SWSR: Notes from Midair

Short Writes, Short Reads

This post marks a milestone of sorts. (No, it doesn’t really but milestones and anniversaries and things are always good setups for being reflective and stuff, so let’s just go with it.)

Sometime in the past week, I published my 50^th entry since starting this Substack. This is actually the 54^th but nobody celebrates the 54^th time they’ve done something or the 147^th day they’ve spent doing it, so let’s just consider this a belated meditation on my recent 50^th.

This was my first post.

I remember what it felt like to write. I remember what it felt like to hit “publish”.

The metaphor in it wasn’t new for me. I had used some version of it a hundred times over the prior 25 years when talking with someone about starting your own business, going out on your own, or being an entrepreneur.

The hardest part of doing your own thing is the jumping. I’ve spent a lot of time around the cliff’s edge and know that well. The leaping is the hardest part.

It isn’t that the actual doing of whatever it is you want to do once airborne isn’t hard or very hard. It’s that the vast majority of dreams of flying don’t die at the bottom of the cliff. They die right there on the solid ground at the top.

I’ve dug some graves up there myself.

When I was in my late 20’s and working in a big ad agency, I had an idea for a startup company. I had worked with a bunch and knew some people in the industry. The contacts were mostly rather soft connections. People I knew but didn’t really have a relationship with per se. Still, there were some I could call.

One was an investor in a reputable venture capital firm that had backed some successful startups and raised a slew of money to invest in more. So, I called and asked if we could meet up for coffee or a drink sometime when he was in the city. He said a quick “Sure!” which I hadn’t really expected to be that easy and next thing you know I was on his calendar for the following week to present my startup idea to him.

“Present” is doing a lot of work in that sentence.

I had a loosely and roughly framed out business concept with an equally loosely framed out rationale and business model… which was, at the time, being… uhh… allowed to ferment…umm… in my head.

So, I wrote a presentation. Met him on the appointed day at the rather swank-at-the-time Plaza Hotel. It was elegant and hoity and the crowd was monied. The breakfast was lovely and very clinky.

‘Clinky” is when all around you, nice little silver spoons are stirring pretty little tea cups and tasteful glasses with orange or grapefruit juice are being picked up and then made to accidentally bump water glasses on the way back down.

I walked the investor through my presentation. I assumed there would be requests for more information and the need to speak with others and probably the casual mention of something I would, of course, have to do which was just routine and had some nondescriptive name like “Filling out an RV-19” or something - to which I would smile almost to the point of chuckling as if I not only knew what an RV-19 was but had filled out so many, I was, of course, now casually dismissive about them. “Hahah, yes, of course. I’ll shoot you over an RV-19 by COB. Boilerplate fine?”

Nope. No RV-19 required. Instead, he finished eating and said “I’ll give you $300k of seed money and an office. You can come up and finish your business plan and get going.”

And it was at that very moment when the two halves of my then-being bid an abrupt adieu.

At the table was my physical being with its belly full of coffee, scrambled eggs, bacon, toast, and a very nice jelly.

Somewhere atop a distant high mesa near a coastline known for its updrafts though was the possible me.

The one with all of the confidence, ambition, and aspiration.

The possible me would not be returning with the physical me to the office unfortunately. Nor would he be meeting up with us later.

That one had been freaked right the fuck out by the opportunity to potentially fly even after having been the one who had sought it.

I turned down the money and the opportunity. I passed on my own deal. I had some mitigating excuses but the truth was - and is - that I had blinked.

Leaping is hard.

Two years later, I “went out on my own” but no matter how much I thought I was ready, I wasn’t.

Two years later, I joined up with a friend as partners in a small business. Tandem flying! That time, it wasn’t me who hadn’t been ready to really leap but the result was the same: I was back to working at a big ad agency.

Meanwhile, as I pretended each day to give a shit whether Old Navy sold more sweatpants or Sprint increased self-reported brand satisfaction among the coveted Digital Trendsetter segment, several of my possible me’s had now been reduced to headstones atop the cliff and were now being bleached white by the same dry winds that colorful hang gliders were using to wheel exhilarating circles out in the currents just past the cliff’s edge.

