In my early 20’s, I was frustrated with life.  While I had good jobs, I felt my life lacked meaning and purpose.  If I could ask my 23-year-old self, “what’s your purpose homey?”  23-year-old Dan would probably answer, “uhhhhhh, getting drunk ON purpose?”

My days consisted of me waking up, going to work from 8am until 7pm, hitting the gym for an hour, watching sports or playing video games over a couple of beers and then going to bed.  Thursdays, Fridays and Saturdays were a little different as they often included a heavy dose of binge drinking out at the bars with friends.

Sometimes, I look back and think fondly of the lack of responsibilities and wild times, but if I’m being honest with myself, those days were often empty and sad for me.  There’s a reason some of my favorite bands back then consisted of Rage Against the Machine, Rise Against, Days of the New, Trapt, and 3 Doors Down – not exactly the most uplifting of tunes.

I also remember not knowing why I was so empty and sad.  I was doing all the same things my friends were doing and yet fulfillment was nowhere to be found.  Were we all a little sad and empty back then?  Not having the emotional intelligence or guts to ask anyone, “are you guys all happy right now?” I continued to follow the crowd.

In an effort to chase down happiness, I’d listen to different depressing music, drink harder alcohol, exercise longer, buy a “cooler” car (a black 1997 Honda Prelude!), and take on a job at a more “prestigious” consulting firm.  When none of that worked, I decided that living in Bethesda, MD wasn’t doing the trick and I moved into Washington DC for “more excitement and adventure.”  After a year of living in DC and still waking up with that lingering sadness in my belly, I bought a house to begin my “real estate empire,” because surely the image of being a homeowner at 25 years old is the key to happiness.  Nope, same icky feeling in my belly.

Ok, ok, I thought, this time I’m going to make the “right” change.  In typical male Neanderthal fashion, I realized what was missing – THE GIRL, I NEEDED THE GIRL!  As luck would have it, shortly after signing onto Match.com, I would wake up one morning to find that the internet gods had delivered a “wink” from a cute, cheerful looking girl who was wearing a tight fitting t-shirt that showed just enough cleavage (but not too much) to think, “this is the answer to my happiness drought.”

Several months later and after going to restaurants, bars, parks, concerts, ice skating rinks, vineyards, and other great places, the euphoria and excitement of dating this fantastic person was over and the emptiness had returned.

Recently, I wrote “The Darkest Days of My Career” about how hope got me through a tragic accident that led to a death at the business I previously ran.  On the opposite side of hope is desperation.  Finding myself with; the house, the car, the job, and now the girl, and still being utterly lost and empty inside, desperation is what drove me to reach out to a counselor and seek therapy.

Therapy gave me the tools to begin to realize that our “outer” game does not drive our “inner game.”  It’s the opposite that is true.  Up until this point in my life, all of my focus was on external factors (house, car, partner, job).  While these are all important for living in our modern society, they do not drive fulfillment, contentment, and/or happiness.  If they did, then why do billionaire businessmen continue to cheat on their wives, why do politicians continue to ruin others to accumulate more power, and why do successful athletes continue to cheat to obtain glory?  These external factors are never ever enough.

16 years later, after years of; therapy, men’s groups, silent retreats, consciousness expanding experiences, daily meditation, and extensive reading on mindfulness, Buddhism and Stoicism, I hold more wisdom than my 25-year-old self.  However, that wisdom does little to diminish the pull towards the external… 

The desire for fast cars has been replaced with the desire for faster mountain bikes.

The striving for prestigious jobs has been replaced with the striving for more prestigious clients.

The search for a nicer house has been replaced with the search for more investments.

The seeking for a wife has been replaced with the seeking for more knowledge.

Today, as my years continue to throw me into middle age, I’m feeling stuck at a crossroads. 

Down one road is a massive highway, stretching farther than the eye can see.  This road is lined with more achievements, more money, and more titles.  From what I can see, the path appears shiny, exciting, and enticing.  Thinking ahead, I know all of these riches are obtainable and I could spend the rest of my life chasing down it’s glory.  However, with the little wisdom I have obtained, I know this road also leads to a literal dead end, lacking the ultimate truth and purpose I seek.

Turning my attention to the other road, I see what appears to be a dirt path through the woods.  As I look closer, the trail appears overgrown, rocks throughout, and with thorns to both sides.  Past the trail opening, there are shadows of some sort, but I can’t make out whether they are friend or foe.  Next to the trail, there’s an old signpost that is barely upright with the words, “truth, this way.”  It’s clear that few have traveled in this direction, for a long time.  The mere sight of it makes me want to turn away and focus my attention towards the other, more inviting road.

And here I remain, fixated on the massive highway, with its bright lights and freshly paved roads, all pointing in a direction that appears so fresh, exciting, and new.  It’s a road who’s curves I know well, providing fleeting moments of joy.

As I begin to fire up my engines towards a rocket fueled flight down this superhighway, I can’t shake the thought of the beaten-up path in the woods.  Turning back, nothing about this route appears glorious, fun, or easy.  I don’t even know where it leads.  More than that, it scares me so much that sometimes I wish I had never seen it all.  But I have seen it and I can’t help but think that the sign saying, “truth, this way,” is right.

Typing these words, I realize, I’m not at a crossroads at all. I am somewhere on the twisting, turning, dark path, taking a break while sitting on a rock, longing for the time when things were simple and my only desire was to obtain a new car or job.

As I snap out of the daydream, my awareness moves to my stomach. There’s no emptiness or sadness, just a hunger for more truth.

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Author Bio: Dan started Fired and Free in 2017, to provide his “truth” after being fired as CEO of the company he started and led. After a diverse 17-year career in management consulting and entrepreneurship, Dan now leads 3Sixty Leadership, where he provides coaching and consulting to business owners with 5 to 500 employees, helping them to work “on” their business not “in” their business.