Live Your Legend | The $100k Question: How to Ask for & Get What You Want
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The $100k Question: How to Ask for & Get What You Want

The $100k Question: How to Ask for & Get What You Want

Ask for something

“It felt like everyone was turning me down – until I realized I wasn’t asking for anything.”

– The man who forgot to ask

Getting What You Want & Asking the $100,000 Question…

A couple of days ago I was walking along Kamari – a little village we discovered when exploring Santorini by rental car. It was lunchtime and the beach was lined with a dozen or more restaurants.

While we were trying to decide where to eat, I stopped at the most appealing place and asked one of my standard questions…

Me: “Kalimera! This menu looks really good. Do you guys have any specials going on?”

Waiter: “Well, we can give you two glass of wine and you can rent our beach chair for free after eating.”

Me: “That sounds pretty nice. There are actually four of us, though.”

Waiter: “Okay, then we give you four glass of wine and four chair.”

Me: “Deal.”

Then he happily sat us down.

One question led to saving about 32 Euro – over half the price of a classy lunch for four. I wasn’t pushy. I just smiled and asked. As a result, he got our business and we got to taste some local Greek wine. Everyone was happier.

As it turns out, getting what you want usually comes down to one question. 

I took a Karrass Negotiating seminar in San Francisco about five years ago. After two days of intensive interactive instruction, case studies and dozens of tactics, they finished with just one technique they claimed would make a bigger difference than anything else we’d learned – the 80/20 rule to getting what you want. Know what it was?


That’s it.

Most people don’t get what they want because they never sack up and ask for it. We build up reason after reason why we shouldn’t. Or we never think to ask in the first place. So we don’t. And we never find out. And the longer we go without asking or finding out, the more reasons we stack against it. The longer we wait, the less likely we are to ask.

And the worst part is that we avoid asking in the first place, not because of what other people have told us, but based on our own negative (and often false) assumptions of what they might say.

We talk ourselves out of all the possibility.

And then we wonder why we’re not making the progress we want to make.

I’ve been asking questions like this for years. Often times I just do it for fun – to see what might happen. And so far it’s saved me well over $15,000.

Once, it even lead to someone writing me a $100k check… 

While my partner and I were building our investment fund a few years ago, we had talked about reaching out to some existing investors to see if they might want to add to their investment. One of them hadn’t gotten back to us.

For weeks, I found ways to talk myself out of following up. He’s too busy. I don’t want to be annoying. I don’t want to be selling or pitching too hard. And on and on. Basically, I was scared of being turned down.

Then one afternoon, I decided I’d just mention it in a casual, short and not so eloquent email…

Hi, [name]

 Just wanted to check in on your thoughts on adding to your investment since we’d like to get things finalized this week. 

 If all is good on your end, then no need to reply. 

 Happy holidays,


Pretty pathetic email, I know. It screams low confidence. But at least I got it out. Then I headed to dinner.

Later that night, I got a short response…

Please make the necessary arrangements to increase our investment by $100k.”

The money was in our account within the week. And to think how close I was to never pressing “send”.

But it’s not all about the money. The numbers just help make the point.

Asking is about giving yourself permission to make progress.

Questions have lead me to new partnerships and friendships, jobs, raises, promotions, business ideas and plenty of unexpected adventures – like having a 1 am nightcap on a $100 million yacht in Portofino only a few minutes after Chelsea and I met the owner (one of my favorite Connect with Anyone moments).

Asking questions is what creates possibility.

So what question have you been avoiding? Who should you be asking? My guess is there are plenty, but let’s start with just one.

For starters, you might ask for…

  • Your boss to create a new job based on your specific strengths and talents
  • A well-deserved raise or promotion
  • Advice from a mentor you’ve been wanting to learn from
  • A discount or scholarship for a course you’ve been planning to take
  • A potential customer in need to give your product or service a try
  • Some unpaid time off or sabbatical to further develop your idea
  • The chance to work from home a day or two each week so you can get more done and have a little more time for your family or passion project
  • An introduction or referral to the person you’ve been wanting to connect with
  • Your first testimonial to build up your brand

Those are just ideas. You know your questions much better than I could. But any ask is huge progress compared to talking yourself out of showing up in the first place.