All those times I told people “The leaping is the hard part.”… It was because I had been too scared to myself once… and then not ready to ride it out another… and then not able to when someone else was the one terrified.

And I was a bit terrified this time too. Were it not for my son, I would almost assuredly still be stuck in the exact same place I was when he and I had the conversation I wrote about in my first entry.

It took months from that conversation for me to leap. But then I did.

And just like I had already known firsthand and had told people for years, it was the first step that was hardest.

Once you are in the air, you’re already committed. You’ve already crossed a boundary most don’t. You are now in a far smaller population: people who jumped off the cliff.

You’ve crossed from one side of a Newtonian principle to the other. An object at rest is now in motion.

Since then, I’ve posted 50+ things. Together, they add up to just over 100,000 words. That is the length of full novel. That total could probably have been cut down to 60,000 and been better.

I’m learning. And that is exhilarating and challenging and awakens you. That’s the joy of hang gliding, I imagine.

That’s the good stuff.

It isn’t all good stuff though. And I’ve long known that too and have described it to friends and been through it and seen it firsthand.

“After you’ve made the leap, at some point, you’re going to hit a wind shear. You’re going to wake up in the middle of the night worried about money or whether you can do it or something. You’re just going to have a moment of beingly suddenly terrified – even though you’re already in the air. And that’s when most people turn back and make a flight to safety.”

And it 100% is.

There inevitably comes a moment when your stomach drops out and all of that exhilaration and excitement vanishes as you suddenly realize you are a thousand feet above the ground and at risk.

I am in that moment right now.

For the last two nights, I have woken up at 5 am and then 4 am with just an agonizing anxiety.

I had been making steady progress toward an eventual point where I can breathe a little without having to panic about whether I will be able to keep doing this in a few months. I had an entirely reasonable and measured set of thresholds that were really meant to be a safety net of sorts… “As long as I can get to here by such and such month, I’ll be okay…” with the unsaid being that “okay” meant “okay to keep chipping away toward sustainable” not “already fine but could be better.”

All of the Twitter fuckery has flatlined what had been at least a modest upward slope. Realistically, rationally, I believe it will be okay. I believe I will figure it out and stay within “okay” – or figure out how to keep flying until I do. I believe that.

It is fear. It isn’t worry. It is fear.

Emotionally though, I was in the parking lot of a not yet open Dunkin Donuts at 4:45 am this morning standing outside my car because I thought I was going to puke.

Wind shears are terrifying. This one I’m in right now has been a real shit sandwich.

This is the moment when someone who has already leapt off the cliff either makes a flight to safety or doesn’t…

The first moment when they are scared to death - and out of the blue.

That’s when you see whether someone wants the dream enough for the nightmares.

While I would have really preferred to have not greeted the new day by dry-heaving in a Dunkin Donuts parking lot before they were even open for business today, I don’t have even an ounce of impulse toward a flight to safety.

If I ever have to give this up… if I ever have to abandon being a writer, it will be a death. It will come with a grief that I will long mourn and maybe never get over.

This chance has been a reprieve of sorts. When I was in college, I was an English major with a concentration in creative writing. I can tell you, it left me with no impulse whatsoever to want to even consider writing or being a writer for a living.

At the time, ADHD was called ADD. And ADD meant a child who couldn’t sit still not an adult who finds it harder than most to do certain things due to a treatable neurochemical inhibition which can easily be misinterpreted as laziness or procrastination.

My recall of that time and those classes is that I wrote few stories over the semesters; liked having written them once I had; but had found it painful to pull them out and put them down.

I remember the pain of it stripped of the joy.

And that is a very ADHD thing. It makes some things torturous… and then it leaves you to torture yourself over why you can’t just find them easier like everyone else does.

All of these years, whenever I thought back on writing classes in college, the overarching feeling I remember is discomfort.

Decades later, color me shocked to be waking up every morning wanting to write and liking it and enjoying the challenge and feeling like it is just my purpose…

So, they won’t get me back on that cliff without dragging me screaming – first, from the air; and then up the rocks.

What’s a little terror.

Thanks for being here. I appreciate you.