’re doing what you think you should be doing rather than what you want to do with your whole heart… you are resisting the truth about who and what you are.” Especially loved Adam’s response too.

Hi Tim,

Absolutely loving all of it! The blog, the podcast and now finally reading Four Hour Work Week.

BUT, it appears the Comfort Challenge on page 93 – getting phone numbers of the opposite sex, only applies to straight people?… hmmm…

Hi! I never commented a podcast episode before. And I listened to all of them!

I just listened to a third of the episode, but I already love it. I don’t know if it will help me, yet. But the idea is great, far better than the other “summaries” of past episodes.

I hope there will be other similar round tables.

Thank you!

Would it be possible to have transcripts of your podcasts?

i think just post and whrite , so simples is good . can i register with pay after a time ?

Like the format. “The failure of the opportunities we have as humans to pursue the things that we love as joy.” Chase Jarvis stuck with me.