Are You a Spiritual Gangster?

My friend, Cheryl, invited me to hang with some friends I hadn’t seen in a while when we ran into each other outside our kids’ school at the end of last winter.

When I politely declined, she asked me what was up…if everything was o.k.

Everything wasn’t o.k. It was the middle of a New York winter, the holidays had been stressful, the side of political conversations at every meal had given me chronic indigestion, friends didn’t seem to understand me anymore, and, in my business, I had to make some tough decisions I wasn’t expecting to have to make so soon.

When I said I wasn’t feeling it. She smiled and shook her head, “You’re cleaning house aren’t you?”


I didn’t know what to say. Ironically enough, Cheryl and I were born in the same place, grew up in adjacent neighborhoods, and ended up here, on City Island, with a population of less than 5,000. What are the odds?

Maybe we get each other so well because we come from the same place or because we can crack each other up with jokes about what it means–or doesn’t mean–to be cosmopolitan or street smart. She knows how hard it is to cut loose from the people and places that no longer serve, to come out of the proverbial closet, and to “clean house” to stay true to your instinct for growth, to do what’s best for you, to stop letting other people–no matter how much you love them–hurt you, play you small, or drag you down when it’s so clear, now more than ever, you need to lift each other up.

She understood exactly what I was going through.

“You know what you are?” She asked me after a moment’s pause. You’re a Spiritual Gangster.”

By now, I know that these two words are pretty popular out on the West Coast. Spiritual Gangster is the registered trademark of a “yoga inspired” clothing brand too; they made the tank I’m wearing in the featured photo for this post. I’m not an affiliate partner, I’m simply spreading the love.

At the moment, it seems to me the best stardust is free.

Their t-shirts made my day, Cheryl’s too, when I bought us both one– takes one to know one and all that jazz–from a boutique I was browsing in Larchmont last spring.

I hadn’t ever heard those two words strung together until the day they came tumbling out of Cheryl’s mouth. When she spoke, I got that chill that runs up the back of my spine when I’m writing with a client who speaks the truth their audience needs to hear.

“I see you. I get it,” she said. “You gotta do what you gotta do. I got you.”

Once a mussel-shucking village, City Island is an anomaly. A weird little town that’s part city, part New England seaside. Nowhere else in the world are people categorized as Clam Diggers or Mussel Suckers depending on whether they were born here or live here. It isn’t unusual to see a waterfront next to a bungalow, a bodega next to an art gallery or a boarded up storefront next to the theater group’s impressive window display.

Like the name suggests, City Island is about mixing up two things that wouldn’t ordinarily go together. City Island, Spiritual Gangster, something about them rings true: both names have range, do away with dichotomizing, create their own meaning, give way to interpretation and self expression. Ever since Cheryl and I met on the sidewalk that day, I’ve been thinking about what it means to me to be a Spiritual Gangster. I broke the term in two. I started with Gangster, worked my way up.

By the time I was five years old, I knew the difference between a Wise Guy and a Wannabe. It was a game my father taught me to play on our walks home from the neighborhood bar he sometimes took me to on Sunday afternoons. It required me to keep my eyes and ears open (while I chalked pool cues and drank Shirley Temples), to keep relatively quiet in the moment and share my observations with him later.

To be clear, my father didn’t want me mixing it up with either type.

Wise Guys had expensive clothes, nice cars, and tons of charisma but at the end of the day, their success (if you call it that) was achieved on the backs of other people. They left a lot of carnage in their wake. And Wannabees? Well, they had nothing they could call their own, no moral compass, no backbone or stability. Destined to ride the coattails of their cronies indefinitely, doing most of the dirty work, with little to show for it. If they lived, and that was a big if, they were going nowhere.

“Better to find your own way,” my father always said.

Growing up, I never quite understood the mass appeal of movies like Goodfellas or The Godfather where these nuances got teased out with such intensity I often had to excuse myself during the more disturbing parts. Like everyone else in my family, I loved these movies but, unlike the others, I loved them with a tangled mix of pride and shame. “She’s too sensitive,” I’d hear them whisper on my way out of the room.

And, as I got older, there was an intellectual component too; like lots of Italians,  I took issue with the prevalence of the gangster archetype as a way of illustrating loyalty and passion. Writ large on the big screen, such portrayals are barbaric and uncivilized. What about all of the Italian artists and scientists? Why keep glamorizing violence?

