The craft, infrastructure, and history of email and newsletters — read through dated artifacts.

Author: Sandra Olson (page 20 of 25)

I Used to Hate Fall (And Other Seasonal Confessions)

The Great Autumn Reversal

I spent thirty-two years being absolutely convinced that fall was a scam. All those people posting pumpkin spice everything and going on about “crisp air” and “changing leaves” seemed to be participating in some elaborate collective delusion. I was team summer, ride or die. Give me sweat and sunscreen and the kind of heat that makes asphalt shimmer. Fall felt like nature’s cruel joke, a beautiful slow-motion death march toward winter’s misery.

I Used to Hate Fall (And Other Seasonal Confessions)
I Used to Hate Fall (And Other Seasonal Confessions)

Then last October, something shifted. I was walking my dog through the neighborhood I’d lived in for three years, following the same route I’d taken hundreds of times. But this time, I actually stopped. Really looked. The maple tree on Elm Street wasn’t just “changing colors” in that vague, greeting-card way I’d always dismissed. It was staging an entire performance. Each leaf was a different shade of gold and orange, some still stubbornly green, others already brown and crispy at the edges. The whole tree looked like it was arguing with itself about timing.

Standing there with my dog tugging at the leash, I realized I’d been wrong about fall for three decades. Not just wrong, but aggressively, smugly wrong. The kind of wrong where you build an entire personality around hating something you never bothered to actually observe.

Illustration for I Used to Hate Fall (And Other Seasonal Confessions)
Illustration for I Used to Hate Fall (And Other Seasonal Confessions)

The Science of Changing Seasons (And Minds)

Here’s what I learned when I finally paid attention: fall isn’t about death at all. It’s about strategy. Trees aren’t giving up when they drop their leaves. They’re making calculated decisions based on decreasing daylight and temperature. The chlorophyll that keeps leaves green all summer starts breaking down, revealing the yellow and orange pigments that were there all along. Some trees even produce new red pigments, anthocyanins, specifically for their autumn show. It’s like they’re saying, “If we’re going dormant, we might as well look fantastic doing it.”

This revelation made me wonder what else I’d been confidently wrong about. Turns out, quite a lot. I’d convinced myself I hated Brussels sprouts without trying them since childhood. I thought I was “bad at mornings” when really I was just bad at going to bed at a reasonable hour. I believed I needed eight cups of coffee to function when four worked just fine. Sometimes being wrong isn’t about lacking information. It’s about not questioning the stories we tell ourselves.

The thing about seasonal changes is how they force this kind of reckoning. Every few months, the world shifts dramatically around us, and we get to choose: adapt our perspective or dig in deeper to our assumptions. I spent years digging in deeper, treating my summer preference like a core personality trait rather than just, you know, a preference that could evolve.

Winter’s Quiet Lessons

My winter conversion took longer, and I’ll admit it’s still ongoing. But here’s what changed: I stopped trying to fight January and started paying attention to what it actually offers. There’s something profoundly honest about winter trees. No leaves, no pretense. Just the basic architecture of trunk and branches against a gray sky. You can see the real shape of things in winter, the structure that gets hidden under all that summer abundance.

I also discovered that winter light is completely different from summer light. Sharper, somehow. More angular. When it’s twenty degrees outside and the sun is streaming through my kitchen window, hitting the steam from my coffee cup just right, I get it. This isn’t the season trying to kill me. It’s the season asking me to notice different things. Smaller things. The way frost forms patterns on the car windshield. How silence has actual weight when it’s muffled by snow.

My dog, by the way, has been team winter from day one. Watching him bound through snow like he’s discovered buried treasure made me realize that maybe the problem wasn’t winter. Maybe the problem was my determination to experience it as a problem.

Spring Skepticism and Summer Honesty

Spring still makes me slightly suspicious, if I’m being honest. All that aggressive blooming and sudden green everywhere feels a bit much after months of winter’s restraint. But I’m trying to lean into the discomfort instead of immediately writing it off. Maybe my spring skepticism says more about my relationship with change than it does about the season itself. Spring is messy and unpredictable, lurching between warm days and random snowstorms. It’s change happening in real time, and change has never been my strong suit.

