It’s Wednesday, February 19, and this week, I’ve got a new edition of Ask a Newsletter Therapist for you. But first…

I’m thrilled about the response so far to The Inbox Awards, presented by Optimism — and there are still 10 days left to apply! If you’ve created innovative strategies for your newsletter, you could win in one of six different categories. Apply here…

If you want to get $100 off your ticket to The Newsletter Conference on May 2 in NYC, make sure you select your ticket type, click “Next,” and then enter promo code INBOX on the checkout page. There are just a few tickets left with that discount code — get them while you can…

—Dan (say 👋 via email or LinkedIn)

All of our newsletters this month are presented by Optimism, an email-first media company. They believe in the importance of bringing positive and informative content to the inbox. Through Curated By Optimism, they’re working with like-minded media companies to drive traffic to publications like yours.

Interested in learning more? Get in touch here.

What Should I Do Next With My Newsletter? A Conversation With Kristen Hawley

Kristen Hawley’s been writing Expedite, a newsletter about the intersection of food and tech, since 2019. But last year, she wrote to me saying that she’d started to feel a little lost with her newsletter. She told me she felt like Expedite needed direction — a clear content strategy to build around, and then the right monetization to layer on top of that.

So we hopped on a call to talk through a few potential paths forward, and I asked her to make two promises:

1.) That she’d follow up with me a few months later to tell me what changes she made to the newsletter.

2.) That she’d let me publish our conversation — plus a follow-up note about what she did and how readers reacted — so that readers like you could learn from her example.

I think it’s so brave of her to be willing to peel back the curtain like that, and I think you’re going to learn a ton from her story. Here’s our conversation

A big thank you to Optimism, the wintertime sponsor for Inbox Collective — they’re making everything in the newsletter and on our website available for free to all readers.

They’re also the proud sponsor of the first-ever Inbox Awards, which honor newsletter operators who are delivering exceptional experiences through email. Your newsletter could win in one of these six categories:

Innovation in Content
Innovation in Design
Innovation in Engagement
Innovation in Growth
Innovation in Revenue
Innovation in Technology

Apply now for your chance to win — it’s free to apply, and the nomination process will only be open until the end of the month.

And thanks again to Optimism for their support of the Inbox Awards. You probably recognize one of their 18 email-first brands, including History Facts, Nice News, and Word Smarts. This year, they’re also expanding their partnership program with like-minded media companies. Through Curated By Optimism, they’re driving traffic to external partners and promoting their great content — and with traditional traffic sources continuing to drive fewer readers to publications, new partnerships like this could help your newsletter or site grow faster in 2025. Interested in learning more about how to partner with Optimism? Get in touch here.

*This content has been promoted by our partners*

From my reading list...

There are all sorts of emails you might send readers, from newsletters to transactional messages. Here’s how to incorporate all of these into your email strategy. (Inbox Collective)

I really liked this map of the current media landscape — I thought this was put together in a really thoughtful way. (Project C)

Here’s another great example of why there’s so much value in side projects. (Please Advise)

ICYMI: Dan Barry, a true pro in the newsletter ad space, wrote a great guide to different newsletter ad pricing models. (Inbox Collective)

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📬 Want to work with Inbox Collective? Here’s how I can help you.

🍰 Interested in attending Dine & Deliver, a dinner series presented by Omeda? Apply here.

✏️ Looking for a new job in the email space? I might be able to help.

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Not a Newsletter - 📬 No. 67 | Ask a newsletter therapist

What Should I Do Next With My Newsletter? A Conversation With Kristen Hawley

From my reading list...

Older messages

Time’s running out to nominate your newsletter for The Inbox Awards!

📬 No. 68 | Lessons from 366 days of email

UPDATE: Now with working links! —> 📬 No. 68 | Lessons from 366 days of email

📬 No. 66 | The Eight Types of Emails

📬 No. 62 | What I learned about newsletters in 2024

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