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optics matter (even when you’re over forty and might forget how to talk)
five days in PDX, building in public, and choosing momentum
Laura Winberry
January 06, 2026 • Estimated Reading Time: 10 minutes
gm and welcome to issue 51. Next week’s issue will mark Babe’s first birthday—hot damn. Thank you for being here for some or all of this weekly ramble. You’re the best.
Last week I wrote a “year in the rearview,” reflecting on a full calendar year of Babe and other fine things.
This week I get into my feelings about the market research trip I just booked for PDX (wherein I go to Portland and talk to people I don’t know and ask them if they’ll fill out my survey and video-document pretty much the whole thing), deciding to run a giveaway in the eleventh hour, the most important tv show happening rn, and further thoughts on cold emailing.
Shall we?
5 days in PDX, some pats on the back, plus optics matter
I finally booked a spot in Portland so that I can finally go and talk with businesses in person and finally (maybe? hopefully? I don’t fucking know.) get some more concrete product market fit validation for this inOregon app I’ve been working on.
And if I don’t? Either this newsletter’s about to pivot like whoa or I have to figure out a different way into the fold of “do people actually want what I’m building for them?”
At least I’ll have spent five days galavanting around a city I like, most likely meeting nice people doing neat things. Oh, and going to dance classes. Because of course I’ve already laid out a 5-class schedule across three different studios and will be planning my days around hip hop choreo.
Here’s the part where I tell you how, in a very on-brand eleventh-hour move, I also decided to run a giveaway through inOregon’s Instagram this week.
 Dec 2025 inOregon stats |  Dec 2025 stats for a local business whose IG I run |
Why? Call it optics, call it signaling—psychology, baby.
As of writing this newsletter, inOregon currently has ~7,200 followers and organic engagement has been steadily growing the last three months. But/and going into the PDX trip with close to 10K followers would simply be… a better signifier. Of what I’m building. Of momentum. Of legitimacy.
So I stayed up til midnight last night planning shit out and sending oddly late DMs to seven local Bend businesses. By this morning I’d already heard back from four, all exuberant about participating and generous in their donations.
Now I just need a few more solid yeses. Then I’ll make the content (reel, post, stories), schedule it, and hope that the results are fruitful for all involved. If you’ll recall from previous issues, it makes me as equally satisfied to grow inOregon (my own shit) as it does to help other small businesses (other people’s shit) grow. Both energize me, and I’m thankful for that.
“If I know one thing in life, it’s to move in the directions which energize you most. Pivot towards the life force, not away from it. Something’s bound to come of you following your own internal cardinals and, regardless, you’ll most likely feel good more often than not along the way.”
Speaking of needing a few more solid yeses
In classic Aries fashion (fucking rams, amiright?), I recently made a list of Oregon businesses I want to work with in 2026—through Frank Mouth. It’s a long-ish but also rather curated list, and I’ve already drafted, scheduled, and sent eight emails to eight different business owner baddies. With more emails to be drafted and sent this week.
I decided that, while most of my current clients came to me through word of mouth, I both cannot and do not want to wait around for more to come my way. It’s not a sustainable model, and it’s certainly not one that I feel I have any control over. Because tbh, I don’t. And while we could tumble into a philosophical discussion about whether or not we actually have control or agency over anything (I think we do, to some extent), that’s not the goal here.
The goal is to make shit happen for myself and for others, even when it feels insane. And I don’t mean in the mythical, elitist “pick yourself up by your bootstraps” kind of way. That’s horseshit. I mean in the “what can you do about this” and then do it (and keep doing it) kinda way.
The “even when it feels insane” aspect? There are many, of course. But one that keeps trying to strut down the runway of my mind in six-inch stilettos looks like this:
There’s another small social media agency here in town (there are a number, but I’m thinking of one in particular). I won’t name them—I actually think they do pretty good work and are probably really nice. I found them through a client of mine whose IG I manage, because they kept leaving nice comments on posts. (I assume this is one of their client acquisition tactics, which is cool. But also, they clearly like the content I’m producing.)
This commenting led me to check out their IG, in which I found a reel about “social media manager red flags to watch out for,” or something like that. And one of the red flags was: if your social media manager is forty years old.
Record stop.
Wait… wtf. Not only are you showing your ageism, you’re also shitting on the majority of business owners who you’re trying to appeal to (who are over forty and run their own social media because they have to). Also: I’m fucking forty-one, assholes. And you will be too someday. OK, not for like 15 years, but still.
I simultaneously found this red flag amusing, tactless, and juvenile. In true Aries fashion, again, it also pissed me the fuck off. Maybe because, as lame as it feels to admit, the red flag has stuck with me like an ear worm ever since. Trying to smize at me from that mind catwalk and say: you’re over 40, girl, like wtf are you even doing running social media and building an app, grow up.
But, at the end of the day, I’m kinda thankful for it. I get to practice shutting it out, ignoring it while I continue to move forward (while getting older, as we all do), and choosing to listen to the amazing feedback that my amazing clients give me. While also listening to (fuck this is so cheesy)… my heart. Because you know what, for the first time in a long-ass time, I love what I do for work. As well as the directions I’m slowly but surely moving in and towards.
I’m also thankful to be forty-one and still finding so much that I’m excited about in life. May we all, always, possess this within ourselves—no matter which fucking year we were born.
I went to the gyno on New Year’s Eve (when you get older you think about annual deductibles) and the bathroom lighting was really good so I took this photo.
Some what-ifs about going to PDX
Even though I’m not going until January 15th, here’s a quick list of some of the things I’m what-iffing about (rational or not, it doesn’t matter) going into what I’m calling my “PDX product market fit validation trip", or, PDXPMFVT for short.
What if:
All the shops I want to go to are suddenly closed
I forget how to talk
I walk into a shop and I’m not wearing any pants
Some of the people I meet like what I’m building
Everyone refuses to fill out my survey
People think the app is dumb and useless
Everyone is too busy to talk with me
I forget how to talk about… anything, including the app
It rains so much the entire city shuts down
Other shit happens
Well, thanks for reading those what-ifs and for letting me write them out. Writing is like diffusing bombs—I feel better already.
forty-one and proud of it
That's issue 51. And omg I almost forgot—HEATED RIVALRY is a must watch. It’s so gay and so beautiful and so important, and I’ll get into the why of these things next week. For now, thanks for reading and for being fucking fabulous. I’ll see you on this mind catwalk next week.
xoxo,
lw
PS: Subscribe now if you're into this messy build-in-public energy. Miss the last issue? It’s right here. Also literally none of this is ever advice. I’m sharing what I learn through Babe, and perhaps you’ll learn from my mistakes. Hopefully, maybe, who knows, ily.