Faccia Tosta, or: How I built a career on cheek and bad impulse control
One day in 2017, I woke up and decided I wanted to get a representation deal with an illustration agency. I didn’t spend months perfecting my portfolio. I had a 24-hour hyperfocus window (ADHD gift, sometimes it’s helpful) and I used it: I pulled together whatever I’d posted on Instagram in the previous six months and sent 73 emails in a single day.
Was the portfolio good? Not really. I got 3 replies out of 73. But one of those replies was from the agency that made me completely financially self-sufficient as an artist within two years of signing.
This is, genuinely, how I’ve built my career: not on talent, but on probability.
Here’s a framework I borrowed from a tech entrepreneur I once worked for: throw a little money at 10 ideas, see what happens. If even just one makes a gazillion pounds, it was worth it.
I don’t have a gazillion pounds to throw at things. But I do have long-standing insomnia, an internet connection and a truly embarrassing willingness to send cold emails. So I adapted it: I plant a lot of seeds. Some grow, most don’t, but because life is uncertain and the future is chaos, this way I’m statistically less likely to end up with absolutely nothing in my basket.
Whenever I talk about my job, people say something like “Ah, yes, but you’ve always been that kind of person”. As if there’s a certain type of human (special, fearless, somehow more legitimate than the rest) who gets to have an interesting career, and the rest are just spectators. I call this the Extraordinariness Gospel, and I think it’s mostly nonsense.
What I’ve observed is that plenty of people who are not the best in their field have amazing opportunities and make a living doing what they love (kudos to them), while plenty of extraordinary artists can’t pay rent despite being genuinely brilliant. The difference, a lot of the time, isn’t talent: it’s who was bold enough to try anyway, and tried often enough that probability eventually did its thing.
(Ok, a lot of the time it’s actually generational wealth and family connections. Entire careers spawned from being born in the right circles are real, and I won’t gaslight you about it, but for us normal people who don’t have the shortcut, boldness still outweighs talent)
But truly, and this is important, “the best” in any creative field is completely made up. There’s no absolute. There’s only scope, target audience, and personal taste. Which means the gap between you and the person who “deserves” the opportunity is probably much smaller than your brain is telling you.
Let’s go back to my seeds, and I’ll show you.
Last year, I was once again pregnant, and I knew that what passes for maternity leave when you're freelance (working "a bit less" with a newborn strapped to your chest) would be better filled with quick brand deals than full publishing projects. Problem: I'd been ignoring my Instagram for three years. Toddler + overbooked illustration calendar will do that. So I focused on reconnecting with my audience, relearning my social media skills, and when my stats were looking okayish again, I started cold emailing brands.
My method, if you can call it that: I looked at the ads appearing in my own Instagram stories. If a brand was advertising to me, they were currently running a campaign. And if their algorithm thought I was their target audience… well, I was probably also their target creator. So I found 10 more brands in the same vein and sent them each a collaboration proposal.
The media kit took me half a day from a free template. I sent 10–20 emails each evening before bed. Most didn’t reply. But the ones that did accounted for a third of my income last year.
Most recently, I somehow ended up on the newsletter of a creator association called FiveTwoNine, and I obviously followed them on Instagram too. I saw on their stories that they were official Adobe partners and were selecting creators to send to Adobe Creator Live, “Reply if interested”. I replied.
I had approximately zero expectation of being picked, but it takes 4 seconds to reply to a story, so I did. I got picked.
I can tell you the event wasn’t life-changing (I even had a minor panic attack while there, thank the goddess for Quiet Rooms), but it did give me two leads that may or may not turn into something real over the next few months. (More on that if they do.)
The through-line in all of this isn’t that I’m particularly brave, or strategic, or good. It’s that these opportunities have to go to someone, and someone might as well be me if I’ve sent the email and most other people haven’t.
What I’ve learned from 30ish years of behaving like this is:
Act on impulse, immediately. I pursue maybe 10% of the random ideas I have, and that’s the ideas I act on right now, before the hyperfocus fades and I talk myself out of it. If you wait for a calm, rational moment to do the scary thing, you’ll be waiting forever
MVP everything. I do not wait until I have a perfect portfolio, a polished pitch, a finished product. I need a bare-bones minimum viable thing: an okay folio, a media kit from a free template filled in a couple of hours, a sketch that’s only a third properly rendered. The people on the other end are not grading you on the presentation. They’re asking: Is this interesting? Could this work? You can answer that question at 60% ready.
You don't need to be extraordinary (very few people are). You only need to plant the seeds: most won't grow, but you only need a few.
With Love and Chaos,
memo
