My Journey into the unknown

As a young child I believed in magic. I believed that one day my teacher would reveal himself to me and show me that I too, was a wizard. He would teach me to harness and hone my abilities, and to use my magical powers to change the world. I was 100% sure that this would happen because as I looked around at how the adults were living, I knew that there had to be more to life.

Years went by and my teacher still hadn’t revealed himself. Yet I couldn’t shake the feeling that there had to be more! As I looked at how most people were living their lives, I refused to accept that this is how life was supposed to be. I saw people selling their time and health in order to make money. They were wildly unhappy, and were choosing a lifestyle based solely on how much money it paid them. I saw empty human shells going through the motions, like automated robots, working jobs that they hated in order to buy expensive stuff. Stuff they didn’t even need, in an attempt to impress people that they didn’t even like.

I quickly realized that I was not the first person to think this way, and I stumbled across a quote that conveyed my observations beautifully:

“Man surprised me most about humanity. Because he sacrifices his health in order to make money. Then he sacrifices his money to recuperate health. And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die, and then dies having never really lived.” –James Lachard


After 25 years of waiting for my teacher, I decided he wasn’t coming. Instead, I realized that he had been here the whole time. Inside of me. He was the voice inside my head that had been whispering “it doesn’t have to be like this”. Year after year he had been gently encouraging me to follow my dreams, no matter what other people would think of me. He was the voice persuading me to reject normality in exchange for a life full of adventure, fulfillment, and magic.

So I have decided to heed his advice. And in the midst of a global pandemic and impending recession, I am quitting my job to embark on a personal odyssey. Why? Because I still believe in magic.

My goal is to prove that we are all capable of extraordinary achievement if we are willing to take the plunge and leap into the unknown. With passion, discipline, love, and kindness as my guides, I am setting sail towards my highest potential. And this page will be where I document my journey.

Step 1 - The Declaration

June 24, 2020

“The scariest moment is always just before you start. After that, things can only get better” – Stephen King

This is the beginning of a drastically different life. I guess it’s the beginning of my life, and an end to the other one. You know, the one I was told would bring me everything I ever wanted.  

In two days I will be walking away from my job at a Private Equity Real Estate Investment Firm. I’ve quit jobs before, but always with the intention that I would find another in the business/finance industry because working in Private Equity was my dream. I was once incredibly passionate about finance, but working in this field no longer excites me. Dreams can change. And when your dreams change, I believe it’s time to change your life. 

This decision has not been easy. It will involve dismantling the identity of the successful young man who works in finance that I have been building since freshman year of college. It means telling my parents, my friends, and my company, that I am walking away from a safe, secure, and well-paying job in the midst of an impending recession. This decision has an associated risk-level that would make my college finance professors scream, and to be honest, it scares me to death.

But it also does something else. Whenever I think about leaving the corporate world, and attempting to monetize my creative and productive capacities on my own, it sets my soul on fire.

I have recently been contemplating what my purpose in life is. And in doing so, I have begun to take a closer and more objective look at my current job. When looked at through a purely transactional lens, I am selling 9-11 hours of my time, ideas, talents, and daily productivity to my employer each day. And since I work 5 of the 7 days in a week, I am effectively selling 72% of my life in exchange for an annual salary.

The above view however, is a gross over-simplification that is negatively skewed. It does not account for the countless learning opportunities I have experienced throughout the past one and a half years, or the incredible mentors with whom I have built strong relationships. My overall experience was positive, but I know in my heart that it is time to make a change.

I know that I was not put on this earth to count money. Instead, I believe my mission is to be contagiously happy and to effect positive change in the lives of everyone I meet. It’s to relentlessly work on becoming the best version of myself, while simultaneously helping others achieve their highest potentials. It’s utilizing my obsession with learning and personal development to inspire, motivate, and teach. I am fully convinced that we are not meant to live lives that are mundane and repetitive, and I will stop at nothing to prove this.

I’ve tried living with one foot in the corporate world and the other in dreamland for the past two years. It’s exhausting and it’s not working. So now, in the face of an unprecedented global pandemic, I’ve decided that it’s time to hurl myself into the abyss. I will be jumping headfirst into the unknown so that I can start living a life I am absolutely thrilled about. I am doing this because I believe that life should be full of laughter, rich experiences, and deep fulfillment. And I am currently lacking in a few of those categories. I also want to prove that everything will work out in the best way imaginable if you simply trust in the universe, and live from a place of love, gratitude, and compassion.

