4 bold questions to live a more purposeful life.

In life, it is not the answers you get that matter, it’s the questions you ask. Questions like What is the meaning of life, and ones that people seemed to have been asking for centuries have only led us to, well basically nothing, besides an ambiguous search into nothingness. Maybe the answer “Forty Two” from Hitchhiker’s Guide to the Galaxy is the only “real” answer we’ll get. If you remember the scene, it was a giant super-computer type modern marvel built way in the future (whenever the time period it took place in escapes me) that was built to answer the age old question. And in front of a crowd of hundreds of thousands the computer said “Forty Two. The Meaning of Life is Forty Two.”  It had 7 Million years to figure it out, and that’s what it concluded. But it’s about as true as any answer, because if you watch the video, the computer complains that the questions is incomplete and cannot be answered but that there is someone who does know the answer.

“What is the meaning of life?” is a bullshit question…

This is a basic layout of an exercise you can practice with yourself routinely to keep the things that you value and are important in sync throughout your life.

Separating yourself from the crowd has shown to be dangerous back before modern day civilizations were as advanced as they are today. But in today’s world, you want to be different, innovative, against the grain; everyone wants to stand out, and most of them do it wrong, by just fitting in, almost unknowingly. And the reason the idea behind ‘dare to be different’ makes a lot of sense is because of the endlessly disruptive environment we are currently living in. New technologies are popping up every day, the internet has changed the way the world communicates, and for the better I hope. But at the time of their inception all these things seemed so… different. With constant change, adaptation is key, without it, you will become the result of modern day “natural selection.”

I recently took a trip to a city not to far from me for some inspiration, amazing food, and fun. I couldn’t help but notice a vast majority of the people (especially between the ages of 18-28) all seemed to dress the same. It’s like they were all trying to one up each other on how much they could look like one another. I felt surrounded by people who were to scared to really be themselves, or just felt they weren’t supposed to be. And authenticity is a rare commodity these days, which is why I cherish it highly. Don’t get me wrong, I met plenty of very interesting people, I have a talent for finding them at times.

In this post, you are going to find out what you want your life to look like. If you recall from a recent post I wrote, I stress people to ask themselves, not what they want TO DO with their life, but instead, what they want their LIFE to look like. Not to other people necessarily, but to themselves, as if visualizing the moments of enlightenment, happiness, and peace within ourselves far into the future to create a vivid image. This helps put your mind in a place where the direction becomes more clear. You can then begin to create the lifestyle you want, but let’s take a deeper dive with 4 more important questions.

Before we start, define what your ideal lifestyle would look like; what is it you picture during your truly high moments of fulfillment and peace.  For some it could be living on a beach going wake boarding 5 days a week and dancing around beach bonfires at night, for others it could be raising a beautiful family of 6 kids in a suburban neighborhood where you grew up, with a loving spouse, and for others, maybe it’s living in the mountains in a small house surrounded by the solitude of the thick piney wilderness, reading books by firelight and living off the land, off the grid. For me, it’s being able to be mobile, to read when I want to, write when I feel ready, and being able to travel and live around the world in, possibly, some very remote areas like an Indochina fishing village, learning about other people’s cultures, but also being able to bring value to many people’s lives, by teaching, and giving back what the many people before me have taught. Also, learning the endless teachings of the culinary arts will always be an important and truly passionate part of my life.

For each person it will be different, and remember, your definition will change as time goes on, and that’s perfectly okay, because the overall is designed to be flexible and interchangeable.

1) If you had to pick one uncomfortable thing, and one pleasurable thing to do every day for the next week, month, year, decade, and the rest of your life, what would they be?

As the stoics would say, life isn’t all about pleasure, and not also all about pain either. But in life, pleasure and pain are merely the nature of all things. Life can die peacefully, but creation is almost always a violent act. Picture birth, blood, screaming… or even a small plant bursting out of the shell of it’s seed, up through the dirt and even the pavement. The universe was created with a massive explosion. This question is designed in part to see what it is you do every day that you enjoy, even if very subtle. Please do not pick something like drinking alcohol, or even smoking weed for that matter, although I’m okay with the latter, and do far more of the former. I enjoy reading for example, but many find it uncomfortable, like a chore.

The uncomfortable part is designed to bring to the surface something you might fear. For me, it’s usually making phone calls to people for whatever reason, or asking questions that I know need to be asked. For you, it can be anything, like leaving your house without your cell phone, or deleting your Instagram (I dare you) or possibly even just starting a bumble account and messaging someone you might think you have a connection with.

2) If at the age of 50, you had to teach something to the people and spend a vast majority of your time on doing so, what would you teach?

This brings to the surface something you truly value. Maybe a truth about life, or a philosophy. Maybe a passion like music or cooking (I love both) or painting or dancing. Maybe you want to teach others how to be a good investor or entrepreneur. Keep in mind, this isn’t about getting paid, or even become a renowned whatever. Just something that deep inside you that you feel is so important about life that want to get it out, and now’s your chance to preach to the people who are ready to listen. It could even just be something that you understand on a truly deep level, like the wonders of scuba diving.

3) Picture yourself at your funeral. What do you want the people there to remember you for?