Give people permission to support your cause.

That’s the beauty of asking.

People usually want to help others. They especially want to support the ideas and people they believe in. Few things feel better. And with the right request and fit, ideally, you’ll be helping them as much as they’ll be helping you. But it’s way too much to expect them to know what you want or need. Make it obvious.

You won’t always get a yes, but at least you’ll know. Then based on the response, you can adjust and make the yes more likely next time.

And here’s the kicker. Since people would rather not flat-out reject you, even an initial no can lead to a smaller, sometimes more useful, yes.

Just be sure you’re ready with a lower level ask the moment you get the initial no.

Maybe they won’t invest $100k or purchase your flagship product, but perhaps they’d be happy to make an introduction or provide a testimonial. Maybe your boss won’t give you four days a week working from home, but after asking, he’ll probably be a lot more open to allowing one day or half a day. The restaurant won’t offer you free corkage but maybe they’ll settle for the private table in the corner with a view.

Always be genuine with your main request, but also realize that anchoring your ask to something big makes the smaller requests much more likely. Expect more support on these lower levels and be ready with options.

When done genuinely, the right ask deepens the connection.

If you don’t ask, the world can’t say yes.

People are funny.

We want things and might even spend months, years or a lifetime thinking about and waiting for them. But our fear – of the unknown or rejection or whatever – keeps us from ever doing the one thing that gives us a chance at getting it.

There are a lot of talented people in our community wondering how to make progress, build their business and make money from their skills, experience and ideas.

I used to wonder the same thing. My “business” didn’t make a dime until the day I decided to put a price on my services. I decided to ask. And people slowly started to say yes.

The sale, be it financial, emotional or any other type of buy-in, is impossible if there’s nothing to say yes to.

So, what can you start asking for? Share your question in the comments.

I’m off to ask for a little faster Internet at the cafe downstairs…



image credit

  • The $100k Question: How to Ask for & Get What You Want - Introverts Power
    Posted at 11:33h, 29 May Reply

    […] And the worst part is that we avoid asking in the first place, not because of what other people have told us, but …read more […]

  • Steve Roy
    Posted at 12:42h, 29 May Reply

    Hey Scott,
    Well said. I think many people are so afraid of either being rejected or having to deal with a little confrontation that they just don’t ask. It does require us to get out of our comfort zones and it’s pretty challenging for many, but like you said, we can’t get a “yes” unless we ask.

    • Scott
      Posted at 13:34h, 29 May Reply

      Right on Steve. What I find so fascinating is how often the thing holding us back is 100% in our control. Pretty liberating once you notice it though!

  • Scott Fox,
    Posted at 14:02h, 29 May Reply

    Hey Scott – love this:

    “If you don’t ask, the world can’t say yes.”


    That’s a quotable quote if I ever saw one. Well said, inspirational, and instructional, too.

    [Adding this to our database at with your name on it!]


    • Scott
      Posted at 23:23h, 03 June Reply

      Very cool! That was a very late stage addition of mine too. Funny how that works…

  • Galen
    Posted at 14:39h, 29 May Reply

    Hi Scott – Great post! Sometimes I get so stuck because I’m afraid of being told “no” by someone but it’s so true that if you are polite and ask nicely there’s no harm in asking anything.

    I think it’s also really important to be persistent. I had a client who I’ve emailed a couple of times now to follow up about a new project with no response. I finally got up the nerve to call them and they were so happy to hear from me. They said they’ve been really busy but they’re very interested and sorry for not getting back to me.

    Thanks for the confidence boost!

    • Scott
      Posted at 23:26h, 03 June Reply

      Isn’t that crazy? You don’t hear back so you try one last time and they thank you for being so persistent. A really important reminder!

