From My Notes App, Vol 41

On invisible decisions, rules that changed without announcement, and learning to trust yourself when nothing feels certain

Hello loves! Memorial Day kind of snuck up on us out of nowhere. Two weeks ago I was wearing turtlenecks and this past Wednesday felt like middle of July, as in I melted into a freaking puddle because of the stifling humidity. All I can say is that after this shitty winter I’m so pleased we are trending in the right direction!

Thank you to all of you who sent us warm wishes and kind encouragement for Murray’s tubes surgery. The day was harder on mom and dad than Murray, but we are through it and doing great. And a lovely weekend followed, mostly outside, catching up with old friends.

More of that is to come this weekend, as we are headed to Newport, Rhode Island for my best friend’s wedding. We’re asking all the Etsy witches to send us beautiful weather so that she can walk down the aisle to her forever guy, who will then whisk her away to a week in Tuscany. I can’t wait to dance, eat and relax. And Monday, if it’s nice, we hope to bring Murray to the pool and let him get all the energy out.

🎧 What I’m Listening To

This weeks round up is about what happens when the rules you built your life around stop working, and you have to decide whether to keep pretending they still do or admit something fundamental has changed.

🎧 Andrew Yang Wants to Give You Money Back on Oversubscribed with Erin & Sara Foster (Spotify, Apple, YouTube) — Andrew talks about universal basic income, AI replacing white collar workers, and why the disruption happening now mirrors the manufacturing collapse of the 80s and 90s. His framing of the “K-shaped” economy felt sharp: some people are thriving and others are quietly falling behind, and that gap keeps widening in ways most people are not prepared for. A lot of workers right now are operating under the assumption that competence and effort will protect them, but the reality is that entire job categories are being restructured faster than people can adapt. His point about needing universal basic income sooner rather than later felt less like policy talk and more like acknowledging what many people are already quietly experiencing.

🎧 Tezza Barton: I Built A $2.5M App That Every Girl Needed With No Tech Experience Or Investors on Hot Smart Rich with Maggie Sellers Reum (Spotify, Apple, YouTube) — Tezza talks about launching her photo editing app to brutal reviews that made her want to delete the whole thing, then pivoting the backlash into a real business that made $2.5M in its first year. What stands out is how honest she is about the failed business ideas, the 250-square-foot apartment, the part where she almost gave up. Most people see success and assume it was linear, but the reality is that most businesses are built through momentum and resourcefulness long before they are built through elegance. Her point about bootstrapping instead of raising money also felt like a quiet rebellion against the assumption that all successful startups need venture capital.

🎧 How Social Media Makes You Money on Built in Public with Courtney Johnson (Spotify, Apple, YouTube) — This episode is about why social media feels so uncomfortable for so many people, and why that discomfort is often the very thing that leads to growth, opportunity, and money. Courtney talks about visibility as a lived experience, not just a content strategy problem. The fear of being misunderstood. The cringe that shows up right before momentum. The internal resistance that makes people want to stop posting right when things are about to work. One line worth remembering: action creates clarity, not the other way around. Most people stay stuck waiting for certainty instead of moving while things still feel messy, and this episode makes a really compelling case for why staying in the game even when it feels uncomfortable is often the exact thing that unlocks the next level.

🎧 We Regret to Inform You That This Episode Is About Firing People with Jennifer Laurie on I Hate It Here with Hebba Youssef (Spotify, Apple, YouTube) — Nobody talks about their first termination the way they should, which is with a little bit of trauma, because we never forget the people we have to let go of. This episode goes into where managers go horribly wrong before they even get to the termination conversation, how bias creeps into these decisions in ways that are really easy to miss, and why the debrief after is the part everyone skips but absolutely shouldn’t. Jennifer is honest about the Googling, the nerves, the manager who was just as lost as she was. A lot of people in leadership positions right now are being asked to make really hard decisions without the training, support, or infrastructure to do it well, and this conversation felt like a rare acknowledgment of that reality.

🛒 What I’m Buying

Making this short and sweet because it's almost the long weekend and we have fun things to do. This week's edit combines a few different vibes, but americana inspiration is the throughline for both Memorial Day weekend and the 4th of July coming up. Red, white and blue are a constant theme throughout, including this incredible striped set (button up, shorts), this navy one piece, this red strapless one piece, this patterned silk maxi dress and so much more.

