life of adventure

Getting Here – A Life of Adventure

 

First of all, this is a summary of my life to this point.  It’s not exceptional and probably mirrors many other people’s lives – there’s been both tragedy and triumph, adventure and boredom.  I don’t write this because I think I’m special, I’m writing it so those interested souls understand where I’m coming from.
So if you want to know my story, read on.

mypath

The Path

I’m a lucky guy.  There’s absolutely no denying it.  As a matter of fact, I’m so lucky that I’ve suffered serious guilt about how lucky I am.

I’ve survived things that other people didn’t, I have a family that’s set me up for success, and people have given me chances in my professional life.  I’ve experienced adventure that I would never be able to describe in words – from freedive spearfishing over a hundred miles offshore, to engaging in firefights outside of Baghdad, Iraq.  From learning to really ride my motorcycle, to sharing some epic diving trips in remote spots with amazing friends.

There’s been no shortage of adrenaline or adventure.  But it wasn’t always like this.

I bore you with an endless list of issues I’ve had, but in summary:  I’ve lost brothers in battle, had romantic interests violently killed, lost family members (most painfully – my father), and endured a variety of failures both personal and professional.

Honestly I don’t do well with failure and throughout the process there have been periods of serious self-doubt that border on depression.  The earth-shattering, soul-crushing kind of self doubt that makes you question every decision you’ve ever made.

Abandoning “my future.”

Early in college a friend died in a Jeep rollover and I stopped caring about college.  They ended up kicking me out on academic probation – apparently final exams are meant to be attended (who knew?).  That failure lead to a shitty manual labor job, living out of a shitty trailer, in a shitty town in Texas.  The level of people I worked with were illegal immigrants (good people) and drug addicts (sometimes good people).

I wasn’t making any money, couldn’t afford my cell phone payments and my student loan payments were beginning to pile up.

Risking my life for a different future.

Eventually I decided to join the military, not really seeing any way out (and it meant I got that adrenaline/adventure fix). I did alright in the military and really enjoyed the camaraderie and the no-bullshit attitude.  What I didn’t enjoy was the lack of real leadership (commanding isn’t leading), insistence on rules, and lack of genuinely motivated and ambitious people (nothing against any of my friends – you were the exception).  Admittedly, I also have a little bit of a problem with authority.

My career essentially ended when I was offered a promotion, and they resorted to telling me I wouldn’t last “in the real world” (meaning being a private citizen). I declined the promotion. The truth is – I was starting to realize that the war my friends and I were fighting was bullshit.  It was ruining our country, drastically increasing our national deficit, and ruining our credibility worldwide. And we weren’t doing any fighting that was satisfying, we essentially drove around waiting to get blown up. Not cool.

I couldn’t bear that level of sacrifice for a cause I didn’t believe in. So I left.

It wasn’t a particularly hard decision, but changing my view of the world was hard. I was coming from a war zone, where everyone was fighting everyday – thousands of miles from their family.  Suddenly I was dropped back into a world full of feelings, caring about people, and sensitivity.  Political correctness had run rampant and it seemed like even the most innocent jokes offended somebody.  I wasn’t a saint nor soft-spoken, but everybody sure did seem overly sensitive.

Adventure Bet

Betting on me.

I quickly found out that you have to work to be awesome in the private sector – there’s serious competition (scattered amongst complete idiots).  So I went back to school – easily made Dean’s list (until I got bored) and worked hard at learning (easy – I love learning). After I finally graduated I found out about Venture Capital, Startups, and Technology Companies and how they can deliver such a staggering amount of wealth to founders and investors.

One of my professors saw a little bit of promise in me and passed my name along to a neat little startup run by some truly passionate people.  There I met friends that I have to this day, and there I also learned alot about how to not manage people, how to deal with difficult personalities, and the in-the-trenches truths about startup life. It was an amazing learning experience and I loved it, but couldn’t wait to get out of it.

Some time in Silicon Valley.

Stanford is expensive and really difficult.  Really expensive and really difficult. I actually had to study and actually had to do homework.  And sometimes, even with a bunch of work I wasn’t excelling – something I really wasn’t used to.  And it turns out I really need friends and colleagues to work through difficult problems, something I was noticeably lacking at Stanford.  Believe it or not, the people I was in class with weren’t on my level.  They weren’t lacking in intelligence, they were all smarter than me – I’m convinced of that.  They just couldn’t talk about some of the deeper things I needed – like: philosophy, the difficulties of working inside of an early stage startup, and the underlying philosophies that had defined life and death decisions (like the ones I faced in Iraq or 100 miles offshore – fighting sharks off of recently speared fish).

