Comfort Challenge #2: Learn to Propose

If you try this comfort challenge, please share your experience in the comments below! I’d love to read them. It’s always a hilarious and valuable exploration of getting more comfortable with discomfort.

Here is the original text of the challenge from The 4-Hour Workweek:

Stop asking for opinions and start proposing solutions. Begin with the small things. If someone is going to ask, or asks, “Where should we eat?” “What movie should we watch?” “What should we do tonight?” or anything similar, do NOT reflect it back with, “Well, what do you want to . . . ?” Offer a solution. Stop the back-and-forth and make a decision. Practice this in both personal and professional environments. Here are a few lines that help (my favorites are the first and last):

“May I make a suggestion?”

“I propose . . .”

“I’d like to propose . . .”

“I suggest that . . . What do you think?”

“Let’s try . . . and then try something else if that doesn’t work.”

If you try this comfort challenge, please share your experience in the comments below! I’d love to read them. It’s always a hilarious and valuable exploration of getting more comfortable with discomfort.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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53 Replies to “Comfort Challenge #2: Learn to Propose”

  1. Love these! This actually caught me right before my next to-do item on my business list: emailing a client who’s not sold on my services yet. Proposing going out now!

  2. This challenge reminded me of an ex boyfriend… I have to laugh now but during our relationship I would be so mortified when he’d ask the waitress what he was hungry for. Like she’s supposed to know his stomach better than his indecisive self and propose his selection. And I don’t think he was making a pass at her either… he he. Anyway this is not a challenge for me because I’m always giving my two cents. But for the poor waitress I might suggest after going through the specials that SHE suggest the most expensive items on the menu. Hah! I always felt so bad for the waitress as my boyfriend would sit there forever trying to make a decision on what he was hungry for. I’m sure she had other patrons to attend too.
    Ugh. I proposed moving on out of this man’s life and it was a great decision! But I bet he’s still doing that same thing to every server at every restaurant.

    1. People who are used to quite expensive restaurants with excellent service often learn to ask the wait staff what they should order. Well-trained wait staff at very good restaurants often are trained to combine their knowledge of what’s best, freshest, or most unique at the restaurant on that day, with what they find out about your tastes through strategic questions, in order to help you find your best dining experience for the evening. In fact, this professional assistance from service staff is part of what you are paying for when you go to a very nice restaurant – yet another reason to leave a very good tip when you go there.

      That being said, some people just have trouble deciding. And not every restaurant is well set-up for this kind of interrogation process.

  3. I love these! Even though I’m no longer in the work world, these will definitely come in handy with real life interactions of any sort. Thank you.

  4. Dude, this is how I live my life. Lol I do find that some people find it a bit aggressive. But I think it’s being confident, certain of what you want, and decisive. Most of all, it doesn’t waste time. We’re all busy individuals. So, let’s be respectful of each other’s time and propose solutions. Great challenge!

    1. Without realizing it that’s how I’ve always approached personal and business life anyway. My girlfriend recently pointed out that people who don’t know me think I’m bossy. Really I find indecision frustrating because it wastes time. So to avoid that I jump in and propose solutions. If people are timid or indecisive then they simply go along with me.

      1. I her you! I am an advocate for making decisions on the spot or offering solutions. I have the ongoing battle with my spouse who (in affectionate terms) is the most indecisive person I’ve ever met. I see the way her inaction to provide solutions or make decisions on the ever growing ‘to do list’ hinders her outcomes and puts her in stressed and frustrating situations. Being responsive, offering solutions and making firm confident suggestions will always make for a productive use of time. Fortune favours the bold!

      2. It is extremely frustrating. I am currently dealing with a person who wants to talk everything into the ground, even after making a plan for moving forward. Once you make a decision, you have to let it breathe and give the other person room to implement it.

  5. Hi Tim, I work for someone who has been a guest on the Aubrey Marcus Podcast, AskGaryVee, and Impact Theory. An author, Speaker, Philanthropist etc. He is also a big fan of yours, and hosts his own large business podcast with Entreprenuer. We are going to be in Austin from March 14th -16th and would love to potentially create some content together, or even get together for a quick intro for future business. I know you don’t generally do interviews right now, but I think he would be a guest you would consider heavily to be on your show. Is there any official channel I can send an email to with all the details? Thank You.

  6. Tim,

    Why did you choose to read from a piece of paper on camera for this blog post?

    Given your attention to detail, I suspect it was a conscious decision.

    Thanks for sharing what you do.

