From Brokeass Writer to Businesswoman — Or, How I Lost My (Two Silk) Shirts, and Still Reached My Income Goal for June (And How You Can Too!)

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 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,



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17 Responses to From Brokeass Writer to Businesswoman — Or, How I Lost My (Two Silk) Shirts, and Still Reached My Income Goal for June (And How You Can Too!)

  1. Linda July 1, 2013 at 1:34 am #

    Hilarious. Love your analogies, Rachel. Your stories are always so vivid that I feel I’ve just been whisked into your world. Thanks for being such an entertaining tour guide! xx

    • Rachel August 16, 2013 at 1:17 am #

      Linda! You’re such a sweetheart to post here! That’s high praise coming from you about the analogies, and the vividness. What a lovely comment. So cool, the idea of being a tour guide. Thank you!!! xo

  2. Jason Hartanov July 1, 2013 at 7:37 pm #

    Great story and narrative. Those shirts were bought when you were at a different consciousness…you up-leveled and the shirts ran away…like the scared little posers they were. You get to buy new shirts that match your new energy…can’t wait to see you in them. Congrats.

    • Rachel August 16, 2013 at 1:18 am #

      How generous of you, Jason! Love your sales-sharp analysis — full of verve and insight as ever. Ha! Shirts as scared little posers! Perfect. Will let you know what new shirts come my way, and for sure wear them when next we meet. Hopefully soon. Thanks for your warmth and support!

  3. marina borawick July 2, 2013 at 3:07 pm #

    i always thought you looked particulary good and “rachel” in your cool t-shirts. i think you should wear those to your entrepenurial gatherings, paired with some nice jeans/khakis. just wear some expensive jewelry. that’s what i do.

    • Rachel August 16, 2013 at 1:20 am #

      Marina! That’s very cool to know it worked with the T-shirts. I do feel so comfortable in them, and fancy myself more rocker than corporate. The key is the expensive jewelry. Great tip. Thanks!

  4. Laura July 3, 2013 at 11:22 am #

    Yesterday I found six bucks under my bed while looking for my cat, who was in the closet, somewhat ironically, lying atop a silk shirt.

    When I was young and had no need for money of my own, I used to find it all the time. Due to god’s rather sick sense of humor, that magic ceased at the exact moment I became an adult and needed to make money to support myself.

    I am hoping that my six dollar find is the beginning of a new phase of money magic for me.

    • Rachel August 16, 2013 at 1:22 am #

      Laura — that is so wild about finding the six bucks while doing something totally other — and there the cat is, in the closet, lying atop a silk shirt. Love! Also soooooo interesting how you just used to find money all the time as a kid — and didn’t need it. And now — that the magic ceased. Well, it sounds like it’s started again for sure. Keep us updated. I also sense…there’s something else afoot, or underneath (or in the closet!) with this story…our money stories are so complex, aren’t they? Should post on that too…thanks for the idea! And do catch us up on your journey.

  5. Daniella July 3, 2013 at 12:23 pm #

    I love your vulnerability in this piece. You rock, my sweet friend. Keep drivin’ on!

    • Rachel August 16, 2013 at 1:22 am #

      Thanks for your warm and thoughtful post, Daniella! You’re such a great supporter, and always give me hope. Yes, onward indeed!

  6. Lori July 6, 2013 at 1:02 am #

    Rachel you are so brave it inspires me. Love your lust for life.

    • Rachel August 16, 2013 at 1:23 am #

      Lori! Thank you for that incredible compliment. Love that you find me brave — and thanks, too, for seeing that lust for life. I feel lucky. xo

  7. dominica July 22, 2013 at 1:06 pm #

    great story. i am sort of glad you lost the shirts because you totally were worthy to be at the biz meetings without them. sporting a kick ass t or tank. yep.

    but….i understand the principle. look good and ppl seem to think you are better.

    but you are not.

    i am more interested in your ability to help me tap into my own vibrant voice and story!

    no matter what you wear!!!

    great story by the way. you totally inspire me to do something different. grow. learn. dig deep.

    thank you


    • Rachel August 16, 2013 at 1:26 am #

      Dominica! Soooo glad you dug the story! Very cool take, too — that somehow losing those shirts was a sign I could still show up to those meetings and be okay. Enough. Worthy. On the other hand, yeah, I’ve experimented and it’s wacky but people really do respond differently — with different clothes, hair, you name it. Fascinating. Also sooo glad you’re more interested in how to tap into your own vibrant voice and story! Clearly you have it all. I hope you are doing something different. Growing. Learning. Digging deep. Let us know! Love to hear your news. Thank you for this beautiful post.

  8. Rachel August 16, 2013 at 1:27 am #

    So honored you pinged this story! Psyched you dig personal stories — and that you were moved enough to share this post. Thank you!!!

  9. Prabhu Tharmarajan May 29, 2015 at 7:06 pm #

    A great story Rachel, I enjoyed reading it and I think it is awesome. Thank you for sharing this post.


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