I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
I talked with a group of publishers a few weeks ago, and they told me they’d just come back from a conference where a speaker told them that the right number of links to include in email was 15. They wanted to know: Did I agree?
And I told them what I know to be true: There is no “right” strategy for email.
There is no right topic.
There is no right format.
There is no right number of links.
There is no right number of emails to send per week.
It’s up to you to figure out what works for you and your audience.
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That’s my first BuzzFeed newsletter. It had just five links. We tested it — and figured out that we could add a lot more!
I was on a call with a client a few weeks ago, and they told me they wanted to build the best possible email strategy in 2024.
“That’s great,” I told them. “But I don’t want you to be thinking about what’s best. I want you to be thinking about what’s next.”
Thinking “best” can lead to magical thinking, to dreaming of blue sky situations where you’ve got all the budget and resources you need. It can lead to planning for a day that may not come.
Instead, take a look at what you’re doing right now and ask yourself: What’s the next thing we can do to make our newsletter strategy better?
It might be a small step, and that’s OK. Some of the best newsletters out there were built thanks to a lot of small steps forward.
The next step may not be perfect. It may just be… what’s next.
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I took that photo, more than 15 years ago, while walking the Camino de Santiago in Spain.
I was rewatching “Pulp Fiction” on a flight the other day. My favorite chapter of that movie is the scene with Winston Wolf, the fixer. Vincent Vega and Jules Winfield get themselves into hot water, and The Wolf gets them out of it.
And I was struck by a thought, rewatching it, that a lot of people think that my job at Inbox Collective is basically that of The Wolf.
Some teams come to me thinking that I’ve got all the answers or magic fixes. I often do not.
What do I actually do? A good advisor isn’t there to have all the answers. My job is to help you ask the right questions — and figure out how to find the answers together.
I’ll admit, it’d be fun to be The Wolf, to be able to come in, survey the situation, and identify a quick fix.
But my job, if I do it well, is to do more than fix the glaring short-term issues. I’m here to help teams build the right strategy in the long term.
All of that starts, not by having all the answers, but by figuring out the right questions.
In the spring of 2019, I was starting to think about leaving the New Yorker to start Inbox Collective. But I was still nervous about it. Was it the right time to leave? Was I ready to take on the responsibility of building a new business?
And that’s around the time a recruiter reached out to ask about a job.
It was a good job with a big title at a major news organization, making more money than I’d ever made it my life. I wasn’t looking for another job, but I interviewed anyway. It was the kind of offer I had to at least consider. I wasn’t sure what to expect.
Within 20 minutes of the first interview, I knew what I wanted to do next.
I wasn’t excited about the idea of taking another job. I still loved my job at the New Yorker.
But more than anything else, I felt excited about the idea of starting my own consulting business — well, equal parts excited and nervous. Whenever I feel nervous, that’s usually a good thing. It’s a signal that I really care about something.
So I started to ask myself: Why, exactly, am I still doing the same old thing if I’m ready for what’s next?
By the end of the month, I told my bosses that I was leaving to start Inbox Collective.
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That’s a photo of me talking to a group of newsrooms in Sydney in fall 2019, a few months after starting Inbox Collective.
For the past decade, I’ve lived just a few blocks away from the United Nations. And yet, until this week, I’d never actually been inside.
If you’re visiting New York, the UN is worth a visit. It’s tough to visit the UN and not feel a little bit optimistic about the future of the world. Diplomacy is never easy, and yes, we’ve got massive global challenges ahead of us, but it’s amazing to visit a place where all the countries of the world have come together to try to solve big problems. World hunger, nuclear disarmament, climate change — the world gathers here, at a campus on 1st Avenue, to try to find the answers.
I was familiar with a lot of the places we saw on the tour. I’d seen the big Assembly Hall on the news. I’d seen photos of delegates sitting around the table of the Security Council Chamber. But there were a few rooms I’d never seen.
One was the chamber for the Economic and Social Council. The room was designed in 1952 from Swedish architect Svem Markelius.
