Ask Better Questions, Get Better Answers (Overcoming Mental Barriers)

Kids can be realllllly annoying at times.

Case in point: The “Why” game.

Aren’t familiar? I bet you are. Let me refresh you.

It goes something like this:

Kid: Why is it so cold outside today?

You: Because the temperature is below freezing.

Kid: Why?

You: Because there was a cold front that pushed cold air and snow over our area.

Kid: Why?

You: Because of global currents.

Kid: Why?

You: Because meteorology.


You: I hate you.

Whether they really are wrapped up in fascination with the world — or they’re just trying to bug you — kids ask dumb questions sometimes.

And guess what?

So do you.

The good news is that if you learn how to ask better questions, you’ll get better answers a lot more quickly and avoid much of the heartache and frustration that comes with trying and failing over and over again.

You’ll never be able to read minds. Stop trying.

I remember the tough middle school and early high school years.

(I know this sounds dumb to some of the older Tribe members — but my 10 year high school reunion is coming up and I’m freaking out about it.)

One of the most difficult things that young people deal with at that age is social interaction — especially when it comes to attracting the opposite sex.

I just didn’t know how to get girls to like me.

I read hundreds of articles online and in magazines…

I tried ordering info products to teach me…

(I had to run to the mailbox before my mom found out I was buying DVDs about “Sexual Communication” — scary, looking back!!)

I saw other guys having success — but nothing really worked for me.

So I’d beat myself up a lot.

I’d ask myself questions like:

“Why doesn’t she see how awesome/funny/etc I am?”

“Why does she like HIM and not me?”

“How can I get better at sports/stronger/ better looking to make her notice me?”

Invariably, as you may have guessed, none of these questions led to any life-changing revelations.

They just made me even more depressed. I had to learn how to ask myself better questions before I could start getting the answers (and results) that I wanted.

How to ask yourself better questions

Being truly, 100% honest with yourself is VERY hard because we have a psychological tendency to deflect blame project it onto others. This often becomes strikingly clear when we get rejected.

Think about all the times when you haven’t gotten the result you were looking for. Now, pay careful attention to the questions you ask yourself — and the answers you give yourself in return.

You ask yourself:

“Why aren’t I progressing faster?”

Your brain answers:

“Because I don’t have [insert resource, ability, knowledge, etc].”

You ask yourself:

“Why don’t people like me?”

Your brain answers:

“Because I’m not [smart enough/sexy enough/interesting enough].”

Notice how the way you ask yourself questions affects how you answer them?

What if you were to change the questions ever so slightly — and reframe the same challenges in a new, more positive light?

For instance, rather than asking why you weren’t progressing as fast as you’d like, you simply asked yourself:

“HOW can I make faster progress than I am now?”

Woah. That changes everything. Now, instead of a list of negative responses — you get positive ones with actionable takeaways.

“Well…I could make some more phone calls.”

“I need to spend more time studying.”

“I need to wake up an hour earlier.”

THESE are the types of answers that actually create positive change — but you have to be asking the right questions first…and that might require overcoming some limiting beliefs.

Your turn!

Leave me a comment below and give me an example of a limiting belief that you have — and tell me how you’re going to ask yourself a better question to overcome it.

For instance, if you’ve always thought to yourself. “I’ll never make $100,000/year” you might rephrase that as, “What type of value can I provide for other people that will make me $100,000/year easily?”

Can’t wait to hear your answers — I’ll jump in and help if you’re having trouble thinking of a good question to ask yourself.


Daniel DiPiazza

Daniel is the founder and CEO of Rich20Something.

A millennial business mastermind, he has successfully started three consecutive freelance businesses and scaled them to over $100K in revenue with zero startup capital. His work is regularly featured in Time Magazine, Fortune, Entrepreneur, Business Insider, Fox News, and Yahoo! Business.

His debut book, Rich20Something, publishes on May 2, 2017.

  • maxkreienbaum

    In regard to me thinking about changing careers I often ask myself “But, what if I fail?”. However, I should probably rather ask myself “What can I do to make sure I won’t fail?” to see opportunities instead of obstacles.

  • For me, limiting beliefs have always been a reflection of personal achievement and social skills.  They include statements I tell myself like, “If I COULD be doing more, I SHOULD be doing more, and shame on me for not working harder.”  (That one may seem like a good motivator to some, but for me it just makes me feel incredibly guilty and depressed to the point that I just sort of crumple inwards instead of allow it to propel me into action.)
    Or “If I’m not famous, then I’m worthless.”
    Or “If I put myself out there even once, I’ll just end up embarrassing myself, and everyone will reject me, and I’ll become a social pariah until the day I die because I’ll just be a laughing stock just like I was in middle school/high school, and nobody will ever love me.  Ever.”
    Or “I have to completely wow everybody, meaning my entire process has to be done in secret and not ask anyone for help, because the only way to get people to love me and be successful is if I fill them with awe.  If they see me asking anyone for assistance in any way, then they’ll know that I’m flawed, and they’ll use those flaws to criticize me and shut me out, because I’m going into this with a baseline of everyone already hating me.”

    …So, yeah.  That’s essentially what rolls around inside my head a lot of the time, and I still don’t know how to shut it off.

  • One of my limiting beliefs is that I need to be successful right away. Rephrase: What can I do to be more successful tomorrow than I was yesterday?

