Self-Expression, Being “Weird,” and People Pleasing.

By: Jen Shoop

I’ve been subconsciously threading a needle for the past few weeks, absorbing pull quotes and essays and moments of insight that pertain to self-expression, being “weird,” and people-pleasing. A few screens from the kaleidoscope:

+I wrote a year or two ago about a quote that arrested me: “People-pleasing is an unconscious attempt to control someone’s opinion of you.” The message rankled and disturbed, as I considered myself a “people pleaser.” I hate to let people down, I am quick to affirm, and I prefer people to feel comfortable and accepted for whatever they bring to the table, which usually means I will subjugate my own comfort/preferences to theirs. For a long time, I believed this was a neutral or even positive trait: wasn’t it a good thing to put the needs or wants of others first? It had never once occurred to me that this impulse could bear any negativity, let alone the subtext of “a desire to control.” Reading that quote, however, was like staring in the mirror for the first time. What was I doing? Why was I making myself smaller to accommodate the perspectives or wants of others? One of my biggest break-throughs in my adult life has been recognizing that I cannot control the way other people will react. I will admit that I still anticipate and worry about their responses, but ultimately, I have learned to repeat those words to myself when I am bracing for impact and they have helped me recenter on what I can control. People-pleasing relates here, as I have been coaching myself into seeing that I am not responsible for the emotions of other people, and that I am allowed to take up at least as much space as the people around me. On a very practical level, two mnemonics that have helped me in this regard are: 1) Reminding myself that I do not need to affirm everything someone else says. This often means physically biting my tongue to suppress the instinct to say “mhm” and “oh, yes!” as someone else is talking. 2) Using the words: “Hm, let me think about that,” instead of immediately springing into a response conditioned by my companion.

+Luisa Weiss wrote a lovely little essay on living amidst dust and protective drapes while her home is being renovated, and I had a major aha! moment reading this passage in particular:

“There’s a certain narrative that goes around, mostly on social media, about how women, especially ones with small children, should let go of perfection, let their houses go uncleaned, embrace the clutter. Implying that there’s something regressive about cleanliness, a connection between a tidy home and a life wasted. Speaking only for myself, of course, I would like to point out that for some of us, the cleanliness isn’t about achieving perfection or presenting some sanitized version of life to the outside world. It is far more about soothing some internal distress signal. When I see clutter, I see problems that need to be dealt with. Bills that need to be paid, clothing that needs to be folded, work that needs to be done. Tidiness allows my mind to rest. And my mind at rest is able to think about things that matter.”

I nodded vigorously at this. It’s funny, because I look back on when my son was born and I remember absolutely exhausting myself trying to maintain a tidy home. I would clean bottles and do laundry while he was sleeping, even though I felt on some level — almost a guilt-riddled level — that I should have been prioritizing my own rest. But I couldn’t. Living in a tiny New York apartment at the time, there was nowhere to hide the mess. There was no laundry room to dump dirty clothes into, no counter space to spare for bottles to wash later, no play room to shut the door on. It just had to be done in order for me to live in any kind of peace. For years now, I have felt like I “should have” not worried about the dishes so much, that I “should have” known to hire a housekeeper to help at that time. Perhaps so, perhaps not. I’m not advocating that any new mother deprive herself of sleep or overextend herself, but I am aware that, at the time, I was doing what I needed to do in order to nest comfortably with my new baby. I was making my way through a chaotic time the only way I knew how: by exerting care and determination to make things feel better and more orderly every single day. And I have told myself for years that I was prioritizing the wrong thing, was near-injuring myself for trivial reasons. And yet. Weiss’ note is a reminder that sometimes we do things that feel almost countercultural because we need to do them. I, too, found tidying my apartment akin to “soothing some internal distress signal.” This relates to the foregoing point on people-pleasing (or on going along with what feels socially condoned at a given moment) in that sometimes it is good to interrogate why we feel internal tension — cognitive dissonance! — over a decision we have made, or an opinion we hold that feels contretemps. A sort of internal: “Hm, let me think about that.”

