The Only Way Out Is Through.

The other day, I had the other-worldly experience of stumbling upon a recording of myself pitching my technology business at a start-up event in Chicago several years ago. I had my entire spiel down. I could pitch my business in my sleep, and it was studded with the start-up patois of the time — “on-demand,” “real-time,” “micro-feedback,” “lightweight,” “cloud-based,” etc. I was so accustomed to answering customer and investor questions that sometimes I felt as though I was floating above my own body, listening to myself speak with conviction the same rehearsed lines to the same common questions, and I would simultaneously be wondering or worrying about something else — what were we going to do about the bug in the latest release? I really need to close that account!

It was not always that way, with the phrases sanded down smooth as glass.

The start of it all is physically painful to remember, gritty and uneven as it was. Telling friends and family that we were leaving our well-regarded, salaried jobs to pursue something entirely different left me gray with nerves. I didn’t yet have the words to explain what we were doing succinctly, or with eloquence, or with the passion I later learned to project. I would stammer. My first few pitches were loose and messy, javelins flung blindly.

Over time, the operation tightened. I learned to anticipate and often pre-empt questions and, later, objections. I became more sophisticated in understanding what would resonate with each stakeholder in a given pitch — that is, we had our investor pitch, our customer pitch, our generic start-up pitch, and then within each stakeholder category, there were further striations. In the customer category, we had a pitch for executives, a pitch for HR people, a pitch for end users, and we had strong opinions on who we’d prefer to pitch to from the lens of whether we would be able to close the account. We even further honed the customer pitch by industry, hitting on different elements when presenting ourselves to small businesses vs. non-profits vs. start-ups vs. enterprise-level organizations. It was like plucking chords on a guitar. I’d assess the audience and set myself up in the right key.

At some point during this period, a college friend of ours visited and we brought him with us to 1871, the co-working space from which we ran our company. He had business to tend to that morning and so did we. I remember heading into that work session with something like dread that, as we passed through the turnstiles, began to rust into steely determination. I was anxious about him overhearing me in my presentation to a new potential customer. It felt like a high-stakes performance. Here was my opportunity to prove to someone close to us, who may have doubted our ambition, that we were serious business people! That we were out there, selling meaningful solutions to real businesses! In some ways, he was a stand-in for the critics I imagined snickering at us behind our backs.

I know now that no one was snickering. Or — I doubt very much that anyone was. Or — if they were, I forgive or dismiss or ignore that naysaying because there was nothing laughable about the effort we put in. No, the discomfort and defensiveness was born and bred by yours truly. I was on an imaginary tightrope I’d conjured entirely myself.

I took a deep breath and jumped on the call and nailed the pitch. I knew my friend was in earshot the entire time, and I could tell he was eavesdropping. But when I was done, he said nothing, and neither did I, and the day unfolded and eventually we dismissed ourselves for happy hour drinks, at which point he said, “You were awesome today. I listened to you. I’m so impressed.”

It felt lovely, to earn that imprimatur. But I was startled by the fact that I already knew I’d earned it, even without him ever saying anything, or letting on that he cared. I realized that when I’d shut my laptop earlier that day, I’d assessed myself and emerged satisfied.

I guess I’ve been thinking a lot about beginnings and endings and renewals this year. About how even as I have moved towards more and more stability in every category of my life over the past few years, how many times I have also started again. How often I have looked, bare-faced, at myself and found myself wanting or — put more gently — in development. How often I have seen myself as a novitiate, even in things I have done before, like becoming a parent for the second time, or renting a second apartment in NYC, or buying a house for the second time, or running a business for the second time. Some stuff sticks. I find myself better equipped to identify bad actors and shady opportunities, for example, or perhaps just more willing to trust my instinct. As a result, I am far less likely to be taken advantage of. Perhaps I was more inclined to intellectualize my way out of spot-on intuitions the first go around, more prone to say, for example, “This agent feels weird to me, and I can’t put my finger on why, but…he must be good! He works for a reputable firm!” The second time around: “Something is off, let’s cut bait.” Ditto in parenting matters. I am far more likely to advocate for my children now if I think something is off, first opinion be damned.

In some ways, the principal gift of experience is realizing how little you actually know and how much you must rely on gut feel to make your way through. And that humility is a good thing. I often tell Mr. Magpie that the older I get, the less I know for sure, and I think that makes me circumspect about my own perspectives in a positive way.

So just a line out there, for any of my Magpies at the start of something, in the throes of self-transformation, feeling insecure or uncertain or overwhelmed: there will be a day where you will find yourself in a groove, where the words will tumble out easily, or where you will simply realize that you’re doing your best and that it is enough. And there will be another day where you find yourself back at the start of the path, in slow and steady ascent. Hang in there. The only way out is through.

Post-Scripts.

+On the imagined criticism we all carry with us.

+On failure more generally.

+You are enough!

+On realizing it’s OK to lower expectations.

+”Never grow a wishbone where a backbone ought to be.”

+“Beyond a wholesome discipline, be gentle with yourself.“

+It’s never too late to begin again.

+The sense of an ending.

Shopping Break.

+This mini dress is currently in my cart. J’adore! With tall black boots?!

+When I first started working, I saved up for a DVF wrap dress and then bought several over the course of my more professional tenure. They are still in my closet and I bring them out every season. Timeless, flattering, ageless! Outnet has one of them on sale in a fantastic fall print here. Boss lady vibes!

+This Clara nightgown for a little lady!!!

+This shearling trim puffer is currently 20% off and I’m super tempted.

+Reformation is killing it at the moment. Major Khaite vibes for under $200. (And don’t forget this knockout dress!)

+These rain boots are super chic.

+Just bought Tilly some new dog shampoo. Didn’t know Ouai catered to our furry friends!

+Speaking of Ouai, I still swear by their texturizing spray if you do a beachy wave. My hair is on the longer side right now (getting it cut on Friday!), and I’ve been wearing it in loose waves a lot lately. That means I’ve been taking a temporary break from my beloved one-step and instead washing my hair at night, letting it air-dry as I sleep, and then curling with my Hot Tools 3/4″ curling iron before finishing with the Ouai spray. It really works so well!

+Fantastic toddler Target find – love a shawl collar on a little boy!

+My girlfriend works at Marc Jacobs and is bringing me this ultra-chic crossbody when she visits from New York this weekend! ZOMG. Will be wearing all fall.

+This Ulla dress would be so chic with tall boots — and currently 50% off!

+Such fun water glasses for a holiday table.

+Mango is offering 30% off a bunch of their fall pieces — top picks are this SEA lookalike and virtually all of their on-trend knitwear, including this fair isle and this herringbone vest.

+I have a fair isle sweater from years and years ago similar to this under-$50 score that I have been wearing a TON this season — usually just tying around my shoulders for a little pop of pattern! Looks so cute against olive green in particular.

+Isabel Marant shacket vibes for about half the price.

+Clever collapsible silicon coffee cup — stocking stuffer for a busy traveler?

+This $59 blouse is serving up major Doen vibes.

+Speaking of Doen — wow.

+Just bought Mr. Magpie this rugby shirt.

+Still a few of these Ganni-inspired quilted coats available ($40!)

+Handsome herringbone blazer to pair with jeans.

+Chic tortoise hair clip!

+These suede boots are fantastic + versatile.

+These heart earrings are so chic and nostalgia-inducing for some reason. It reminds me of my beloved Elizabeth Coda Callen locket book. (Did anyone else collect those books?)

+These flats are absurdly fun. Sort of like a printed version of my velvet furlanes.