There is no path: lessons from a monk and a billionaire

April, 2014 at a small conference in Toronto: I know that I’m on the wrong path in life, but I don’t know how I’m supposed to find the right one.

One of the speakers at this conference is a Hindu monk who dedicated years of his life to meditation. He seems to have deep insight into the human condition. You can almost feel his presence in the room.

Another speaker is a billionaire. He knows more about the world of business and commerce than anyone I’ve met.

It’s a very intimate conference and I have the opportunity to chat with them one-on-one.1

Separately, I told the monk and the billionaire, “I’m lost right now. I’m modestly successful, but it feels wrong. How do I find my path?”

I assumed that both men would offer very different answers. To my shock, they gave nearly identical suggestions. It felt like I discovered the secret to success. I was giddy.

Here’s the path they laid out:

1)   Spend time getting to know yourself and your authentic desires. Use open-ended questions to search deep within yourself. For example:

  • How would your life change if you suddenly inherited $100,000,000 dollars?
  • What would you do if you only had six months left to live?
  • What do you want your life to be like when you’re 90?

They both advocated taking this process slowly. They promised that with reflection comes clarity.

For several months, I spent Sunday mornings in a café with just a pen and paper to learn more about myself.

2) As you start to connect your vision, describe it in lucid detail. This can be done with words, magazine clippings (think vision boards), clays, paints, or whatever medium resonates with you.

Personally, I like writing, so I described the life I wanted in words. It involved growing my speaking business, vacationing in Costa Rica, giving back to the homeless, and building a thriving social circle.

3) Once you have a clear vision, reverse engineer it. In other words, figure out how to get from point A to point B.

If you want to become a rock star, perhaps you begin by researching different instruments. Then, you buy a guitar. Next, you learn how to play it. After that, you make a few musician friends….

The important part is to have each step lead to the next.

With time I figured out how to increase my stature as a speaker, book a trip to Costa Rica, work with the homeless, and host weekly dinners at my apartment.

4) Finally, take action. If you fail at any point, return to your vision for yourself. Let your vision flood you with energy, inspiring you to overcome your setbacks. Continue taking action.

Both the monk and the billionaire found success following this path.

The monk claimed (and seemed) to be content. He felt he was on the path to enlightenment. The billionaire claimed (and seemed) to be happy and felt like the world was his oyster.

So what happened when I tried this?

I followed this path for two years. In that time, I achieved almost everything I set out to.

But through the entire process, I felt weirdly hollow. More than that, I still felt lost.

It’s not that the path the monk and billionaire laid out didn’t work.

Though it made me successful, it wasn’t my path. The moment I tried to follow their paths, I unintentionally departed from my own. If your goal is to fully engage with life, you can’t follow someone else’s path; you have to blaze your own.

Think about it for a moment. Truly successful people tend to have two things in common:

  • They are passionate about their pursuits (which boils down to self-awareness and self-confidence)
  • They blaze their own trails, allowing their lives and their work to be expressions of their truth.

Barack Obama, Mother Teresa, and Steve Jobs all changed the world, but they did it in dramatically different ways. They did it their way.

When I realized that the monk’s and billionaire’s paths wouldn’t work for me, I tried something else. I paused and asked myself, “Do I know what the first step on my path is?”

I did.

In fact, I knew the first few steps. They were: end a relationship, leave a city, and quit a job.

If you look deep within yourself, you’re likely to find the first step on your path. If you can’t see the second step (and often, you can’t) trust that it will appear after you’ve taken the first. And if you can’t find the first step, take a step – any step. Sometimes you have to walk down the wrong path to recognize the right one when it appears.

Your job is to stumble around until you can tell which way is forward. From there, trust yourself…



  1. You may be asking, “How the heck did Jason manage to get invited to a conference like that?” I was asking the same thing. Honestly, I am the exact opposite of a self-made man. Yes, I work hard. Yes, I try to care about my clients more than most consultants. But still, virtually everything I’ve done that succeeded was a result of the people who invested in me. In this case, one of my friends worked hard to get me an invitation to this life-changing conference. I remain extremely grateful.

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17 thoughts on “There is no path: lessons from a monk and a billionaire

  1. Hey, Jason! Great read, and mostly I align with the “blaze your own trail” ideology. There is something I’d like to add, or at least ask if you’ve considered: You point to Mother Theresa, a woman from a faith tradition/lineage of which I am intimately familiar, and from your writing you point out that set out to blaze a path by following a passion **her way**. If you’ve read her words and studied her path, she states that her life was a calling, a task she didn’t think she could do without some grace to assist her. And, what’s more important is she dedicated her efforts to the the “Big G” (or, God). She never took credit. I feel in these chaotic times that when we set out to do something, if we put energy behind our passions and actions to be of service to Something Bigger than ourselves, then that Something Bigger fills in the details and helps direct our sails. And I call that the “flow state”. Some, like Mother Theresa, may call that the Grace of God. I just thought I’d throw that out for ya 🙂 Some hold the belief life is 100% on their terms, but I sense we can *live into* a calling. Seems to soften the egoic “My way!” mentality that, when I’ve applied this philosophy, ultimately leaves me empty at the end of achieving goals. ~ “At the end of my life I hope to stand before God and say, “I have nothing left; I used everything you gave me” ~ Erma Bombeck.

