Stepping Off the Precipice

I have once again stepped off the precipice and joined the ranks of the self-employed.

The last few months have been ones of seismic change for me. I started working with a Coach in November 2015. We spent the first month or so just figuring out what it was that I was passionate about, and how I could turn that passion into something that I could actually get paid for. She pushed me to think about what I really wanted to do. Then she pushed me a little harder to “think bigger.”

In thinking about what I’m passionate about, I found the “deathbed” analogy very useful. I imagined myself, in great detail, lying on my deathbed facing that black, implacable wall of death (to borrow from Harry Chapin) and asked: what is the one thing that I most wish I would have done?

Granted, that wish will probably change as I move through life, but I found it was a useful exercise to get me started in the right direction.

I thought about this deathbed analogy and, over the course of a month, a new life started to take shape. One in which I was able to earn a living doing what I wanted to do, mostly managing my time on my terms, with the financial freedom to do what needed to be done, but also giving me the free time to focus on the things that are important to me – my wife and my family.

A key component of my transformation were a handful of books my Coach recommended, including $100 Startup and Born for This, both by Chris Guillebeau, and A Whole New Mind: Why Right Brainers Will Rule the Future, by Daniel Pink. Both of these authors advocate a different way of looking at and finding our place the new economy (which I loosely define as the post-9/11 era).

For me, I went back to my Epiphany – the day in the park with my children, looking up at the sky, when I realized that I love teaching people to do stuff outside. I knew that I would find my passion if I could find a way to combine these factors: public speaking (an educational component), working outside, travel, and working with people.

Then I asked myself, is what I’m doing now moving me towards that goal? Is it making me happy? And, like Steve Jobs said, if the answer is “no” too many days in a row, then it’s time to do something different.

I enjoyed my restaurant jobs for a few years. But over time, and as my children grew older, my job was taking more and more of a toll on my relationships. I realized it was time to move on. There was a catalytic event that really put things into perspective for me, and allowed me to feel what it would be like without my current job – and I discovered that I had a wealth of ideas I needed to more forward on, and that being tired from working nights was prohibiting me from bringing my best self to bear on what I wanted to do.

After numerous conversations with my wife, we decided it was time for me to to move on. I left my job and, applying the lessons learned from Messrs. Pink and Guillebeau, I brainstormed close to 100 different ways I could work for myself and make money.

This is the “new economy” part of the equation, an economic reality that I like to describe as the “gig economy.” Essentially, if I can cobble together enough “gigs” to create a whole that equals the salary I used to earn from one job, I’ve succeeded.

That’s been my journey for the last 6 months. One of self-discovery. Identifying what I really want to do with my life, and finding a way to make it a reality. Granted, I’m at the very beginning of this adventure. There is every possibility I might crash and burn. But if I do, it’ll be on my terms, and I’ll go down swinging, taking my shot at trying to plan my work around my life.

I’ve put together multiple income streams that I can work on with varying degrees of intensity to, I hope, generate the type of income I need while allowing me to mostly do what I want, when I want, working on things that I enjoy, and finding a way to get paid for them.

That, in a nutshell, was the process of giving birth to my brainchild, the Cleveland Zephyr. It (I hope) allows me to do the things I want to do – work with people, outside, teaching leadership skills, travelling to different parts of the country (and maybe someday the world) , while getting paid to do it. Granted, there are some other side gigs I need to throw in there to make this newest endeavor economically viable, but I think of them as temporary ways to make the money I need while I put together the plan that will let me get paid for doing the things I want.


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