Beyond The First Summit: Mishka Shubaly and Greg Larkin on JUST PRESS RECORD

I realized that if I didn’t leave at 40, I’d be wholly trapped by 50. And it’s not like it wasn’t going to hurt to breakaway. It was just, what did it mean - to me, for me - to stay?

I did the corporate thing like I thought I was supposed to do. I quit the music and quit the friends and (quite effectively!) quit the fun parts of life in my mid-20s, and if I’m being honest, which I’m really trying to be here, I started saying “OK, tell me what to do.” I was lost. I had no clue. I figured these other people I was meeting did. I didn’t know I shouldn’t believe them. Or, rather, I didn’t understand what I should believe from them. But like everything, it’s a journey, and you learn more from stubbing your toes than from their rules of thumb.

It took me 10 years to basically do what they told me I could do in 5, and, lest I forget, what they regularly teased “Oh, but if you’re really good, like so-and-so, you can do it in 2.” Yeah, it took ten years and I - even then - had nothing to show for it. A handful of friends, a bunch of knowledge I was less than half putting to use, a pile of debt, a disaster of a personal life, and some fancy plaques with each promoted title signaling I made it to top it off. IT. But, what was it, exactly?

Sure, other people were happy to tell me what “it” was. Almost unilaterally in terms of what IT meant for them. But that’s corporate life for you. I had everything but my soul intact. I had everything but anything. I had a therapist who, when she asked me, “so who do you talk to about this stuff,” I very un-matter of factly told, “You. I have you. That’s what I pay you for, right? No? I’m being serious, I’m sorry if this sounds like sarcasm, but it’s not. This is why I hired you. I’ve got nobody.”

Greg Larkin, the smartest rebel on Wall Street just before the financial crisis changed his life all those years ago, the founder of the community Punks and Pinstripes, he’s got an expression for this. He calls it the moment “All the trophies felt like atrophy.” And Mishka Shubaly, the rock and roll Bukowski of walking through the fire until you’re sober and undeniably scorched but still inexplicably living, he went through a version of it too, when he finally had some money in the bank and resources at his disposal and recognized, “I’ve completed my psychic job list… what the f*** do I do now?”

There’s a shortage of sharing these stories. I mean, hang out in a bar with a bunch of 40+ year old’s and you can probably hear a thousand of them, but we don’t celebrate them. They’re sad and ugly and full of lost jobs and divorces and figuring out how to cope with our deeply personal inabilities to cope.

It’s not true of every successful person. I’m not saying it’s even the norm. All I can say is that I was meeting an above-average number of people on my journey who had successfully papered over their troubles. It wasn’t everybody. Just, a lot of them. A disheartening amount of them.

I realized I had some wonderful friends who I watched go through their own spectacular disasters too. My therapist helped me realize it. She helped me start to talk to them. But up until that path started forking out and away from their goals and metrics for me, I assumed all the other ladder climbers found the one and only way. Like they knew the truth. The TRUTH. And what they knew was - you just make more money about it. That’ll solve the problems of your s****y kids, your s****y ex-wife, your s****y new wife, your s****ty golf buddies, your s***. Success was proved by money, so make more of it, and everybody wins.

I’m bringing up Greg and Mishka because of the conversation we had on Just Press Record. Greg talks about how the first mountain of our careers is all about knowing the goals, getting the external validations, seeing the metrics of what success is and looks like. He had it (and you can listen or connect with him on LinkedIn for the story, or read “This Might Get Me Fired: A Manual for Thriving in the Corporate Entrepreneurial Underground” which is fantastic), and he felt what followed: the valley in between.

Mishka was there too. He’s got books (and books, and stories, and songs, and - he’s prolific - but seriously, try “I Swear I’ll Make It Up To You: A Life On The Low Road” if you need to know), and when that book money started hitting the bank account, it was like a magic trick. Luckily, he had cleaned up some, and he was on his way to building something he didn’t blow up, but that doesn’t mean you understand what you’re supposed to do next.

So what are you supposed to do next? For me, it was leaving a corporate gig for a small company that would allow me to pursue all of my side pursuits while still doing the core client work I didn’t hate myself for doing anymore. No product pushing, no sales quotas, just get paid for good work by good people and then make the world a little bit better of a place. The Personal Archive project was my path out and through, but I’m still trying to work out where it’s leading.

Not unlike Greg and Mishka, but they’re definitely more than a few steps ahead of me too. Which is a big part of why I wanted to get them together, as you’ll see. Because Greg told us, and Mishka had the reaction I did, that after the first mountain, you have to choose if you’re going to leave it for the second mountain.

All those executive types I watched juggle their s*** while telling me how to do it, they turned around went up the first mountain again. Again and again. Over and over. Miserable and misery-land-sliding, luxury-leased(!)-auto-avalanching, and over-priced-country-clubbing with people I’d rather be dead than hang out with along the way.

Greg told us - there’s a second mountain. And when you climb that one, you don’t have any of the goals or other external signposts anymore. The only job you have on the second mountain is to open up “the miracle window.” It’s where the opportunities come in. It’s where things you know and believe to be true hang out. And your biggest job on the second mountain is to make sure you and the people you care for have access to this new window that doesn’t exist on mountain number one.

The second mountain is where we find purpose. The second mountain is where we let go of the purposes prescribed by others, for their self-interest, and our own self-aggrandizement, in favor of, an open window, I guess.

My miracle window was right under my nose. It was in this Personal Archive here. It’s definitely in the Just Press Record episodes, where I’m introducing other people just to see what happens, and just to explore how any of us might help any of us in any way. My miracle window comes when I connect people and ideas together. The tying of the ends. The facilitations of introducing people, or helping put two things together in a new way. It’s created all sorts of new opportunities for me on this journey.

And that’s a big part of why I know exactly what Greg means. And I know exactly why Mishka has found some peace and is in the spirit of reaching out to friends of friends when they ping him to come on podcasts. The success of the second mountain, the reason we’re on it, is because we survived the first mountain and we ain’t never going back.

If you put the time in, and you’ve gone up and down the first mountain at least once, you’ve got the option to get off and start up the second mountain.

It doesn’t require you’ve had a ton of success (although it doesn’t hurt). It likely requires you’ve at least figured out how to live somewhere within your means, and value your time. I left a corporate gig with a ton of debt, a bunch of personal messes, and hardly much more than the knowhow that I could work my way out of all of it if I just kicked the bad bits out of my life, and that’s exactly what I did. It cost me way more than I had, but, I’m building it back. The miracle window is funny like that.

And once you’re on the second mountain, you can start shifting your attention to your miracle window too. There are opportunities outside of it for you. There are opportunities outside of it for the people you want to help, on whatever mountain or valley they’re on. It might be in some version of a Personal Archive of your own. It might be a connection that’s there that you just can’t see yet. But, I’m positive, it’s going to come from allowing you to do you in a way that takes care of your people that you feel genuinely proud about.

Figure out which mountain you’re on. Make your choice what’s next. And, if you already know how to open your miracle window, keep that open and shout outside to the others. They’re waiting. They’ll be listening, if you can catch their attention (and you can, I’m sure of it).

Check out this conversation between Greg Larkin, Mishka Shubaly, and myself for more, out now on Cultish Creative YouTube or wherever you get your podcasts: