Your Checkered *Present* Is Calling.

Whether it’s the first time, or if it’s just been a while, let’s connect and get to know each other (better) as humans.

1. If we haven’t connected yet, connect with me on LinkedIN. I post some super useful stuff there, as well :)

2. Put 30 minutes on my calendar to chat. No strings attached, whatsoever.

Let’s get to know each other (in many cases after not chatting for a long time) as humans, friends.

Of course, if there’s something I can help you with, just ask and I’ll do whatever I can to ask.

Here’s my calendar link, again.

Don’t be a stranger, friend.

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In this issue: A Checkered Present - And Why It Shouldn’t Stop You from Action

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A Checkered Present

Look, I don’t know if you need to hear this, your friend or family member.

Maybe this is just a PSA of myself being a work in progress.

While you were so consumed with your checkered past, your whole life went by in a flash.

An eventful life, to be sure.

One with many things to celebrate and be grateful for, to be sure.

But still a life where you’ve stopped yourself - maybe even sabotaged yourself - repeatedly from acting (or finishing to act) to do what you need most.

Let me explain.

I don’t have my MBA, so I can’t start a business.

I don’t have enough work experience to be an exec here. 

Who am I to write this book?

Who am I to do stand-up comedy? There are SO many funnier people than me out there. 

Who am I to invest in cool startups? I don’t have much money or industry knowledge.

In short, who am I, what am I, why should I do this, who should even care?

Anyways, I have a checkered past.

WHOOOOW there, cowboy/cowgirl.

Slow dooooown a minute.

First of all, seriously… who cares?

We’ve all got issues. Past, present, future.

Who are you to presume you’re the only one with issues?

LOL.

No, but seriously.

We live in a time when (outside of guilds like law, finance and medicine, which are also eroding in their self-importance - thanks, AI and outsourcing to India and China)…

When tastemakers are largely self-determined.

Hell, even the likes and blue check marks and all that.

But behind this grandiose-sounding self-determination, there lies a dark streak.

We’re all pressured to show a “good face” to the world, a picture of health, wealth and importance.

We always have to be in our Insta-life, or else we fall behind in the estimation of others.

So much for “freedom.” Looks like just another kind of slavery to me.

And what to do now?

Pssst… little secret for you.

A few basic things I’ve learned definitively from coaching more than 2000 clients in the last decade?

Firstly, EVERYONE feels like an impostor.

All the way from the CEO on down to the analyst.

Secondly, few to none of us really, truly “have their shit together.”

Not the Insta-model who does coke and is forced to fight for her place in the pecking order.

Not the tech billionaire who has few to no real friends.

Not even the time management or habit guru whose book you read.

You know why?

Because it’s insanely hard, next to impossible, to have all areas of our lives even visible, never mind in order and running smoothly.

Humans are insanely complex creatures, even those that seemingly know themselves and human nature super well.

Personally I may do my damndest to have things together, but I fall down a LOT of the time.

Unpaid bills, parking and traffic tickets, a million missed opportunities, a ton of missed signals, lack of consistency in business, and so on.

Don’t get the wrong impression. I’m all about transparency, but I also have an ego that gets bruised. Not as easily as in the past (thanks, NYC and Israel and life, in general), but still to some degree.

I can (in theory) blame ADHD, trauma, high sensitivity, the neighbor’s dog or the roaming wild pig in the yard.

But neither my explanation, nor my equivocations are worth a damn.

You know why?

Sure, accountability. But it’s more than that.

I grew up holding myself (and yes, other people) to insane, impossible standards.

In intellectual inquiry, in books, movies, science, women, food, etc.

Even though I grew up without much means, I always found a way to get some little morsel of haute cuisine from Fairway or Zabar’s or Whole Foods.

I was always the tastemaker and cultural and culinary GPS for all my friends.

Nothing to sneeze at, I loved it.

But my spiritual life was shallow, even if growing.

My financial management was poor to non-existent.

Same for career management, time management, relationship management, lack of boundaries, and a million other things.

But I played someone highly functional yet artsy, an author, lawyer-in-training, etc.

I talked too much, drank too much on occasion, went through all sorts of upheaval and self-doubts and career changes and being super-broke.

The vast majority of people just saw me as an artist, an author, someone who knows about art, food, is someone to talk to about interesting things, someone who gets how things work in life.

But most of it was a facade of curiosity hiding a lot of hidden trauma and misery, being broke and living way above my means and essentially hoping for the best, without having a clue about how life really works.

Sad. But also, it was a young man doing as young men do, things that are unsurprisingly typical for the hordes of young people who come to NYC for more than a few weeks or months.

The shit hit the fan far too many times for me to count.

Sometimes, the fan just broke down. I had to move back home to Mom for 2 months at one point. Couldn’t afford rent, etc. $250K in debt from law school, with no bar.

Yeah man, crazy shit to live through. And no magic salve or rich uncle came along to pull me out, either.

And you know what?

I don’t claim to have achieved any sort of nirvana or ultimate realizations about life or any sort of F-U money (yet, at least).

Just something like a semi-stable steady state that can function as neither totally conclusive nor totally delusional.

Based only on things that I can conclude from my life experience, having the benefit of my own brain and perceptions.

I may have written a book or two (4) collecting a lot of wisdom from various masters and stitching that wisdom through with stories and horizontal integration, but that is more or less just to make sense of the chaos within and how I’ve dealt with it using a massive spectrum of tools, strategies, frameworks, conventional and contrarian wisdom from various quarters and fields.

My point here?

The checkered past is practically a guarantee with all interesting, successful people.

The real breakthrough comes when you realize that…

Your present is checkered too.

And that’s totally fine!

Even healthy, to a large degree.

Wealth doesn’t “save” anyone from the forces of human nature or aging.

Success doesn’t inure or cure all self-doubt or trauma.

Titles and achievements don’t erase the emptiness and loneliness one feels without true friends around.

None of the sturm-und-drang of daily existence off the social grid is in any way a handicap or shame.

The dignity of the daily fight for truth, freedom, a paycheck, for a place under the sun, is noble and more than sufficient.

Sufficient for what?

Sufficient for any sort of “eligibility” to not feel like an impostor.

Sufficient to write a book, start a podcast, to let the world know what you think or what you’re working on.

More than enough to go for that job you really want that seems out of reach.

More than enough to go for that girl or guy who’s “way out of your league.”

More than enough to get past whatever trauma, baggage, lack of means and rough circumstances, even if it seems impossible now.

It’s imperative not just to make peace with your “checkered past.”

It’s time to make peace and embrace - your checkered present.

Don’t be stuck in that no-mans land where you sort of embrace yourself, but also keep the present from your friends.

Sure, many things suck and are far from your expectations.

But so what? As long as you can find happiness and joy and gratitude from at least something good in your life (I guarantee you have at least a handful of things that do), you have hope.

You have motivation, drive, a ray of hope, a burst of sunshine, something to keep you going.

And never again, should you need to ask for permission from anyone to go for anything you want in life.

You certainly have mine, if you ever needed it! :)

Look, even for all my checkered past and challenging present, despite all the baggage and challenges and massive debt and relentless demons I have, I somehow went for the girl (and married her), wrote the books (7, so far), built the business (2), got in over my head to all sorts of crazy adventures, but still survived (thank G-d).

I have no illusions that any of the business or career stuff amounted to anything so special, but 6 careers in, it’s certainly been interesting and curious.

If I could do it, despite all my excuses and equivocations, I’d venture to say, you’ve got no excuse to at least not try.

Whatever I can do to help, I’m here.

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My Offer:

Put 30 minutes on my calendar to chat. No strings attached, whatsoever.

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