Sometimes, We Bet on the Right Thing

Tips for branding your newsletter, my Book of the Month spring pick, and thoughts on marriage and friendship.

May 04, 2026

Today’s post is free for everyone because Book of the Month sponsored it!

Happy Monday to you! Today, I’m thinking about how sometimes, we bet on the right things. We took a gamble in hope, and we were right all along.

It is my seventh wedding anniversary today, May 4th.

We were married at an age that makes people gasp when I say it; quite young. But today, I sit and stare at the ring on my finger with joy and deep satisfaction that I bet on the right person. Sometimes, we just get it right.

Inevitably, our lives are full of betting on the wrong things; sometimes this comes as a horrible, unforeseen surprise, sometimes we should’ve known better. This is part of being alive. And while the times we get things wrong make for great television and riveting paperbacks, the times we nail a life-altering decision on the head don’t always get celebrated for the miracle they are. We should probably celebrate much harder when we pick the road that proves itself right — whether that be a person, a position, a place, etc.

I could write a million words about the person Connor is. His work ethic, his ever-growing stack of books & how carefully he reads each page, the smell of his coffee each morning, how he dances on a dance floor (with fervor), how he handles people who wrong him, how he cares for every living thing, his green eyes, the way he articulates thoughts with such care, and his hand reaching for mine in the crowded streets. But I’ll save them all for myself today.

I think about how many funerals we will hate to go to together. How many nights we will hold each other. How many times we will do our dishes. The homes we’ve never seen that one day we will thoughtfully arrange our things in. The color of our children’s eyes. The way our hair will turn grey and how we will have a quiet house, but all the same memories to relive.

I hope to do so many big, exciting things in my life. But the one I am most looking forward to is experiencing an ever-deepening lifelong love with him.

Announcing a new look for Feeling!

Another thing I am betting on is Feeling! I’ve wanted to make a magazine since I was in elementary school, and last year decided the risk was worth taking. Feeling! has been on Substack since 2023, but last year I started pretending it was my job until it actually became my job. Despite this, I’ve never gotten around to actually developing a brand for the publication.

I am a graphic designer and have drawn plenty of logos for others, but for some reason, I never could get my own design down how I liked. I knew what I wanted, but sometimes you need a talented eye to help pull together your concepts because you are in too deep. So I asked, Hailey, who is my graphic design superstar and has been helping with Feeling!’s graphics since September, to take a stab at it. And she made everything more wonderful than I could’ve imagined. I’m excited to show you!

The design problems:

I felt my current placeholder logo didn’t pack a punch. I wanted something more timeless. Something that would work in print, and across a few different business ideas I had.
The colors were more playful than I wanted. I was ready to commit to my very favorite, red, in all its vibrant glory. I wanted red to lead the charge, and a muted blue to partner with it.
I think I had just outgrown it — I felt disconnected from the design — and that means readers would too.

The inspiration:

Vintage print Postcards
Old movie credits
Archival New York signs
Print menu designs
Antique greeting cards

The final results:

Hailey took all my pain points and all my inspiration and created something I absolutely love. Here is the new Feeling logomark:

We’ve maintained the “!” as the main character she is. The overall type is custom-made and unique to the publication. I want it printed on my forehead backwards so I can look at it every time I look in the mirror. I love it so much. I can see it on a print magazine! Can you imagine that? Here are the variations of the mark:

If you like it, tell Hailey in the comments! She is incredible!

As I was putting together this reveal, I thought through a few things I prioritized in the rebrand process that may be a timely help if you are working on your newsletter branding. Here they are:

Start with inspiration outside of Pinterest, in order to preserve a unique vision. Start with art books, a trip to the library, a museum visit, or browsing packaging at an antique store. Take photos and save them together in an album!
Good brand design answers these two questions: What is your business’s purpose? Who is your target customer?
Articulate, in writing, who exactly your readers are. What do they like? What lights them up? What are their hobbies? You need to design for them, not for you. Make sure you have a thorough understanding of who you are trying to attract to your brand.
Lead with color. Strong color tells a story. Pick a few and stick with them for all your graphics. Often, in brand design, you have a primary and secondary color, supplemented with a dark hue and a light hue — a family of 4 to five brand colors.
Simplicity and clarity are key players. Don’t get lost in the design sauce.
Put personality into the small details: illustrated icons, a mascot, custom dividers, titles, etc., and your readers will feel it.

