Musings + Essays

On Pessimism.

By: Jen Shoop

*Image above not really a propos of today’s post, but I couldn’t stop staring at the gorgeous photo above via Danielle Frankel’s bridal collection, and the model seemed appropriately introspective, so here we are.

When Mr. Magpie and I were running our technology business, we worked out of 1871, a co-working space and start-up incubator in the River North neighborhood of Chicago. We participated in countless events and programs there and so had multiple occasions to cross paths with and attend various talks by its CEO, Howard Tullman, a serial entrepreneur and investor himself. One of the sentiments he repeated across those interactions was: “Pessimism is always cooler. Be different.” The message was that it can be harder, and more vulnerable and suspect, to be ambitiously optimistic. And that there is something lazy and self-aware about pessimism: yes, casting doubt or pointing out flaws can project discretion, hard-earned apathy, and even intelligence, all while protecting oneself from the likelihood of failure. But it is a pose, an inertia. (Sartre practically branded the affectation.) To do the thing — to muster the optimism required of any new venture, new dalliance, new relationship, new foray — demands emotional output that far outweighs the negligible effort of saying “Nah, that won’t work.”

I wonder sometimes if he issued this pronouncement as a matter of good business: he was, after all, on the hook for driving memberships at 1871, and encouraging us starry-eyed entrepreneurs to dare to think big and stay positive was one way to discourage us from throwing in the towel on our various endeavors and, in turn, discontinuing our memberships.

But I must say that the notion has stuck with me, emerging on more frequent occasion than I’d have anticipated.

Like when I tuned into the HBO “Selena + Chef” episode I mentioned two weeks ago, where a bright-eyed and gleeful Jose Andres talks lovingly to his ingredients and celebrates, well, everything while dancing his way through a shortcut Spanish omelette-souffle. His joie de vivre was contagious: I couldn’t help but smile, and I found myself waxing poetic. “You just don’t see people express such positivity or optimism that often. I love it,” I told Mr. Magpie.

Or when Mr. Magpie and I occasionally, and with jocular tenderness, remind one another to exercise a “yes, and” mentality, whether we’re running through the options for dinner delivery or deliberating over a parenting matter. The slogan is hangover from a training I had the opportunity to participate in years ago at a retreat for non-profit leaders: a comedian ran us through a series of exercises, one of which was to practice the principle of “yes, and” — a core tenet of sketch/stand-up comedy in which performers affirm and build on the pronouncements of their colleagues. So if John says: “Oh my gosh, I just found a dead mouse!”, Judy must say: “Yes, and it’s starting to smell.” In so doing, she validates the work of John and keeps the narrative moving, generating new opportunities for plot development and comedy. I can’t tell you how often, after the training, I would observe colleagues (and sometimes myself!) handily throwing shade or negating or nit-picking at ideas rather than operating in a “yes, and” headspace to move towards a solution. It is easier and cooler to be the pessimist in the room, telling everyone why XYZ won’t work. (“Thinking is difficult,” wrote Carl Jung, “that’s why most people judge.”)

More recently, I had the opportunity to listen to a group of mothers discuss their experiences with parenting in the context of this pandemic. There were some interesting experiences, tips, and suggestions circulated, and then one mother cleared her throat, laughed, and somewhat pointedly stated that, unlike the rest of the mothers that had previously spoken, she was going to “keep it real” and admit that everything was (to summarize and borrow the words of Alexander): “horrible, no-good, and very-bad.” I knew how she felt. I have experienced the same exhaustion and frustration at various points in this pandemic. I have struggled. I have wondered how other parents are making it all look so easy. And sometimes it is healthful and helpful to say: “This is really hard” among peers. In fact, we’ve done it here on this blog many times in meaningful moments of catharsis. But her tone — the way she chuckled to herself and told us she wasn’t going to sugarcoat or kumbaya her way out of the reality of things — felt like a reproach.

