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20 Questions You Should Ask Yourself BEFORE 2023

20 Questions You Should Ask Yourself BEFORE 2023

We can’t get good answers without asking good questions. 

It’s the questions that elude us because we don’t think in terms of which questions ought to be asked. We go on living, answering the same daily questions. Ninety percent of our thoughts - or more - are the same thoughts we had yesterday. So we never break out of our current trajectory.

We simply float along in life as the people we think we are without ever realizing we could have been more, we could have loved more, achieved more, become more. This ‘breaking free’ starts with asking questions.

Before you set your annual goals, and it’s a great exercise to set annual goals and put them on paper, answer the following questions. 

Figure what you really want, and what you’re willing to do to get it. Figure out what you want to remove from your life, and commit to getting rid of it. Figure out who you have to be, today, to become who you can become tomorrow. 

We can all be someone better. We’re all heading on a path that’s at least a bit of a degradation from the path we could be headed on. Stop that path today, start a new one in 2023.

The Questions


If you continue living exactly as you are will you end life proud of how you’ve lived or filled with shame and regret?

  • What in your life right now brings shame?
    • Write it down, commit to getting rid of them. Just don’t do these things. They’re a weight on your soul, but also your future. They drag you down and minimize who you will be 10 years from now. Free yourself from shame, from doing things that make you hate yourself.
  • What makes you proud of how you’re living?
    • If it’s not yet a habit, make it one. Commit 18 months to doing these things (lifting, running, eating right). Forget about ‘how tough it is’. If you want to improve, win, evolve, just fucking do it.
  • What are you doing that you hate that you’re doing it?
    • This is in line with the first thing, but think deeply on this. Chasing loose women? Do you lack honor? Watch porn? Are you lazy, do you put things off, do you spend money on stupid shit? Write your list. Keep it private. Commit to not doing these things.

What are you doing right now that you want to stop doing? Something that doesn’t get you closer to your goals, but may push you back?

  • This doesn’t have to be something you hate that you do or even something that brings you shame, but something that simply doesn’t improve your life or who you are. It can seem insignificant to others, but you can feel it’s weight, even if it’s slight, it slows your progress.
    • This could be how you train, it could be the limiting thoughts you have (this is the one for me), it could be gossipping, it could be envy, it could be a worldview you hold that doesn’t help you.

What beliefs do you currently hold that hurt you?

  • Do you see yourself as a victim? Do you think the rich (outside of politicians) cheated their way to wealth, and that wealth isn’t accumulated on merit but on being evil and birthright? Do you think anyone who’s lean and jacked simply has better genetics?
    • I’ll answer this for the both of us, any belief that places the responsibility for your achievement on someone or something else, hurts you. Any belief that puts the responsibility for your success in life on your shoulders, helps you.
    • Commit to seeing the opposite of these beliefs. Remove any belief that hurts you, that holds you back, that makes you envious or lazy or justified in your lack of success.

What beliefs do you currently hold that help you?

  • Double down on these beliefs. They’re the opposite of the above. They understand the reality of the world, that you can build the life that you want if you have discipline and good decision-making over a long period. Man up. Take responsibility for your life.

What habits can you put in place that will improve your life?

  • Physical - training, when’s the best time to do it to ensure it’ll get done?
  • work/focus - how do you structure your work time to get the most done in less time?
  • Be specific. Write them down and write down when in the week or day you’ll do them.

What is it in your life that you want to do or become that you don’t fully believe you can do or become?

From what I’ve seen in talking to the super successful is that the primary difference between them and those who simply try, is belief. They understand that if they make the right decisions and do the work, they’ll achieve some great things. The rest of us hold onto a belief that we’re not quite good enough to become who we dream of becoming. It’s a belief we have to destroy. It doesn’t make sense. If we do the work and make the right decisions, we’ll achieve great things, it’s just math. Decision + work = result. Good decisions + work over time = great results.

One way to get rid of the negative belief is to alter the desire. To be honest, I want to be wildly successful. I want fuck you money and the freedom that comes with it. That desire, however, pulls me out of the present, it casts a shadow over my current life, leads to daydreaming, and doesn’t really increase the quality of my work or my decisions. Getting rid of that desire and replacing it with a grand goal for the company, a true vision for my life, allows me to be free to make the right decisions, it adds a ‘lightness’ to be able to focus on the moment and do the work.