Half-Off Sale for 24 More Hours

Last week, I announced a one-time-only half-off annual subscription sale that ends today. I am leaving the sale open an extra 24 hours because some readers had a difficult time with the link. We problem-solved and discovered that it only works on the desktop version of Substack using this exact link. Sorry about any confusion — I have little control over the Substack checkout logistics!

I hope this gives you more time to opt in, in case you were having trouble. If you run into any issues, feel free to send an email back or a dm on Substack.

I have kept my monthly rate for subscriptions at $5 since 2023, which is the lowest Substack lets you go. Since I’ve kept my subscription rate so low, I’ve never offered a sale.

But for one week, I will do this massive sale, and then I will never do it again. Here’s why:

I am building something new, and I’d really like to make it accessible to you. If you’ve enjoyed this publication for a while, this drastic discount is a way to jump on board for the best experience possible.

This is the cusp, the perfect time to join in, because so many new features are coming out (starting in May).

The paid annual subscription ($25) will offer:

Access to the new “Hosting with Feeling!” column, all about how to do the human parts of hosting
Full access to the “Design Dive” column, which includes how-to guides for designing your space with intention
Access to the up-and-coming full-service graphic design and digital design workshops
A membership to our card-writing matchmaking service (launching in May), which included exclusive discounts to Feeling! Press products)
My entrepreneurship diary of sorts, detailing this new brand launch from behind the scenes, and direct access to “office hours” for any of your burning creative small business questions

I am grateful for your support every day, work hard to create a publication that is of value to you, and I am hopeful that a half-off discount will allow as many readers as possible to join in the party without a strain.

Here is the link to get the sale price.

The stack of fiction next to my bed is growing, thanks to Book of the Month! I think I’m a better writer whenever I’m in the middle of a good fiction book, so my goal this year was to read more fiction. Book of the Month’s subscription allows you to choose brand new fiction works, exposing you to new writers (and new favorites) consistently. This month, I picked Good Joy, Bad Joy by Mikki Brammer, which is a moving and sometimes really funny story about the enduring friendship between two very different women in the midst of a terminal diagnosis.

Readers of Feeling! can pick up their first copy for only $5, and a free cute boat tote here. Perfect for toting your hardcover around!

✸ I think parties need more play. But, there is a strategy to picking a board game that doesn’t make everyone immediately check out. I wrote out my strategy and my tried-and-true board games for livening up any gathering.

✸ Mother’s Day is rapidly approaching, and I have made you a very thorough list of gift ideas, including a chunky birthstone ring and custom candy boxes.

✸ I recently interviewed the CEO of my favorite fragrance brand, Dedcool, about how a fragrance is designed through the lens of feelings. Her experience of making the intangible, tangible is a fascinating read.

I made a Mother’s Day gift guide full of some really thoughtful gift ideas, but wanted to slide in a few more favorites for your consideration, as the holiday is coming up on Sunday.

I know Mother’s Day can hit a wound, a loss, or a pain point for many. I know the sting holidays can have after you have lost a loved one or are navigating a familial fracture. I often write about the principle of giving away what you don’t have (giving friendship when you feel lonely, giving away joy when you feel depleted, etc.), and I think it carries across this holiday as well. It’s an excuse to give a mother whom you know some supplementary love and care. A woman who was like a mother to you, a friend who has recently entered the throes of motherhood, a coworker who loves to talk about her kids, or a veteran mom whom you admire. They could all use a thoughtful note of encouragement, and maybe a gift, too.