I’ve been wondering about this interaction and about the lines between pessimism and keeping it real and optimism and performance and denial. It’s a spectrum, isn’t it? And it’s hard to tell where people fall along it, and why. Perhaps that mom the other day wasn’t a pessimist — perhaps she was just having a day and not in the mood to be told about the small and winning ways people were making lemonade out of lemons. We’ve all been there. (Remember? The play-doh? AHHHH. If I’d been asked about parenting in the aftermath of that afternoon, I would also have been snappy.) Maybe her admission was a relief for other mothers on the call. “Ah, phew, so I’m not alone,” they might have thought.

But maybe it achieved the inverse. Maybe it brought the mood down. Maybe it made other mothers feel smaller, less secure, too bright-eyed and bushy-tailed. Maybe it made them feel foolish, or desolate. Of course, it was not that woman’s job to support the mental wellness of a group of strangers. She was, I have to imagine, speaking her truth, or some version of it. But there we were: a group of women exchanging experiences, and the mood suddenly curdled. I didn’t know what to make of it. It was a strange moment where I felt twenty-two things at once.

It did present me with the opportunity to think about where I’d like to fall on the spectrum, though. And the sweet spot for me lives north of “keeping it real,” reaching towards optimism.

How about you? What are your thoughts on “the spectrum” between pessimism and denial?


+Maje is offering an extra 20% off already-discounted pieces, like this ultra-chic longline cardigan. Love the sporty athletic stripe trim! There is a mom in my daughter’s school pick up line that wears this coat (now heavily discounted as a part of the promotion) frequently and zomg she looks amazing.

+In case you ordered a HHH nap dress with the latest launch (I bought the Nesli in the green trellis), I have it on good authority that this $32 bra (which gets rave reviews on its own) works with the neckline.

+I’m going to be needing this coverup for the summer.

+A tip for gaining perspective in a tricky situation.

+I can’t stop thinking about this trench coat.

+Such a chic top.

+This vine topiary!

+This mini tech detox really worked for me.

+Would love a piece of investment jewelry from Aurelia Demark — this heart bracelet engraved with the names of my children? Too sweet.

+Me, in shirt form.

+Love this maternity dress.

+I have one of these alpaca sweaters in a cropped fit — love the newer longer silhouette!

+Just the dreamiest tweed jacket. (The pearl buttons!)

+I never knew I needed a proper sewing box until I laid eyes on this one.

+Cute personalized crayon boxes — good for little gifts / travel. Also cute for stowing miscellaneous toys with small parts/accessories (thinking of some of mini’s Barbie accessories)!

+These monogrammable scallop-trim sweaters!!!

+My forever quest to live in the present moment.

+Thinking I might need to order one of these chain stitch sweatshirts for my little man.

+Love these affordable ribbed leggings for littles in the blue set.

+I’ve always wanted to be a writer.

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12 thoughts on “On Pessimism.

  1. I had to sit with this post for a bit! I am perpetually a “glass half full” person, but the past year has certainly challenged my outlook and responses. It’s been particularly challenging to lead a staff that is all across the spectrum you so aptly identified. My empathetic listening muscle has received quite the workout! Love the “yes, and” concept — I’m now thinking about how to incorporate it into trainings and conversations in the workplace and at home. It feels like less of a “pep talk” which can be exhausting and more of encouraging food for thought if employed constructively.
    I had a recent conversation with a staff member about using the terms “good” and “bad” to describe a struggling student’s school day to the parent. I encouraged her to shift to “easy/smooth” and “hard” moments rather than summing up the entire school day in such black and white terms. After all, aren’t our days a spectrum of moments themselves? These are the situations that require honesty (often VERY hard to hear) paired with encouragement. Striking the balance is difficult indeed.
    Just a few of my many thoughts on this subject! xo H

    1. Hi Heidi – I love the idea of shifting away from a “good/bad” binary. The people management aspect of this conversation is SO challenging — how do you accommodate different personalities/affects/outlooks on life while focused on goals/bottom-line/success metrics? Landon and I spent a lot (!!!) of time researching and thinking through the mechanics of providing real-time employee feedback in our former lives as tech entrepreneurs in “people tech/HR tech.”

      Anyway – thanks for chiming in!