  7. Tim, there is an app called Deconstruction based off of your language learning principles. Is it yours?

  8. I love this! I want to live in a world where people are more open about sharing what they want, because mindreading is damn hard— see Mindwise by Nick Epley. It’s one of Derek Sivers’ favorite books.

    It reminds me of how people say things like “does anyone want the last cookie?” What they are really saying is “I would like the last cookie.” In my experience using more direct language helps build trust.

    Perhaps it sounds robotic, but often in relationships I’ll directly ask— “are you seeking advice or do you just want me to listen?” This helps for situations where someone is vocalizing a problem but may not want a solution, they just want a listener.

  9. I find the suggesting thing very effective. Its your idea, and your will. But your friends get to ‘sign off on it’ and so they’re happy with that. They’re allowed in on the decision in some way.

  10. The hardest thing for me to do is to remember to catch myself the moment I should make a decision or propose rather than absolve.

  11. This was one of the first things I put into practice while still reading The 4-Hour Workweek years ago – and it has saved me countless (i.e. literally, thousands) of unnecessary emails, IM’s, WhatsApp/iMessage/SMS messages! Whether it’s a business or personal context, suggesting options or indicating my preference is much more productive then just asking “what/when/where”. No more, “let me know when you’re available” – but “let me know when you’re available – I can do Date/Time 1 or Date/Time 2 or any time Day 3”. The next reply leads is a confirmation – ending the exchange – 99% of the time. Simple and powerful. Thanks, Tim!

  12. First, I think this is great advice. I have done this for decades. Within my friends groups, it’s always worked out well. And I think me making a definite proposal gave permission to others to do likewise. I was always more interested in a prompt decision than getting my preferred option.

    With my family it is a whole different story. I am the youngest of four children. I am perceived as selfish when I make a simple proposal. I have actually been told that my proposal puts others in the position of “having to say yes” to things they don’t want to do. No amount of me asking for someone else’s proposal seems to get things moving. When I began this decades ago, I assumed my family would get used to it but it still causes friction.

    I have usually used the form, “I want to do xxx…” Perhaps if I changed my language to something with less potency than “want”, it might go down better. I will try, “May I make a suggestion?”, or “I suggest that . . . What do you think?”

    1. The problem is – you can’t always use May/I suggest in family situations – this mellow stuff is usually shot down quickly in such situations in my opinion – (Also its too formal – i have yet to come across an alternative for informal occassions)

  13. Like this strategy, and realized I do a lot of “what do you think?”. So I tried this in a slightly different way. I said, “I’m hoping…”; and then I said, “here are my thoughts”. I love that I don’t really need to stay tuned for a lot of back and forth, and that any response contrary to what I’m hoping for will probably include reasons and thoughts that should be considered. It’s a much better way to advance meaningful discussion.

  14. LOL! I’m more like Hermione, pushing my ideas forward all the time. I’ve had to stop myself and let other people chime in.

  15. I am a recovering people pleaser – trying to improve on that, and to speak up more, so this challenge is perfect. I tested it yesterday during a zoom call. At mid point, the host asked if anyone recommended a next topic to discuss. I spoke up. I have a subject to propose. Points! But, then quickly from old habits, followed it up with a, but we don’t have to do that today. Ugh. Baby steps. What typically happens to me is I keep quiet, don’t say anything, and end up feeling resentful. Or I feel like I am being too aggressive if I do and controlling the conversation. Reminds me of the sponge bob “I don’t know, what do you want to do”… “I don’t know, what do you want to do” dialogue. So annoying.

  16. I started doing this many years ago (before ever reading 4HWW). I realized that it is unfair to ask other people’s opinions first if I don’t even know what I want; that makes others responsible for my success or happiness. So I decided I should form an opinion before I ever ask for other opinions. This applies to dinner, work situations, relationships, and every other part of my life. I have noticed that many years later, I still sometimes lapse back into asking for other people’s opinions first. This tends to happen in situations where I think I don’t have a right to have an opinion.

  17. This is timely. In a recent conversation with a guy I am dating, he said his ‘beef with me’ is that I ‘control situations.’ Triggering words aside, we broke it down to I have strong opinions and share them, especially when he asks me what I think, which is considerate, but in this case it had been eating away at him. Perhaps this IS the challenge for me, to share my opinion and then ask him what he wants to do, with a loooong pause. However, it’ll probably be with a different guy, because his most frequent answer has been “I don’t know” or “It doesn’t matter,” which is not productive. But, this balance, especially in a relationship, seems to be the allowance of space for people who maybe need more time to make a decision, especially up against someone as decisive as I apparently am. Thank you, Tim!

