8 Weird Questions Successful People Ask That You Don’t

We live in a world where everyone is secretly copying everyone else. It’s become so endemic in our society that we barely even realise we’re doing it.  Our desire to be affirmed by others leads us to live within ourselves. Rarely demonstrating the true range of skills and creativity that exists within us all.

To bravely step out of the shadows and live a life for you is the first step towards a successful and happy life.

We’re so wired towards safety and conformity that when someone does step outside of the norm they are first ridiculed but later worshipped.

Just look at the great entrepreneurs of the last 15 years and imagine someone pitching Uber, Airbnb, PayPal or Twitter to you as a startup.

Be honest. What would you have said?

They were all unique in their different ways and as such provide little to compare them against to ensure success.

There is safety in crowds but not much excitement. To live as an outlier on your own is to push yourself beyond what is comfortable. That can lead to failure but it’s the only route I know that leads to true success.

The saying:

   “What got you here won’t get you there”

suggests that sometimes you need to look at something in a completely different way to get to the next stage of success.

If you want to stand out from the crowd then it makes sense that you need to do something different from the crowd. In short, you have to get a little weird.

Don’t get me wrong, I believe being weird is the biggest compliment I could ever receive. To be weird is to be unique which is to be you. That’s right….you. Not a version of you that you think others want to see but the version of you that frees and liberates you.

In order to find a deeper level of success in life we have to ask ourselves the weird, unique questions that only the successful few ask.

Tim Ferris said:

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have”

So here’s an opportunity to get uncomfortable and ask yourself these 8 weird questions that successful people secretly ask, that you don’t:

#1. Who scares me?

Your comfort zone is a state in which you feel in control, at ease and familiar. Well, growth happens outside of this, and that is largely determined by who you spend your time with. So ask yourself:

Who scares you a little? Who scares you a lot?

When I joined a men’s programme a few years ago I was surrounded by men who scared the living crap out of me. They challenged me in ways I just couldn’t challenge myself. They were doing things that inspired me but scared me too.

They called me out to do and be something better than I was being. This was tough but I would never have left my job without them. I wouldn’t have committed to my relationship without them.

I would have run to safety but because of them I realised what needed doing and that was something I couldn’t do on my own.

successful people

#2. So what?

So you want to make lots of money. So what?

You want to use the money to buy a nice house. So what?

You want to have a family and somewhere to bring them up in a safe and loving environment. OK, now we’re talking.

“So what” helps to challenge you to go deeper into why you’re doing something in life. If you don’t feel truly connected to a project just ask yourself:

So what?

Do it again and again until you say something you can’t say “so what” to. That’s when you know you’ve hit on something important and touched on why you’re doing it.

THAT’s why I’m working so freaking damned hard.

THAT’s why this project means so much to me.

THAT’s why I love her.

Successful people are deeply connected to their why. This helps to drive them forward in the good days but particularly during the bad.

#3. What am I just rubbish at?

It’s important to distinguish between what you’re awful at from what you need to improve at. There are some things we’re rubbish at and it’s likely we’ll always be rubbish at. So stop focusing on improving and get someone to help you, or even better, do it for you.

If you’re rubbish at motivating yourself to go to the gym, get a personal trainer.

If you’re rubbish at website design then hire a developer.

If you’re rubbish at planning, hire a virtual assistant.

Admit what you’re rubbish at and find the support you need. This creates space and time for you to focus on your strengths and developing the skills that you can improve upon.

What are you rubbish at that you need to hand over to someone else?


#4. What would my dad disapprove of?

In his book Way of the Superior Man*, David Deida talks about living as if your father was dead. How differently would you live your life if you weren’t living up to his expectations of you?

Living up to his expectations can have a negative effect on your ability to move beyond the constraints that those beliefs have upon you.

What are you withdrawing from in life caused by your dad’s disapproval?

Maybe taking a chance on the new city would challenge his need for safety.

Maybe admitting to a failed relationship would challenge his Puritan beliefs.