And summer? Well, I still love summer. The difference is that now it’s not the only season I love, which somehow makes me love it better. It’s like finally admitting that pizza isn’t the only good food. Suddenly you can appreciate pizza for what it actually is rather than what you need it to be. Summer gets to be long days and fireflies and the specific exhaustion that comes from too much sun, without having to carry the weight of being the only season worth experiencing.

The truth is, I probably needed to spend thirty-two years being wrong about fall before I could be right about it. Some changes in thinking require time, the way some flavors require the right season. I couldn’t have appreciated autumn’s strategy and winter’s honesty when I was twenty-five and convinced that comfort was the highest goal. Now I know that discomfort often points toward something worth noticing.

The Long Game of Observation

These days, I try to approach each season like I’m meeting it for the first time. What does March actually feel like when I’m not busy waiting for it to become April? What happens if I let December be dark and quiet instead of fighting it with string lights and forced cheer? It’s a small practice, but it’s changed how I think about more than just weather.

The seasons keep changing whether we pay attention or not. But paying attention, really paying attention, turns out to be its own kind of season. One that doesn’t show up on any calendar but changes everything about how you experience the ones that do.

I’m curious about your own seasonal revelations, the assumptions about weather or time or change that you’ve discovered were worth questioning. What season took you by surprise? What did you think you knew for certain that turned out to be more complicated than that?

Money Moves I Made This Year (And What They Actually Taught Me)

The Credit Card I Finally Canceled

You know that credit card you keep meaning to cancel but never do? Mine was a Chase Sapphire Reserve that I’d been paying $550 annually for since 2019. Every January I’d tell myself I’d use the travel benefits enough to justify it. Every December I’d realize I hadn’t.

This year I finally pulled the trigger in March. Not because of some grand financial awakening, but because I was irritated at seeing the charge hit my account again. The customer service rep tried to downgrade me to the regular Sapphire. I said no. She offered to waive the fee for a year. I said no again, which surprised us both.

The weird thing? I felt guilty for weeks afterward. Like I was admitting defeat or giving up on some version of myself who travels constantly for work and racks up points at fancy hotels. But that person doesn’t exist. I drive to most meetings and stay at Holiday Inn Expresses when I travel for fun.

Buying the Wrong Mattress on Purpose

Our old mattress had developed what I can only describe as a crater where my partner sleeps. We’d been talking about replacing it for months, doing that thing where you research extensively but never actually buy anything.

Instead of getting the $1,200 foam mattress we’d bookmarked seventeen times, I bought a $400 one from Costco. Not because we couldn’t afford the expensive one, but because I was tired of optimization paralysis. Sometimes good enough is actually good enough.

The Costco mattress is fine. Not life-changing, not terrible. Just fine. And you know what? Fine is working out better than I expected. I sleep the same amount. My back doesn’t hurt more or less. The only difference is we have an extra $800 in our checking account.

The Subscription Audit That Revealed Too Much

In June, I went through our credit card statements and found $127 in monthly subscriptions I’d forgotten about. This wasn’t the usual suspects like Netflix or Spotify. This was the meditation app I used twice, the meal planning service that made me feel guilty about not meal planning, and something called “CreativeLive” that I genuinely could not remember signing up for.

The meditation app cancellation was easy. The meal planning one required a phone call where a cheerful person asked why I was leaving and whether there was anything they could do to keep me. I explained that I don’t meal plan and never will, which seemed to confuse them more than it should have.

CreativeLive turned out to be a photography course platform. I apparently signed up during a 2 AM rabbit hole about learning portrait photography. The course is still sitting in my account, 0% complete. I kept the subscription for another month out of shame before finally canceling it too.

Investing in Something I Actually Understand

After years of putting money into index funds because everyone said I should, I bought individual stocks for the first time. Not because I think I can beat the market, but because I wanted to understand what I was actually investing in.

I picked five companies whose products I use regularly and whose business models I can explain to my grandmother. Apple, Microsoft, Costco, Johnson & Johnson, and Visa. Nothing sexy or revolutionary. Nothing that’s going to make me rich quick or fund early retirement.

The portfolio is up about 8% since I started it in May, which is fine but not the point. The point is that I actually read the quarterly earnings reports now. I understand why Costco’s membership model works and why Visa makes money on every transaction. It’s made me more curious about how businesses actually operate, which has been worth more than whatever return I’m getting.

The Emergency Fund That Wasn’t Emergency Enough

We had $15,000 sitting in a savings account earning 0.01% interest. Financial wisdom says this is smart. Inflation says this is expensive. In September, I moved $10,000 of it into a high-yield savings account earning 4.5%.

The extra $400 per year isn’t going to change our lives, but it bothered me more than it should have that our money was actively losing value while sitting in a “safe” place. The high-yield account is with an online bank I’d never heard of six months ago, which feels slightly risky and slightly grown-up at the same time.

I kept $5,000 in the local bank account because some emergencies need immediate access to cash. This feels like a reasonable compromise between paranoia and optimization, though I’ll probably second-guess it until something actually breaks and I need the money.

None of these decisions feel particularly wise or foolish in retrospect. They just feel like choices I made with the information I had at the time, which is probably the best any of us can do. If you’ve made similar money moves this year, or completely different ones for completely different reasons, I’d love to hear about them.

The Projects That Actually Mattered This Year

The Database That Nobody Asked For

I spent three months this year building a customer feedback database that our product team swore they didn’t need. They had spreadsheets, they said. Color-coded ones. What more could you want?

The Projects That Actually Mattered This Year
The Projects That Actually Mattered This Year

But I kept watching our support team drown in those same spreadsheets during our weekly triage meetings. Sarah would pull up one file, then another, then realize the data she needed was in last month’s version, which lived in someone else’s Google Drive folder. By the time she found what she was looking for, the meeting was over and the customer complaint was three days colder.

So I built it anyway. Called it a “learning project” in my performance review, which is corporate speak for “I’m doing this whether you like it or not.” Three weeks after launch, the product team was using it daily. Sarah sends me coffee shop gift cards now. Sometimes the best projects are the ones nobody thinks they want until they have them.

The Newsletter That Almost Wasn’t

Our internal newsletter died sometime in March. Not officially, it just sort of faded away like a houseplant everyone forgot to water. People would ask about it in Slack occasionally, usually followed by shrugging emoji and someone changing the subject.

I volunteered to revive it, mostly because I was tired of hearing the same questions repeated across five different channels. “When’s the next all-hands?” “Did anyone see that article about our competitor?” “Why is the coffee machine making that noise again?” Basic stuff that used to live in a shared space but had scattered into a dozen private conversations.

The trick wasn’t writing it, it was making it feel human instead of corporate. I started including photos from people’s desks, weird overheard conversations from the kitchen, actual updates about projects instead of management buzzwords. Response rates went from zero to 89% in two months. Turns out people will read almost anything if it doesn’t sound like it was written by a committee.

The coffee machine noise mystery got solved in week three, by the way. Loose screw in the grinder. Tom from facilities fixed it in ten minutes, but only after I mentioned it in the newsletter and half the office started leaving sticky notes on the machine with theories.

The Training Program That Worked Too Well

Training new hires used to be pure chaos. Not the fun kind, the expensive, inefficient kind where people would spend their first week asking the same questions that the person before them asked, and the person before that. We had a wiki, technically, but it was organized like a fever dream and about as helpful as a chocolate teapot.

I created a structured onboarding program that paired new people with mentors and broke everything down into digestible weekly goals. Nothing revolutionary, just basic human psychology applied to workplace reality. Week one: learn the systems. Week two: shadow your mentor. Week three: start taking on small projects with backup.

