Trade Comfort For A Compass: How To Lead An Adventurous Life – Year 1 – Introduction

I’ve never been what anyone would consider a bad*ss. Is it legal to at least admit that I’d like to be one?

My journey to an adventure filled life began several years ago and it’s only now in 2025 that I can look back and begin to chronicle the journey. Although I know I haven’t ‘arrived’ (laughably so), I know that I’ve made significant efforts and learned A TON about the journey along the way, including a lot of the ‘Why do I even want to do this, anyway?” My hopes are, though, that the words I’m offering here will inspire others like me who are paddling upstream in an attempt to change our own misconceptions about ourselves to become a version of ourselves that closer to who we’d consciously like to be. I think it’s these kinds of articles that I wish I could have read back in 2020 around the time I began.

This is the beginning of my story.

So, back to that first question. Can I become a bad*ss? That question actually begs another question first…what IS a bad*ss (or at least what do I personally mean by it?) Well, in my personal pursuit to become one I’ve learned that there are different types depending on who you ask. One might envision a handlebar-mustache-toting, tattoo covered Harley rider. Others might describe a 28 year old Wall Street genius with a fast car, large black book and an even larger bank account yet others might consider folks like Ernest Shackleton or anyone who’s actually made it to the top of Mt. Everest. Although all of these might in their own way be correct, it was this third of many different types that I lifted up in my own heart. The ADVENTURER. That man that could speak several languages, but only when required. He could survive in the outdoors and relished all the thrills nature could offer. He was well traveled and collected experiences over cash. He could handle himself in any fight, but always preferred peaceful resolutions when possible. He was also a man with the strength to give back that stemmed from a sincere gratitude for life and humility in world perspective. And, perhaps most importantly, his LIFESTYLE reflected every one of these qualities. He wasn’t a ‘weekend adventurer.’ Dare I even say it out loud…a contemporary Indiana Jones?

The problem was that it became painfully clear that there was no formalized path to follow per se – no Learning Tree Annex Course on “How to be a world adventurer.” I had to create my own – and the path to create the path proved to be more difficult because it kept changing. I would try a certain direction and then found that either it wasn’t working for me or it was proving not to be genuine. OR…it WAS proving to be successful but once I got the fruit of my labors I found out that I wasn’t always wanting the fruit after all. But, these are all things you only find out after the fact. And that had to be ok…even if it didn’t always feel ok.

During those first few months of my journey, I knew that the first thing I needed to do was complete an honest assessment of myself. It wasn’t likely that I would be able to become something that I…well…just wasn’t. I began to ask myself WHY I wanted to make these types of changes. I reflexively spouted out the superficial reasons of wanting to be liked and respected by both women and other men. But these answers, although somewhat true, left me feeling a bit hollow, like they just weren’t telling the true story. What I eventually figured out was that there were certain character traits and lifestyle details that I longed for, but I never gave myself the permission to take on or pursue. It wasn’t about being liked or respected by others. It was more that I felt like I was one person on the inside which was inconsistent with the person that I acted like (and even often times thought like.) It was about aligning my thoughts and actions with the person that was inside of me wanting to be released.

I then hit a wall that nearly sank the fleet, so to speak – the cold realization that I truly wasn’t the person that I wanted to be. It doesn’t always feel good when you don’t measure up to someone else’s standards. But, when you don’t measure up to your own (especially in some embarrassing ways) it can be a bitter pill to swallow. My own manhood and masculinity came into question. Aspects of my personality that I was once proud of became cheap, carnival consolation prizes compared to the holes I was seeing in my very character. It was a cruel mirror.

Immediately after that self assessment, I took a quick inventory of my current resources available and what I was starting with personally. I felt a desperate need to see what I had to work with. I had a Bachelor’s degree in Art History, nothing in my bank account, a ton of debt and three sons now out of high school (so few direct parental responsibilities.) I owned my own treasure hunt design business of 20+ years (though was flat-lining thanks to covid). I had just turned 50, stood at 5’5”, with a bad back and could have easily lost 70 pounds (though not effortlessly.) I had done a stint of gymnastics in college and new that my body responded well to working out. I had learned some German, Spanish, Japanese and Ancient Greek. Beyond those details, that was all I had to work with. That was my ground zero. I hadn’t really ever even camped, held (much less fired) any weapon, hadn’t traveled or had ever been in any physical fight in my life (and that last one I hope that remains true for my future years, as well.)