Maybe investing more in your own development would challenge his frugal nature.

When you live your life based on his beliefs they cease becoming solely his. Now, they’re yours too.

What do you need to do that would liberate yourself of his expectations? What is it you could do that he would disapprove of?

#5. What boats do I need to burn?

What if you didn’t have a backup plan?

In 1519 Spanish explorer Hernán Cortés landed on Mexican soil. His surprising call to “Burn the Boats” is still quoted to this day because he was declaring that it was “do or die”.

We’re often asked what our plan B is but how different would you approach plan A if there was no plan B?

Where are the unnecessary safety nets you’ve prepared for yourself and how can you remove them from your life?

Doing so will give you that extra motivation and fire in your belly to go after what you want.

Create a situation where you need it, as opposed to want it. Needing something creates a deeper motivation than wanting.

#6. Who do I need to tell to fuck off?

Everyone has an opinion; some of them are worth listening to and some are not. Trying to accommodate and please everyone’s advice will have you running round in circles.

If you’re creating anything meaningful in life then you’re going to polarise people. There are going to be people who love it and those that hate it.

successful people

It’s hard to accept but the sooner you can let those opinions go, the sooner they will stop holding you back.

If you believe in what you’re doing then learn who to listen to and who needs to take a long walk off a short pier.

#7. What do I believe in that no else does?

There are countless stories of successful people who had an idea everyone thought was mad.

Someone gets a new idea, by its very nature it challenges the norm. It challenges how we look at things, at ourselves and our needs.

Successful people can see beyond the status quo and imagine a different world. Not everyone else sees the world as they do, and until then they will be thought a fool.

The difference between thinking someone a fool and knowing the truth, is time. Until then ask yourself what is your crazy idea that everyone else thinks is completely bonkers.

Successful people take that idea and make gold out of it.

#8. Where can I fail today?

Success is on the other side of failure. If you’re not failing well enough you aren’t succeeding well enough.

Byron Katie says that there isn’t anything you can’t have in life that you aren’t prepared to ask 1000 people for.

Embracing the perceived failure that comes with that is just a state of mind. Thomas Edison famously said that he didn’t fail, he just found 10,000 ways that didn’t work. That simple reframe could be all it takes to “fail” gloriously.

Where can you fail today? Because afterwards, I guarantee you’ll be closer to succeeding, even if it doesn’t feel that way.

After all, what’s the alternative?


I hope this post was helpful. Do you have any other questions you would add? Let me know in the comments and please share this post with a friend if you enjoyed it. For regular content like this just click subscribe below.


To your success



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About the Author

Writer and coach, Mike writes about the struggles and triumphs of how to be a modern man. He writes to support these men, and the women that love them. Click here to learn more.

Leave a Reply 11 comments

Jasmine - September 4, 2017 Reply

I love this! I need to ask myself some of these questions more often! Especially the one that says what can I can fail at today hahaha I love that but it’s so true!

Jasmine 🙂

Jillian Schleger - September 4, 2017 Reply

Do you know how many fluff blog posts I read? Too damn many.
I adore your post.
I have to be honest. You pissed me off in the first part. I didn’t like where I thought you were going.
The reminder that we are too comfortable in a crowd. The truth that we rarely step away from ‘the norm’. And the harsh reality that we copy and follow the masses – although I do believe it’s the Artist that steals to manipulate and make his own.
The fluidity, structure, and resolution of persuasive concepts, both new brilliant gems and other not so new, was a satisfying read!

Melissa Wuollett - September 6, 2017 Reply

Very interesting, never would have thought of asking those questions!

Ramona Spires - September 6, 2017 Reply

Can I say how much I love this post? These are questions I wished I asked myself much earlier in life. I learned that stepping out of my comfort zone was the only way I was going to truly live.

    Mike Matthews - September 7, 2017 Reply

    Thanks Ramona. Yes of course you can say that 😉 Glad you liked it and yes growth happens outside your comfort zone. Similarly it took me some time to realise it.

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