What I learned from sending 20 personalized letters (with Starbucks gift cards)
Hiii friend …
No cash flow tips or org charts today - just a vulnerable behind-the-scenes story that reminded me why rejection is just part of the job.
Earlier this summer, I did something kind of crazy / bold.
I made a list of 20 businesses that I’d love to work with and painstakingly drafted two-page personalized letters to each business owner accompanied by a $10 Starbucks gift card (I kid you not - the only ‘template-y’ part of the letters was the closing paragraph lol).
You see friend, I wanted to find a memorable way to reach the people I wanted to work with that wasn’t just another email that would probably get deleted because it was full of emojis and em-dashes (thanks ChatGPT 🫠).
So, I started mailing five letters per week and anxiously checked my email Inbox regularly to see if anyone reached out. For context - the “ask” was to email me to book a coffee IRL or virtually.
When no one wrote back…
After three and a half weeks went by without a single acknowledgement email, I won’t lie - I felt a bit dejected. And embarrassed. And so I spiralled (of course).
“Do people really not want to work with me?”
“I need clients for the fall - what am I going to do?”
“I’m better at my job now than I’ve ever been.
So why did I have seven clients four years ago… and only one now?”
You know… the usual lol.
But then I gave it another few weeks… because.. we're talking snail mail here lol. And in the end, four people reached out:
One person was interested in working together and sent an awesome email detailing what she’d like to accomplish so we're talking about that now (yay!!!!!!!),
One person said “let's chat once things have slowed down over here” (fair but also YAY),
Another person said “thanks, but no thanks” (got it!) and
The fourth person said they'd love to do coffee IRL when I’m in their city next (great!).
Why I’d still do it all over again
Now, a lot of (normal) people would look at this situation and say - you only heard from four people so that means you wasted A LOT of time / money printing personalized envelopes, drafting letters, editing letters, printing letters, buying gift cards, buying stamps, stuffing letters and then mailing those letters out to 16 businesses.
But not me. After recovering from my premature shame spiral, I was honestly pumped that four people got back to me. And I might even end up working with one or two amazing businesses as a result.
Yes, it was a massive time investment for me - to the tune of 29hrs (and, NO, we’re not doing the math on my hourly rate x 29 lol….).
Yes, I was disappointed that certain people didn’t respond. There was one business in particular I really wanted to work with - I spent way too long on their letter - and I never heard a thing. I still kind of hope they have it pinned to a wall in their office somewhere haha.
Here’s why I’m sharing this:
We don’t talk enough about how often we hear “no” as business owners.
Not just from potential clients - but from:
A potential buyer for your business who says it isn't worth half of what you think it is
A past client who gives you a three-star Google review after you went above and beyond on their project
A current client who says “no” to your proposed plan to help them with ABC so you have to go back to the drawing board (at your own expense)
A warm lead who says “no” to your lunch invite
A trusted team member who leaves for a competitor you basically trained them for
A long time client who complains about the amount of their bill
It’s easy to feel like rejection means you’re failing.
But honestly? It just means you’re trying.
And you’re probably braver than most.
So if this hits a little too close to home…
Here’s your reminder, friend:
Keep going. Keep showing up. Keep putting yourself out there.
Whether you’re writing letters, pitching new services, or pricing a 6-figure proposal that makes your stomach flip - this is what real leadership looks like.
And I promise: the right people will eventually say “yes” (I know - I'm talking to a few of them this week 😉).