Also on my radar is this light blue dress with matching earrings and light gold heels. This tomato printed mini is giving me Wishbone Kitchen vibes and I love it so much. I need this golden retriever golf hat for my next round. And these unique tortoise shell sunnies. This patriotic set (top, shorts) from Target just arrived in time for my long weekend in Newport and it's SO comfy. Plus you'll find a ton of very affordable shoe options for summer (like these LOFT favorites). I also want to remind you that I rounded up all my recent purchases and gifted items right here, and I also shared them on social right here.

👣 What I’m Coaching: Competence Is No Longer Enough

On Wednesday, Meta laid off 8,000 employees via 4 a.m. emails after reportedly telling teams to work from home so there wouldn’t be a scene at the office when the notifications hit. At the same time, the company is aggressively reorganizing around AI while flattening management structures in the name of efficiency. It’s a pretty jarring moment for a lot of professionals who spent years believing career safety came from being dependable, promotable, hardworking, and loyal to the institution they were helping build. The corporate ladder many people spent decades climbing is getting shorter in real time.

One of the stronger observations I read this week was in an article by Hanna Goefft about recent graduates entering the job market. She writes about how companies increasingly want people who can adapt quickly, integrate AI into workflows, communicate strategically, and continuously reposition themselves as the market shifts. And this is becoming one of the biggest conversations in my coaching sessions lately, but not just with recent grads. With mid-career professionals who are quietly realizing the rules changed without announcement.

The professionals navigating this era best are not necessarily the smartest or most technically competent. They are the ones willing to evolve before they are forced to. The ones building visibility, relationships, adaptability, and leverage outside a single employer long before a corporation suddenly decides efficiency matters more than loyalty. A lot of my clients right now are dealing with a version of the same question: what happens when doing your job well stops being enough? When being good at what you do no longer protects you from being flattened by a reorganization you had no visibility into?

I think competence used to buy you stability. Now it buys you time. The real work is figuring out what you are building while you still have it.

📚 What I’m Reading

There is a very specific flavor of existentialism quietly taking over the internet among ambitious people. The conversation feels less focused on “how do I achieve more?” and more focused on whether the version of success people optimized for actually feels worth the level of exhaustion, performance, and self-abandonment it often requires to get there.

✨ In Defense of the AI Girlboss (The Cabro’s Substack, Catherine) — This piece perfectly articulates the internet’s growing discomfort with ambitious women monetizing expertise, especially in emerging spaces like AI. Women are often expected to share expertise freely, but the second they profit from that knowledge, they become suspect. We’re entering a labor market where adaptability and AI fluency are increasingly becoming survival skills, yet women speaking authoritatively about those shifts are often framed as opportunistic instead of informed. The internet seems deeply comfortable with women working hard, but far less comfortable when they openly benefit from it.

✨ The Truest Technology is Human Connection (Alexis | The Breadwinners Substack) — This piece is about two founders who left stable corporate careers to build intimate, offline communities centered on real human connection, and it made me think about how many people are quietly craving depth over scale. One line that stuck: "We're living through a crisis of connection disguised as a golden age of connectivity." The friction, she writes, is the point. It's where the good stuff happens. I think a lot of adults are realizing they don't just want audiences anymore. They want people they can actually call on. Real friendships. Real rooms where they don't have to perform. This partly explains why newsletters, dinners, retreats, and smaller communities feel so emotionally resonant right now. People are exhausted by optimization and hungry for something that can't be replicated by a platform.

✨ What Would You Do If You Actually Had a Full Day to Think? (Life at Play Substack, Gina Kawalek) — This piece is about creating a full day designed to help high-achieving people pause long enough to question whether they still want the life they spent years building. Gina writes, "most of us didn't design our lives. We accumulated them." And that feels painfully accurate. Promotions, routines, cities, identities, expectations, obligations, and suddenly you wake up one day realizing you've built an entire existence without ever stopping to ask whether it still feels aligned. I deeply related to the idea that most people don't actually lack answers — they lack the space to hear themselves think.