It worked so well that HR asked me to expand it company-wide. Then other departments wanted their own versions. Suddenly I was running training sessions for people who’d been here longer than me, teaching them how to teach others what they already knew. Meta-training. The kind of project that starts simple and grows tentacles when you’re not looking.

The best part was watching the mentors discover they were better teachers than they thought. Jennifer from accounting, who swore she “wasn’t good with people,” ended up leading the most popular sessions. Turns out expertise and patience are a powerful combination, even if you don’t realize you have both.

The Process Nobody Wanted to Document

Every company has that one process that lives entirely in someone’s head. Ours was client onboarding, and that someone was Marcus, who’d been here since the office had carpet instead of concrete floors. Marcus knew everything, remembered everyone, and had exactly zero interest in writing any of it down.

The problem became obvious when Marcus took his first vacation in three years. Client calls went unanswered. Contracts sat in limbo. The rest of us scrambled around like chickens with our heads cut off, trying to reverse-engineer decades of institutional knowledge from email threads and prayer.

I spent two weeks following Marcus around with a notebook after he got back, documenting every step, every exception, every “oh, and if this happens, then you do that” moment. He thought I was being paranoid. I thought I was being practical. We were both right.

The documentation ended up being forty pages long. Forty pages of processes that had been living in one person’s memory, vulnerable to vacation days and job changes and the simple passage of time. Now it’s a shared resource that three people can execute instead of one. Marcus still knows things the rest of us don’t, but at least we won’t lose everything if he decides to retire to that cabin in Vermont he’s always talking about.

What Sticks Around

These projects all have something in common, they solved problems that were hiding in plain sight. The database made visible what was scattered. The newsletter connected what was fragmented. The training program scaled what was working. The documentation preserved what was fragile.

None of them were flashy. None of them will win innovation awards or get mentioned in company press releases. But they’re the kind of work that makes everything else possible, the infrastructure that lets the exciting projects actually happen.

Looking back, I’m proudest of the things that other people now take for granted. That’s probably the best measure of whether something was worth building, not whether people notice it, but whether they’d miss it if it disappeared.

What are you working on that nobody asked for but everyone needs? I’m curious about the projects that don’t make it into status reports but somehow make everything else work better.

Things I Quit That Actually Made Life Better

The Morning News Ritual That Was Slowly Poisoning My Brain

I used to start every morning with a doom scroll through news apps while my coffee got cold. You know the drill: check the headlines, fall into a rabbit hole about some political scandal, emerge twenty minutes later feeling like the world was ending and my day hadn’t even started yet.

Things I Quit That Actually Made Life Better
Things I Quit That Actually Made Life Better

The breaking point came when I realized I was getting genuinely anxious about events I had zero control over, in places I’d never been, involving people I’d never meet. I was carrying this low-level stress all day, like background music you don’t notice until someone turns it off.

Now I check the news once a day, usually after lunch when I’m mentally prepared for it. If something truly important happens, trust me, someone will tell you. The world kept spinning without my constant surveillance, and my mornings became infinitely more peaceful. This works especially well if you’re someone who absorbs other people’s emotions or if you find yourself arguing with strangers on the internet before 9 AM.

Illustration for Things I Quit That Actually Made Life Better
Illustration for Things I Quit That Actually Made Life Better

Why I Stopped Saying Yes to Every Social Invitation

For years, I thought that being a good friend meant showing up to everything. Birthday parties, work happy hours, casual hangouts, weekend plans that popped up via group text at the last minute. I said yes to all of it, even when I was exhausted, even when I’d rather stay home and reorganize my spice rack.

The revelation hit during a particularly loud restaurant gathering where I spent two hours making small talk about nothing while secretly calculating how much this mediocre pasta was costing me. I wasn’t enjoying myself, and I definitely wasn’t being good company. I was just… present. Like a cardboard cutout of myself.

