betting on yourself
betting on yourself
taking risks, creative generalists, doing the thing
Greetings from the deep, deep depths of this heat wave. I’m getting myself through these subtropical temps by picturing the summer we deserve: one synonymous with late rooftop sunsets, backyard aperitifs and live music, a fresh breeze on a maritime getaway…
I don’t identify with summer in my core essence, but I do like to try and lean into who she is. If I could personify summer: she’s an energetic daze who doesn’t let you sit still too long. She’s undisciplined fancy, the one who comes and goes as she pleases, here to distract you from your normal whims. Found in an after-hours drive from a coming-of-age movie and the hush of an unexpected rainstorm. When the party’s done and over, she’s a melancholy lull (à la Lana Summertime sadness and Charli I think about it all the time).
There’s a time for rest (winter). And there’s a time for restlessness.
I used to think this kind of restlessness was a me problem until I started talking about it with other creative types. Plagued by this never-satiated curiosity of endless possibility. What else is out there—what else are we capable of? (So many things. Highly recommend my friend Michelle’s Creative Juicy where she chats with a range of guests about their career paths.)
You can’t do it all, but you can try. A simultaneously freeing and frustrating truth as someone who wants to do it all. People say getting started is the hardest part, but to me it’s actually a few steps before that: you can hold onto an idea forever. You get stuck between an idea and reality if you’re not first willing to bet on yourself (and that idea).
Nothing quite propels you forward like a stubborn (sometimes delusional) belief in what you have to offer. Nothing makes life feel quite so alive as when you take a risk.
Adulthood strips us quickly of the childlike fearlessness we used to have while learning how the world works. We know we’re not supposed to touch a hot stove, to cause a scene in public. How often are you leaving your comfort zone these days? I find the best way I exercise the ability to take risks is to experiment. It’s the best way to get to know your metaphysical safety blanket. For example: last week I tried a drop-in ballet class as a total beginner. It was literally breaking my brain to follow along (and embarrassing to feel bad at something) but it was a fun enough challenge for me to want to go back. In contrast, I tried a boxing class in 2017 and haven’t been to another one since.
Such challenges are necessary for growth. Sometimes it helps to visualize it. I jotted down a list of topics I want to write about and a list of topics I would never write about, in an attempt to understand some of my own boundaries. How far am I willing to go? When is something out of bounds because of self-preservation, and when does it become self-sabotage to my own growth?
And…what’s the worst that could happen?
My friend Joy Mao finishes up her artist residency this month and we celebrated as she signed the lease for her very own studio (!!!). To an outsider, it seems like the natural next step. But there’s so much wrapped up in such a decision. It’s not just the financial considerations—money comes and goes. It’s a psychological and yet very real leap of faith. Instead of focusing on the worst outcome, it’s hoping that it’s all going to go somewhere. A commitment that says maybe I can do this thing.
Fear inevitably shadows hope. But I’m inspired by anyone hopeful enough to make a leap. It’s welcome proof that life is still in motion. If you tune into the world with that mindset, you’ll see people all around are taking risks. A new job, a change in relationship status, a big move. A new restaurant, a first date, a closet switch-up.
Taking a risk means betting on yourself, no matter the outcome. Or at least that’s how I’m trying to think about it now. I think back on all the dates I dreaded going on and how they’re just proof that I’m betting on finding someone worth my time, one day. Or the first time I cut my hair short and found a new freedom in being able to redefine my appearance. Why join my self-critics in expecting my own failure? Every time I think something is out of reach, or shut something down before even trying, I’m reframing it as betting against myself.
The worst thing that can happen is simply learning from what I did wrong. The career mishaps I made early on are ones I will never make again, like showing up to the Hearst Tower as a naïve student without a portfolio. (Hard lesson learned: never ever show up empty-handed.)
Now I’m older. And wiser! And trying to look past the fear of things not working out and instead trusting that they will. What does it look like to bet on your own success? IMO, you have to:
Forge your own path
Betting on your future requires not asking for permission from others to do so. I remember feeling crazy when I turned down a full-time offer after my first design internship with nothing else lined up. In hindsight, I would never trade that experience of blindly navigating freelance for a season. It taught me the hard way to get everything in writing in order to get paid for your work (even someone you’re supposed to trust can screw you over). And even though I’ve worked full-time for the last 6+ years, people still come to me for freelance advice, which is kind of comical because I’d wouldn’t exactly recommend doing what I did back then.
Make investments in yourself
This applies to time, money, relationships. Whatever you’ve established as the things that matter to you. Continuing to prioritize those things help create a safety blanket so that you can try new things with confidence. Full time or freelance, I’ve always prioritized friendships and travel. Every job I’ve taken has been thanks to a connection. Every major trip has taught me something about myself and how I see the world.
Embrace (or at the very least, accept) rejection
My friend Clem sent me this piece on Ask vs. Guess culture, which tied in well to my musings this month. “There is no penalty for asking.” Why are we (I’m speaking for myself and other self-identified Guessers) so scared of NOs? I signed up for a flower delivery service on the street simply because they stopped me…and I said yes! (I respect the grind of selling IRL to New Yorkers actively ignoring you.) The most constant rejection I face is failed self-promotion online, which is honestly so low-stakes. A lowercase whispered no. I’m constantly impressed by and learning from the Askers around me. One yes is all you need to keep on going.
Prioritize your support system
I’m so skeptical of leaders who don’t acknowledge how important emotional support is. It doesn’t matter how ambitious or achievable your idea of success is: it’ll be lonely where you’re going if you’re lonely along the way. The people you want around you are the ones who are rooting for you to succeed: the ones betting on you, too.
Believing in = betting on yourself and making smart course corrections when necessary. Loved this episode with Julia Collins and Everette Taylor on Aurora James’ podcast. “How many no’s do you have to get?”
On repeat Predictably: the holy trinity of Chappell, Sabrina, Charli. This song deserves to be blasting from your car stereos this summer:
Last watched I Saw the TV Glow, rewatched How to Lose a Guy in 10 Days (I was inspired by Sabrina’s Andie Anderson dress) and Inside Out 2. (The visualization of sense of self!!!…the personification of Anxiety...)
Last read Finally finished The Art of Gathering and it changed the way I think about hosting. Made it through half of Growing Up in Public: Coming of Age in a Digital World for our Hearth book club, but think it’s better suited for prospective or current parents. I’m testing out the art of subway reading with The Writing Life and have some Emma Cline queued up for plane Kindle time. Fun summer reads!!!
One last thing If you have friends doing a new thing…your support means everything! Go to their shows. Leave a comment. Text them. :) On that note, Sophia from OOSO sent me a pack to celebrate their recent launch (yay!). I’m slightly partial to the green tea flavor (it is indeed BRIGHT HERBACEOUS ENERGIZING) but both were great accompaniments to our summer dinner party.
As always, thank you for reading. Follow along with my summer travels over on IG for day-to-day fun. P.S. Any tech folks also going to Config this week? See you there! x