✨ Hilary Duff’s Commencement Speech for Northeastern University Is Dividing the Internet (Cosmopolitan) — Hilary Duff basically told graduates that not every opportunity, paycheck, or impressive next step is worth saying yes to if it disconnects you from yourself. The internet immediately pushed back that saying “no” is a privilege, which is obviously true to an extent. But I also think people underestimate how expensive it becomes to spend years building a life around work that quietly conflicts with your values, identity, or actual desires. Burnout, resentment, health issues, nervous system dysregulation, career pivots that require starting over — those things are often the downstream cost of repeatedly saying yes to opportunities that look successful from the outside but feel deeply wrong on the inside.

🌀 Spiral of the Week: Do I Want a Simpler Life or Do I Just Want Relief?

This week’s spiral is brought to you by the increasingly aggressive amount of bread-baking, chicken-owning, slow-living content currently dominating our social feeds. Suddenly everyone wants a garden, a slower morning, less screen time, a tiny bookstore, homemade soup, and to disappear to a coastal town where nobody asks them to circle back on anything ever again.

And honestly? I deeply understand the fantasy. I save all those posts. But I also think the internet keeps flattening this conversation into “women secretly want to become trad wives,” which I fundamentally disagree with. I don’t think most women want less ambition, less independence, or less agency. I think they want relief from carrying 700 invisible responsibilities while also performing high achievement, emotional regulation, beauty, productivity, motherhood, partnership, self-optimization, and career excellence simultaneously.

I read a piece this week by Megan Schnarr about why so many high-achieving women are suddenly baking bread and choosing slower lives, and it articulated something I’ve been watching build. She writes about how women operate on a monthly hormonal cycle, not a 24-hour one like men, which means our energy naturally fluctuates week to week. Instead of honoring that, we’ve been trying to keep up with constant high-output, always-on lifestyles that keep our nervous systems in a permanent state of stress. Eventually it catches up! And because of that, a lot of women are quietly asking themselves whether they want a simpler life or whether they just want to stop feeling like they’re drowning. And I’m not sure the answer is always clear.

👀 What I’m Scrolling & Saving

These are the posts that actually stopped me mid-scroll.

These made me smile when I was having some hard days. This too.
Do you agree? I certainly do.
A love letter to what Jennifer Hyman built at Rent the Runway.
Obsessed with this girls style and aesthetic.
I don’t make the rules!
Ahhh, who feels seen?
Everything Meredith creates makes me hungry.
This sandwich recipe will certainly be a summer go-to!
Great reason to always shoot your shot.
This had me chuckling so hard!
I want these to be my summer plans, too.
Cannot wait to try this in Charleston next month.
This might be my favorite creator ever.
You just know every girl watching this wants to be wearing this exact outfit.

💬 The Group Chat Says: We're All Outsourcing Our Own Answers

My group chat has been discussing how many decisions we make in a single day. Not just the obvious ones like what to cook for dinner or which meeting to prioritize, but the invisible ones. The mental load ones. Should I follow up again or let it go? Is this worth pushing back on? Do I actually want to go to this or am I just saying yes out of obligation? etc. By the end of the day, a lot of us are so decision-fatigued that we start second-guessing our own instincts. We go looking for external validation. We poll the group chat. We scroll through advice. We ask the internet. We consult frameworks, coaches, podcasts, newsletters, and apparently now we are naming AI agents and treating them like trusted advisors who can confirm what we already suspected.

I read a Career, Reconsidered essay that goes into detail around our hunger for external validation and how we are outsourcing our own answers to anything that sounds confident enough to make the decision feel less like ours. And I think she’s right. The question that keeps me thinking is: what becomes possible when you stop doing that? When you trust that the thoughts you keep returning to, the instincts that persist even when you ignore them, are not random noise but actual signal trying to tell you something? People aren’t lost because they lack information. People are lost because they have so much coming at them from the outside that they have stopped being able to locate their own voice underneath it. Sometimes the smartest thing you can do is turn off the noise long enough to hear what you actually think.

✌️ That’s A Wrap

As we head into the first official weekend of summer, I’m leaving you with this absolute BOP I’ve been playing nonstop (thank you TikTok). I will be blasting it on my way to Newport and I encourage you to do the same. You can catch me in all these beautiful little restaurants this weekend.

Also, have you read Lena Dunham’s Famesick: A Memoir? I haven’t, but have heard such interesting things about it, so I’m adding it to my TBR.

Have a lovely long weekend!

xo,
Kelsey