Over the next few months, years, and hopefully decades, I will be documenting my experiences as I attempt to live the most irregular and unreasonable life imaginable. I will be sharing my journey through writing and other mediums. I’ll detail the days where I feel on top of the world, and dissect the inevitable days where I am overwhelmed with anxiety. Committing to openly sharing my experiences publicly both terrifies and excites me. But if my trials and tribulations can inspire at least one person to change their life for the better, it will have all been worth it.

I anticipate that many people will not understand my decision. Some will question me out of love, others out of fear, and countless will think I am acting like an entitled millennial. I will probably be labeled as naïve and unrealistic. I certainly hope so, because that means I will be doing something right.

Knowing that there will be many challenges and unavoidable headwinds, I take comfort in knowing that I will be exchanging monotony for constant excitement. I will be giving up security for spectacular adventure. And most of all, I will be replacing apathy with a sense of the pure exhilaration that one only feels when chasing their dreams.

As I sit here on the eve of quitting my job and announcing my quest, I find myself repeating one of my favorite quotes of all time. In the words of the legendary Theodore Roosevelt:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”


These words give me the strength to leave my old identity behind. This is my declaration, and it’s time to step into the arena.

Step 2 - Extreme Ownership

July 22, 2020

“Life shrinks or expands in proportion to one’s courage” – Anais Nin

I did it. I actually followed through and quit my job. Are we surprised? Honestly, a little bit.

Talking about my dream life was a lot of fun while I was gainfully employed and enjoying the benefits that came with a handsome salary. I’ve always considered myself to be somewhat frugal, but I’d be lying if I said I didn’t fall into the rhythm of nearly daily Amazon purchases justified by my relatively secure income stream. I felt like I deserved another health supplement or another fancy juice subscription because I was sacrificing so much of my overall wellness by sitting in a chair for 11 hours a day without much exposure to sunlight.

Side note: When did we collectively decide as a society that we would go to work just as the sun was rising and often work until the sun was down? Like excuse me but human beings were designed to have plenty of exposure to the sun. We need UV exposure and all the ancillary benefits that come with it to be happy and continue living. Hasn’t anyone read the research showing that people who live in rainy cities without much exposure to sunlight are more likely to become depressed? But I digress…

A good challenge or a wild adventure always sounded fun and exciting when I would daydream about it from the comfortable box I was living within. I filled my free time with books and movies on “The Hero’s Journey”, and I couldn’t wait to answer the call to adventure in my own life. Cheesy superhero movies have always been a guilty pleasure of mine and I think it was because they all are driven by the narrative of a normal person becoming extraordinary. What I wanted more than anything else was a life full of adventure. One with exciting challenges and obstacles that were going to reveal what I was truly made of. I wanted to prove to myself and others that I could do anything. And now that I have actually answered the call to adventure, quit my job, and thrust myself into the most uncertain time of my life, I have two main observations.

First, I am now radically responsible for my daily outcomes and personal progress. If I am having a bad day, that’s on me. I can no longer blame my frustration on the fact that I am doing work that doesn’t fulfill me. If I am feeling empty and unfulfilled, that means I haven’t found my purpose yet which probably means that I haven’t been spending enough thinking about how I want to contribute to the world. Choosing to spend an entire day watching Netflix doesn’t count by most metrics as “searching the world for my purpose”. And while there’s a time and a place for relaxing, I think I deserve to feel lazy if I am choosing to shirk my responsibility instead of figuring out what I want to do with my life. I am now fully in charge of my schedule, my life, and my happiness. I have extreme ownership of who I end up becoming, and I am finding this to be both incredibly inspiring and extremely terrifying at the same time.

Second, I am discovering how much self-worth I previously derived from my old identity. Being relatively successful in terms of traditionally accepted metrics such as salary and job status felt pretty good. But now that I have no job title, no salary, and no idea what the next few years of my life will look like, I am realizing that my self-worth needs to come from within. And so I am creating a value system for myself where I am assessed primarily on the quality of my character and on my willingness to be uncomfortable.

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”  -Tim Ferriss

Additionally, I am cultivating and honing aspects of myself that are inseparable from who I am as a person. I am realizing that traditional metrics of success can be taken away from me at any time. A house, a car, a job, even loving relationships with friends and family can vanish in an instant. But something that can never be taken away from me is my work ethic, my virtue, my tolerance for uncertainty, and the amount of self-love I posses. These are all aspects of myself that I will retain no matter what happens. Even if I somehow end up homeless and you get a call from me asking to sleep on your couch, I’ll still have all personal progress I worked hard to achieve. I will also have the contentment that comes with knowing that I am continuously learning and perpetually improving. And while this extreme ownership and desire to keep evolving is a lot less comfortable than playing it safe, it will be what brings tears of joy to my eyes as I lay on my deathbed and reflect on how my life turned out. No matter what happens, I take comfort in knowing that my life is going to be one hell of a ride. 

