The questions you ask yourself determine the answers you get. The answers you get determine the decisions you make. The decisions you make combined with the circumstances you start from create the life you have now.
As Socrates said: “The unexamined life is not worth living.”
So, examine your life. Don’t just let life happen to you. Question your reality and use the answers to guide you. If you can’t come up with any questions yourself, here are some to get you started.
What Important Truth Do Very Few People Agree With You On?
Peter Theil, co-founder of Paypal, an initial investor in Facebook, and eccentric savant billionaire asks this interview question to all his new hires:
This question sounds easy because it’s straightforward. Actually, it’s very hard to answer. It’s intellectually difficult because the knowledge that everyone is taught in school is by definition agreed upon. And it’s psychologically difficult because anyone trying to answer must say something she knows to be unpopular. Brilliant thinking is rare, but courage is in even shorter supply than genius.
If you want to get different results than everyone else, then you can’t think like everyone else. Some conventional wisdom makes sense. Some pieces of conventional wisdom, many pieces, are cemented in our minds because someone asserted them repeatedly. The wisdom becomes part of the crowd and the crowd becomes mad.
If you look at the way most people live, they suffer not because they lack individual talent, but because they lack an individual worldview. Because they have a deep desire to fit in, they make the same exact moves everyone else does even if those moves lead nowhere good.
This reminds me of a game I used to play — lemmings. All the lemmings would follow the leader of the lemmings no matter where it went.
If the lead lemming made it safely to the end of the round, you’d win and all the other lemmings would follow. If the lead lemming fell off a cliff into a pit of fire, so did the rest of his crew, even though they saw him fall in first they kept going.
The goal of this question isn’t to become a contrarian for the sake of being a contrarian. The point of this question is to get you to think. Thinking for yourself entails risk.
“The prospect of being lonely but right — dedicating your life to something that no one else believes in — is already hard. The prospect of being lonely and wrong can be unbearable.”
In some shape or form, you have to take risks if you want to get disproportionate rewards.
So, what’s my answer to the question?
I don’t think true contentment is possible. I think we will all end up in a never-ending chase over our desires or regret over not achieving them. We can only choose the lesser of those two evils.
Ask Yourself the Same Question 5 Times in a Row
Whenever you try to sell somebody something, they’re usually going to throw an objection at you:
‘I don’t have enough money,’ ‘I don’t have time to use this’, ‘now’s not a good time’, etc. But usually, the truth lies behind the initial objection. Either they don’t trust you, they don’t trust the product, or they do trust the product but don’t trust themselves to follow through with using it.
Good salespeople get to the root objection and offer a solution to it if they can. You can use a question to go through a similar process when unearthing your own problems. Whenever you’re struggling with something, or even when you think you want something, ask yourself why?
I was always afraid to take the next step in my business and start creating programs. Why? Because I wasn’t sure if I could deliver on my promises and I didn’t want to become a sleazy course salesman. Why? Because I didn’t want to ruin my reputation. Why? Because I care about my reputation?
Because ultimately I’ve attached my identity to the results of my work.
A failure in business makes me feel like a failure as a person. I created a solution by consciously separating my identity from my work, offering a generous no-hassle refund policy, and creating the best programs possible.
When you’re struggling with something in your life, drill down to the root cause. Often, you’ll find a similar answer. Most of your hesitation in life comes from attaching your identity to the outcomes that happen in your life.
You’re afraid you’ll have to become someone you don’t want to be to succeed. Maybe you think you’ll have to compromise your character. Often, you’re worried about the blow to your ego and no longer being able to use ‘potential you’ as a crutch.
Getting to the root of your motivations, fears, and problems is a tricky battle, but one worth fighting because it can unlock answers that finally move you in the right direction.
How Can You Achieve Your 10 Year Goal In 6 Months?
This is another question from Peter Thiel to get you to stretch your thinking and understand where you’re hedging and playing it safe instead of just going for it. There’s a heuristic called Parkinson’s Law that says you’ll fit a task or a goal into the timeframe you give it.
Most of us continue to kick the can down the road. I’ve done it many times. It took me five years to quit my full-time job. Looking back on everything that went down, I probably could’ve done it in two or three years.
I lived by a rule called the 5 Year Rule. I even wrote an article about it. So many people told me that was how long it took for success that it became my destiny.
Now, don’t get me wrong, getting your freedom, and living your dreams in five years is awesome. And you can also fail by trying to do too much too soon. But this question is a great exercise in thinking because it shows you how much you limit yourself.