  18. YES to this. At work there is always someone who “asks” what meeting time will work for 30 different people instead of just suggesting a time. Or one of my favorites, we were on a tour bus in Hawaii and the driver asked everyone on the bus when they wanted to stop for lunch, instead of just telling us what time lunch was. I realize these gestures are coming from good, accommodating intentions, but it just creates unnecessary confusion and stress for the person asking.

  19. I love this idea. I have a hard time making decisions because I never want to make the “wrong” choice when it comes to picking anything with friends. I tend to take it personally when I suggest something and the place/event turns out terrible. I am currently working on this with my psychologist. I like the “Let’s try . . . and then try something else if that doesn’t work.” Let’s see how this goes!

  20. I like to use “I recommend” or “I highly recommend….what do you recommend?” It seems to get folks to put more thought into suggestions.

  21. I like the concept, but not in all cases. The key for me is … who is the decision maker? Proposing to a decision maker is a challenge, because, well they want to make the decision. When you propose to a decision maker, just be ready to not always have your proposal approved. Otherwise, go for it!

  22. This practice works very well in the right circumstances.

    I remember reading of a submarine commander that would expect this of those in his command. He would provide a high level direction to the next in command and expect them to take on the responsibility of developing and implementing the detailed plans to follow the command. The subordinate would then respond to the commander, providing his plan in language such as “Sir, I intend to”…. If the commander was satisfied with the plan he would just respond with “carry on”.

    With colleagues I have found that they readily accept my suggestions for ideas or plans rather than get stuck in the roundabout discussions of options. So I can usually pick where I would like to eat.

    But with my wife, I have learned that we have different tastes in restaurants. So I have learned to avoid making the suggestion of where to eat.


  23. Gah. As an executive assistant by trade, I’m a big fan of the “propose a solution” approach (or multiple solutions, with predicted outcomes, from which they can choose). My personal experience is that, as long as the other person is pretty easy-going in general, in many cases proposing solutions works great.

    However, if you’re working with someone who is a bit of a control freak, or someone who likes to externalize their own internal discomfort, they’re highly likely to respond to your proposition with no’s and complaints, and yet they’re unlikely to propose alternate solutions to replace the ones they’ve shot down.

    I find this hugely frustrating as it puts me in the position of then having to either:
    a. try to guess what they’ll agree to in order to move forwards (not always possible, and usually not what I want), or
    b. get them to make a proposal of their own (which they rarely want to do).

    So, I’ve learned categorize people in my mind into two categories:
    1. Those with whom I will propose solutions/options/decisions freely, because it makes things go easily and quickly with them, vs.
    2. Those with whom I insist on a mutually agreed-upon plan FIRST before starting anything together. If I place the decision-making process in the very beginning, then I can decide whether it will be worthwhile to engage further, or not.

    That eliminates the frustration almost entirely for me.

  24. I’ve been subconsciously practicing the “learn to propose” challenge for quite a while especially with the where to eat situation. I get to try all the new places I’ve heard of and my eating buddies seem relieved to be free of the burden of deciding where we go.

  25. Type A Personality here. Proposing solutions, making decisions and leading come naturally and with ease. The challenge is playing along, letting it go, waiting patiently for things to reveal themselves. Working on it and looking forward for that exercise.

  26. Great summary of the concept. My wife & I often struggle with this when neither of us has a strong opinion about something.

    It is also a tool that I have regularly used as a project manager to work with stakeholders who have different opinions about something and you need to get to some sort of common decision. It gets them to move from their position to another position and then it gets easier to get to a solution.

  27. My wife and I would go back and forth deciding where to eat until I came up with the simple solution of letting our kids choose since we couldn’t make up our minds.

  28. The best opening line for a proposal imho is “how about we do ….?” Not sure that reads well, so an example Is: “how about we eat at Yen Yen?”

  29. And now for something different:

    In times of corona, have you tried to completely avoid touching your face with your potentially contaminated hands (and by that means avoiding contamination yourself)?

    Difficult? Impossible? Here is how you do it:

    1. Define or build a virus-free scratching instrument for yourself, e. g. a pen with a pen cap (without the lead of cource, you don´t want to write on your skin). Or the corner edge of one credit card in your purse. Or the edges of the temples of your glasses. Or thousands of other possibilities of covering a defined part of a tool before and after scratching.