“Why can’t you just enjoy the movie?” My father would ask. “They’re some of the greatest movies ever made and you have to go overthinking them. What about the Italian actors, aren’t they artists?”

Yes, of course, the actors are artists. And, true, I have a tendency to overthink, especially when I begin to judge my feelings, believe they’re too much, stuff them down or, worst of all, ignore them.

What did people who weren’t Italian get from these stories? I wondered. Why weren’t the people in my family as disturbed as I was by the brutal killings?

“It’s just a movie,” my father would say and I couldn’t quite wrap my head around the notion that the dynamics I was seeing play out before me on the screen weren’t real. How could they be so riveting, have such mass appeal, if they weren’t true?

If we didn’t see a part of ourselves in the actors and actresses why did we continue to watch?

Had my father encouraged me to see the mafia plot as a metaphor, maybe I’d have understood. Mind you, I never expected this of him; literature has never been, and likely never will be, his thing.

On the page, the closest equivalent is taking Faulkner’s dictum to “kill your darlings” seriously. In the garden, it means snapping off the heads of waning flowers, cutting the weakest rose stems, snapping off the smallest basil leaves to prevent seeding too soon, hacking off the yellowed arms of the tomato to strengthen the rest of the plant. In your diet, it may mean saying no to wheat, sugar, alcohol, and excess, even when you “love” the comfort they bring you.

It means clearing the clutter in your closet, your heart, and your mind.

It means letting go of what isn’t going to get you where you want to go.

As I began to play with what the term Spiritual Gangster means to me, I realized there are Wise Guys/Gals and Wannabes in every neighborhood and every network, metaphorically speaking. Being able to differentiate the two is a valuable, transferrable, skill. Whether the person boasts a library full of rare and interesting books, a network full of impressive connections, a list so big it makes your head spin or a seven figure business, you best have your own set of values front and center before you get caught up in the drama that always ensues when you bet against yourself.

The truly scary part? You can bet against yourself without even knowing it. This happens when you either don’t know who you are or you’re slow to reveal yourself for fear of getting hurt or hurting your chances. At what?  You’re not quite sure. You keep a lid on your self, sooth that same frustrated self with the story that sucking up crumbs, if that’s what you’re offered, is your best course of action.

Someone else, something else, always knows better than you.

If you’re about to tell me the variety of crumbs you truly enjoy or you’re justifying your identification with the last paragraph with a lame excuse you’re passing for a really good reason why you’re different, drop me a line; tell me all about it.

I will not hesitate to call your bluff.

Lie detecting is a huge part of what I do as a writing coach. It’s how I get results. Trust me, you want a writing coach that doubles as a lie detector because audiences are giant, multifaceted, magnificent, human, lie detectors.

Imagine standing in front of an audience not knowing who you are or, worse, pretending to be someone else knowing all the while it’s just a matter of time before they sniff out the real you.

That would be terrifying.

But I digress.

When I work with speech and book writing clients, you’d be astounded at the sheer number of inconsistencies we hammer out on the page. The following are just three examples I see over and over again with slight variations in detail. The bullets are samples of me speaking to the writer in the margins.

  • Careful, you said your goal was to create better communication in corporate environments but in the story you share, you’re blaming the other person. 
  • Watch it, this feels like a bait and switch.
  • Sure you don’t want to be a little more forthcoming with your personal story? Your work is built around the premise that people need a bold authentic self to share but instead of sharing your own, you’re bouncing your readers out and about with too many quotes from other people.

This vetting is painful sometimes. So is the creative process. Ask any new mother. I remember how relieved I felt, pregnant with my second child, reading Spiritual Midwifery and learning that many women in labor actually think, say, feel, they’re going to die. Thankfully, the positive aspects of modern medicine mean most of us don’t and, of course, parts of us do.

Don’t let the pain stop you. You wouldn’t be doing whatever it is you’re trying to do if things were really all that great back in your comfort zone. Creating is the fuel for your rise and until you’re doing it–the work of finding out what you really think and feel and testing it against an audience–metaphorically speaking, you don’t have a self yet. You don’t have a body of work or the intellectual property you can hang your hat on. You haven’t staked your claim. And that makes you vulnerable (and not in the good Brené Brown way).

Believe me when I tell you the pain that ensues from that kind of vulnerability is ultimately far worse than the pain of giving birth to yourself. Giving birth to yourself has rewards: your blog, your book, your new speech, your best copy yet, your thought leadership. Not someone else’s, yours.

