Perplexed and Awed.

“You may not see it today or tomorrow,

but you will look back in

a few years and be absolutely

perplexed and awed

by how every little thing

added up and brought

you somewhere wonderful — or

where you always wanted to be.

You will be grateful that things didn’t

work out the way you once wanted them to.”

I found this quote a few months ago, took a screenshot of it, and have revisited its buoyant message on occasion in the weeks intervening. Though I feel that my life is in an upswing at the moment — as though my husband and I are birds in ascent — the feelings of failure and ambivalence that lived so close to the surface just a short year or two ago are never far from my thoughts. I wrote a bit, somberly, after Christmas about how growing up has felt like a gradual tempering of emotion. Until I was in my late 20s, I felt unbridled in every sense of the word: I could do anything, be anything, go anywhere, feel what I wanted to feel at any time, any place. Now I feel situated. Centered, maybe, if I am being generous with myself. I understand better the constraints of the real world, the unlikeliness of certain kinds of success and reward, the probability of certain kinds of disappointment and loss.

Let me speak more openly about what I mean from a professional standpoint (though I have other achingly personal griefs that I could share here, too). I am aware that, taken from a thousand foot view, Mr. Magpie and I have led highly charmed lives, and that the shuttering of the business we built together must seem like a petty gripe in the grand scheme of things.

“At least you had the privilege of starting a business; do you know how few people even have that option available to them?”

“But you turned out just fine — you now live in Manhattan and are on to other amazing projects! No harm, no foul.”

“It’s an insane blessing that you were even able to take two years to explore entrepreneurship on your own! A rarity! An indulgence!”

I tell myself these things all the time. And they are true. And poignantly so now that I better understand the inequities of the startup world and how it and the financing apparatus around it inherently bias certain categories of people and business. I know this because Mr. Magpie and I fall into a lot of those privileged categories — and still we were unable to find success as quickly as we needed to in order to sustain our company. The unvarnished truth is that it takes two things to succeed with a new business: capital and connections. The business itself can and will evolve and grow until it achieves “product-market fit” over the course of many years, and often, the final product is far afield from where the founders first planted its earliest iteration. But to buy yourself the time to get to that magical “fit,” you need deep pockets and an impressive rolodex. If you are missing or slight in either of those, it’s impossible to succeed. In our case, we did not have sufficient resources in either category. We were fortunate to have enough capital to start the business, forgo salaries by living off of savings, and raise a small pre-seed round of money. But our connections to the VC world were slight, and to the circle of “angel investors” that often take care of funding rounds under $1M, even slighter. In order to network your way into that crowd, you usually need to have attended an elite business school, invested in businesses yourself (i.e., be substantially privately wealthy), or been in some meaningful way professionally or socially connected to That Set. We had done none of those things.

On the connections side, Mr. Magpie and I had built strong relationships in our respective careers, but neither of us had lived in a specific professional field long enough to have a robust black book. If, for example, I had built a career in, say, accounting technology sales, and had worked in that domain for ten years, building countless relationships to individuals and businesses in that orbit, attending professional symposia and conferences, etc, etc, I might have had a chance to anchor my business (at least early on, in the “MVP” stage) there with “insider” information. I might have said: “I am building an HR technology specifically for sales professionals in accounting technology.” And then I might have carefully crafted my pitch and designed my product to cater to that micro-market as a kind of proof of concept. Once I’d closed enough business (we learned that around $5-10K in monthly recurring revenue would have been enough to turn heads for the type of business we had), I could then turn to my VC cronies (if I’d had them…) and sell the idea based on the traction I’d seen, extrapolating that if we’d had this kind of success in such a small corner of the market, imagine what we can do if we expanded sales to x, y, and z!

Alternately, if I had previously worked at a major, respected consumer packaged goods firm and had strong enough relationships with the right people there, I might be able to sell a small “pilot” program to my former company as the “proof of concept” and that might be enough to yield some financing.

But. Mr. Magpie and I had neither of those kinds of connections. We were well-liked in our respective professional paths but lacked a sufficiently wide or deep net in order to establish a kind of market specialty or land a “big fish” win early on.

And so. Our chances of sustaining ourselves until we had achieved product-market fit were slim before we even started. And they are even slimmer for those without the considerable advantages we had when we started out.