    2. Scratch using this instrument and enjoy! (regardless wether your hands are contaminated or not, you should be safe)

    3. Enjoy even more safety by doing this for another reason: In the course of the next few days you will find out that your awareness and willingness of not touching your face rises exponentially by this little shift of attention and habit. Personally I have reached 100 % compliance in less than two days without being brutally strict to myself. It´s now a sticking habit and I don´t need the scratching tool more than a few times per day. I literally never touch my face with my hands unless I have washed them immediately before (washing my hands is the last thing before I go to sleep, so that period is covered, too). If I can do it, you can do it, too!

    4. Start using this approach today. It will possibly become more and more relevant in the next weeks and months.

    5. Of course you don´t forget the other good habits, eg washing your hands often, avoiding big events with a lot of people and so on.

    Disclaimer: I am not a doctor. I am not really an inventor either, just a successful imitator of the first ape, that scratched itself using a tool 😉

    @Tim and all readers: If you like this idea, please verify it and spread it. The idea is totally cheap and could be instantly and easily applied by all people in all countries all over the world.

  30. Hi tim i am really dealing with alot of stress n anxiety, missing deadlines and other things. I live away from my family and really wanted to express my feeling. I follow u so thought you would be the right person to take advice on how should i get up back. I know you are busy but a word or so will make my day

  31. One of my favorite techniques is the Strawman. This is where you make a suggestion or write a draft of a thing, with no regard to it being good. If it’s merely mostly coherent it’s great for a start. I did this with a business procedure and in two more half hour meetings it was approved and filed. Since I didn’t have any attachment to it, and everyone knew that, they felt free to tear it apart, and make the right thing.

  32. Hello Tim Know you’re busy and just wanted to post this one more time. I am a Postgrad Student in the UK and I have a chance to write a Dissertation (thesis, US) about a specific company, and would love to make it about your Podcast. It’s a 10K word essay about a topic to explore —involves a 3 month relationship.

  33. I love it! So often we hear “I’m open to anything” or “either way” which is just lazy. I love taking initiative and someone who takes initiative especially in a relationship.

  34. This is great! I’ve been trying much harder this year to look people in the eyes as I pass by on busy sidewalks. Hasn’t led me the love of my life yet, but the world works in mysterious ways 😉

  35. Tim, I love this challenge. Since taking this on, in the last week, I have had some incredible outcomes: 1. Meetings with 3 entrepreneurs to help me with scaling up the business I work in, one from a member of the Paypal mafia. 2. Sold a piece of real estate and put in an offer on another piece of real estate 3. New work contract including a moving benefit package and probably the most important of all, got my kids to do the dishes.

    All the best in Austin…

  36. Someone close to me “identity hidden to protect the guilty”, would ask me what I wanted to eat. I would counter with what I was in the mood for only to have him decide on what we were getting. Which felt like an open disregard for my feelings. This happened…often. So I stopped proposing, seems like the simplest and most efficient way. Sometimes the only way to win is to not play.

  37. Practiced this for the last few days.

    What worked great for me are beginning with “what if we…” and “how would you feel about xx.” These phrases help sidesteps the “yes but not really” facial expressions that I sometimes get when I ask “can I make a suggestion”

    My learning: For high stake things such as asking my org leaders to cancel public events during COVID-19. Highly recommend checking in on leaders and help them address their top concerns first. I made the proposal without doing that, and got “I don’t have time for this” as a response. In short, when a mountain is worth climbing, gotta help the gate keepers first so they can help me get there.

    I did this exercise with myself, too. It’s quite soothing to turn on the “Inside Out” mode during this intense time and have an inner fairy to ask “what if we go for a walk?” Or “how would you feel about going ‘fuck it’ for the next 10 minutes and come back later?” I said yes to most of these proposals.

    I also didn’t ask anyone’s permission, and just offered my joy&clarity toolkit for everyone to take or leave. The feedback has been amazing. Offering it here [Moderator: link removed.]

    1. Forgot to say, SUCCESSFULLY got two spaces to change to online programming because of this exercise 🙂 thankful for this team

  38. I’ve been practicing this challenges for three weeks now. My friends and colleagues are thinking why I start to behave so bossy? I think if I were a boy to propose everything it would be normal but as a girl to have your independent ideas is not as tolerance as a guy does. Interesting. But I like and enjoy this challenges a lot and will continue do so. Walk you own way and f* the rest noisy.