It’s a beautiful room, featuring wood from Swedish forests. But there’s one particularly unique feature of the room: The ceiling is unfinished.
That’s on purpose, our tour guide informed us. It’s a subtle reminder: The ceiling is unfinished because the work of the UN will always be unfinished. There will always be more to do.
Here’s to whatever work and whatever challenges lie in the year ahead.
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I took that photo of the Economic and Social Council chamber on a visit to the UN.
There’s this great piece of research out from the teams at Trusting News and the News Revenue Hub. They worked with five non-profit newsrooms that serve communities in five different states — Connecticut, Michigan, Pennsylvania, Texas, and Wisconsin — to test messages around the work these newsrooms do and how they operate. All five tested out similar messages.
There was no clear trend across participants, which is to say that each newsroom had different messaging work best for them.
This tells us that each organization is unique and has a unique relationship with their audience. We plan to test this more in the future, but for now, this indicates… that every newsroom should assess their own data and audience feedback regularly and tailor their messaging accordingly.
It echoes something I advise my own clients: Don’t just assume that what worked for someone else will work for you. Use the work you’ve seen from others as a starting point — but then test out those ideas and see what actually works for you and your team.
Everyone wants to go as fast as they can go. Everyone wants to find ways to move a little bit faster. Many are willing to cut corners.
But resist the urge to chase shortcuts.
The good stuff takes time: Building relationships, testing new ideas, talking to your audience. There are no shortcuts there — you’re going to have to do the work, and the work doesn’t always happen quickly.
Be patient, and embrace the work. It’s the way forward.
I’ll often talk with newsletter operators who tell me they want to launch another new thing: Another course, another ebook, another product.
But the question I always have to ask is: Have you gotten everything you can out of the stuff that’s already out there?
I’ll see newsletters with great engagement that are missing obvious monetization opportunities, like running ads or affiliate content.
I’ll see operators with a paid membership who aren’t promoting it nearly as much as they could — even though with every new member they get, they’re getting more value out of a thing they’re already working on.
Forget about launching new stuff for a second. Look at what you’re already doing — is there an opportunity there to get more out of the work you’re already doing?
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That’s a random snippet of emails in my inbox at the moment. (I’m not trying to pick on any of these particular newsletter operators!)
I had a call with a client last week about their newsletter strategy. “I feel like we don’t have a complete picture of what our audience wants,” they told me. “What are we missing?”
I’ll tell you what I told them: Building a strategy is like putting together a 10,000-piece puzzle. Every time you do something — like sending an email, running a survey, or talking to readers — you collect a few more puzzle pieces. But you’ve got to be patient — it takes time to collect enough pieces so you can start to see the full picture.
Your goal is to do something every day that helps you discover a few key pieces of your puzzle.
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That photo of a puzzle comes via Unsplash and Hans-Peter Gauster.
There’s a great story in the New York Times this week about Michele Lowe, a former advertising executive, who now coaches rabbis on their public speaking skills and helps them improve their sermons.
I’ll quote this section directly:
Some of Ms. Lowe’s clients are confidential, concerned to be seen as needing a crutch. At first, Dara Frimmer, a rabbi at Temple Isaiah on Los Angeles’s Westside, was reluctant to share that she had sought help on a sermon.
“There is a fear that rabbis have to be wholly original and brilliant and poised and always have the right words,” Rabbi Frimmer said. But she came to realize that turning to community in a time of need was a profoundly Jewish ideal. “With great pride I wrote at the bottom: ‘Thank you to Michele Lowe.’”
Everyone needs a little help sometimes — even people like rabbis, who spend their careers speaking publicly. Rabbis lead public services and private services. They stand before their congregations at bar and bat mitzvahs and at weddings. They spend time with their congregants during moments of joy and sorrow.
And yet: They still need help! It takes courage to be willing to ask — and to truly listen to the advice being given.
No one has all the answers. Everyone — even the pros — has questions.
Always be willing to ask.
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That’s the outside of Sixth & I, a synagogue in Washington, D.C. The photo was taken by Ted Eytan and is used here thanks to a Creative Commons license.