Self aware as you may think you are, if you aren’t creating, chances are, you don’t know exactly what your brand persona wants to be and that’s o.k. We all start somewhere.

What’s not o.k? Waiting around expecting it to knock on your door and introduce itself to you. Or waiting for someone else to tell you what it is, to give it to you.

A brand is not something you can buy or know in its entirety before you’ve lived it. Go live, create, bring yourself into being. If you’re scared, be honest with yourself about that and do what it takes to enlist the help of a professional writer.

Take notice where the light comes in, where you begin to feel all of the energy you want to give to the people you serve, all the possibility. Go there.

Like all great writing, you and your brand are best discovered as you go develop big, bold, messy relationships with other people who have feelings too.

See what happens.

Go when and where your instincts tell you.

Do something that takes guts not because you care what people think, because you don’t.

Don’t try to solve an equation. Don’t get too caught up in seeking. You won’t find an answer. What you’re doing isn’t about being right. The artistic process doesn’t work that way. You need to dive in and get messy. Get your hands dirty, feel alive. Feel like you’re going to die. It is all good, even when it doesn’t feel so hot.

Like in the childbirth analogy, chances are you won’t die and, of course, parts of you will. Like a tomato plant, those are the parts that need hacking if you’re going to grow up ripe and juicy.

Juicy, not cheesy.

You want the audience to feel that together you’ve peeled away the thick skin, you’re energized by the zest that lives there, that the juicy parts you share are nourishing and energizing to them as they go about doing their own work.

You sharing you must be done in such a way that it makes your audience feel less alone.

Whatever you do, it’s important you discover something you didn’t think you knew. Or something you’ve known all along but were too fearful to admit. Your audience will feel the discovery, the truth of it. 

Creating is the only way to figure out who you are, where you stand, and what you truly value. Your value will spring forth from there. Your authenticity depends on it. If you don’t know who you are, if you can’t wrestle it down into a communicative form that can be easily consumed by audiences, how will anyone else?

If you don’t draw a line in the sand, how will you know it when you’re crossed or when you’re just plain cross? It will happen. And when it does, you need to understand it is –to use a spiritual term–a blessing that can help  you discover that other elusive A, alignment.

A business associate, friend or family member steps over the line, betrays a confidence, crosses the boundaries you’ve clearly delineated, disregards your agreement, plays you small, says one thing and does another, disappoints you yet again, what do you do?

When you don’t know who you are or you’re afraid to reveal who you are or there is a power differential in play, you wait. You hope the relationship will get better. You tell yourself it will. Out there, in the distance, are your just rewards. Surely, they’ll be yours after you jump through a few more hoops, eat a few more crumbs, earn more trust, rock more projects, work even harder for that promotion, demonstrate–for the umpteenth time–you’re a team player, do a few more favors, receive–even more–rave reviews, and time and again make your good intentions known.

What do you do if you’re a Spiritual Gangster?

You don’t steal from your literal or figurative family or rat on your friends, ever; those rules are instinctive to you. Like Cheryl and me, you learned long ago to be street smart and look out for your friends stealthily; most times they don’t even know you’re watching. You know you’ve invested plenty in the relationship. You’re loyal, schooled in solid rules of conduct, and amongst associates, family, and friends, you behave well. You do the right thing. You share. You protect.

And you aren’t anybody’s fool.

When you’re a Spiritual Gangster you have faith enough to stand in your power. You trust that you’re supported. You know your integrity—your freedom and your growth–is worth more than another pair of golden handcuffs.

You’re worth your weight in gold and then some.

You’re through waiting for acknowledgement from on high.

You know the work of rising has more to do with who and what you let go of than who and what you hang on to.

You recognize the difference between fantasy and reality. And when you spot that fantasy that’s so tantalizing in your minds eye but is doing more harm than good for you on the day to day, you know what you’re going to have to do.

You’re going to have to kill that darling.

You can love it and let it go.

You’ll be all right, I promise. Walk away.

You may feel you’re slaying a dragon. Metaphorically speaking, you are.

When you’re finished, bring it back to your self as proof.

Stand in your own light; it’s far, far, more magnificent than you previously imagined.

Consider yourself—your true family, your children, your real friends—all the love that’s wholly yours at the end of the day—worth every penny you stand to lose, every tear you’ll shed, every lesson you’ll have learned. And bask in the glory of what it feels like to move one step closer to your self, one word, one post, one scene, one chapter, one little death, at a time.