    1. Thanks, Christine, I appreciate the note. I think you’re right: a lot of people find contentment and happiness when they focus chunks of their life on external motivators – giving back, serving God/the Universe, working to improve the quality of life on earth, etc. Strangely, and I think this is what you’re suggesting, is that it also seems to enhance people’s success. Pretty beautiful, when you think about it.

  2. Hi Jason,

    Great read. I’m currently stumbling around a bit, but starting to take some steps. Sometimes even small steps seem large when you need to take them! Anyway, thanks for writing. Catch up soon!

    1. William! Hey man! Stumbling around is good. Lean into that. It took me a long time to realize this, but a few steps on the wrong path can be pretty valuable too…

  3. I love this Jason! I think it’s so easy to get sucked into advice or someone else’s path because if it worked for them, surly it would work for me! Even if it’s simple stuff, but it starts with, “you should travel more/date more/move to a new city/quit your job, etc.” That should word means it’s their agenda, and it’s important to look out for that. Not only should from other people, but from yourself. I’ve often tried to talk myself into something based on “shoulds.” It’s hard to go against the grain, but that is what makes us all unique.

    1. Tonya- BINGO! So many budding, “High performers” (a nauseating phrase in and of itself) waste their time reverse engineering other peoples success. Habits, morning routines, etc. It’s not that there’s no value there – there is – it’s just that your path is yours, not theirs. No other path will work. When you find the courage to leap, thats when you start to become the people we all admire. I look forward to seeing what you create. And you’re totally right about the “shoulds”….

  4. This is really good. I have spent a lot of time waiting for the right thing to push me into action. I like and want so many things that I have a hard time choosing what is right for me. I like what you said, sometimes you have to walk down the wrong path to recognize the right one when it appears. This is SO good. I just simply need to try. I need to spend time figuring out what it is that I want, act on it, and if it is the wrong path, turn around and try again. Thank you for sharing.

    1. Amanda – EXACTLY! A lot of us are so overwhelmed by desire and excitement and possibility that we never even take the first step. In truth, we always need action. Maybe pause for a moment or two to figure out which action will be the highest leverage, and then do it! If it works, terrific! If not, no sweat, you can always tweak a variable and begin again.

  5. Very thought-provoking, Jason! I’m a big believer in each person having their own unique path, and I surely don’t give a lot of thought to what monks profess since I don’t have the luxury to meditate all day and not deal with real world issues.
    Oddly enough I’ve been asking myself similar questions within the scope of my Buddhist practice, and I’m trying to live honestly in a way that I won’t have regrets when I’m old, nor feel the need to drastically change if I stumble upon a sum of money.

    1. That’s cool. You know, the monk thing is funny. I’m really interested in monks and other contemplatives and the wisdom they can share. But a quiet part of me wonders, “Are they missing the point?” If we really are spiritual beings having a human experience (and I suspect we are…), then isn’t the point to have a HUMAN experience? To go out and drink to much, to be messy, to balance the kale smoothie with a big ass cupcake? I don’t know. Maybe the next time I meet a monk I’ll ask. 🙂

    1. Maike –

      I’m so touched you’ve taken the time to translate my article into Portuguese. Thank you! If you don’t mind, would you be willing to link back to in addition to Rockstar Finance? Thank you!

      1. Absolutely Jason! I cited and linked since when I published the text. Thanks for allow it. I hope you keep doing a great job.

  6. Interesting… I left this browser tab open as I thought it might be useful but never read the last part, completely changed the article! In a good way!

    Just for clarity… are you saying that those four steps didn’t work for you as a system/process? Or that you choose the wrong things to put into it?

    I would see how kinda using both together could be helpful, although not being so uptight about the four steps and leaning more to just doing what feels right to do next.

    1. Hey Mark – great question. The four steps work remarkably well as a process, especially if you’re disciplined. The fact that they work though presents a new problem unto itself; if you use them to walk down someone elses path (like I did), then you’re likely to end up someplace you don’t want to be. Personally, these days, I tend to just wait until I can see the first step, and then take it, without the sort of intensive planning or discipline that used to define my life. Not sure if that answered your question, or only made things more confusing. 🙂

  7. You mentioned ‘end a relatkonship,leave a city and quit the job” ..does it have to be that way ?

    Would that not amount to ‘fleeing’ a situation and then work on yourself when actually all the experiences are a”Work in progress”.

    1. Hi Betty – I’m not 100% sure I understand your question. If I do understand you correctly, you’re asking: does one truly need to make such drastic changes? Doesn’t that just amount to running away instead of addressing the problem? If that’s the question, here’s my take: first, no. In most cases, I think people should make small, strategic changes. Those tend to be more sustainable and gentle. As far as whether or not making big dramatic changes amounts to fleeing instead of fixing a problem, I think it varies. In my case, I was living in the wrong city, dating the wrong person, working in the wrong industry. I could work to make myself accept those things I suppose, but I think the stronger move – for me – was to foster deeper alignment.

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