The Ask Challenge… or how to have the best chance of getting what you want

Last month, I travelled to the East Coast for a friend’s wedding. On the morning I was headed to the airport, I had convinced myself that 45 minutes would be enough time to shower, wash/dry my hair, change the sheets on my bed, water my plants, and wash the dishes. It was total madness. There was no way in hell I was getting any of that done in less than an hour and half, and even though I cut every corner I could, and I still was late leaving for the airport.

That was the first in series of events involving really unfortunate timing. The Lyft driver I had that morning was dead set on driving between 5-10 mph below the speed limit (I kid you not… it was like I was on a hidden camera show, and the producer wanted to see what it would take to break my spirit). And there was more traffic than I expected. And my driver accidentally took me to the arrivals level so I also had to figure out how to get upstairs to departures with the least amount of lag. Which I did, and, while this may seem like a bit of hyperbole, it’s times like this that I am convinced I would be an amazing contestant on The Amazing Race.

Anyway, by the time I was inside the terminal, I had 38 minutes to check my bag and get through security and sprint to my gate. That timing detail is important because my airline’s bag-check cut off was a strict 40 minutes before the flight – so, technically, I was already screwed.

When I got to the check-in line, it was short, but it was not moving, at which point I knew I had a decision to make. I could either quietly, nicely, fairly wait my turn and (probably) miss my flight, or I could be brave and start asking anyone who would listen if they could help me out. The bottom line was that I had more to lose by not asking than to gain by being quiet. So I sucked it up and started asking.

This is what happened: 1) Two passengers in line at gate check were annoyed and tried to shame me for my lack of planning, BUT they let me go ahead so I didn’t care. 2) Airline check-in agent late-checked my bag without even blinking an eye. That was my biggest perceived obstacle so in my mind I was almost home free. And then… my first road-block, 3) The passenger directly in front of me in the security screening line denied my request to go ahead of him; 4) but then, I was able to switch to a different line and had success with all of the 8 passengers who were in front of me letting me go ahead. Incidentally, even though I had legally skipped to the front of the line with the permission of all interested parties, the TSA guy gave me a lecture about how it was not fair that I did that. I’m not a dummy so I kept quiet while I silently explained to him how wrong he was.

So in case you weren’t keeping count, of the 12 people I asked for help, only one was a flat “no” and only two others gave me a hard time.

Which made me wonder….how often do people want (or need) something but not even consider asking for it? I think I am pretty good at asking for what I want, and still I don’t ask nearly as often as I could. I suspect, without even realizing it, many of us are trying to avoid seeming greedy, or entitled, or needy, or selfish or thoughtless. Or we just don’t want to be a burden.

But the thing is most people aren’t going to be able to psychically know what you want or need, so you need to know how to communicate those things. And luckily, there is a method for doing this that was devised many many eons ago. It’s called “the question.” ?

The good news is that asking is a mental muscle that can be strengthened. And I think the key to being a successful asker is to not be attached to the answer – the outcome. If you can get to the point where you don’t really mind if the answer is yes or no, asking becomes a really low-stakes activity. Then, if you ask and your request is accepted, you’re ahead of the game, and if you ask and your request is denied, you’re really no worse off. Win-win!

My airport experience was a perfect example. I could have decided being comfortable and avoiding judgement were more important than putting myself out there with a simple request, and I likely would have missed my flight. In that situation, making the decision to ask was easy because the stakes were high enough that they outweighed my emotional discomfort.

But the true elite-level asker doesn’t only ask when the stakes are high. She asks when she sees an opportunity. And of course, whatever the outcome of the request, she is respectful. When you see asking in this light, so many cool opportunities present themselves.

Here is a short list of asks to get you thinking.

  1. Help… with anything… the dishes? A pending move? A project… the list goes on
  2. Information… where did you get that? …Or how can I…? Or why are those beans $80?
  3. Directions… where the eff am I anyway?
  4. Perks… do you think you could bump me to business class… Can I have more paid vacation time?
  5. Feedback… how am I doing? …how’s my work? …how does this look?
  6. Love… could you give me more quality time, kisses, talking, sex, etc.?
  7. Comfort… would you stop kicking the back of my chair? …would you please be quiet during the movie?
  8. Discounts… what kind of a better deal do you have for me?
  9. Raises… I deserve a raise….would you give me one?
  10. Favors… could I please go ahead of you in line because I didn’t give myself enough time to catch my flight? Sigh…

These of course are just a few of the many ways I challenge myself to do the (sometimes uncomfortable) work of asking for what I want. There are so many ways to apply this skill. But my point in bringing it up is to offer a gentle reminder that asking – even when it feels uncomfortable and especially without attachment to the result/answer – is a skill that can improve your life in so many ways.

Incidentally, on my return trip to LAX, I was at the airport almost two hours before the flight (lesson learned). While in line at security, two people asked if they could go in front of me. Not only did I let them by, but it felt so good to help out another person. So remember, in some ways, you are giving people a chance to feel good when you ask them for something. Hopefully, that will make your future requests a little easier to make.

Can you think of any outrageous requests you made in your life where the answer was yes? Comment below…

photo of legs and feet resting on luggage at LAX
This picture was brought to you by the art of asking. If not for my asking – and, of course, the kindness of strangers – this photo would not have been possible.

About The Author

Anne Stericker

City-dweller, designer, writer and lifestyle consultant practicing the art of living well in the 21st Century. Fixated with good coffee, great design, and any little thing that makes life better.


  1. KJ Luker | 10th Aug 16

    So right on Anne. It’s been a good thing to teach my kids (and myself): You don’t get if you don’t ask. The spiritual masters talk about that on many levels….

    • Anne Stericker | 10th Aug 16

      It is so simple, which maybe is why it is easy to forget… Love you, KJ!

  2. Diana Faust | 10th Aug 16

    So great– I love the reminder list of asks at the end! A great phrase to use when negotiating with someone in business deals, after they offer you a price, is “Is that the best you can do?” Yesterday AT&T phone rep offered me $20 credit for a billing snafu. I remembered to ask “Is that the best you can do?” And she came back offering $60! I was happy with the $20, but asking got me $40 more! ?

    • Anne Stericker | 10th Aug 16

      Diana, that is such awesome advice! Thank you for commenting! And congratulations on your $60 credit! Love it.

  3. gryffud | 10th Aug 16

    My brother has long been a proponent of the “5 No’s a Day” theory: If you don’t get at least five No’s a day, you’re not asking for enough! Which would lead to conversations at the end of the day, if he hadn’t fulfilled his quota: “Will you bake a delicious pie for me?” “No.” “May I have a pet swordfish?” “No.” “Will you carry me to the park?” “No.” Etc.

    I think you’re right about not getting too emotionally invested in the outcome. A “no” to your Ask doesn’t mean you’re a bad person or a failure.

    • Anne Stericker | 10th Aug 16

      hahahahah! I love this! Thanks for the laugh, Larry! And totally agree.

  4. steve heller | 11th Aug 16

    Riffing off of “gryffud” above … My cousin has said to me “If you’re not getting rejected, you’re not trying hard enough! It applies to girls and also to jobs/clients.” He’s … right.
    And of course so are you Anne.

    And for that matter, Jesus quotes from the jewish guy, that fit your post:
    “Everyone who asks receives, and everyone who seeks finds, and to those who knock it will be opened.”
    [Jesus, Luke:11:10]

    • Anne Stericker | 15th Aug 16

      Steve, I love this comment! You are so funny and smart! And thanks for the Jesus quote… I can NEVER get enough of them. 😉

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