The Liminal Space

On my June birthday nearly twenty years ago, I handed in a resignation letter.

My clients and colleagues expressed their admiration for my bold move. Some called me brave. I was surprised - I thought they’d say I was nuts. After all, I had spent more than seven years establishing myself as the face and the force of this creative firm. One that I had no equity in. Now, I’d simply be walking away.

Some of you may recall this tale from my LinkedIn postings, but I promise I take it further here, so keep going!

I had recently realized that I'd let this role define me. I'd forgotten who I was, what I wanted to create, who I wanted to be. It had drained me of my time, my energy, the space I needed to think for myself. I simply had to make this change. It would turn out to be the largest, most uncomfortable gift I’ve ever received.

By Independence Day, I was poetically and suddenly free of a high-level role that I'd allowed to define my entire existence. My first major leap into the unknown.

The morning after my final day, I woke up alone. I relished the calm and the silence. But as the afternoon wore on, a creeping sense of dread set in. I didn’t truly have a plan. What I did have, intentionally designed over a six-month period prior to resignation, was room to maneuver. Time, to stop and breathe.

I want to be completely honest about that flexibility, because many don't have a luxury like that right now. You may have been shoved into the unknown, without a net, during a brutally uncertain era for creative professionals. I know that being pushed feels entirely different from choosing to jump.

And sadly, most of us race breathlessly to get to the other side.

When a gig ends or burnout hits, the immediate reflex is to lace up and sprint toward the next contract, the next title, the next zoom, the next brief. Take any call, change the channel, sign on the line, get that next paycheck. We tell ourselves we’re just being practical. We blame financial anxiety, not wanting a gap on our resume. We hear our parents’ voices. We fear our peers' judgment.

But if you can pause in the quiet, one arm akimbo, the other hand lifting up to check your pulse…. Here, you can get completely honest with yourself.

I know how terrifying it can be as a mid-to-senior careerist to suddenly stop, let alone listen to your heart. It asks inconvenient questions. Brings up old dreams, along with annoying mantras and idealistic manifestos from your 20s. It directly threatens the comfort and familiarity of the identity you’ve carefully spent decades stitching together. The very act makes you want to overcome it, feel prideful in your power over it. The brain barges in like a tag-team partner, slapping back the feelings and barking its same old clichés about bills, adulting, survival.

I spent that summer shaking off the chattering monkeys in my brain, and exploring every corner of Prospect Park in Brooklyn. I started reading books that felt too "woo-woo" to mention out loud to my friends and former colleagues. I laid down in the grass, looking up at a giant, open blue sky. I finally acknowledged the double life I’d been living.

For years, I’d been doing improv comedy shows weekly, in front of large crowds, at a time when the scene was booming in NYC. It was a way to shake off the day, plus I love to laugh and I love the minds of fellow comedians. The expressive, honest, deeply present version of myself who conjured new worlds and characters instantly out of thin air, in collaboration with other poets & geniuses - that guy started to contrast with my service-oriented, career-driven, professional buttoned-up straight-arrow self. The dissonance became too significant for me to ignore.

Now that I was free, I threw myself into that vibrant, creative community. Collaborating, taking big swings, coloring past the lines, learning how to fall on my face, getting right back up and trying again. My perspective - my entire life - took on a completely new shape. The more I invested in this direction, the more discoveries and surprises I experienced about what was possible. Eventually, I'd find a way to combine my previous career experience with this new work that gave me life. The benefits were exponential. The path began rising up to meet me, because I was moving forward, with purpose. Onward I went, with confidence, in my own skin.

I’m writing this to you because I see so many incredibly talented, seasoned creative types standing at that exact same spot I was twenty years ago.

Some are frozen, staring at an attractive next step up the same ladder they’ve been on, but unable to utter the word "yes". Some are panicking in the aftermath of a layoff or an impulsive resignation. Others are just persevering through days that all feel the same, trying not to risk making waves during such a tumultuous era.

I’ve been there, right where you are. And more than once - in fact this story is just one example of the many in my life and the lives of those whom I admire, that I’ll share, where we pushed past our own resistance, persevered through the hard times, found the people and resources we needed, and rewrote our next chapter.

So far you’ve seen me use words like pause or stop. Leap. Listen to your heart. Yes, I may have taken a summer off to wander in a park, but I promise you I’m not delusional. I understand how different this process can look for each individual. The path isn’t always clear, it’s not easy, it’s often non-linear, it can happen in fits & starts - but what I am advocating for is making a practice of returning to yourself and getting what you need to take informed, intelligent risks that open up possibilities. So this isn’t about career reinvention as much as it is about ongoing continuous realignment.

I hope to inspire you to dig deep, to reach further, to keep going - but I also want to help you along the way, gathering the resources and building community, so we can all lift each other up. We’re living in unprecedented, transformative times and we’ll need each other to find our way through.

And for all my storytelling, look - even after twenty years in active pursuit of my dreams - I need this too. This year I finally made the conscious choice to create more than I consume. I’ve got a novel outline that I haven’t run with yet. A giant idea for an animated series that I want to self-produce. And much more - an endless list of ideas, collabs, creative projects I still want and need to bring to life. All while balancing my existing work and, most importantly, quality time with my family.

Thanks for signing up here. Thanks for reading all this. I know how it can be. Like everyone else, I’d rather quick-snack on the junk food - listening to podcasts at 1.5 speed, watching all the YouTube videos with the captions on, scrolling through the Insta reels - and just let my mind wander.

You either point at the braggart on screen and say, sure YOU could do that but MY life won’t allow that, buddy. Or, you do get inspired and jot a few notes down (sometimes I’ll text myself or send myself yet another screengrab of an Insta post). Only to never revisit that notion again. I’m pretty tired of this routine.

Behind the scenes of this weekly missive to you, The Courageous, I’m designing something more deliberate and action-oriented: small, highly confidential, focused cohorts of mid-to-senior level creative peers. The aim would be to help you find objective clarity on what your next chapter actually looks like. We can learn together, take real action in between sessions, and be there for each other providing support during setbacks and celebrating our wins.

The doors won't open just yet, I'm still in construction mode. The timing is on purpose - I want your input. So if you're either sitting in that uncomfortable liminal space, or if you’re ready to stop avoiding what your heart’s been telling you, reply directly to this email.

Drop me a line and tell me what you're working through. And tell me what came up as you read this. I read every single response.

You’ve got this.

Onward,
Kevin
Founder, THE COURAGEOUS