14 Questions. No Lying. Start With the One You Are Avoiding.
134: Questions that will change YOUR life.
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Every result in your life (good or bad) comes down to the questions you ask. The one you asked. The one you didn’t ask yourself. The one that made you think. The one that gave you a perspective you had not considered… What is this about? Questions. Once you start asking yourself the right questions, your life will begin to change.
Questions You Should Ask Yourself
1. Will I be glad I did this looking back?
Watch the video before you go any further. It is a good one, and the framework itself is powerful. The full interview is available by clicking here. Back to our question. When was the last time you asked yourself this question? Reflecting on our past decade, we made some big decisions using this framework to simplify how we justified our choices. Especially the high-stakes decisions. Ones where failure meant real pain.
To get the most out of this. Make sure to use this question in the right context. Such as when it comes to life-changing stuff, getting rid of bad habits, or doing something you were afraid to do. Running through different variations based on what matters most to you. If we had to pick the three most effective questions from this post. This would be one of them.
Why do you want to ask yourself this question: Because regret is the most avoidable pain there is. It is also one of the hardest to get rid of once it takes hold.
2. What would I do if money were not a problem?
Since we have not been dealing with money problems for some time. We can reflect back and say that the period after that initial realization can be tricky. It is similar to setting your goals poorly and overachieving every single one. Zero satisfaction mixed with the confusion. Sort of a strange emptiness where you don't know whether to celebrate or worry.
The answer you want to find with this question is the one that aligns with your current lifestyle. The bigger the gap between where you are now and where you want to be. Means you will have to work harder to get there. Not rocket science when you think about it. Those who are already living the way they would with a few more zeros in the bank account? They are the ones winning. Because it means their current lifestyle choices are not selling them short or forcing them to cope with a life that doesn’t match what they want.
Why do you want to ask yourself this question: This question kills the belief that you need more to start living the life you actually want. Most overestimate what they need. Then they use that big vision as a coping mechanism. One that will stop them from ever starting.
3. What brings me an enormous amount of joy and happiness?
Less is more. For us? Happiness comes down to few things. Once you dig into them, all of them are based on freedom. It took us years to process this and internalize. Because the answer is rarely on the surface. Meaning you have to know yourself well enough to get there.
How do you use this question? Take a laptop (or replace it with any other materialistic item). That laptop you want. The one that feels like it would make everything better and make your work easier. Now ask yourself why you need it. Because you give yourself a simple reason, such as that it is the best or it has a great screen you "REALLY" need. Dig deeper. Ask yourself is that a real reason? Or is it because you know you can carry it anywhere and use it however you want.
This is not easy to pick up. But after some reflection, you will realize it was never about the laptop. It is what a laptop means to you. The deeper meaning behind it. It might mean that you can take it and work from anywhere you want… Or the complete opposite. It is subjective and all of us are different. When you dig past the surface-level thinking. It is all about the freedom that a laptop provides. The same approach works for every other item or the thing you want. Dig deeper.
How to get the most out of this:
Pick 3 - 4 things that bring you 80% of the happiness.
Find the pattern. What do they share?
Keep asking yourself why they bring you happiness. What is the meaning behind them? What you think you value and what you actually value are rarely the same thing.
Why do you want to ask yourself this question: The deeper you go into your work and daily life. The more pressure and confusion there will be around the things that matter to you. We all know that it has never been easier to lose this sense of what brings you joy. The purpose of this question is to find deeper meaning and figure out what actually carries weight for you.
4. Who inspires me?
It took us years to process. Years before we managed to shape it into something that actually made sense. Before you ask yourself… What does this have to do with improving my life? The answer is everything. To give you more context, ask yourself why you spend time with the people you do.
The answers will come down to:
They make you feel good.
You trust them, and they have your back.
They share similar ideas to the way you think.
Let's say you are one of those who follow our principles for being more social. There is a good chances you have multiple groups of friends. Look across all those different groups. What you will notice is that they all share similar patterns, with at least 2/3 of the answers from the list above. For those wondering what any of this has to do with inspiration. It is the same mechanism behind it. The people who inspire you and the ones who impress you. They all share these patterns…
The ones you WANT to know more about.
Write down a few people you find inspiring. Cross-reference them. What do they all have in common? Chances are, they share at least 60-70% of traits. The patterns you keep noticing across all of them? That is your answer. Pay attention to it.