Step 3 - Fastening my Seatbelt

September 5, 2020

“Go ahead, light your candles, burn your incense, ring your bells, and call out to God. But watch out, because God will come. He will put you on his anvil, fire up his forge, and beat you and beat you until he turns brass into pure gold.” – Sadguru Sant Keshavdas

My new life feels like I am permanently riding a roller-coaster. I’m not talking about some weak little Disneyland type ride. I’m talking about X2 at Magic Mountain. Going over the edge of the drop section upside down and backward with fire shooting at me. Yeah – it’s like that but on steroids.

While this may sound exhilarating and fun (to be honest it usually is), it can be downright awful on occasion. Being completely in charge of my fate is the sharpest double-edged sword I have ever experienced. It is empowering beyond belief when I am feeling creative and inspired and it’s during these times when I feel unstoppable. Sometimes it even seems like the cliché phrase of “anything is possible” might actually hold some truth.

But unfortunately, those great days are frequently followed by some of my worst. I’m still trying to figure out how I can be feeling so spectacular one day and so terrible the next, but I have yet to find any answers.

As much as I hate to admit it, I have many days where I don’t want to get out of bed. Coming from a self-proclaimed morning person, this usually means something is seriously wrong. On these mornings I often feel overwhelmed and lost. These mornings are when the most insidious of questions slowly bubbles to the surface.

“Are you sure that quitting your job was a wise decision?”

This isn’t spoken like a good friend asking me an honest question. Instead, it cynically slithers out from the darkest part of my mind and is spoken with venom and mocking. Spoken with the same obnoxious tone as the quintessential “I told you so”, this question’s only intention is to break me.

And if I am being honest, it sometimes does.

I’ve cried more times in the two months since I quit my job than I have in the past five years.

Yes, that statement just came from a 25-year old man and yes that statement is hard to admit publicly. But the amazing part about what I just said is that 4 out of the 5 times my tears have been tears of joy and gratitude.

Every aspect of my life has been enhanced since I decided to follow my dreams. The highs have been higher and the lows have been lower. I think this is because I no longer have anything to latch onto in terms of external validation. I can no longer impress people by telling them where I work or how great my benefits are.

When I have bad days now, it’s just me, my negative thoughts, and the increased probability of becoming homeless. Ok – maybe I am being a bit dramatic here but the most realistic option of having to return to the corporate world scares me even more.

The most interesting realization I have stumbled upon since quitting my job is that I can now see that my past life was a game of “escape the room” that no one mentioned I was playing. I first heard this concept in an Aubrey Marcus podcast and below is something I wrote after listening to it:

“One day you wake up and see that you are in a standard room. It looks like every other room you have been in throughout your life, so you assume it is normal. Nobody tells you that the purpose is to escape from this room. Instead, they tell you that your entire existence should fit inside these four walls. All of your questions and protests are met with “that’s just the way it is.” But you know deep in your heart that this is not true. And as you begin to have a look around, you start to notice clues that support your intuition.

You begin to realize that there are actions you can take and items to uncover that reveal more and more about how to escape. You notice that the countdown clock on the wall has plenty of time left so you begin your search at a leisurely pace. You make some progress, but not as much as you know you could if you were trying your hardest. Why rush when you have so much time left?

Minute after minute goes by and what started as casual curiosity turns into apprehension as you start to wonder if you’ll be able to escape in time. You begin to search furiously for anything that will allow you to break free because you are so sick of living inside of this damned room. You start cursing yourself for not trying harder earlier to figure this out and you feel hopeless, dejected, and worn down. 

As you slump against the wall you accidentally knock a picture off the wall that has been right in front of you the whole time. As you reach down and pick up the broken frame you notice a key was hidden inside it. In utter disbelief, you insert the key into the door and your jaw drops as it gently swings outwards.

You have no idea what to do next, but you are finally free. You are relieved, terrified, ecstatic, and for the first time in a while, you feel truly alive. You don’t know what to expect, or what’s going to happen next. You don’t know anything about what awaits you in the outside world. The only thing you do know is that you weren’t meant to stay in that room. 

It is with this thought that you take your very first step outside the room. Despite being scared and alone, you feel a sense of purpose and direction as you enter the incredible unknown.”


