The (Non) Art of Wanting To Scream Into Your Pillow

...and then recalibrate and get back to work

Thank you so much for subscribing to the exclusive version of the WELCOME TO THE SOIRÉE newsletter. Here you’ll find my brutally honest musings about this entrepreneurial journey—ones that I often don’t even share with myself (sometimes you just got to keep yourself on a need to know basis, and I *don’t* need to know…), helpful guides that I’ve made just for you, and a chance to be an active part of this crazy journey. Want to see a new feature on site, hear from someone in particular, think there’s a cool brand we should check out, or have tips for something new we should try? I’m a solo founder, so now, you’re my team!

What’s on the menu?

  1. From the Raw Bar, an honest essay about the pros and cons of quitting your job to go off on your own, the constant internal battle of “is this even worth it?” (spoiler alert: it is), and my thoughts on pivoting, “cutting your losses,” and when to push through versus when to shut the computer, take out a pen, and reacquaint oneself with the ever intimidating “drawing board.” (This essay is the second installment in the (Non) Art series. If you want to read the first one, check it out here!)

  2. Some books and shows I’ve loved this month.

  3. A comprehensive guide of cooking substitutions that you can save to your phone, print out, or get tattooed on your forearm to save you when you’re in a pinch.

  4. A few questions that I have for you!

The (non) art of screaming into your pillow

Your internal monologue is going to change from Taylor Swift lyrics to “I can’t do this.” It will play on loop in your head from morning till night and you’ll either get used to it or go crazy by the rhythm. 

You’ll lose sleep making lists and writing essays and plans, trying to fill empty spreadsheets in your head until the wee hours of the morning or the night or whatever construct time is…at this point, you’re too tired to care. 

As a result, you’ll lose your mind too. 

You’ll lose money working from every bar and coffee shop down Bowery. Having gone to them all, you’ll cross an ocean and do the same on the King’s Road. $7 oat lattes are an investment when you need three to find the will to live…they’re even more so in pounds. 

You’ll lose time walking from one place to the next and your feet will hurt. 

You’ll lose your taste in music listening to every founder’s origin story podcast until they all sound exactly the same. (Postscript—you’ll later realize that the “bootstraps narrative of a liberal arts white man coding in his garage” is the same in Comic Sans as it is in Windings or in a studio somewhere in the Bay Area).

You’ll lose the vegetables in your fridge because they’ll always wilt before you have the time or energy to roast them. 

You’ll lose therapy sessions waxing the same fears and complaints week after week. (Postscript—Yes, it is still…hard).

You’ll lose your computer battery starting at blank screens when you just can’t remember how to write words or you’ve run out of them after writing too many of them for too many days straight. 

You’ll lose your appetite from a gut too full of anxiety knots.

You’ll lose your core strength having had no time to go to the gym that you overpaid to join.

You’ll lose your bank account paying a rent with too many zeroes at the end, so instead you’ll keep booking flights trying to locate the sense of self you once had that now changes daily…hourly. 

You’ll lose friends who just don’t want to hear about the big idea that you have nothing to show for anymore and are tired of your constant bailing on plans because of “work” when you allegedly make your own schedule. 

You’ll lose every reason that you had for deciding to do this in the first place….

Some days. 

But then there are those other days…

This essay isn’t meant to be a pity party—some “woe is me” product of too many therapy sessions ill spent. Because see, there are things you’ll gain too. I’ll list them and in the process you…or more likely, I…will do the long division and soul searching necessary to figure out if this soul-sucking new reality is actually worth it. Is it finally time to scream into a pillow and cut our…my…losses?

Because, first of all, you’ll gain freedom. 

After years of being chained to your laptop, triggered by incessant Slack notifications—a sound that will haunt you for years to come—now, your life is finally your own. Sure, you’ll gain ulcers trying to figure out what to do with that freedom and migraines trying to rewire your brain for a new kind of discipline, but hey, at least in July I did it with my best friend from a cheap Airbnb in Provence. 