Picture the type of people who you would want to be at your funeral. It can be anybody, from your dearest childhood friends and family members to your most passionate cult zealots and acolytes (kind of a joke.)

During the funeral, what are things you want people, even if not discussed in it’s entirety, to remember you for. It’s one thing to have a good speech made about you, especially by someone who knew you better than anyone, but most speeches at funerals don’t truly speak to the overall memories of the people who you’ve met in your travels. Your secretary, let’s say, will have a much different opinion about you than your Sensei or Mentor, or your college buddy Joe.

Imagine what the people there would be thinking of you, what you did in your life, what type of person you were, how you influenced them, and how you helped others. I also want you to think about the people who are almost happy to see you go. I know this sounds a bit odd, but you can tell a lot about somebody by the people who despise them. The haters as they say. What made them hate you? Was it petty? Did you hurt them? These questions don’t need to be specific, but at this current moment, sometimes thinking about those who would rather see you fail can ignite the flame in your heart much bigger than those who you influenced. This question is important because it forces you to stay true to what you value, and it will hopefully make you remember that in life, it really isn’t the opinions as it is the actions and examples that truly influence the world.

Think deep. Another way to put this in a more mindful scenario would be to imagine a video made of your life, where a camera and crew followed you around almost endlessly in your day to day life documenting it, in the most non-narcissistic way possible. Then this video is shown to your grandchildren, or great grandchildren. I know we all have our ups and downs. No one is perfect and that’s what makes it perfect every time.

4)Fast forward to a hopeful reality of laying on your death bed, and think now of something, if you never do it or fulfill it, you will strongly regret. What is it?

There you are. Sitting in your hospital bed. The heart rate monitor slowly beeping away. The medicine keeping you alive by keeping you numb courses through your veins. But you know it’s the end…

Many great people throughout history had their great “last words” whether they were meaningful or not, it was still like the ending of a movie. The final scene fades out, and your conclusive emotions and wonders start to set in. How could it end that way!? I wish they told us more! But maybe these are the thoughts that play in your own head at the same time. Or maybe they won’t. Maybe, just maybe, you’ll be sitting there as the light shines through knowing you did your part on this earth. You put your best foot forward as nature intended.

As Seneca once said, “Life’s like a play; it’s not the length, but the excellence of the acting that matters.” As is it with movies and songs, and any form of art for that matter.

It’s also realizing that your time on this earth is limited, and in the grand scheme of things, we exist for very short period of time, yet we all have the power to make an impact. I was once struggling in my financial practice, I sat down with one of the highest level executives in our company to discuss how I was doing after roughly 8 months. Emphasis on the roughly part. Instead of him laying into me and making me feel like crap for not trying hard enough, he gave me a few good tips, told me about when he was my age, and then told me something that stuck with me forever. He said “You got one chance on the rock, you better make it count.” At first, the words echoed in my head painfully, but after a while I realized how true this is. I did end up leaving the company about 10 months later, the whole industry in fact. But that was for several, mostly personal, reasons.

It’s hard to think about what you might regret laying on your death bed. I can tell you right now there is the short and the long of it. Short would be something you might regret if you don’t do it very very soon. But the long is the important part. The long is also the harder question to ask because it can be such a vague regret. Like ‘oh man I wish I just invested in stocks more’ or ‘I wish I just went out to the bar less with my high school buddies’ or even ‘man I wish I would have done what I really wanted to do instead of being complacent in my decently paid corporate job for 45 years’… I think you get the point. It’s not just about money or societal success (like houses, cars, status) but also, more importantly, about personal fulfillment. Maybe you were the best damn engineer at NASA but all you ever wanted to do was write a series of fucking fantasy novels… but you never did. Meanwhile you’ve surrounded yourself with people who would look at you like you were crazy if you even said something along those lines, and your final words before the light took you simply fell on deaf ears. The travesty. A disservice to your true nature.

But we can only blame ourselves for the things we didn’t do. And no matter what you tell yourself at this very moment, the excuses you make, the fears you succumb to, the lies you tell yourself, the bullshit jingle you play on repeat in your mind; when you’re sitting there on your last few breathes of air, the truths will surface, and you will be faced with your final ending. And as the credits roll, for a moment, you will either ponder on what could have been, or you will await death with utter curiosity as you drift into the void. I hope you choose wisely.

forever a student.



  1. I love this article Kyle! Really makes you wonder about life and what is important, and I know we are all here to share and grow and learn from each other and I’m so thankful that I ran into you again and we actually had a conversation about the important things in life and this article gives perspective in a way that really influences emotions.

    Liked by 1 person

  2. […] I hope you enjoyed this article and I hope it has taught you a thing or two that you can apply in your daily rituals and your journey for living a better and more fulfilling life. […]


  3. […] When it comes to wealth in life, the determining factor is the metric by which you measure yourself. I don’t need to get very specific, but we all know someone who has a bunch of money and is still sad, or clearly broken, and we all know someone who is fairly impoverished financially, or maybe comfortable at best, but finds the simplest things in life joyful and is always kind to others. Which is something I always saw in my Grandmother. I’m not saying that one is better than the other, the point is to look at your life and determine what it is that truly matters to you while also making sure you aren’t setting yourself up for failure and misery. And in time, your values will change, so it’s always good to routinely ask yourself. […]


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