My classmates at Stanford were brilliant kids, with brilliant kid worries, and I was 28 wondering what I was doing there.  To complicate things, the classes I was involved in were clearly taught by the B-Team.  Don’t get me wrong – the professors were smart, well connected guys.  But it quickly become clear that my entrepreneurship professor hadn’t ever built a company (believe it or not) and that my comp-sci teachers were overwhelmed by the amount of student requests.

It turns out that Stanford Summer Intensives aren’t my learning style.  Another failure, not in grades, but in real learning.

 

Home from Adventure

Home, whatever that means.

So I returned home to find out that there weren’t any developers willing to leave their cushy jobs to work with me on developing the “next big thing.”  And it shouldn’t have surprised me – these guys had awesome work environments already, great salaries, and challenging work ahead of them.  And I was an unproven guy without easy access to capital or any real mentorship.

So I ended up taking the advice of others and took a job.  It turns out I was pretty good at the job and actually had a bunch to contribute.  I found that I understood and contributed to sales, sales strategy, and marketing but wasn’t a huge fan of sales as a career.  More importantly, I brought an attitude of getting shit done – and it turns out that’s a really rare thing in the business world.  The business world is full of meetings, and politics, and hot air.  I was able to bypass most of it and operated by being friendly and nice, but frank and proactive.

The banality of home.

Boredom.  The only way I could stay engaged was to push hard at my job – not sleeping much, not working out, staying plugged in all the time, and sacrificing everything but the job.  If I started to enjoy any other part of my life again – I’d find that my work wasn’t important.  That feeling – that what I’m working on isn’t important is something I really, really couldn’t stand.  I was craving risk, adrenaline and adventure again.

So I started a company on the side, with an amazing co-founder and we decided we were going to attack the construction space.  The chance of failure is remarkably high – something to the tune of 90% or more.  But I’ll be goddamned if that’s going to stop me.  At the time of me writing this, things are moving but we so early that any prediction would be foolish.

Passion.

I had it, but it wasn’t wrapped around what I was doing in my day job. As a matter of fact, the stuff that I was working on (in my day job) was boring by any standard and was only really inspiring as it was a source of learning.  But when I was offshore, sailing, diving, fishing, spearfishing, exploring – I was really in my element.  If I was waiting on a monster wahoo to come in, or fighting off a shark, I was having the time of my life.

And even though I craved adventure,  I wasn’t prepared to make the monetary/professional sacrifice to move to something I enjoyed more.

Another Adventure Event

The Event.

I got a call from my sister, who was working in the Congo.  I had a habit of answering like a complete jackass, we had a great relationship – we laughed alot and  had so much fun that we were actually pretty embarrassing to be around. This one was different though, she was serious and tense – I picked up on it immediately.  Something was really, really wrong. The good news is that she wasn’t crying – so she was relatively composed and her life wasn’t in immediate jeopardy.

I’d prepared for this a million times over, she was in a sketchy situation and I was ready to drop everything, empty a couple of bank accounts, and go over there with the express intent of buying a couple of weapons and finding my sister.   I could operate with the best of them and I really didn’t give a shit – it was a lawless place, the kind I liked…  But that wasn’t it at all.

My Mom had a heart attack.  She was visiting my sister in the Congo when it happened.  Immediate grief and a sudden sinking feeling.

I’d already lost my Dad to work, stress, and a generally unhealthy lifestyle.  I couldn’t lose another parent that way.  The night I received the call, I couldn’t sleep.  I couldn’t do anything.  Completely helpless, I decided I wasn’t going to let work, other people’s opinions, my projects, my desire for wealth, or anything else stand in my way.  I was leaving to go sail and live a pure, simple life and I was taking my Mom with me.

So here I am, ready and (for the first time) willing to give up money and work to practice what I’m going to preach to my Mom – the value of time, following your passions, and experimenting with better ways to live.

If you’ve made it this far, I really appreciate your attention. I hope there was some value in the preceding words, that you’ll subscribe as I share my experience preparing for this transformation, and that you’ll stay with me as I continue to move forward.

I’d like to connect with you – and the easiest way to stay tuned is to subscribe by clicking here.

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10 replies
  1. jeremy
    jeremy says:

    Wow, tough choice you made. I admire your courage, not sure I am ready yet for that kind of adventure but I am sure you and your mother will find true happiness thanks to your decision. Just taking it must already have made you feel real good. Good luck for the next steps!

    Reply
    • Nate
      Nate says:

      Thanks for the feedback jeremy – believe it or not, the decision wasn’t too hard. I think following through with it is going to be the hard part, hence this blog. Hope you stay tuned and enjoy!