So when I say that closing the business flung us into a kind of situational depression, I mean to say that the experience revealed to me so many raw truths of the world that it was hard to swallow it all at once. I saw that maybe the “American Dream” is a kind of figment. I saw that hard work and clarity of purpose do not always yield reward. I saw that sometimes a straight line is not the shortest distance between two points — meaning that it makes intuitive sense that a good and honest idea will flourish, but that there are invisible constraints and machineries in motion that favor certain kinds of businesses and ideas and shun others (i.e., why there are so many home meal preparation startups?!). And maybe, too, our idea was just not that good. And so I saw a kind of creative failure in myself I’d never seen before, an artistic impotence. And I saw that a particular vision of success that Mr. Magpie and I had long clung to was unlikely for us. And I was embarrassed, and frustrated, and stressed by our financial losses, and uncertain of when or how I would ever be able to rebuild my professional career now that I’d gone “off grid” to pursue something on my own.

We felt as though we were drowning. I felt for the first time in my life lacking in direction and ambition, an alien kind of listlessness invading my personal space. (This, from a textbook Type A Gal.) I didn’t recognize myself. I remember telling Mr. Magpie: “One day we’ll look back and understand why we did this and where it took us.” And we’d both nod glumly at each other, neither truly believing it.

Yet here I am, roughly two short years after we decided to move on from our business, and though I still do not fully understand “why we did that,” I am relieved at where it has taken us. I am startled by the fact that I can grasp both the morose discoveries unveiled in our shared entrepreneurship experience and the shining optimism of the quote I shared at the outset of this post and find both to bear an equal measure of truth. Because while I am hardened by our experience starting a business, I am also “perplexed and awed by how every little thing added up and brought me somewhere wonderful.” Above all, I am grateful things didn’t work out the way I once wanted them to.

Because I am here, now, and happy.

I share this today with a twin pair of hopes. First: that I might use this post as a kind of closure on this topic, as I have agonized over it for too long. My father often tells me, in various permutations: “Never look back.” He said this after we sold our home in Chicago, and even after we more recently sold our SUV — the last remaining vestige of our life in IL and all of the dreams we pursued while there. Keep moving, Jennie.

But, second, and more importantly, I share this post with another intention: I hope that if you are drifting in the throes of disappointment or grief or frustration, you might permit yourself to see that your hardships will give way to something better, even if you can’t fully believe it right now, and even if you want to groan and roll your eyes as I did two years ago. Just open that door for a minute and let it stand before you: the possibility that in a few years, you might stand perplexed and awed at where your present has taken you.

Post Scripts.

+This post reminded me of a great quote by Colin Powell that I discussed a year ago.

+Mango is having a nuts sale and I currently I have this slouchy sweater and these snakeskin boots in my bag. Also love this soft lilac color and this chunky knit. (THE PRICES!)

+Dreaming of this top-handled bag in the powder blue. No idea what to wear it with but I’m confident I could create a look around it.

+Another reminder that you are enough.

+Love the length and Gucci stripedness of this midi dress. Startling in proportions in a good way!

+A chic and well-priced sweater.

+Found these marbleized-effect Native shoes for mini on sale for only $28! Bought them immediately.

+Love this acrylic bookcase. Mr. Magpie and I need to do an assessment of our toy/book/clothing storage solutions with micro on the way — we need to make better use of the space we have so that we can stow toys and clothes and books for two! The acrylic bookcase above caught my eye because it’s narrow and clear — and therefore won’t look too bulky or dark tucked into a corner of mini’s nursery.

+In a similar vein, it dawned on me recently that I might be able to maximize storage by adding this etagere to our master bathroom. Then I can repurpose the bins I’m currently using to hold overflow towels and toilet paper for other purposes…

+How darling are these plates?!

+OK, this is a chic upgrade from the Qi I bought Mr. Magpie for Christmas…

+I did splurge on these velvet Miu Miu slides (on super sale! — more sizes/colors also on sale here and here). I bought them as a present for myself post-delivery in May. I figure I’ll need some fun shoes to prance (ha!) out of the hospital in. That said, I also found these for only $23 as a chic way to get the look for way less….

+Speaking of pearls: this is fun, and my beloved Lele Sadoughi pearl headband was restocked here and here!