If you actually started to brainstorm and plot out how to pull off a goal in a shorter period of time, you’d come up with a bunch of amazing ideas that might not literally cut your time frame in 1/12th, but it can and will give you some ideas to move forward more efficiently.
Think about how much you sell yourself short, limit yourself, and expand your timeframes so long that you’ll probably never get anything done. Try this exercise and use the answers to create a plan you can use right now.
What Are You Afraid of Realizing About Yourself?
For me, it’s that I’m predominantly driven by insecurity veiled as ambition. The issues I write about are issues I’m addressing and working to fix for myself. I think any self-improvement writer would admit that if they were being honest.
I’m afraid that I’m constantly going to chase the dragon and try to fill the void, only to die with everything I’ve ever wanted in a material sense but still feeling that void. I’m afraid that I’m not okay as I am right now, in stasis, without having to ‘achieve something.’
But I’m going through the process of separating the wheat and the chaff when it comes to my own life and I’m inviting you to do the same. I openly admit that I have no perfect answer and only make suggestions without any guarantees or promises.
With that, I turn the question to you (in fact, leave it in the comments if you are bold):
What are you afraid of realizing about yourself?
What are you hiding from? What’s blocking you from coming to fully realize yourself? How are you lying to yourself and why?
I look at life as the process of trying to be less wrong than trying to get everything right. My opinions and worldviews shift because I shift. The things I write are a timestamp of my thoughts at the time and my life is a working practical philosophy.
You’re either unconsciously or consciously creating a map for your future. The map that leads to the most realizations about yourself tends to be the most painful one. But, as I’ve always said, pain, frustration, anxiety, and other negative emotions can be positive signals if you use them well.
What Would You Do If You Weren’t Afraid to Fail?
Sure, ambition can be hollow and driven by insecurity. But ‘contentment’ and ‘security’ can be driven by apathy. And that apathy is ultimately derived from fear.
Say what you want about self-improvement and it’s hyperbole, but we live in a society of terrified people. What are they afraid of? Here’s a thought from one of my favorite thinkers:
“We’re all going to die, all of us, what a circus! That alone should make us love each other but it doesn’t. We are terrorized and flattened by trivialities, we are eaten up by nothing.” — Charles Bukowski
We spend our entire lives wasting time with trivial BS because we’re afraid of facing life head-on, chest out, shoulders wide, brave yet vulnerable.
What would you do if you weren’t afraid to fail? If it’s not close to what you’re doing right now then you know it’s time to stop BSing yourself. Sure, you have bills, health insurance, your kid’s college fund, but you have an abundance of free time to do the things that scare you.
At least, you think you have an abundance.
The Yoga teacher I’ve studied from for the past six years suddenly died. She was in perfect health. During Shavasana pose, at the end where you lie down and relax, she’d always read a quote, many of which talked about surrendering to the present moment so that you could overcome your fear of failure.
She took a dream and a Yoga mat and turned it into an empire of her own. I’m sure she made a ton of money from the channel, but you could tell she just loved to do what she did. She had to overcome her fears to do that, and for overcoming her fears she got to lay to rest knowing she was the person she was meant to become.
That’s the goal. Not money. Not fame. Bravery.
I can’t give you some magic recipe for your fear of failure. But I can tell you that you’re going to die. And I can also tell you that there is a version of you that can exist if you started doing some of the things that scare you.
Why Not You?
I’ve finished some of these online programs that teach you skills like how to make money blogging, self-publishing books, starting businesses, etc. I pulled it all off and live my dream.
I can’t explain the exact underlying mechanism of how I got motivated, but I just sort of asked myself:
Why the hell not dude? Some people pull it off. Why not you?
And I just held onto that feeling. I held onto it when I launched my first product that sold zero sales. I held onto it when I barely made a dime for my first couple of years of writing. The alternative looked worse to me — stuck in a cube having to listen to people I didn’t want to fucking listen to.
So I weighed my options and chose ‘Why not?”
A lot of these questions are just different little derivatives to help you deal with your fear. The fear you feel because you tie everything so close to your identity, so close to your ego. Your ego tells you all the reasons why you shouldn’t do something. Counteract it with ‘Why the hell not?”
And the underlying attitude of a phrase like that is the key to propelling yourself forward. You’re serious about your goals, but at the same time you’re just like ‘screw it.’
What’s the point of being so serious, so timid, so stuck in a state of pragmatism that’s really nothing more than a failure to understand that you’re a speck of cosmic dust and that it’s insane you’re even here in the first place.
So, why not?
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