+A week or two ago, Megan Stokes solicited “unpopular opinions” from her followers, and the answers spanned from “not liking Taylor Swift” to “not understanding why people with garages don’t park in them” (HA!) amongst other contrarian views on ambient pop culture, technology norms, and lifestyle conventions. The prompt was interesting because it again reminded me of all of the inputs that filter through our consciousness, sometimes without us even registering them. As a frivolous example: I love makeup. Sometimes I feel that I should disabuse myself of my affection for this superficial product category, as I understand, conceptually, the problems it can entail with regard to self-image, reality, comfort in one’s own skin, etc. And I have mixed feelings on my daughter’s occasional curiosity about my lipstick collection. And there is even something in me that feels like “serious women” — or “women of substance” — don’t wear makeup. But, at the same time — I love it. I find it fun! I enjoy trying new products! I could watch beauty TikToks for days! People are so creative! I believe it can be about self-expression and artistry! Why shouldn’t I make myself feel a bit prettier with dramatic lashes? And so why is it that, in the presence of many friends and acquaintances, I feel as though the desired response is: “Oh, I barely ever wear makeup.” To be clear: makeup is not the hill I die on, but the example is demonstrative. I’m talking here about a small, personal enjoyment, and I should feel comfortable saying, shruggingly, “Oh, really? I love it.”

+One of my favorite Instagram follows is Sam.Moooves. She is a bright light, full of warmth and energy and positivity. She often reminds her followers to “be you — be weird” and recently shared a post that read: “You are not meant to live like the others; you are meant to live like you.”

A scattered breadcrumb trail this Tuesday morning reminding me — to be myself. To live my one wild and precious life as me.



+On responding to hurt feelings.

+A podcast on apologies that changed my life.

Shopping Break.

+I wrote last week that these leggings are matte enough to take you from the fitness mat to brunch (they do NOT look like athletic wear) and I also wanted to mention that this white tee from Outdoor Voices is the same way. I wear it casually/with jeans all the time. Love the shape/fit.

+While we’re talking OV, this fitness dress of theirs is a bestseller. Love it in the navy. I also found this adorable toile/floral fitness dress over at Dillard’s!

+Sam Edelman is really killing it this season. Love these everyday flats (remind me of Mansur Gavriel) and these platform espadrille loafers! I have a nearly identical pair from last season that I loved wearing during these transitional months with shirtdresses. Like, imagine paired with this divine creation, which you could also dress up with heels/sandals.

+Are you traveling anywhere for spring break? I feel like these white linen pants (under $130) would be chic as a beach cover up. (Especially over our favorite swimsuit!)

+Cute white eyelet skort for a little lady.

+This dress sparks joy.

+These sweatshirts remind me of the much more expensive ones from Sloppy Joe’s.

+We’re almost to warmer weather. Time to buy some acrylic drinkware and melamine plates!

+Apparently these relaxed trousers from Jenni Kayne always sell out – just restocked!

+About to place an order at Saie, as I just finished a tube of their slip tint and immediately need to reorder. I also LOVE their highlighter — I actually have it in the lilac, which is not as scary/futuristic as it sounds, but I think I want to try in another color, too. And this brightening under eye concealer caught my attention…

+Obsessed with this “secretary desk.” So chic! Adds such dimension and personality to a room.

+Cheerful spring top from J. Crew. Comes in green if you’re still hunting for a last minute St. Pat’s day moment.

+Super love this dress in the army green — looks like La Ligne, but under $150.

+My current top pick for my daughter’s Easter dress.

+Magpies love a blue and white stripe (no one more than me though!)

+An oversized beach towel for your summer adventures/picnics.

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9 thoughts on “Self-Expression, Being “Weird,” and People Pleasing.

  1. Wow — as a lifelong people pleaser, I’ll be chewing on that first point for a while! Especially love the mnemonics you’ve shared — I’m going to test these out.

    I also love the passage of Luisa’s that you shared here — I had the same reaction when I read it in her newsletter! Side note: if you haven’t read her book My Berlin Kitchen, I highly recommend it. Such beautiful writing and as a gourmand, you’ll love the food-related parts as well. I read it a decade ago and think it might be time to revisit it!

    PS — I haven’t bought anything from Outdoor Voices in years (after going hard from 2014-2018ish, and I still wear some of those pieces!) but that tee has been on my wishlist for so long! I think this is just the push I need to try it. Also intrigued by the Exercise Dress 🙂


  2. I still am very behind on your posts for 2023. Yet the ones I read such as today’s always is what I need. I am learning how to be an adult. It’s not an easy process and your posts give me pause on how to rethink situations.
    I did see a headline re Marie Kondo and tidying up. Your post reminded me of that.