  • Akshay Nanavati
    Posted at 15:05h, 29 May Reply

    LOVE this Scott! Like Jack Canfield says in his bestselling book the Success Principles, one of his principles is “ask, ask, ask.” It is amazing what we get when we actually step up and ask for things, and just believe that anything is possible. By just asking for it, I have gotten two sponsors for my run across the world, Omegawage and Newton Shoes (some of the best running shoes on the market) and I have gotten free nights at hotels in the Caribbean. Why? Because I asked for it 🙂 As always, love your work Scott. Really looking forward to meeting you at the WDS soon!

    • Scott
      Posted at 23:26h, 03 June Reply

      Well done!

  • David Firth
    Posted at 15:06h, 29 May Reply

    Powerful essay, Scott. Thank you!

    You asked for examples for what I’ll be asking for. My primary ask is ‘You’ll love participating on my Conscious Consulting School and I’d love you to be there. Will you come?’

    Inspired by your post, I realize I now have a follow up to No (for some candidates): ‘How about we talk about me doing a version of the School for people inside your organization?’

    I don’t know if that’s a bigger ask rather than a smaller one, but it’s a great alternative!

    Thanks again.


  • Anna
    Posted at 15:07h, 29 May Reply

    Scott, wonderful post, thank you! As long as I remember myself, I was afraid to ask. “What if people will think I am so and so for asking about it?” Doing that made me frustrated with myself, but I couldn’t work up the courage to ask.

    Steve, you are absolutely correct, it requires us to get out of our comfort zone, and up until recently it was a huge task for me. Once I realized how much I lose by not asking, how many wonderful opportunities I passed up, things got easier.

    • Scott
      Posted at 23:28h, 03 June Reply

      For sure – experiencing a little loss from not asking helps a lot 🙂

  • Tope Fabusola
    Posted at 16:39h, 29 May Reply

    I have been meaning to get incentives to further my career lately. I held back because I was worried I would be inconveniencing others.

    I think now I should at least ask first.

    Hey, what am I thinking again? I am asking from now on!

    Matthew 7:7.

    One love, Scott!

  • Loreena
    Posted at 17:10h, 29 May Reply

    Time! Asking for time to myself, to help me achieve what I need to achieve has been a tough one for me. Knowing it’s ok to put myself first. Although I know I’m not the only wife/mother/person who struggles with this it somehow seems like the hardest thing to ask for. I’m working on it though 🙂

  • Jill Prather
    Posted at 17:52h, 29 May Reply

    OMG! I just slapped myself on the head. As a person terrified of being rejected so never asked for much, your article blew away my fear.


    Faithful reader

    • Scott
      Posted at 23:29h, 03 June Reply

      Well I’ll take that as a good thing – now you gotta let us know what you do with it!

  • Sum
    Posted at 18:09h, 29 May Reply

    Often, people do not want to reject you outright. They are silent – basically not responding to calls, messages and mails and not even offering feedback afraid of really leaving a trail or of keeping you guessing. How does one cut through this impasse ? “It felt like everyone was turning me down – until I realized I wasn’t asking for anything.- The man who forgot to ask”. Does it mean that you have to evaluate what you are asking ? Is that not judging yourself and hence taking a little beating on the self-confidence ?

    • Scott
      Posted at 23:37h, 03 June Reply

      It’s a tricky spot for sure. One option is to just be totally up front with them and let them know it’s totally cool if it’s not your thing and you’d really appreciate knowing why so you can continue to improve and find the right fit with the right people going forward. You could turn your ask to asking for the why not. Not so you can sell them harder but so you can learn. Let them know you realize they might be hesitant to say no or give the real objection. But you have thick skin and would really appreciate hearing it. You could even mention what you think some of their objections might be so they feel more comfortable. That can help a lot with opening them up.

      Of course do that in a nice friendly concise way 🙂

  • Steve
    Posted at 18:46h, 29 May Reply

    Great article which I can relate strongly to.

    I used to be afraid to ask for fear of rejection. But after a while, I came to realise, I don’t have to take rejection too hard and personal – that any rejection is to the request and not towards me.