Then came the task of fully describing the man that I truly wanted to become – that Adventurer that I felt was inside of me and who longed to take the reins of my life. I thought that this part would be easy, not taking more than an hour at most. It took a month of on and off soul searching. I made a long list of characteristics, that was constantly being revised, that got very specific on a variety of life and personal topics. I knew I wanted a mobile lifestyle that enabled me to travel the world as my own curiosity and work would take me. I made a list of skills that I wanted to acquire across several disciplines from foreign language mastery to outdoor survival schools to Jiu Jitzu. I knew I had to work on my own character and temperament – to become more self disciplined, less emotional in decisions and actions, as well as weakening my tendency to quit when things get challenging. I also eventually learned that I wanted to develop a new set of friends and people in general that I associated with in my life – to develop a certain circle of friends that were passionate about their own pursuits. I even wrote down details about the physical changes (my appearance) I wanted to make.

After the list I created came the very difficult task of deciding which of those characteristics I valued most – I knew that I needed to prioritize. I couldn’t be everything, perhaps even lucky to attain a few. I had to remember, this project wasn’t about becoming someone else, it was about discovering who I truly wanted to be…and then giving myself the permission to be that person. With that, I crossed a few of the items off the list, concluding that they didn’t feel or seem genuine with who I was deep on the inside. Immediately after I knew that I needed to honestly consider which of those characteristics were achievable (considering my own resources and age.)

So, by now I had a full description of the exact adventurer that I wanted to be. The adventurer that I felt was inside of me, waiting to have his turn in the driver’s seat.

And then I stopped.

I asked myself the question – what if I only ACT like an Adventurer, but I don’t BECOME a Adventurer? And are they the same thing? Was I only looking for the feeling or the self image or even a self imposed title? Then the word ‘poser’ camped out in my mind. I knew it wasn’t about mastering a couple languages on Duolingo and traveling to Europe every Summer with an occasional hike at the local state park. I wanted to BE a certain person and not LOOK or ACT like a certain person merely. This journey was never about trying to be someone I wasn’t or to be a ‘weekend adventurer’, as preciously mentioned, but rather having the courage to be the person that I WANTED to be…and this great experiment was going to be about whether or not I was going to be able to pull it off. Or, in my case, HOW MUCH was I going to be able to pull off?

This quickly turned into somewhat of a mind bender. I mean, how do you become something you aren’t…but you are? I knew that I needed to be in a head space to be WILLING to do ANYTHING, and that scared me. I then encouraged myself by looking at some of the characteristics and skills that I either already possessed or gained. It wasn’t much, but knowing that I wasn’t starting out with a zero helped some. Some.

It was far too overwhelming to try and change everything at once. I didn’t have the time, nor the money (to say nothing about the emotional energy) to face every fear and insecurity that was having a staring contest with me. There was no way that I was going to be able to tackle every tentacle of that Leviathan at the same time. I decided to delineate every characteristic change to make and skill to acquire on a master list. I then tried to get an individual plan to change each of those things in a realistic and systematic way. Some I knew I could address immediately while others were going to be lifelong pursuits.

All that analysis took close to a year, but I didn’t wait until I was done to begin taking action. I acknowledged my history of suffering from a paralysis-of-analysis so I just started DOING things randomly. Money was still an issue but I couldn’t let that stop me from doing what I could. I did things that I never did before and tried to break outside of my comfort zone in different ways. I started going on overnight camping trips (mind you I hadn’t camped in over 30 years and had NEVER camped alone.) I checked out a local MMA gym to talk to the owner about the best martial art to potentially learn, based on my future lifestyle. Additionally, I knew that I had body image issues so I went to a nude beach a dozen times until I stopped caring what I looked like. I began working on my weight (which proved to be its own demon, and fodder for a separate article assuming I get the courage to write it.) I did some traveling with a buddy and shot a semi automatic weapon in the woods for the first time. Don’t worry, that tin can had it comin’.

The more I did, the more my ‘end goal’ began to take shape and the easier it was to come up with my master list. I was learning what was feeling genuine…and what was feeling false. It was good to learn both. Then, one day I met Quinn. Someone I’ve known for 25 years and yet never met. Someone that never existed. Someone that I’d never get to speak to or shake hands with, but who would personally inspire me to grow beyond who I thought I could be…

CLICK HERE TO CONTINUE – Trade Comfort For A Compass: How To Lead An Adventurous Life – Year 2 – Meeting Quinn