  2. I love this post! Thanks for that Carl Jung quote too. I do not have eloquent thoughts — am mid move right now (!) but I am going to file away the sentence of “I’m going to keep it real” as a phrase to be used sparingly in a group setting, as it seems to imply others are not. It’s kind of like how I try never to say “at least” or “it could be worse” when others are complaining or confiding in me because because I just don’t find empathy in those phrases. I consider myself a realistic optimist and don’t think that is necessarily a contradiction. Hope springs eternal. 🙂

    1. !! Mid-move! How are you even forming sentences? Thinking of you! Thanks for chiming in here — will also ban “at least” or “it could be worse.” I think I’m good at avoiding that already but will make a mental note to fully excise those two phrases. I find them especially common in conversations about parenting — “oh, just wait until baby A is crawling! at least now they…” So bad!


    2. Ugh! “Just you wait,” my least favorite form of parenting advice, and so prevalent! I greatly appreciate the friends who can tell me things to look forward to! Even when I was in my third trimester “When the baby comes and you can find time to sleep you’ll be able to get much more comfortable.” Or more recently, “When he starts walking it will be easier on your lower back because you won’t have to carry him around as much.” (Both true!) And comments like, “Oh you’re going to love reading him chapter books and teaching him how to be kind to others” are truly balms to my spirit. 🙂 Motherhood is very hard, I don’t mind a future bright spot to dream about as I read “The Very Busy Spider” 900 times in a row.

      1. I love that – going to have to tuck away the “things to look forward to” suggestion in my conversations with my mom friends. So positive and encouraging!


  3. I lend myself to vulnerability. That can look both pessimistic or optimistic, given the day. Context and setting matters. In passing with a colleague in the hall? I likely won’t air my grievances. With girl friends on a group chat? Yeah, that’s okay. Read the room.

    Vulnerability and absence of pride are connected, and I value both in any meaningful relationship.

    1. Hi Christina — I think you are so spot-on about the importance of context/reading the room. (Perhaps that was the underlying issue in the parenting circle moment I mentioned above.) And I appreciate the provocation that we don’t necessarily live as pessimists or optimists in absolutes — perhaps we move along the spectrum depending on context, experience, current conditions, etc.

      As always, great food for thought.


  4. I’ve tried so hard in this first year of motherhood to keep a “both/and” paradigm. It’s a concept I first learned in an organizational leadership class in grad school. I can love my daughter to pieces and feel so blessed to have her here and also hide in the shower crying because parenting with no help 11 months into a pandemic is treacherous. I’ve found it’s so important to allow for both. As someone who struggled for years with infertility, there can be a tendency to only allow for feelings of gratitude towards finally having a child. But parenting is just as difficult, no matter the journey.

    1. Hi Tricia – I love this concept. My sister shared a helpful conceptualization of this mentality when she talked about holding empathy for others in one hand and awareness of one’s own needs in the other. They can seem on the surface often incompatible but it’s about acknowledging and balancing both. I am now thinking similarly about the notion of “keeping it real”/being honest in one hand and aiming for optimism and positivity in the other. One does not negate the other.

      I’m sorry to hear of your challenging fertility journey — I have several good friends who have been on that road with you — and am so glad that you have come to the realization that you are allowed to feel much more than gratitude as a parent, regardless of the path that led you to motherhood. Your note here reminds me of how important it is to let myself feel it all, let it all out — not meter or suppress or judge. Thanks for this!


  5. This is one of my favorite posts you’ve written. “The sweet spot for me lives north of ‘keeping it real,’ reaching towards optimism.” This articulates my very feeling, that I’ve never put an exact finger upon.

    I have my pessimistic moments for sure, and I end to cry them out, to myself and those close to me, before trying to return to seeing the world as a sunny place. Sometimes that trying feels arduous–how difficult it is to reach for the sunbeams when you are in the pits. But ultimately optimism just feels better in my soul. And in my attraction to friends, partners, even acquaintances, I would say optimism is among the top, maybe the top, quality I look for.

    Thank you for helping me ponder this today! I always find your words to help things sit even clearer inside myself.

    1. Hi Jaclyn – So glad this resonated with you! It was a really interesting subject to contemplate and begin to unpack for me as well. You are so right that it can be arduous to find the silver linings, but it always makes me feel better when I’m in that zone.


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