    Its hard at first but after some time getting used to asking, I got a lot of freebies, offers, people more than willing to share (surprising), just by asking!

    • Scott
      Posted at 23:37h, 03 June Reply

      Awesome – yeah it’s pretty wild what people are willing to do. Really fun to discover!

  • Tina
    Posted at 19:08h, 29 May Reply

    I want to ask my employer to let me do my job remotely. I am seriously thinking about moving from the east coast to the west coast for personal reasons.

    • Scott
      Posted at 22:36h, 29 May Reply

      Well Tina, what’s the risk in asking? What’s the risk in not asking? That usually makes most decisions pretty clear to me. Let us know how it goes!

  • Eme
    Posted at 23:17h, 29 May Reply

    Whoa! I wrote about this on the most recent post on my blog! Freakily similar.

    I help cake decorators grow a more successful business (or at least thats the plan:)). And because most don’t have money, means or even knowledge to do the internet thing and fancy marketing, this is one thing you can do without having to have money or tech knowledge. You can ask! I have asked celebrity TV teachers to come teach for me, I have asked shops to give me free products to try, I have written letters that said things like “I am not well known but I know my stuff dammit! I want to be on the lineup of your speakers…”
    When you ask, things happen.
    I remember seeing someone on TV, liking what he said and stood for and asking him to do a foreword for my book. He didn’t know me from a can of paint but he said yes!

    And Scott, you are “spot on” about two things 1. people are usually helpful and 2. You may not always get what you ask for but you will always learn something and often get something better down the line.

    Awesome post Scott. You made even more sense of what I tried to say in the Learn This One Thing report: Asking gives people the opportunity to support you and you give yourself permission to progress.
    This post is a huge validation for me as I am a newbie blogger and I wondered if anyone really needed to hear what I had to say…
    So I am asking…
    Could you please, maybe, check out my post and read the Learn This one thing report and leave a comment.

    • Scott
      Posted at 23:40h, 03 June Reply

      Your example adds a ton to this post Eme. That’s exactly what I’m talking about! Thanks so much for the detail and congrats.

      Great ask on your post btw. I’ll go try to find it!

  • Peter Simoons
    Posted at 01:17h, 30 May Reply

    Asking is so important and every now and then it is good to be reminded to ask and this is a great reminder. Now just need to think a little about “how to ask”. But then, I already have No and if I don’t ask it will never turn into a Yes

    • Scott
      Posted at 00:29h, 04 June Reply

      Well put – anything is progress at this point!

  • Joe
    Posted at 02:23h, 30 May Reply

    Very simple and profound. Just ask! Dont know why it is sometimes so hard to do – paralysen by fear, thoughts of inadequacy, positional power and past mistakes

  • Darren
    Posted at 05:34h, 30 May Reply

    Love this article, Scott! It was such a relevant topic for where I am in my business growth, and life in general. I have been asking more in the last couple of years and with surprising results. But what you wrote made me realize there is MUCH more I can ask for, and how I can go about doing it.


  • Mike Goncalves
    Posted at 08:40h, 30 May Reply

    Thanks Scott, definitely a great reminder. Interesting as well how we can apply the “ask” concept to many other areas of our lives. Don’t know much about someone? Ask them about themselves. Don’t know how to do something? Ask those who know. Don’t know how to get somewhere? Ask for directions (I know, tough one ). 🙂 One of my recent “asks” was asking those in my community to share my newsletter and material with family and friends if they felt they could benefit from my work. My assumption is they did as I noticed an increase in my newsletter subscription. Such a simple request yet so powerful. Thanks for the insight, good stuff as always. Cheers!

  • Jeremy
    Posted at 11:33h, 30 May Reply

    Thanks for the powerful and empowering reminder.

  • Rebecca Beaton
    Posted at 16:11h, 30 May Reply

    Thanks Scott! Really loved this post, it’s SO true. It’s often surprising what we get when we ask. Reminds me of Jia Jiang’s talk at WDS last year… overcoming (or at least working with) the fear of rejection has been a big piece on my own journey and is so key to becoming successful. Thanks again!