    On a different note, what recommendations would you suggest for being a guest at someone’s house? I like to bring local one of a kind gifts…such as I brought trivets one year which a local artist in Georgetown, CO makes. Another year CO aspen leaf ornaments. And last year CO tea towels from cat studio. I am running out of ideas and am looking for about half a dozen for our family in Australia. I welcome suggestions and do you have a review of summersalts swim wear or hunter Wellington’s? I still need/want before our trip.

    1. Thank you so much, Michelle — I absolutely love that my musings meet you at the right moment. So fulfilling to hear that. I am also learning how to be an adult — we all are. This reminds me a bit of the quote I borrowed a few weeks ago: “The truth is, most of us find out where we’re headed once we arrive.” Reading this made me feel so much better. It reminded me that all of us are just feeling our way through our lives, no matter how “buttoned up” and “organized” people may seem.

      On your gifts question — wow! What thoughtful items you’ve purchased for people in the past! So special. I would check out some of the pretty pieces from the following small businesses:

      Proper Table —
      Saddle Stitches —
      Hotel Lobby Candles —
      Hammett —
      RoundHouse —


      1. Oh and PS – Have not tried Summersalt but I know a lot of Magpies LOVE. I would definitely rec ordering to try based on how Magpies have raved about this brand in the past. And I love Hunter wellies, but personally prefer the styles with shorter shaft lengths. I used to own a full-length pair and they were so long on me, they hit like mid-knee and just looked so strange proportionately. If you’re taller, I’d say go with the classic/tall, but if you’re on the shorter end, look at their mid or low shaft lengths;

        These boots are really made to last, though. I bought a pair in college that I wore until a few years ago when I realized I hated the length. They hang tough!


      2. Thank you Jen! All of these are great. I’ll keep you posted in what I end if up. Am leaning towards Summersalt for a suit. And for boots I’m 5’4 so not super tall or that short. Average. I’m liking the idea though of short ones for this trip only for packing purposes. I promised Favourite Human Male I would pack light this trip. Which is probably good because I’m going alone this time and meeting him there. A bit nervous for flying solo on such a long flight.

        1. You got this!! You’ll be fine!! I agree on the shorter shaft Hunters for travel! Bon voyage / safe travels, friend!


  3. The flip side of this that I’ve been dealing with recently is when I’ve encountered people that don’t accept mine and my husband’s choices, such that I feel compelled to acquiesce and adjust myself because the urge is to people please that way and in line with their outlook.
    It’s painful and icky and stressful.
    Strangely though, this time — even with considerable grief — I’ve been able to recognise that it’s the “old programming” that is being tapped into with this and the reason it’s been so difficult and uncomfortable is because I really have done a system upgrade away from people pleasing. It’s been so arduous to do so but I’ve managed to make so much progress that now when I’m up against it, it’s a whole new mix of feelings. But there’s also a blessed and delicate silver lining that I’ve never experienced before which is: I actually do like me and the pain now is less about disappointing others and I feel the painful tension instead of not disappointing myself. It’s a new thing for me to look at myself as being valuable in things rather than cannon fodder.

    From your beautiful piece here, I’m wondering if maybe the extra facet of the kaleidoscope is how we need to work on pleasing ourselves as important members in the equation? I rarely do this and I think, ultimately, it’s because I never before thought that I was worth it and I didn’t like myself enough to do so. As I get better older I feel more and more tender towards myself while also working on being more compassionate with others; the road of life is long yet fragile so I want to be generous and thoughtful no matter what.

    Love your writing so much, Jen. Thank you! xx

    1. Aoife, I absolutely adore what you’ve shared here. First of all, incredible that you’ve been able to complete “a system upgrade away from people pleasing.” I think what you’re feeling is the pain of growth. I think the Internet’s big sister, Tinx, had something she shared about this awhile ago, on the sensation of “leveling up” or “away” from a person you used to be, and how that growth often (unfortunately) means some friendships/relationships will fall apart or fade. And that’s OK. Easier said than done, of course – I still have angst over friendships I’ve outgrown; I feel badly that I’ve moved on or had to proactively step away to do what’s right for me. Honestly, though, I wouldn’t want it any other way. The fact that I care about those people and how they feel is a sign makes me realize that I am a compassionate person. I don’t ever want it to “be easy” to move on from a friendship, or grow out of a relationship pattern, or whatever. It means I’m living with my heart. But, like you, I’m trying to honor my own needs/wants/etc. It’s a balance and anyone who says its easy or has a “quick fix” out of it — well, I don’t know I fully trust them.

      Anyway, thanks so much for sharing this vulnerable set of reflections!


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