Now I’m ruthlessly selective about social commitments. I say yes to things that genuinely excite me and no to everything else, without elaborate excuses. When you show up to fewer things but bring your actual enthusiasm, people appreciate the quality over quantity. This approach works best if you’re an introvert masquerading as an extrovert, or if you’ve ever found yourself hiding in someone’s bathroom just to get five minutes alone.

The Productivity System That Made Me Less Productive

I spent an embarrassing amount of time perfecting my task management system. Color-coded calendars, detailed to-do lists, apps that turned my daily habits into games. I had spreadsheets for tracking spreadsheets. It was productivity theater at its finest, and I was both the star and the only audience member.

The system itself became the main task. I’d spend thirty minutes each morning organizing my day and another twenty minutes each evening reviewing what I’d accomplished. I was managing my productivity more than I was actually being productive. It’s like spending so much time planning a road trip that you never leave your driveway.

These days, I keep a simple notebook and write down three things I want to accomplish each day. That’s it. No apps, no color coding, no elaborate systems. Somehow, I get more done with less planning. This works particularly well for chronic over-planners and anyone who’s ever spent more time organizing their digital workspace than actually working in it.

The Comparison Game That Nobody Wins

Social media turned me into an amateur anthropologist, constantly studying other people’s highlight reels and wondering why my regular Tuesday didn’t look like their carefully curated vacation photos. I’d catch myself measuring my life against strangers’ Instagram stories, which is roughly as useful as judging your cooking skills based on magazine food photography.

The comparison extended beyond social media too. I’d walk through Target and wonder why I couldn’t afford to casually drop two hundred dollars on home decor like the woman in front of me apparently could. I’d read about someone’s career success and immediately catalog all the ways I was falling behind. It was exhausting, and more importantly, it was completely pointless.

I deleted most social apps from my phone and started treating other people’s lives like movie trailers: interesting to watch, but not representative of the full experience. My life didn’t get objectively better, but my satisfaction with it increased dramatically. This strategy works best for natural comparers and anyone who’s ever felt inadequate after scrolling through LinkedIn.

The Perfect Timing Myth That Kept Me Waiting

I used to wait for the perfect moment to start things. The perfect time to learn guitar, to start that side project, to have difficult conversations. I was waiting for some mythical alignment of circumstances where I’d have enough time, energy, and mental space to do things properly.

Spoiler alert: that moment never comes. There’s always something else competing for your attention, some other responsibility that feels more urgent. I realized I was using “perfect timing” as sophisticated procrastination, a way to avoid the discomfort of starting something new or potentially failing at it.

Now I start things badly and figure it out as I go. I began learning Spanish during the busiest month of my year, started writing consistently while working a demanding job, and had that overdue conversation with my landlord about the leaky faucet on a random Tuesday. None of these moments were ideal, but they were available. This approach works especially well for perfectionists and chronic over-thinkers who mistake planning for progress.

These aren’t earth-shattering changes, but they’ve quietly improved the texture of my daily life in ways I didn’t expect. If any of these sound familiar, maybe there’s something here worth trying. What have you stopped doing that made room for something better?

Why You Should Fail at Making Sourdough (and Other Creative Disasters Worth Pursuing)

The Beautiful Disaster That Started It All

Three months ago, I decided to make sourdough bread. Not because I needed bread, mind you, but because everyone on the internet made it look so effortlessly rustic and satisfying. You know the photos: perfectly scored loaves with those Instagram-worthy ear formations, sitting on marble countertops next to mason jars of bubbly starter.

Why You Should Fail at Making Sourdough (and Other Creative Disasters Worth Pursuing)
Why You Should Fail at Making Sourdough (and Other Creative Disasters Worth Pursuing)

My first loaf looked like a deflated football. Dense as a brick and about as appetizing. The starter I’d been nurturing for two weeks? Dead as disco by day ten. I’d somehow managed to kill what is basically immortal bacteria that has survived since ancient Egypt.

But here’s what surprised me: I wasn’t disappointed. I was hooked. Not on bread making, necessarily, but on that specific type of creative failure that teaches you something you didn’t know you needed to learn.