  • Brian Comstock
    Posted at 21:51h, 30 May Reply

    Scott –

    I was sitting at a software conference two days ago with Pat Hughes, a friend of yours from Santa Barbara. He and I were having a great conversation and he brought up your name and started telling me about LYL and the amazing progression he has witnessed from the early days. He commented that you and I have a lot in common, and he suggested I check out your blog. So, here I am, and I’m fired up on what I’m reading. So, here is my question:

    Can I join you on a run or workout of your choice as a way to be able to connect with you and hear a bit more about LYL in person?

  • Debashish
    Posted at 10:02h, 31 May Reply

    Thought provoking post, Scott. It reminds of the TED talk by Amanda Palmer.

    I am considering the idea of crowd-funding to help me quit my job. I might have to pay $25k to my employers to quit my job in the next 3 months. If not, I might have to stay on till the end of next year. Is this too big/daring an ask?

  • Daniel
    Posted at 19:10h, 31 May Reply

    I’ve been asking and asking for the last two decades, and still trying to find someone willing to help.

    Though, due to some serious financial issues many years ago, the main help I would need now is for someone to co-sign for some school loans, since I’ll need loans above and beyond the standard ones. I sent out tons of e-mails, and talked with everyone I know who could possibly do that. No one has even considered it…

    Beyond that, my financial woes have gotten me all the way to the bottom of my “backup plans” list.

  • Bond
    Posted at 23:12h, 31 May Reply

    Scott, this is a great read, thank you very much. I am immediately going to implement the Karrass 80/20 rule that you shared, it is brilliantly simple, I had to laugh! Also, after years of timidly thinking that the “world must certainly know” what I want, and what would make me happy, you summed it up with, “If you don’t ask, the world can’t say yes”! …um … duh!? I spent a lot of time waiting for the “yes”, only to realize that I never clearly asked the questions that needed to be asked along the way! Good luck with getting the faster internet at the cafe downstairs, that’s beautiful… and inspirational!

  • Taina
    Posted at 13:53h, 03 June Reply

    Hey Scott and everyone!

    Thanks for the post, it prompted me to ask for something. Please help me win 5000 € in a poster design competition where the winner is chosen by voters. It’s really easy: just click ‘tykkää’ (like) underneath my poster at the link below:

    Winning this would make some of my art & design projects possible.:)

  • Jeff
    Posted at 17:49h, 03 June Reply

    If you don’t ask the answer is always no! Great point and great points throughout the piece! Thank you!

  • Mieke
    Posted at 01:48h, 05 June Reply

    Thank you for this insight… I so hoped that your truth was wrong! But it makes me want to cry my eyes out because it is so true! I always assume I will be turned down, so somewhere I just stopped asking… This hurts but this will help, so thank you for posting! 🙂

  • Jamie Walker
    Posted at 09:32h, 05 June Reply

    I have just started looking at your website and this article confirmed what I’ve learned myself and tried to teach my children. My version of “If you don’t ask, the world can’t say yes.” has been “If you ask you might receive. If you don’t ask you won’t receive.”. I’ve found out over the years that if you ask you are very likely to receive but if you don’t ask you won’t receive. I’m looking forward to exploring more of your website.

  • Dave
    Posted at 21:20h, 08 June Reply

    Hey Scott,

    This is truly the best advice ever. I was told the same thing at a leadership seminar I attended years ago in Cabo.

    My buddy and I decided to test it out at the Hard Rock Cafe in Cabo by asking the band to let us come on stage and play with them. Sure enough they said yes, and while they kicked us off pretty quickly once they realized we sucked, it was clear proof that just asking will get you way farther than you’d ever imagine.


  • jibran
    Posted at 09:34h, 10 June Reply

    Hi Scott,

    I had a question I’d like to personally direct to you, it relates to to Questions to Find Your Passion worksheet. I completed it and would love to follow up with you about it and see if an analysis on your end was possible. You are an expert at what you do and would love to hear your thoughts since you have been at this for quite some time.



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