I keep returning to this passage whenever I am having a bad day. It always makes me feel better when I realize that everything I am trying to accomplish is supposed to be challenging. I am facing life on the outside of the room and I am in completely unchartered territory. As sad as it is, I feel our society is designed to keep us lazily content inside the traditional four walls. We aren’t supposed to know the full extent of our capabilities and instead, we are supposed to settle for a comfortable but limited existence. If, however, we manage to find a way out, we will never be the same.

Steve Jobs, one of the most innovative and brilliant minds of the 21st century, explained the same concept beautifully in his Stanford commencement speech:

“When you grow up, you tend to get told that the world is the way it is and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family life, have fun, save money. That’s a very limited life. Life can be much broader once you discover one simple fact. That is – everything around you that you call life was made up by people no smarter than you. And you can change it. You can influence it…Once you learn that, you’ll never be the same again.”

I resonate with this quote so much because I know for sure that my life will never be the same. Now that I have escaped the standard room and seen how incredible life is on the outside, I will never go back to accepting things as “just the way they are.”

And despite my emotional state often bouncing between ecstatic/joyful and overwhelmed/anxious, I will continue to choose this life 100% of the time. I do this because I have found that the majority of life’s beauty is hidden in the tails of my emotional distribution.

Step 4 - stopping to smell the roses

October 20, 2020

Inhale through the nose for four seconds. Hold for four seconds. Breath out through the mouth for four seconds. Hold for four seconds. Repeat. 

These are the thoughts that are flowing through my mind during my morning breathwork routine. It’s a lovely Tuesday morning and this breathing technique, called box breathing, is part of my morning ritual.

As I sit outside and bask in the rays of the morning sun, I notice that something feels different today. My mind instantly begins investigating, searching for the root cause of this strange feeling that’s welling up inside of me.

Hmmm, we’ve felt this way before, but not for a long time. Mild euphoria, an acute awareness of how beautiful the sunrise is, lack of tension in muscles, overall sense of wellbeing….

Like a caged animal, my mind erratically begins to jump back and forth between searching for the answer and asking increasingly panicked questions.

 Why aren’t we rushing around? Don’t we have to get to work soon? Why aren’t we questioning everything? What the hell is going on? 

It’s precisely at this moment that it suddenly hits me – I am, for the first time in a long time, truly happy. 


For any reasonable person reading this, it may seem strange that my mind didn’t know how to handle being happy. But sadly, after living through 5 months of apocalyptic Corona Virus news paired with feeling like I was failing in the “life purpose” category, my mind had grown accustomed to being miserable.

And so, on that fateful Tuesday morning, it took me longer than I’d like to admit to realize that everything in my life had become fantastic.

Let’s do a quick recap for anyone who may be joining us for the first time:

Gregory’s Big Adventure into the Unknown

Step 1 – Walk from my job in Private Equity

Step 2 – Experience serious anxiety about the future

Step 3 – Document said anxiety in a podcast called The Dare to Dream Podcast

Step 4 – Experience pure terror related to not knowing what’s next

Step 5 – Consider what it would feel like to be homeless

Step 5 – Serendipitously team up with my business partner and co-found a nonprofit

Step 6 – Realize that we know nothing about starting a company

Step 7 – Panic. Repeatedly.

Step 8 – Consider joining a monastery

Step 9 – Begin to make legitimate progress with the nonprofit and start seeing it as a viable career path

Step 10 – Begin training as a neuro-transformational coach

Step 11 – Start enjoying every single day (including Monday’s!) and begin to feel fulfilled

Step 12 – Question everything and spend a whole day too stressed out to do anything besides clean the house and stress eat

Step 13 – Experience three consecutive weeks in which I feel like I am on the right path and that quitting my job was the best decision I have ever made

Step 14 – Write this article


In six days, it will have been four months since I quit my job. As I sit here and reflect on what has changed, I am chuckling to myself because the answer is everything. My job, my attitude, my belief in myself, my energy levels, my weekly routine.

In other words, my entire life has changed.

Sure, I still have challenging days, and yeah – there’s plenty of times where I doubt myself. But for the first time in my life, I feel like life is happening for me and not to me. It’s this beautiful feeling that has allowed me to get out of my own way and start living the life I always dreamed about.

And since quitting my job four months ago I have:

  • Started the Dare to Dream podcast
  • Created a personal website
  • Published my writing publicly on said website
  • Co-founded a nonprofit

I share this list not in an attempt to brag, but to detail what became possible for me once I took a leap of faith and started living my life on my own terms.

