Losing One's Shirt:  A Selfy in Service of Entrepreneurial Risk

The Liberation of Losing One’s Shirt: A Selfy in Service of Entrepreneurial Risk

Two silk shirts — one fiery red, the other dove grey with psychedelic blossoms edged in peach piping — gone.


Last I saw them, they were laid out on a chair on the deck to make room for the cleaning lady. But the cleaning lady didn’t come. Apparently I’d gotten the day wrong. So I brought the stack of clothes back inside. Minus the silk shirts. Where did they go? Did I imagine they were on the deck chair? Did I have early onset Alzheimer’s? Did someone steal them? I called the drycleaners. No silk shirts. I searched high and low. No silk shirts.

(Pause) Let me explain. These silk shirts equaled success in my mind. They were the most expensive shirts I owned. I bought them to wear at all these entrepreneurial conferences I’ve been attending the last two years. I bough them to help prove I belonged in the new world of Business People even when I didn’t feel worthy. I left my Brokeass Writer tore-up Blondie T-shirts at home. What did it mean that the silk shirts disappeared? Did it signify that I still felt I didn’t belong? Was this a mindset problem? Or a fluke?

When a chick loses her shirt, it’s not the same as when a guy does.

There’s shame involved for a woman. There’s no opportunity for an Abercrombie & Fitch softcore porn moment here of a bare male (teen) torso. When a girl loses her shirt…it’s degradation. It’s exposure. It’s a mistake.

I dreamed the silky shirts blew away down the hillside. Fluttered down the steep rural slope like banners advertising a colorful, opulent world, full of treasure chests, gold flasks and silken fineries. They got stuck on palm trees. Wrapped around cacti.

But the next day, I searched the grounds high and low and found nothing. The silk shirts vanished.

Then it hit me. I’d lost my shirt. TWO of them! I was a living idiom!

According to Cambridge Dictionaries Online, losing one’s shirt means losing a lot of money, “especially as a result of a bet = money risked when you guess the result of something.”)

I’d just stepped up to a new level of investment and risk in business training. Talk about gambling! I was terrified I was a fraud. That I wouldn’t be able to make the payments. That I was a failure. Less than. Naked in my exposed inadequacy.

I took a deep breath. Talked with my business coach, supporters. And made a decision. A narrative decision. This is my story. And even if one angle comes my way, I can choose to dismiss it. I chose to laugh. I chose to enjoy this crazy real-life manifestation of my fears that I couldn’t succeed in my new money goal after decades of inhabiting the tender skin of a brokeass writer. And then…

I let those silk shirts fly away down the hill, never to be seen again.

Risk is part of growth. You can’t avoid it. Especially if you want to rewrite your story. We humans are wired for challenge. Not overwhelming, impossible challenge. But appropriate, stimulating challenge that invites us to step into our higher selves. The next stage of development. A larger arena.

What I know now is that I can lose these two silk shirts, and still be okay. I can earn more money, through standing in my value as a messaging and book mentor — and taking the actions that constitute a business. Making those scary and necessary asks. And…

I can buy a new silk shirt. Or two.

How about you? Are you avoiding growth in your business and creativity? Are you saying no to challenges that would help you break through your stuckness? That would stimulate your sense of your own worth and possibility? What if you took the risk? Could you let go of your shirt?

I’ve let go of two. Got back into action, making calls, making asks, gunning for my June goal along with my bigger goal of helping entrepreneurs let go of boring messaging and tap into their own vibrant voice and story. And I’m still here.

I’m still offering complimentary 20-minute Message Makeover calls for a limited time. Why not take a chance? E-mail me at info@writersonfire.com with Message Makeover in the heading.

Remember — a steady job is the new risk. Entrepreneurship is where it’s at. Come join — creatives and corporates alike. The water’s fine. And even better on bare, naked skin.

Yrs in truth,