Illustration for Why You Should Fail at Making Sourdough (and Other Creative Disasters Worth Pursuing)
Illustration for Why You Should Fail at Making Sourdough (and Other Creative Disasters Worth Pursuing)

The Art of Productive Failing

If you’re someone who gets paralyzed by perfectionism or finds yourself avoiding new creative pursuits because you’re worried about not being immediately good at them, I have a weird recommendation: pick something you’ll probably fail at, and fail at it on purpose.

Not everything needs to be a side hustle or a skill that adds to your LinkedIn profile. Sometimes the most valuable creative experiments go sideways, teach you about materials you’ve never worked with, or show you how your brain solves problems when there’s no pressure to succeed.

My sourdough disaster sent me down a rabbit hole of fermentation science, which led to making kombucha, which led to growing my own scoby, which somehow resulted in me having strong opinions about water pH levels. None of this was planned. All of it was ridiculous. Most of it failed spectacularly.

Three Failures That Became Unexpected Teachers

After the sourdough incident, I started keeping what I call a “failure journal.” Not in a self-flagellating way, but as a record of experiments that didn’t work out as planned but taught me something interesting anyway.

The watercolor disaster of June taught me that I have zero patience for waiting for layers to dry, but excellent instincts for color mixing when I’m not overthinking it. Now I keep a small watercolor set on my desk for five-minute brain breaks between meetings. Those loose, imperfect sketches capture more life than anything I labored over.

The great pottery wheel fiasco of August showed me that my hands apparently have no muscle memory for centering clay, but I discovered I love hand-building techniques. Pinch pots became meditation. Coil building became problem-solving. I never did master the wheel, but I made a set of wonky bowls that hold soup better than any perfectly round ones I could have bought.

Then there was September’s attempt at learning ukulele through YouTube videos. My fingertips couldn’t handle the strings, my strumming sounded like an angry cat, and I never made it past three chords. But those twenty-minute practice sessions before coffee became a surprisingly effective way to wake up my brain. Sometimes I just hold the thing and pluck random strings. It’s not music, but it’s something.

Who This Approach Actually Works For

This isn’t for everyone, and that’s fine. If you’re someone who finds deep satisfaction in mastering skills systematically, or if unfinished projects stress you out more than they energize you, this probably isn’t your path.

But if you’re the type of person who has seventeen browser tabs open at any given time, who gets excited about learning new things but bored once you’ve figured out the basic mechanics, or who tends to abandon hobbies once they start feeling like obligations, then strategic creative failure might be exactly what you need.

It’s particularly good for people who work in fields that demand a lot of precision or have high stakes for getting things right. There’s something liberating about doing something where the stakes are exactly zero, where “messing up” isn’t just okay but actually the point.

The Practical Magic of Purposeful Incompetence

Here’s what I’ve learned about making creative failure work for you instead of against you: treat it like research, not performance. Keep your experiments small, cheap, and time-bound. Give yourself permission to quit when something stops being interesting, even if you haven’t “finished” it.

Set a timer for weird constraints. Spend exactly fifteen minutes trying to draw with your non-dominant hand. See what happens if you try to write a poem using only words that rhyme with “orange.” Attempt to cook something from a cuisine you know nothing about using only ingredients you already have.

The magic happens in that space between intention and incompetence, where you’re trying something real but not trying to be good at it. Your brain starts making connections it wouldn’t make otherwise. You notice textures, sounds, processes, and problems you’d never pay attention to if you were focused on achieving a specific outcome.

My sourdough starter is thriving now, by the way. Not because I got better at following recipes, but because I stopped caring whether the bread looked like the photos. Turns out, even ugly bread tastes pretty good when you made it yourself and learned something along the way.

What’s the thing you’ve been avoiding because you know you’d be terrible at it? Maybe it’s time to find out just how terrible you can be. I’d love to hear about your beautiful disasters if you decide to try any of this.