Here are a few more ideas to complement the full guide:

The beaded phone wristlet from Joiana is another gift that hits the useful + elevated sweet-spot. It’s an exciting accessory for the mom who constantly takes her phone out to take pictures.
These lightweight oval gold stud earrings are a timeless silhouette at a really great price point. For classy moms, these will become an everyday staple.
I’ve recommended Soft Service’s really amazing nighttime hand cream many times because it works wonderfully and is in the best-designed vessel I’ve ever seen. It’s a pump that serves as a jewelry dish too. They outdid themselves by releasing a “Mother of Pearl” version of Theraplush hand cream in a shimmery new vessel. It’s something mom will absolutely use, but wouldn’t think to treat herself to something so luxurious. The best kind of gift (actually useful, but elevated).
If you have a tea/coffee/sweet treat kind of mom, Dona’s cardamom tea concentrate is a gift they will actually use every drop of! Combine the concentrate with foamy milk for a decadent latte treat that takes seconds to whip together. Pair with a bar of dark chocolate, and you are set.
You can ship fresh white orchids in a box from UrbanStems. The package arrives, magically, intact and fresh, like you just went to a greenhouse down the street and picked them out. This is a great option if some distance separates you from your recipient, but you want to gift something fresh and thoughtful. They also have really lovely Mother’s Day bouquets that are on sale all week, guaranteed to arrive for the holiday.
Photo evidence from my living room — look how beautiful the orchid is!
For statement-jewelry-kind-of-moms, the shell statement ring is perfect for summer. It’s funky, also super lightweight, and would be complemented well with some
If you are looking for something a bit fancier, I will introduce you to the brand “Flamingo Estate,” and their luxury rosemary clary sage hand soap that smells like it came straight from a garden and arrived at your doorstep. They also sell fabulous soap bars (the peppermint is my favorite) if you are going for a bathroom-to-spa gift set.

Launching next week, all paid subscribers will have access to subscribe to the Friends of Feeling! Match-Making Service. There will be a brief “application” period where you can apply to be included in the program.

The idea is that handwritten notes, kind words, and thoughtful intention are ever-increasing in importance and essential to life. I want to help connect you with a new, one-of-a-kind friend!

The application will include questions about what you value most in a friend, your interests, communication styles, etc.

Not a robot, not an algorithm, not AI, not a spreadsheet, but a committee of coffee-fueled New York girls will be reviewing every application, printed out and on a coffee shop table somewhere, and making matches by hand, giddy about the new friendships!

My friends and I will review every application and bring our various perspectives to help match the best potential friends. My committee includes an HR worker, an ed tech consultant, a marketing manager, a graphic designer, and more really thoughtful and interesting people who value friendship highly. After you have a match, you will be connected via email, where your pen pal relationship can begin!

Members will also be the first to receive snail mail discounts from Feeling! Press, launching this summer, to fuel their pen pal journey.

Out of curiosity, I asked the Feeling! chat “If you had to summarize in a few words, what’s the most important quality in a good, long-lasting friend?”

Here’s what you said:

Gabriella Owen: Mutual Respect and encouragement
Chelsea Ferruzzi: Shared Humor
Maggie Bergevin: Someone who can be your container in the times your thoughts, worries, dreams, and hopes need to be held, and someone who in turn trusts you contain them.
maddie: Someone who sees you holistically, believes in and supports your growth when you inevitably stray from who you want to be
Sydney Morgan: Safety to be your true self
Marigold: Consistency
Cassandra Jackson-Baker: Generosity of spirit. Someone who accepts no relationship is perfect. There will be ebbs and flows in every friendship, but no matter what they respect you and think fondly of you.
Rachel: Compassionate, curious, and funny
Eve: Genuinely kind to you

There were so many more great answers. See them below:

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Available in the Substack app and on web

Thank you all for your thoughtful words. My favorite part of making this newsletter is talking to you directly. It means a lot to me when you leave a comment, thought, or feeling. Truly, the best place on the internet.

Thank you, Hailey Howe, for your lovely work on Feeling! Magazine Graphics! You made this Monday Letter magical!

P.S. Telling my Substack friends before anyone else…new secret Instagram for the upcoming greeting card business is here. Substack is nicer than Instagram, haha, I would love to have you join the journey and see some familiar names!

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