      Reply
  2. Pukka
    Pukka says:

    You write very well, I look forward to hearing how your adventure develops. I have been a sailor since I was a kid, I am currently in a job that isn’t really going anywhere and isn’t as fulfilling as it once was. I love the thought of giving up everything and heading out on a boat to explore the world.

    Reply
    • Nate
      Nate says:

      Thanks! The financial aspect of giving up what you’re doing and heading out is the hard part. Realizing that you’re not worth nearly as much to an employer after a 2 (or 5?) year break is a tough pill to swallow… The key to that is getting rid of consumer debt – car payments, mortgages, etc.

      Reply
      • Cameron
        Cameron says:

        Good luck on your journey! I was starting off 5 years ago with no money and a dream to buy a sailboat and go cruising. In about a month I’ll be ready to leave and will be gone for a year. If you need any help or advice let me know.

        It seems that you’re starting off great and doing what I did – selling my dream to anyone that will listen. This may afford you some great things. I’ve had family gift me some money (not a huge amount, but enough to make a big difference), and I’ve had work let me take a year long leave of absense, etc.

        Reply
        • Nate
          Nate says:

          Cameron, that’s awesome. I’m impressed and I hope you stop by occasionally, I’ll definitely follow your progress

          Reply
  3. Jason
    Jason says:

    Hi Nate, my name is Jason and I am currently a senior in high school living in southern California. I have been following your blog and Instagram page for about 3 months now and have really felt that I am connected with your ways of thinking . In this story you stated that you went through a very difficult time in Texas and had trouble with where your life was going. About 2 years to the date I had the same feelings. I felt bored in California, not with all the activities that are available, I am actually quite the adrenaline junkie myself with, surfing, the ocean, dirt bike riding, and snowboarding, but I had the feeling of loneliness and I was sick of how so many people could be so superficial and not give a shit about others. I have always based my relationships with people based upon how sincere they are with me and others. It got so bad that I had almost attempted suicide. I was in a terrible place at the time, but through some close friends, I was able to make it out. After my bout with depression I thought about dropping out of school and just running away, but I have always wanted to follow my father’s footsteps and travel the world like he did during the mid 80’s. My father was able to be hired onto a sailboat and basically sail the world while being paid. He had a few duties that included making a dinner for the family that hired him on and to home-school their two sons. He traveled through some very fascinating places such as Papua New Guinea, Australia, and some extremely remote places in the Southern Pacific. Fast forward to today, I’m in the middle of my senior year, I just finished my last season of high school water polo and have been accepted to my college of choice. The depression is 100% gone but it definitely changed my way of thinking to the point where many teachers have noticed that I think like someone much older than my current age. My current goals are to get through the rest of high and then proceed to go to college and receive a doctorate in physical therapy. My lifetime goal is to do exactly what you currently plan to do. Sail the world either on my own or with a few of my closest friends. I am about a decade younger than you but I honestly feel that we share some traits with how we look at society and what we want in our personal lives. I apologize for writing such a long “comment” I got a bit carried away but I appreciate the time you take for your blog and hope you continue post as much as possible about your adventure. Jason

    Reply
    • Nate
      Nate says:

      Jason, that’s pretty deep stuff man. And I hope you don’t ever apologize for sharing things or thoughtful comments.

      I’m certainly not anybody to give advice, but I can tell you something about high school and college: life doesn’t get better, but you will get better. So hang in there. Your ability to cope with pressures of society, friends, family, etc will get better. Your ability to understand people and their motivations will get better. And your ability to understand yourself and your own motivations will get better. If you think, and it appears that you do, you will find those things are incredibly important in your life – in many ways they define your life.

      One other note: I’ve long been criticized for having a short attention span, taking large risks, being impulsive, and quickly moving from one thing to the next. Don’t be discouraged by this kind of criticism. It’s healthy and humbling to hear (you need to hear it), but it’s equally healthy to give other people’s expectations the proverbial “middle finger” and live your own life. Don’t take criticism from people who aren’t where you want to be, only take criticism from people who have lived the life you want to live. The world needs all types: daredevils, conservatives, scoundrels, straight-edges, felons, victims, leaders, and followers – everyone plays their part.

      The world is a big, beautiful place full of other cultures that have different values. Our (American) culture isn’t the most healthy, the smartest, or the happiest – which isn’t something that they teach in school. If someone tells you that – kindly remind them that our nation was built on the backs of slaves and on the bones of Native Americans. Keep that in mind if you feel like you don’t fit in. In fact, in a culture that’s so screwed up – it’s a badge of honor to not fit in. Wear it proudly.

      Cheers, thanks for taking the time to write. And I don’t apologize for the long comment/response ;)

      The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.

      – GEORGE BERNARD SHAW, Maxims for Revolutionists

      Reply

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