5 Deep Questions to Ask Yourself If You’re Desperate to Change

Contemplation + action = results

You spend a ton of time in your head, but how useful is that time? Mental chatter throws you off, constantly, doesn’t it? Sometimes you feel like you have little to no control over your mind at all.

Instead of trying to fight your racing mind, try using it to your advantage. Make that time valuable by asking yourself questions that will lead to a better life.

I use this process often.

When I feel doubts, when I want to move in a certain direction but feel unsure, or when I’m lacking confidence, I’ll ask myself smart questions to counteract negativity.

I ask myself positive questions when I’m fired up about a goal. I’ll ask myself how I can take things to a new level.

Either way, the questions you ask yourself are important because the answers to what you want are out there, but if the quality of your questions sucks, then you’re going to get bad answers.

“Why me?”

“Why can’t I get ahead?”

“What’s wrong with me?”

You’re always going to find what you’re looking for. Stands to reason you should always look for a way up or a way around whatever stands in your way.

Let’s take a look at some of the questions I’ve asked myself again and again. Questions that can help you figure out your next move, too.

Why Not You?

“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes … the ones who see things differently — they’re not fond of rules, and they have no respect for the status quo […] The people who are crazy enough to think that they can change the world, are the ones who do.” — Steve Jobs

Success requires a level of delusion.

I remember taking an online course for successful blogging. In the first module of the course, the instructor flat out said most people will not finish the course and become a successful blogger. I’d seen the writers who did graduate from the program and they were quite successful.

I made it up in my mind that I was going to finish the course and make a name for myself. That’s exactly what I did. And I did it by asking myself this question — “Why not me?”

You’re a good person, right? You’re reasonably intelligent, have some innate skills, and deep down you know you could stay motivated if you found something that clicked.

So, why not you?

We live in this society where people either become admirers or denigrators of successful people. Either we outsource our identity to the heroes we worship or we show disdain for what we can’t become. Few people ever decide to become one of those people.

I ask the question “why not?” all the time. I’m going to attempt to write a New York Times bestseller. Why not? At age 30, with my skillset, this seems more than possible. I’m going to build a seven-figure business, for the challenge and not for the money, just to see if I can do it. Why? Why not?

You probably have some crazy-ass dreams. Go for them. Why? Why not?

It’s so sad that we get caught in this box of fear. Self-doubt does create this palpable feeling of being limited. I won’t deny how difficult it is to overcome. But, hell, don’t you owe it to yourself to try and keep trying until it works?

You don’t need to achieve world domination, but you could be in the position of the people you admire one day. You could max out your potential and live a pretty damn good life.

I know you feel doubts and I know those doubts can be crippling. I know it’s tough. But keep that question in mind when you feel those negative feelings.

Who Could You Be If You Weren’t Afraid to Fail?

“Someone once told me the definition of hell; on your last day on earth, the person you could have become will meet the person you became.” ― Anonymous.

Visualization can be a form of mental masturbation. Some people daydream about who they could become and never do anything about it.

That being said, having a vision for your life, combined with action, is the key to reaching high-level goals. I think about that quote often. I want to reduce the gap between the person I end up becoming vs the person I could’ve become.

Spend some time not just passively daydreaming, but actively visualizing yourself in scenarios where you’re the self-actualized version of you. Not arrogant, but confident. Not free of fear, but courageous. Make the vision both realistic and aspirational at the same time.

You’ve heard anecdotes about athletes using visualization — golfers mentally playing every hole of a course, basketball players imagining free throws. The power of the mind is something we’ll never fully understand, but its presence is undeniable.

You don’t have to be some super talented human to imagine how amazing life could be if you simply maxed out what God or the universe equipped you with.

Even now, after spending 5 years working on a dream, I might be at 20 to 30 percent of my full capabilities, if that. The point isn’t to reach perfection but to try in vain and celebrate your growth along the way.

You can’t escape your mind. And, even if visualization doesn’t work right away, you can keep doing it over and over again until it does.

Visualization can turn into a decision. Burn that question into your brain, drill it, repeat it, obsess over it until you decide to act on it.

Why Do You Care What Others Think About You?

I have often wondered how it is that every man loves himself more than all the rest of men, but yet sets less value on his own opinions of himself than on the opinions of others. — Marcus Aurelius

To this day, when I get a negative comment on my writing, it stings. I still don’t like getting rejected. I don’t like feeling embarrassed. But, I’ve found a way to overcome those feelings to build my career in spite of the naysayers.