Why do you want to ask yourself this question: On the surface, it looks like you are searching for a role model. But that is wrong… You are not. This question helps you to look for characteristics and patterns that impress you. The ones you want to possess yourself.
5. How do you spend your weekends?
A question that might completely throw you off at first. Yet powerful because it shows you how you value your time. We always find it funny when people say their work drains all their energy. They spend five days waiting for the weekend just to do nothing. Thinking that something different will happen during those 48 hours. In the end? Netflix. Video games. Watching sports or wasting time any other way.
Now imagine waking up one day and the work you hate is gone. No emails. No meetings. No colleagues talking about their pets. Just you and your time. Basically, your weekend… But permanent. Are you still doing everything the same? Or are you finally giving yourself permission to do something that actually matters and will move you forward?
Weekends are there to build your future life. 48 hours that show you what your life could actually be if you put your foot down and get serious enough. Something you want to think about... Often.
Why do you want to ask yourself this question: For those who are still locked into a strict Monday - Friday schedule and looking for an escape on the weekends. This one is for you. How you spend your weekends tells you everything about what you actually value and where you are headed. This question might be the wake up call you didn’t know you needed.
6. Where do you see yourself in the next 5 years?
No one teaches you to ask yourself this question. It is something you need to revisit every year, especially now that we live in a time of rapid change where nothing stays certain for long.
What makes this question powerful is that it forces you to actually stop and think. It helps you reverse-engineer what you are doing right now. If you know where you want to be in five years. It means you have to determine what you should be doing now to reach that goal. Why only 5 years? Because a 5 year plan is close enough to feel real. At the same time, it is far enough to require effort and real change. Plans for 10 or 20 years are unrealistic because too many variables are at play.
Why do you want to ask yourself this question: There is no fancy answer here. This question works because it makes you think in layers.
The answers will come down to:
Where are you now?
Where do you want to be?
What has to happen to close that gap?
7. What would I do if I knew I could not lose and everything worked out in my favor?
It took us 30 years to realize that it is impossible to lose. It really is. That comes with a big "IF" and there is no denying it... But if you follow the rules of the game. It is hard to deny that you will make it. The hard pill to swallow is that the world is full of mediocre performers living lives you dream about.
This question? All about alignment. Lost on how to answer this? Start with the one thing in your life you would change first. Look for the things that you would do differently. If your answer is work you are already doing, the things you are building, and the life you are living. You might be one of the lucky aligned ones. Which is a massive positive. If the answer is something completely different. Then you need to look for the reasons that are stopping you right now.
Why do you want to ask yourself this question: It exposes what you actually want in a scenario where nothing is working against you and there are no limitations.
8. One thing in my day to day that could be simplified?
It doesn’t matter what it is. Your diet. Your job. A routine you repeat without thinking. Always ask yourself: how do I get the same results or better… By doing less? The whole concept of simplification should be based on this. Or finding a way to spend less energy, less time, and less money getting there
Why do you want to ask yourself this question: Out of every question here? This is the one that anyone can act on immediately. Low effort - high ROI.
It’s easy to say ‘simplify.’ But it’s very difficult to do it. - Elon Musk
9. If I continue to live the same life I am living right now until the end of time. Would I enjoy it?
Everyone falls for the illusion that success by other people's standards means you are doing things right. It is a massive lifestyle trap. Especially when you consider that the average person is out of shape, full of debt, living to impress other people, and has no idea what they actually like. The question is powerful because it forces you to ask whether you are actually doing what you should be doing. The only way you will ever feel like your life is truly yours is by doing the things you want to do. Not for the others. Not to fit the society norm. Not to be like everyone else around you. Once again. Only the things YOU want to do.
Why do you want to ask yourself this question: It connects all the dots. Most people live day to day in ways imposed by those around them. Thinking that something will eventually change. The power of this question is that it puts you in a position where something has to change. Not later, but now. At the same time, you have to be the one driving that change forward. Ask yourself are you really living the life you want to live, or are you living someone elses story?
10. If I wake up tomorrow with $0, would I do the same thing I am doing right now?
The older you get, the more you realize that there are multiple ways to reach your goals. You also realize that your way might not be the best way to achieve them. You might even realize that instead of taking 4 steps to achieve what you want, you could do it in 2 steps, but there is ____ (insert your own) reason you are not doing it. This is just a high-level overview of what this question is all about. The answer you get will tell you a lot. At the same time, it is one of those questions that can be either surface-level or go as deep as it gets. We are leaving this one open on purpose. The answer will tell you more than we can.