You’ll also gain a sense of pride. You did the first hard thing. You left the career that was breaking you. Broke up with the job that was making you cry—the one a million girls would die for. You took the step that no one thought you would. Yourself included…maybe most of all. At that point, that was the hardest possible thing. Have there been harder things since? Yes. Will there be even more difficult ones to come? Also, yes. But look, you broke the seal. Every upcoming challenge is your reward for accomplishing that one. You get to do this. You leveled up. The game has higher stakes now, and isn’t that more fun?

You’ll also gain a lot of unsolicited advice. Some of it, good. Bits of it helpful. Most of it either not or simply wildly inapplicable. But see, advice is kinda like thrifting. You have to sort through a lot of Granny Dearest’s two cents, but once in a while you come across a Dior. A diamond in the rough. 

Along with that hypothetical Dior, you’ll also gain a lot of new, very un-hypothetical friends. Passion begets passion. You’ll join an accelerator and find people who finally really get it. All of the “its.” The struggles, the tiny victories that feel like a f*cking Nobel Prize after weeks of lateral movement, and the random acronyms that now have taken up real estate in your brain.

You’ll find a run club with more of this same heavily-acronymed breed and find a sense of community because of it. You’ll connect with a whole new world of people who you’re surprised to find…actually want to help. As fast-moving and scary as this world can sometimes seem, it’s also significantly less “dog eat dog” than you thought it would be. The population here in this new world seems to be the first to realize that there actually is enough room at the “top” to uplift your fellow aspirational idiots/entrepreneurs without feeling threatened by their wins. 

On top of that, you’ll gain a new best friend. Yourself. Those 7 words were typed by shaking hands, because, besides for setting a few high school track & field records, I never thought that I’d ever say that I was really proud of myself. For a different sort of illness acronym-riddled brain like mine, I simply didn’t expect that to be in the cards, but here we are. Do I have a 30 Under 30 in my social bio, a top spot on ProductHunt, a braggable number of followers, or a successful closed investment round to my name? Nope. But as many gallons as I may have cried this week…and last…I’ve learned more in the past year than in all of the others put together. I’ve grown into a person with somewhat of a backbone and steady sense of self who can pitch and speak and hold her ground without giggling nervously, apologizing, or downplaying. And, I’ve learned my worth in a way that no number of annoying situationships or bad dates could have ever taught me because—Hey, if I can’t bet on myself, why should anyone else bet on me? 

You’ll also find even more discipline. For a recovering commitment-phobe like myself, the idea of sticking with something for a year is not one that comes naturally—especially when by every book’s standards, I should be ten steps further than I am by now. But the reality is that the book reads differently for everyone. That’s why there are so many of them. For the first time in my life, I’ve actually stuck. Dealt with the personal and interpersonal confrontations that old me would have run from screaming. Caught the sand that feels like it’s falling through my fingers every day and built every iteration of a sandcastle with it. Have all of them had a steady foundation…definitely not. But I’ve tried them all so I know what not to do next time.

So here we are. In true Type-A fashion, stress crying in a coffee shop with a list of pros and cons. Still desperate to cry into a pillow, embarrassed about sobbing while on Zoom when my accelerator workshop partner asked how I was doing last night, but also aware about the fact that no matter how many times I’ve said “I’m done” in the past 10 days…I’m not. Because, if you look at the net value, this list balances out to an incontestable answer. If it wasn’t this hard, I wouldn’t love it this much. Feel this alive. Activated. Passionate. For lack of a better word, obsessed.

So, will I scream into a pillow in T-30 minutes when I get home? Yes. Sometimes you just have to. But will I also wake up, recalibrate, and do it all again tomorrow? Pivot…again? Untangle something else? Put out yet another fire? Call it quits in my head while I keep chugging along? Also yes. At the end of the day, it’s the things that make you want to scream into your pillow that are the most worth it.

Welcome to the content corner…

Taste by Stanley Tucci (please, if you listen to anything I say ever…for the love of god, food, and all things good, LISTEN TO THIS BOOK! It feels like you have the king of cuisine himself waxing poetic about pasta in your ear and there is nothing better in the world.)

The Romantics—it’s a short series that just came out on Netflix about Yash Raj films and the history of the Bollywood industry and watching it and getting to go to the premiere felt so nostalgic, made me feel so proud to be brown, and had me dancing in my seat.

The lazy patissier’s guide to baking substitutions

A few questions…