You free yourself from desires like this simply by being aware of them. See their flaws, the negative impacts they have. When your focus turns to building and creating, you end up making better decisions and doing better work, which will end up leading to better outcomes. 

What desire in life do you have that ends up repelling the outcome you want?

  • Sometimes a desire can be too strong. We’re blinded. We want success so bad that it hurts our decision-making, it crushes our energy, our joy for our life as it is. We want a wife so bad that we’re desperate, and women can smell desperation from a mile away, it’s a more effective repellent than bad hygiene.
    • Be very careful about the things you desire. First, they ought not to be things. They should be process-focused. They shouldn’t add weight to your shoulders. They shouldn’t make you make bad decisions. They shouldn’t degrade your life as it is right now. They should bring you into the moment, rather than making you regret things you’ve done in the past or spend time wishing for things you want in the future.
    • Get rid of these desires through awareness. Be real with yourself and your desires. Are they helping or hurting you?

What things are you doing right now that are making you soft?

  • Men can’t be soft. If you teach your sons one thing, it ought to be to be tough. Toughness enables you to endure the shit storm that is life. It’s being both Stoic and antifragile, and just plain old tough. If you’re doing things that make you too comfortable, be weary of them. Think about removing them or at least using them as a reward only.

What can you add to your daily life to make you tougher?

  • There are things a man ought to be doing daily, namely actively experiencing pain. The pain of training, the pain of running, the pain of extreme temperatures. Our modern life can be devoid of physical pain. Humans need it. A soft man is a useless man, a man who’s fated to fail.

What about your life as it is right now do you love most?

  • Guard it. Guard them. Appreciate it or them. The reality is we need nothing. We pursue things because humans need forward motion, but if we have a good relationship or two, good people in our lives, food, and a roof over our head, there’s little else we need.

What would the perfect day look like with what you have in your life right now?

  • That is, the perfect work day, maybe with some training, some time with the Mrs., some laughter. Think about this. It’s achievable. And you can technically have this day every day.

It’s time to leave normal behind. It’s time to leave who you’ve been behind. We’ve all been a shadow of who we can potentially be, myself included. I have habits and beliefs that hold me back, and I’m removing them and replacing them with better habits. Enough is enough, commit to this shit.


What do you want to achieve in 5 years? Think big, grand, ideal. And…

  • Place no limitations on this.

What’s the most important skills you can have (2-3) that will help you reach your goals?

What are the 5 best books you can read that will help you develop said skills?

If you have your own business, what is the biggest goal you can have? What’s the grandest vision you can create for the company?

  • Explore other verticals. This doesn’t mean lose focus of what you have to achieve first. Just think bigger, and sometimes bigger means broader.

Maybe the most important question, and this pertains to hiring: what do you suck at? 

  • Answer this, then find someone who’s good at it and hire them.

What can you change about your day to ensure that you operate optimally?

  • A few things for myself:
    • Set a timer when you’re working on a single task, get up and move, do push ups, when the timer goes off. When the timer’s running, focus on nothing but that task (I’m doing that right now).
    • Release your desires and focus on what has to be done. Desires, for me, add weight. They don’t necessarily pull me toward that thing. You have to want to achieve something, but then you have to release it completely and just play.
    • Have a firm end to the work day. A work day that never ends leads you to push things back to the end of the day, and then they never get done.
    • Workout at 5am. Wake up at 4am. Get that shit over with so you have the rest of the day to get shit done. Don’t have the workout hanging over your head when you should be focused on work.
    • Study the skills and mental models that will help you succeed.
    • Write 1-3 things you’re grateful for everyday. In the pursuit, you forget about what you have. Appreciating what you have makes you light, it gives you happiness and energy and we work better with both.
    • Kill doubt.

Find the Answers

We don’t ask these questions enough. If at all.

They’re important questions. Life is short. We have the answers to these questions, but because we fail to ask them and really think about the answers, we never get the focus, productivity, joy, and happiness that we should have.

Figure out exactly who you ought to be, what you will achieve, what’s important in life, what you have to remove from life, and be free to win.

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  • Good article helps to make alpha male

  • “Stoic and antifragile” – Best part of the post. I try to get this across to my son and the Boy Scouts I mentor all the time.


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