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Turning A Life Crossroads Into an Intersection

"I'm heading towards a career crossroads." I said those words to a co-worker seven years ago. I was at a pretty low point in my career - and life - and had just uncovered the realization that what I was doing for a living did not feel like a good way of living.

At that time I was in Year #15 of a 22-year IT career. I was building systems and managing people within a 35,000 employee global corporation. I felt like a speck. And the treatment I received often reinforced that notion. I didn't care about the work I was doing and my work didn't seem to care much about me as a person, either.

As I slowly opened my eyes to that sad reality, my squinting vision ahead showed me there was a crossroads in the distance. I had no idea what was on the sign post, nor how far away it was. But it was good to know it was there. I was awake.

At various junctures along the way I thought I might've arrived.

Stones Along the Path

A few years after I left that Big Corporate job, I was having a blast working in a just-beyond-startup-mode IT company. I was engaged and working with lots of great people. Yet there was no "me" in the job. I was helping someone else build their dream. I was still marching towards that crossroads.

After becoming president of that cool tech company, and experiencing burnout multiple times, I realized that I needed to make another turn. In late 2016, I slowly transitioned out of what I had imagined to be my dream job and started dabbling in consulting. I loved the idea of it and had some early success in helping small business owners based on my experience. But I wasn't truly energized by it and I ended up taking a "step down" job.

Then, in mid-2018, just about a year and a half ago, I made a sharp turn. Without a plan in place, other than to finally arrive at the crossroads, I resigned from my last corporate job. (Optimistically, the word "ever" belongs at the end of that sentence.)

Ok, so enough with the history lesson. Thanks for following along.

A New Discovery

Here's the thing I didn't realize:

All that time I was looking for a magical crossroads that would show me where to find happiness, I should've been looking for an intersection.

At this point, dear reader, you may be thinking "what's the difference between a crossroads and an intersection?" Fair point. They're pretty synonymous.

What I discovered is that, in this metaphor that was so important for my evolution, a crossroads is something that is "out there". It's created by others. It has signs that tell you your options. And those options are predetermined.

On the other hand, an "intersection" can be something completely different. It is the place where things come together, where they intersect. The root of the word "intersect" comes, in part, from the word for "cut". I have taken this to mean how I can cut away the things that don't compel me and discover how the things that light me up come together, how they intersect.

What's Come Together ... So Far

Nearly 18 months into my life as a solo entrepreneur, and a full year (at least) since I thought I'd finally arrived at the crossroads, I have found a charmed intersection.

  • I have long loved humor and have devoted myself to hundreds of hours of learning and playing in the realm of improv comedy. It is a huge part of me.

  • I also love helping other people grow by learning more about themselves and how they can bring their gifts forth to the world around them. I devoted hundreds of hours more towards building my skills as a coach to help with this.

  • I am fascinated, in large part by my own evolution as a human being who is jam-packed with feelings, with the ways that we connect with ourselves and others on the deepest levels. I'm not yet at hundreds of hours of studying the field of emotional intelligence to better understand how these skills can be developed. But it's getting close to that.

  • As a leader - of my life, of my business, of people in my past jobs, and in the world - I place a huge value on taking a leadership perspective into every day. (My improv troupe's name notwithstanding...)

  • As a Gentle Man, one who recognizes his own sensitivities as well as his tremendous courage, I feel so strongly that men have a tremendous opportunity to bring balance to the world. By taking a step back, we can allow a huge step forward, one that is more fulfilling - and more powerful - for everyone.

So here I am. I'm at the intersection of Improv + Coaching + Emotional Intelligence + Leadership + Gentle Men! It's a fantastic mix of things I love and I feel passionately that it is something that can help our world.

So... what does your intersection look like?


Jim Young is at the intersection of coach, improviser, pro-feminist man, Dad, entrepreneur, experimenter, big old ball of feelings, dark chocolate lover, and so many other things.

He offers one-on-one and group coaching to people who are seeking to lead a robust and adventurous life that creates harmony and joy. His passions for life, business, and leadership are all focuses for his coaching.

Jim also provides innovative programming based on improv and emotional intelligence to help people and organizations create stronger relationship and leadership capabilities that help them thrive.

If you are interested in learning more about how Jim can help you or your organization, get your email intersecting with his via


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