Crafting A Meaningful Life Outside Of Work

When I worked in corporate, I was trading 5 for 2.

Life was all about the weekend.

Which I’d spend chasing the next high at the bottom of a bottle and inside the magnetic strip of my Amex Platinum card. 

My job had no meaning, and I didn’t like it, so I might as well enjoy the hell out of my life these two days.

These two days were my attempt to give meaning to spending five days doing what I didn’t like to do. 

It worked deceptively; each swipe of the card, each step deeper into the bottle, provided a little blast of happiness and an escape from my life. 

But quick highs fade quickly, and I’d feel empty again before I knew it.  

I sprinted from one finish line to another, always looking for the next race, always trying to fill that void.  

It was a superficial existence, and I fooled myself into thinking it was living. 

I had a success-sized hole in my life, and I was handcuffed to a job I didn’t like to support an empty lifestyle. 

When I was in prison, well, I was in prison. 

It’s a world unto itself, with its own rules, language, and overall feeling of being disconnected from real life. 

I didn’t have the responsibilities of the outside world, but I had the stress and trauma of being incarcerated. 

Each day is a matter of routine, and each check mark on your routine is one micro-step closer to the door. 

It was a surreal existence that I was able to eek a life out of because I began what would later become “Blank Canvas: How I Reinvented My Life After Prison” and I dove head-first into trying to understand myself and give meaning to the suffering. 

Prison was still prison, but I had direction. 

After prison, I landed a job working the front desk of a gym in the Lower East Side of Manhattan. 

I was grateful for the job, but I didn’t love the job.

Unclogging toilets, wiping down treadmills, and dealing with angry members weren’t much fun.

Plus, there was no meaning, a sense of purpose, or fulfillment.

However, I was writing my first book (Blank Canvas) and attending Toastmasters meetings to keep the commitment I made when I was in prison to conquer my fear of public speaking. 

I wrote for two hours every morning before work.

I attended Toastmasters meetings on my day off and was soon elected the president of the Brooklyn Premier Club. 

The toilets still got clogged, the treadmills still needed to be wiped down, and the members still got angry. 

But their impact diminished in the face of the life I’d created outside of work. 

I had joy, purpose, meaning, and fulfillment that had nothing to do with my employment. 

Work was a means to a larger end. 

Today, I run my own business where I write, speak, consult, and coach. 

I share the lessons learned from blowing up my life and reinventing it from scratch so others can connect with their own sense of purpose and craft joyful, meaningful, and fulfilling lives. 

I’m fortunate and grateful every day to earn a living by living my life calling.

I still write for two hours every morning and now I’m paid to speak. 

But here’s the thing:

I have a new project I’m working on with my wife that’s adjacent to one of the aspects of my business (writing) but entirely outside my wheelhouse and comfort zone, for that matter.

It’s totally foreign to me, but it has a higher mission attached to it. 

In honor of our two special needs cats, we plan to donate 25% of the net sales of this endeavor to charities focused on special needs animals.

It’s providing my wife and me with a deep level of connection, a massive mission, and a deep sense of joy, meaning, and fulfillment. 

My work (vocation) has created even deeper levels of work (passion project). 

What I’ve learned:

  • Externals will never fill me from within. 
  • A superficial life is an existence, but it isn’t living.
  • Accepting short-term highs in lieu of long-term joy and fulfillment is a terrible trade. 
  • There’s enough time in the day to meet my financial obligations and feed my soul.
  • Sacrificing short-term highs in exchange for a long-term sense of purpose, meaning, and fulfillment is an excellent trade. 
  • I may not be able to control the circumstances, but I control how I respond to them and how I decide to show up within them. 
  • If work doesn’t provide me with a deep sense of joy, purpose, meaning, and fulfillment, it’s incumbent upon me to create it elsewhere. 
  • Even when my vocation does provide a deep sense of joy, purpose, meaning, and fulfillment, there’s still an opportunity to expand into other areas of challenge and growth and create even more meaning in my life. 

My corporate career didn’t provide what I desired, so I chased what I thought would, and I know so many of us do the same. 

I also know so many of us live, as Thoreau said, “lives of quiet desperation.”

My life changed when I stopped chasing externals and running from my authentic self and instead began the journey of going within and creating from what I discovered.

And I didn’t have to go to prison to do it. 

📣 If you’re ready to get unstuck and master midlife so you can craft your remarkable 2nd act, check out the Midlife Mastery Program.