  • @George I totally relate to what you said about the “shoulds.” I feel that I put a lot of expectations and obligations on myself and don’t stop to think if they’re based on something I really want to do (or will help me get to that) or if they are based on what I think other people want me to do. And sometimes when I ask the other people what they expect it’s not what I thought it was. Lately I’ve been working on trying to prioritize what is really necessary and what would only be nice to do if I have time. It’s helping to reign in the to-do list paralysis a bit. What have you tried in the past when you have gotten to ” the point that I just sort of crumple inwards instead of allow it to propel me into action”?

  • Rich20Something

    Shelly Najjar Love it, Shelly. I also have a fear that I’m not moving fast enough or that I’m not taking the most direct route towards my goal.

  • Rich20Something

    @George Thank you for sharing that. It’s deep stuff and takes courage to talk about 🙂 I want to piggyback on what Shelly Najjar is talking about re: “shoulds” — I too have dealt with this.

    Here’s a question: Why do you judge your own progress based on what you see other people do? Why shouldn’t you be allowed to go at your own pace?

    I’d be interested to know your thoughts.

  • bmbenson2

    Very honest

  • Rich20Something What do you do when you feel that fear? I remember the bamboo post but I don’t think you shared how you allow yourself time and learn patience. For me sometimes this is limiting how many “inspiring” stories I hear like “Michelangelo was 26 when he started carving David” or making sure I immediately stop my thought process of “I’m that 26, what am I doing with my life? I’m such a failure” to trying to appreciate his talent and being okay that mine lies elsewhere or may take longer to develop. Sometimes when I compare myself to someone else, my pity party keeps me from appreciating that person which isn’t helpful to either of us. It’s something I’m working on now, so if you have any tips, I’m sure they’d be very helpful.

  • Rich20Something Shelly Najjar  Sorry it’s taken me a while to respond to this.  I’ve been needing to organize my thoughts.
    “What have you tried in the past when you have gotten to ‘the point that I just sort of crumple inwards instead of allow it to propel me into action’?”
    Well, ashamed as I am to admit it, these sorts of feelings have led me to consider/attempt suicide more times than I wish to remember.  Or I’ll just lie in bed and not want to face the world for the whole day, maybe longer.  Sleep can help me get out of some of the worst parts of depression, but it doesn’t fix the core issue.  The truth is I don’t have an answer to this problem.  This is where I’ve been stuck my whole life.
    “Here’s a question: Why do you judge your own progress based on what you
    see other people do? Why shouldn’t you be allowed to go at your own
    I guess it’s because I see other people my age or younger who have gotten so much success, who seem to have things figured out, that I feel like I should have stuff figured out, too…especially since I grew up valuing intelligence (or rather, “having all the right answers”) as being a chief virtue.
    When I was growing up, good grades–the kind of accomplishment that got rewarded–came very easy to me.  I was raised with the motto “if you do well in school, you’ll do well in life.”  And somewhere along the way, I interpreted that to mean a very black-and-white lessons of:
    –“The ONLY things you will EVER need to know to succeed in life will be taught to you DIRECTLY by your teachers at school, so don’t pay attention to anything else”
    –“Life will be as easy for you as school is.”
    Of course, both of these are flagrantly wrong, but I never learned how wrong these mindsets were to have because thinking about our own inner monologues and limiting beliefs and whatnot wasn’t something taught in our school curriculum.
    And since grades were so easy for me, I never really learned how to work hard at anything, since I thought grades were all there was to life.  I graduated thinking that since I put in my end of the bargain, a good life was supposed to just be handed to me somehow.  And when it wasn’t, I started to realize in retrospect just where I had been failing at everything else.
    I was socially awkward growing up.  I literally had no friends in middle school or high school.  I would leave school at the end of the day and go home and be by myself.  I was never invited to go anywhere with anyone else.  No parties.  Never went to prom.  I had ZERO social life and just as much social skills.  I was in the Boy Scouts for a number of years, but it was clear that the other boys in my troop didn’t really like me, either.
    I was constantly ostracized by my peers, made to feel worthless for being so different in so many ways (I enjoyed learning and engaging with my teachers, where other students saw school more as a prison or a joke; I was White in a school district where Whites were a racial minority; I was (and still am) very overweight; I didn’t speak Ebonics like most of the students around me; I didn’t like sports; I didn’t like the same music as everyone else; I struggled to accept myself as both gay AND Atheist while living in the Bible Belt; the list goes on, but I was basically a huge nerd), and so that’s what I learned to accept for myself:  weird and worthless.  Undesirable.  A waste of space and a huge inconvenience for everyone around me.
    All I’ve EVER wanted in life is to feel like I belong.  I just wanted to be able to hang with the cool kids, to feel like I’m loved and accepted.  I want to be one of those people that others look up to and come to for help or inspiration.  Music became an out for me, but not even the cool kids in music have ever wanted to have anything to do with me; I never was interesting enough and still just too socially awkward.
    So for my entire life, my entire sense of self esteem and confidence has been based on how other people view me and treat me.  I know that this isn’t a healthy model to have since I can’t control what other people do, but I have no idea how to want anything else.

  • Adam YN

    Quick question, I am at this time, on holidays, finished my Year 4, waiting for next semester and I want to make that paper in a sustanable way. I know my interest but I follow a lot of alternatives that seem to be faster paper.
    Q : Why am I not starting cause my barriers are “learn a new language” instead of “put 1-2k and see what happens” ?

  • Kate

    Amazing. This is so great.

  • ScholastykaBardzoszajba

    I can so incredibly relate to this and have just yesterday been feeling suicidal again. My question is how do I get enough money in 10 days to stay alive? With no car or Internet connection other than on my phone. Thinking in progress.. .. ..thinking.. .. Still thinking lol