How? I continually ask myself why I should give a damn what anyone thinks. Again, I drill down and try to understand why I care.

  • Sometimes you think people’s criticisms of you are accurate. Sometimes they are accurate. You have flaws and shortcomings. Exposing yourself to the world will highlight those flaws and shortcomings, no question about it
  • You’re wired to constantly monitor your social status, pecking order, and standing in the tribe because of your caveperson brain
  • You’ve been socially conditioned, on top of your brain’s wiring, to fit in with your peers, the Joneses, and society at large.
  • Sometimes you actually care about the opinions of others because those people are important to you, e.g., your parents.
  • You understand that tall poppy syndrome is real and that leveling up may require you to shed relationships or change them

What do you do when you find the answers to why you care about the opinions of others so much?

You’ll remind yourself about the nature of the people you seek approval from. Would you trade places with the people who’re opinion you care about? No. Are other people inherently better than you? No. Are they just as neurotic and self-critical as you? Yup.

This won’t cure your fear of rejection and embarrassment, but it will decrease over time when you level up yourself and continue to analyze the nature of others, trust me.

You will care. And you’ll still be afraid of ostracism. But you’ll just decide you’re going to deal with those situations as they come. The pollyana form of self-improvement teaches you that you can eliminate negative feelings prior to, you know, actually doing anything. This is incorrect.

The road to success is paved with a plethora of negative feelings. But once you realize negative feelings are just part of the game, not some scary monster you need to vanquish first, then you just go about your business knowing these feelings will come up.

What Kind of Person Are You?

“It is what a man thinks of himself that truly determines his fate.” — Henry David Thoreau

Have you taken the time to consciously map out your moral code, your understanding of the way the world works, your values, and your standards for the people you want in your life?

How well do you understand yourself? Do you even know what you want?

I’ve had the benefit of both keeping a journal and writing in public for years. These two activities have helped me shape a solid worldview where I am pretty self-assured about my life.

I don’t know exactly what the future holds or what I’ll want, per se, but I have principles I live by tastes I’ve developed and standards that help guide my decision making.

Spend time not just thinking about, but writing down answers to questions like these:

  • How does the world work and what are the rules of thumb/heuristics that come to mind?
  • What type of people do you want in your life — friends, romantic partner, colleagues, network?
  • What are your values? Rank them.
  • What’s your moral code?
  • What kind of life do you want to live?
  • What, or who, do you admire?

Asking yourself these questions is just the start. You’ll learn the most about yourself in the process of trying to achieve your goals. You’ll learn whether or not your moral code is legitimate when it’s truly tested. The world itself will show you whether or not your understanding of it is correct.

The combination of contemplation and action creates this sense of certainty. The greater sense of certainty you have, the bolder and more confident you become.

And that’s what you want, really, above all else, is confidence. That feeling that you can exert your will over your own reality. You can get there, but it will require this sort of inner work over and over again while also growing your competence in the real world

What is the Meaning of Life?

“The unexamined life is not worth living” — Socrates

Even though you’ll never know the answer to the question, contemplating the meaning of life gives you the perspective you need to live more freely.

What the hell are we doing here? How did why get here? What’s the point of all this?

Different people get different answers. There’s only one wrong answer — the nihilist’s answer who concludes that the randomness of the universe means life itself is meaningless, thus, one should not try to do anything useful in life at all. What a shitty answer.

My answer?

So far, I’ve come up with this — the meaning of life is to be useful and honor the universe by harnessing its power as much as you can.

Sometimes I get very deep and philosophical, reminding myself that I am of the same matter that created this insane science experiment that is the universe.

I believe in a creator of some sort because the sheer wonder of it all leads me in that direction. And, I think that creator wants me to put as much positive energy into the universe as possible. Because of the ludicrous nature of reality, I decided to go all-in on pushing its limits.

Why the heck not?

Contemplating the scope of the infiniteness of all this helps you…chill out.

Why are you so stressed all the time? You’re already dead in the eyes of the universe. Why care about the opinions of others? They’re dead too. Why not shoot for the stars? There are trillions times trillions times trillions in the sky.

Do you realize how insanely crazy and cool is it to be alive? To be a part of all this?

Remember that and do what you will with that information.

Grab your free checklist here The Ultimate Guide to Discovering Your Natural Talents and Strengths. Wanna keep in touch online? Follow me on Instagram here.

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