"In the business world, the rearview mirror is always clearer than the windshield.”
My business coach gave me an assignment last year that I still haven't quite forgiven.
Record all your sales calls. Then watch them.
… … … 😫
I said “ummmmm” 27 times in a half-hour conversation.
TWENTY. SEVEN.
I know because I counted. While simultaneously hating the sound of my own voice and wondering if it was too late to quit and become a barista.
***
Here's the thing nobody tells you when you start a business without a sales background, a business degree, or apparently, … a working vocabulary. You find creative ways to avoid the uncomfortable stuff.
My method was the clock.
I'd watch it during calls and engineer the conversation so we'd run out of time right before I was supposed to give a price.
“Whoa, look at that. Gotta hop to another call. I'll send over a quote via email.”
I did this more than once. More than a dozen times, honestly.
The rearview mirror on that period is painfully clear now. Sweaty palms, awkward “ummmms,” and my elaborate time management scheme … all of it was really just insecurity and self-doubt.
***
That’s the thing about the rearview — it's only clear because I'm past it now.
At the time, I found all sorts of craziness to justify my aversion:
“Not a salesperson. Hate sales. Never going to be comfortable. This is dumb. People hate being bothered with calls. I should just do everything by email.”
But after tons of practice and way too many painful watch parties, sales calls stopped being so bad.
And if I'm totally honest about why, it wasn't just the repetition.
It was getting crystal clear on what we do better than anyone else.
That’s what gave me the confidence stop trying so hard. Suddenly, I wasn't selling anymore. I was just listening and sharing something helpful.
When you're fuzzy on your offer and positioning, every sales call feels like a performance. You're scrambling for the right words, hoping to win someone over.
That's exhausting. [ And also where the “ummmms” tend to show up. ]
When you can confidently say: This is who we help … This is what changes for them … This is why it works … the call stops being a test you might fail.
It just becomes a conversation.
***
Every year brings something new that’s awkward and uncomfortable. Guaranteed. That’s just part of running your own business.
But sometimes the real struggle is just being too close to see things clearly.
Your offer.
Your positioning.
Your messaging.
Your branding and website.
If any of that looks fuzzy right now, that's a great place to start.
Let's have a conversation.
Promise, I won't count the “ummms.” 😉
Get Your Brand Scorecard
***
You really need to see this …
I'm co-hosting a webinar for my friend Laura Lopuch next Thursday.
And if getting clients is your Achilles' heel right now, you have to see what she's built.
She works 11–13 (total) hours per week …
Doesn't post on social …
Doesn't run ads …
And still starts 3–4 qualified client conversations every month.
Her secret?
A structured cold email system, backed by AI research and targeting, that does all the heavy lifting for her.
She's sharing the whole thing LIVE ( with me! 🤩 ) on April 2.
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Victory Points
By: Mike Shary
My board-game-loving, copywriter extraordinaire and mentor, Dad ❤️
Love Letters: a deduction & player elimination card game for 2-6 players
Love Letters is a fun, deduction card game where every decision feels bigger in hindsight than it does in the moment.
You’re trying to get your “love letter” into the princess’s hands by staying in the round longer than everyone else. Or by ending with the highest value card still in play.
On your turn, you draw one card, play one card, and carry out its effect. That’s it.
A guard lets you guess someone’s card. A priest lets you peek. A baron forces a comparison. A handmaid protects you for a turn. The whole game runs on a few simple roles, but every play changes what everyone thinks they know.
That’s what makes it so good. You make a choice with partial information, hoping it’s the right read. Then the round ends and suddenly everything looks obvious. You realize why that discard mattered. You see what another player was protecting. You understand the risk you should have spotted two turns ago. Love Letters turns hindsight into the whole experience, which is why it keeps pulling people back for one more round.
Branding works the same way. Looking back, it’s easy to see why a message landed flat, why an offer felt muddled, or why a competitor’s positioning was stronger. Looking ahead is WAY harder. An expert brand strategist helps you read the table before the round is over, so your message isn’t just clear after the fact, but persuasive when it actually matters.
If you enjoy quick games with deduction, bluffing, and constant second guessing packed into a tiny deck, Love Letters earns its place in your collection.
Make it a great week! 🙌
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