Last September, a woman I’d never met sat me down and extracted confessions I’d never said out loud.
That I once needed my mum’s boyfriend’s cousin’s wife to smuggle a note to a cartoonist I was too frightened to email directly. That I pitched The New Yorker every week for 6 years before they took a single cartoon. That the best career advice I ever got arrived as a 5-page email from a Pulitzer winner I’d written an email to from Perth, fully expecting silence…
Somewhere around the part where I described seeing my first cartoon in print, she typed “Why am I crying?”
That woman was Carly Valancy. The interview ran on her Substack under the title “People get things because they ask,” which is the sort of sentence that seems obvious right up until you actually try it. This Thursday, the tables turn. She’s my guest on Draw Me Anything.
Who is Carly Valancy, you ask?
Carly is what happens when a Broadway performer takes a hard left into tech startups and comes out the other side with a philosophy. At 30, she reached out to 100 strangers in 100 days; it rearranged her life so thoroughly that CNBC wrote it up. Now she runs Reach Out Party, an 8-week mastermind where ambitious creatives finally send the emails they’ve been drafting in their heads for years. She hosts Anti-Networking events, co-runs a growth consultancy, and writes a good omen, a Substack read by 5,000+ people about how everything good -the job, the marriage, the big break- traces back to 1 person being brave enough to ping another.
Here’s the bit I love most: When Carly was 9, she wanted to be a cartoonist!
Her camp counsellor taught the cartooning class, and his dream was to be published in The New Yorker. She didn’t become a cartoonist. She became something arguably more useful: the person who gets everyone else to ask. But somewhere in there is still a 9-year-old who flips through the paper wondering who drew the cartoons. Which, I suspect, is how she found me.
I’m doing her Reach Out Party this year. Yes. A 40-something Australian who considers asking for a glass of tap water an imposition is now formally enrolled in an American asking academy. In Australia, requesting things sits somewhere between poor form and light treason; Carly has spent 7 years proving it’s the single highest-leverage thing you can do in a day. One of us is wrong, and I’m paying her to find out which.
On Thursday at 10, we’ll get into:
What a professional asker can teach a man who apologises to furniture
Why “networking” is a filthy word, and what she does instead
The 100-strangers-in-100-days experiment: what worked, what was mortifying
How to write a reach-out that doesn’t read like a LinkedIn ransom note
What thousands of scary drafts have taught her about what people actually want
When: This Thursday @ 10am EDT (4pm in Spain, where Carly will be enjoying considerably better weather and food than the rest of us)
Where: Live, right here.
Come with a question. If her whole thesis holds, you’ll get something just because you asked.
‘til next time!
Your pal,
PS: If you know someone who’s been drafting the same scary email since 2019, restack this and send it to them. Consider it your reach-out for the day.









So just ask. Got it!
reading this makes me so giddy