The (Non) Art of Taking a Deep Breath and Starting from Scratch

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Trying to roll my R’s…(r)unning, (r)eality checks, and (r)ecalibrating

In the grand scheme of life, there are many things that seem inconsequential—scoff worthy, even. But it’s just that. It’s only when they’re looked at in the grand scheme. Or to use the phrase that rings in every rookie founder’s ears after 10 too many demo calls—when you look at them from a 50,000 ft overview. Because, in the moment, [bleep] if those things aren’t the absolute end of the world as you know it. 

On this list of inconsequentials? 

• That one argument you had with your best friend—Neither of you can remember what it was about now.

• The guy you swore was the love of your life but who slowly stopped reaching out and you thought it was because you told him that you didn’t actually like baseball or The Office or his haircut that one time—You don’t remember his name anymore (and in the movies the girl doesn’t actually end up with the self important drummer from high school).

• The 10lbs you gained during quarantine. So did everyone else. You lost 5 of them and went shopping. Your style is now much better than it was at 22.

• The quarterly review with your boss that made you cry. You don’t work there anymore.

• Or that one calc assignment you just didn’t do. You still graduated with a 3.9 and frankly don’t even know how to do long division now, so what of it? In the decade since allegedly learning it, no one has held you at gunpoint and asked you to find the integral or derivative of anything. 

Another bullet point to add to the list? Any given 6 month period of time. 

Sure, it feels massive when you’re packing to go away for that long, waiting to hear back about a job, missing someone, locked in the house with only sourdough starter to entertain yourself, or when measuring the start of a relationship. But on their 33rd wedding anniversary, I don’t think my parents can tell you about every 6 month breakdown of their lives. 

That said, in the moment, when you’re trying to start a company and every week that goes by feels like launching too late, like everyone is lapping you, and like you have nothing to actually show for your time, damn does 6 months feel like a lifetime. 

But see, 6 months ago, I was making a whole lot of mistakes trying to build a company that just wasn’t working…and 6 weeks ago, absolutely everything changed (don’t worry, it’s for the better!)

Just to recap, in the past month and a half:

• I got a puppy and with it, a taste of what being a single mother in NYC feels like (Spoiler Alert: It feels like a lot of crying calls to your own mother and thankfully even more cuddles on the sofa while working from home).

• I tackled one of the toughest mental health and disordered eating episodes I’ve had in a long time with the kind of strength and control that I think teenage me would be seriously proud of, considering that she refused to say the word “bipolar” (calling her highs and lows a product of being a “Gemini”) and now I’m working to fight to be an advocate for mental wellbeing in this wild world of “tech bro hustle culture” extremism.

• I found a sense of team, camaraderie, and community that I didn’t even know I’d been aching for by joining Pitch and Run, Endorphins, and Dirty Bird Run Club and re-falling in love with a sport that used to keep me up at night and now just makes me feel full, happy, and strong, the way that it should. Because of their support, I ran my first half-marathon ever on Sunday (a sentence I never thought I’d say!), but was able to come back from limping the first 5 miles to finish with a 1:51 because I had Kayla and Karen by my side. (I also just want to shout out a few of the other new friends who I now don’t remember what life was like without their hugs and little votes of support (both IRL and virtually), so big big love to Bailey, Amelia, Vicky, Kate, Emily, Brooke, Tyler, Hannah, Christina, Del, Cait, Sammy, Rob, Meg, Kate, Carl, and so many more!)

• And finally, I pivoted BIG time. SOIRÉE, the one stop shop for all things “dinner party” became MOM FRIEND, a GPT-powered virtual assistant that provides life advice, support, and immediate answers to 20-somethings navigating life’s difficult transition periods, when I finally realized what a true taste of product-market fit felt like at SXSW in March. (We’re launching soon, so please text “HEY” to 202-991-3227 to join the waitlist!)

So, for the sake of real time trusted narrator documentation, here’s a list of the 6 lessons that I have—ermmm, I am desperately trying to—learn from the past 6 months. 

Disclaimer: I write these knowing full well that I will be doubled over laughing at my naivete 6 months from now. 

1. Starting your own company does not make you your own boss. It may be really fun to say but fundamentally it’s untrue. The customers are your boss. The investors are your boss. You may not be hired by, but you are indebted to, both. So when you haven’t launched and thus have neither, you are not your own boss. You are unemployed and playing make believe. Don’t flatter yourself. 

1. No matter how many times people tell you that your idea, product, mission, vision, or market will change over time or to “fail a lot and fail fast,” you won’t believe them. I wish I had. The founder mindset means believing in what you’re building with your whole heart, which is great. That said…99% of the time, “they” are right. Don’t keep spinning your wheels, chugging in the wrong direction, because you “told a lot of people” about your product. No one cares. At the end of the day…you can’t solve a problem that no one has. Reid Hoffman’s whole idea of “if you’re not embarrassed by the first version of your product, you’ve launched too late” is frustratingly true. There is absolutely no way of gauging what people want, how they want it or if they want or need anything at all without giving them something to see. Hold. Try. Remember the old adage about assumptions? Throw spaghetti at the wall to see what sticks. 

2. Stop reading. Boy, did I think I looked cool carrying around a tattered copy of The Lean Startup like a Warby Parker-clad Jehovah’s Witness. I didn’t. Reading is great but once you’ve read 3 of those “let me be your startup spirit guide” books, all the rest are pretty much the same in a different font. Don’t waste your time, no one likes the “smartest person in the room,” and unfortunately in this world, unless you are literally curing cancer with an app, you’re not going to be the biggest fish. In the same vein, don’t know the things you don’t know. You come off more trustworthy, self aware, and competent if you respond to a question with “I’m not sure, but here’s how I’ll figure it out” instead of making something up with a lot of big words and acronyms. In the wise words of Kendrick, “Be humble. Sit down.” There will always be more books to read or content to consume but it’s all too easy to get sucked into believing that you need to have taken notes on every page of The Hard Thing About Hard Things before you start. You don’t. It’s better to read the targeted specific achievable things you need as you need them…and all of Paul Graham’s essays.

1. Celebrate wins! This sh*t is HARD and there is no “done.” As such, no one will give you a milestone to celebrate, so you have to give them to yourself. It can be as small as writing the email you had been putting off because you didn’t know what to say or just getting time on someone’s calendar. Be proud of yourself! You are doing a hard thing!

1. You can’t carry everything all at once. Learn to juggle, but put a few balls down. Big companies can do what they do because running them is a team sport. Sure, there may be a team captain, but they have the same 24 hours in a day as everyone else, so it’s naive to believe that you—as one singular person—can have a team’s worth of hours in your one day. It’s important to know how to juggle a lot of moving parts, but it’s just as important to know what to prioritize, what to delegate (if you can), and what is simply a “later problem” because not everything needs to happen this second. Even if you’re doing this solo, your time has value. Act like it. 

1. Things change fast. Starting over happens over and over. I learned that the hard way. It can be scary and demoralizing and frustrating to feel like you’re back at square one. When that happens you just need to remind yourself that you earned this “square one” by completing the previous level. You wouldn’t know what to do here if you didn’t get lost and unlost over there.