Why do you want to ask yourself this question: If you are someone living in a comfortable situation? Good job, steady income, things working out your way… It is easy to stop questioning things. Money has the power to make things feel right even when they are wrong. This should strip that away and give you a proper overview of where your time and energy are actually going.
11. What is the one thing I am spending A LOT of my money on?
There is nothing to hide here. Be honest with yourself. Pull up your card statement from the past few months and look at where the money actually went. It should be clear. For us? It connects directly to few things that make us happy. Which is a good sign. It means our spending is aligned with what actually matters to us. The alignment is all that matters.
This question is a quick reality check on whether you are buying things for yourself or to impress others. If most of your money is going towards your quality of life, you are doing the right thing. If it is not… You need to rethink your priorities or stop living someone else’s life.
Why do you want to ask yourself this question: Because most people have no idea where their money goes. This question gives you that overview. Revealing your real priorities and not the ones you are telling yourself you have. What you are looking for is simple. Does my spending pattern match my values? If they do… You are in control. If they don’t, you have just found the reason it never feels like you have enough.
12. What is one thing I can't stand and want to avoid at all costs?
For us this comes down to masses, noises, and people we have no interest in being around. Positive? It is easy to avoid them. Negative? It is impossible to cut yourself off from society. To the point that there is no good reason to do so. Cutting yourself off from everything will only hurt you. But knowing what drains you gives you clarity.
Everyones answer to this question will be different. The power of this question is in realizing how little you actually need to feel fulfilled. At the same time, how much of what you hate and want to avoid have you been exposing yourself to? Your answer should not be based on defense mechanisms. Purposely avoiding something because you find it hard or don’t want to expose yourself to uncomfortable situation. It should be based on something you have complete control over and refuse to waste your energy on.
Why do you want to ask yourself this question: Everyone tells you what you should add to your life to make it better. No one tells you what you should remove to make it better. Funny enough - removing things is often the easier and more efficient path.
Someone is sitting in the shade today because someone planted a tree a long time ago. - Warren Buffett
13. What is the one thing you are avoiding but know should be done?
Around 2010 for us it was affiliate marketing. We knew the opportunity was there. It was easy, and you didn't have to be a rocket scientist to make the money. Much more so if you were in the right circles. Instead of going all in… We split our attention between 2 - 3 things at once. The results? We ended up in the same place we would have reached with affiliate marketing. Except it took 5 - 7 extra years. Think about what else we could have done with that time. Massive opportunity cost. There is also a good chance you know at least ONE thing you should be doing right now. But you are not doing it. The question is why and what is stopping you? Those quantum leaps everyone talks about? They are usually built by using this question and challenging yourself.
Why do you want to ask yourself this question: The biggest leaps in your progress come down to 1 - 2 things that you know you should be doing. But you are not. The funniest (or saddest) part is once you start answering this question. You know exactly what you should do. Everyone does if they can look deep down. Answering this question and admitting that you are avoiding something (becoming aware) + putting it out to self-accept it and embrace it will provide you with clarity and sharpness.
14. Who are you?
Last question on the list. On purpose. On the surface, it is the easiest one here. But once you start going deeper and looking for the answer… It becomes the hardest. Be honest with yourself. How many times have you asked yourself?
Who am I?
Not what you do for a living. Not what others think of you. Who are you? Do you know what you like? Do you know what pulls you out of bed each morning? Or do you think you know? All the previous questions could fall under this one…
Do you know who you are when no one is looking?
Why do you want to ask yourself this question: Because your answer will tell you everything you need to know about yourself. If done right this will change your life. Good luck.
Disclaimer: None of this is to be legal or financial advice of any kind.
These questions are SO GOOD. Especially the "Pick 3 - 4 things that bring you 80% of the happiness." triggered something for me. In this phase in my life, I'm having a stronger sense of who I am and what is important to me (and indeed, it is less rather than more!), but I still struggle with staying true to that at times, because it is quite different from how other people close to me live their lives! These questions are a great reminder to stay authentic. Am saving them to work them out properly later! Thanks for sharing.
Asking the difficult questions. Solid write up.