I firmly believe that this is how we are supposed to live. We all have a dream that is worth pursuing and I believe that it is through the active pursuit of our dreams that we find happiness and fulfillment.


Bronnie Ware worked as an end of life caregiver for many years. After comforting over 500 patients during their final moments, she wrote a book about the top five regrets her patients confessed while on their deathbed. They were:

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me 
  2. I wish I didn’t work so hard
  3. I wish I’d had the courage to express my feelings
  4. I wish I had stayed in touch with my friends 
  5. I wish I had let myself be happier 

Number one is why I stopped drinking alcohol. Number three is why I’ve started being radically honest and authentic about who I am and what I want. Number five is the most challenging for me, and something that I constantly work on improving.

Bronnie Ware’s wish (and my own) is that everyone who reads the above list will realize which parts of their life they need to change and to do so before it’s too late.  

Maybe it’s spending more time with friends and family. Maybe it’s taking yourself a bit less seriously or taking a few more vacation days. Whatever it is, we all have the power to drastically change our lives in an instant. All it takes is one single decision and a willingness to step into the Unknown.

I believe that we are all meant to live a life that we are truly in love with. That’s why I have begun training as a neuro-transformational coach and made it my mission to equip others with the tools to discover and live their dream. But more on that later. For now, I will leave you with a few things to ponder.  

Life is too short to do anything else besides relentlessly pursue your dream.

So go for it.

Step into the Unknown.

Hurl yourself into the abyss.

Burn the ships.

Start living your ideal life today.

Step 5 - Becoming A Problem Solver

December 25, 2020

““I prefer to be true to myself, even at the hazard of incurring the ridicule of others, rather than to be false, and to incur my own abhorrence.” – Frederick Douglas

It’s Christmas morning today which means it’s been exactly 6-months since I quit my job. The phrase “time flies when you’re having fun” comes to mind but it falls flat compared to what I have experienced since June. Something that describes my experience more accurately would read: “Time moves at the speed of light when you are wholeheartedly chasing your dreams” 

It’s been six whole months and I am not the same person who started this journey. So what’s changed? 

Practically everything. 

I still make corny dad jokes and cookie dough is still my kryptonite but I am not the same. Many aspects of my being have fundamentally shifted. I learned more in the past six months than I have in the other 25 and a half years of my life and it has transformed who I am as a person. Two of my favorite changes are as follows.

First, I have greatly reduced how much time and energy I spend caring about what other people think of me. There will always be a part of me that seeks approval from the people I care about most, but I have made enormous strides in genuinely not caring what people outside my closest circle think of me. 

Looking back, I used to care so much about everybody thinking I was cool. It kills me to realize how much I was letting other people’s opinions and judgments get in the way of my dreams. I was hiding my true self from the world simply because I thought other people might judge me.

A few days ago I did something I never thought I would do. I posted a shirtless transformation picture on Instagram. Yes, I became that guy. But it wasn’t a physical transformation that I was trying to highlight. It was the complete character upgrade that I had undergone since quitting my job that I was most proud of. And the fact that I was able to post such an authentic and emotionally vulnerable post on social media gave me all the proof I needed to confirm the following: 

I am no longer letting other people’s thoughts and opinions inhibit me from achieving my dreams. 

The second shift that I am most proud of is that I have become a problem solver. There are two kinds of people in this world: those who solve problems and those who ask other people to solve problems. 

While I was in the corporate world I was the latter. I was constantly surrounded by people who were more experienced than me and it was quicker to ask my boss “how do I do this?” than trying to attempt to find the solution on my own. This led me to seek out someone else’s help first thing whenever I encountered a new situation that I hadn’t dealt with before. 

Developing that habit is what caused me so much anxiety during my first few months as an entrepreneur. Every single day I was encountering new situations that I had never dealt with before, but now I had no one to turn to for help. I could send an email to a mentor or call my dad but there were simply too many new tasks to get done to ask for help on all of them. 

So I learned to solve problems on my own. And I became more comfortable with having no idea how to do something. My mindset shifted from “I don’t know how to do this” to “I don’t know how to do this but I will figure it out.”

This small shift has been invaluable. If I could only choose one lesson I learned from the past six months it would be this one because it means that no matter what situations I encounter in life, I will be okay. 

As I write this, my business partner and I are ramping up fundraising efforts for the nonprofit we started. Do I have any fundraising experience? No. Do I know exactly what to do next or how to run an online fundraising event? No. 

What I do know is that I will learn on the fly and figure it all out. This newfound confidence comes from becoming a problem solver and knowing that no matter what happens next, I will never stop chasing my dreams.