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 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.
I had a moment last night with my newsletter. I wasn’t sure what to do about the intro section — I knew there should be an intro, but I wasn’t sure what I should say. And I felt stupid for not knowing: People pay me every week to help them figure out stuff like this! Why couldn’t I figure it out on my own?
And then I thought about a conversation I’d had with a client earlier in the week. They were feeling a little down, so I gave them a pep talk. It seemed to help.
And I thought: Could that be the intro?
So I wrote it up last night, but didn’t schedule the email. I wanted to read it again this morning.
This morning, it still made sense. It gave the newsletter something it didn’t have before — a bit of life, a bit of personality. It made it sound more like me.
I think I figured this one piece of the puzzle out today. And I know there’s a lot more to figure out.
But just figuring that one thing out made me feel a little lighter — the weight of this one task, however small, has been lifted.
Every few years in the email space, someone will put out a big piece of research that says something like this:
“After extensive testing across thousands of newsletters, we’ve discovered that purple call-to-action buttons drive nearly 2.3% more clicks than blue and red buttons, leading to significant improvements in long-term conversion rates.”
And for months after, though most users won’t notice it, suddenly it seems like every ecommerce email has changed their CTA buttons to purple, even in cases where purple isn’t one of the brand’s primary or secondary colors.
I’m worried the same thing may happen after this interview I did with Hanna Raskin, publisher of The Food Section newsletter. As I wrote in the intro to that Q&A:
In May 2022, [Raskin] told readers that she’d randomly remove 15% of her free list, but readers who chose to pay for a subscription would “avoid the axe.” It worked — she saw an immediate bump in subscriptions, and that growth has steadily continued for over a year.
I’m nervous that some newsletter operators will read this and make it the new purple button. They’ll think: The lesson here is that random acts of aggression against my list are a great way to convert readers to a paying subscription!
But the next time you see a story like this, don’t simply copy and paste.
The best teams see stories like this and think: I wonder if we should change the way we present our CTAs? Or: I wonder if we could try alternate marketing messages that would work for our audience?
They look at their data. They talk to their audience. They work on honing their voice.
And then they go out and test different tactics to see if they can create something that resonates with their unique audience.
Don’t just plug purple buttons into your newsletter. Test, don’t copy.
It’s hard to make time for everything you want to do. I know I’ve got a big list of things I’d love to do one day — new projects, new adventures. I don’t have time for it all.
So it always comes back to this big question:
What is it you really want to do?
• Do you want to read more? • Do you want to learn a new skill? • Do you want to run that first 5k or 10k? • Do you want to launch a new project?
You can’t do all of it. You can’t choose everything.
But you can make time for some of the stuff you want to do. Maybe it’s not as much time as you’d like — maybe it’s just 20 minutes a day. Maybe it’s an hour or two a week.
This year, I started writing a quarterly review of my business.
Every quarter, I take 20-30 minutes to go into a Google Doc and jot down a few thoughts on the quarter’s work. What worked well? What am I excited about? What needs work? What’s on the horizon? I write it all down.
The more of these I write, the more I can track my progress over time. I’ve got my spreadsheets to show me the hard numbers — but the quarterly review is a way for me to track how I’m feeling about the business.
It doesn’t take much time, but as I progress, I’ll be able to better understand the trajectory of Inbox Collective — what I did and why I did it. It’s another tool to help me hold myself accountable and to build a better business.
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The data is great, but it helps to be able to track the bigger story alongside it. To that point: At top is a photo of a chart, taken by Isaac Smith for Unsplash.
Earlier today, I typed this very website into my browser — https://danoshinsky.com — and nothing came up.
There was an error message on screen. So I typed in a different URL, and then a third. Those pages loaded correctly — it was just my website that wasn’t loading.
A decade ago, this would’ve been a crisis for me. I would’ve spiraled, and started frantically Googling stuff to figure out a fix. It would’ve ruined my afternoon.
But I’ve seen a few things at this point. I’ve had website errors; I’ve dealt with a few tech situations. I’m no IT person, but I can handle a few small things.
So I went through the options, and within about two minutes, had figured out the issue. I hopped on the phone with my hosting service, and three minutes later, my website was up and running again.
It’s nice to know that I can handle certain small issues like this. But it’s also a nice reminder: The older we get, and the more stuff we run into, the easier it is to handle problems like this.
The first time you run into something, it’s a crisis. But the third time you’ve dealt with it? The fifth? The tenth?
It’s not a crisis — it’s an issue. It’s something small you can handle.
You’ll learn how to handle it, and the next time, it won’t seem quite so bad.
Sometimes, change happens slowly. You start to feel the changes coming, but they’re not coming all that quickly. You can see the transition period happening. You can prepare for the change.
And sometimes, it just happens.
You’re looking around and notice that everything’s suddenly changed. No warning, no advance notice — it’s all different.
But no matter what changes, or how fast it changes, remember: Things will always change.
There’s this lie I’ve been telling myself for the past decade: Once I get through this next stretch, things will get easier.
But I know what’s going to happen. After this stretch of work, after this stretch of travel, after this stretch of busyness, things aren’t going to slow down. Things aren’t going to stop.
There’s always going to be more.
Things don’t magically get easier at the end of these stretches. There will be new challenges, new problems.
There’s always more.
But the good news is: Even though it doesn’t get easier, that doesn’t mean it’ll get harder. You’re always learning and figuring out new ways to solve problems. New obstacles appear, but you’re also learning more about how to get past them.
No, it never gets easier. But you’ve gotten through hard things before. You’ll get through these, too.
At age 30, in my annual Things I Believe post, I wrote:
You don’t need to be able to predict the future — but it helps if you can see what’s coming around the corner.
I certainly don’t know what the future holds. But I think I can see certain pieces that will matter in the decade ahead. I think small, curated, in-person events will matter. I think relationships will matter. I think expertise will matter. I think that there will still be a desire to learn new skills — that will matter.
You should do the same. Try to identify what’s coming in the next month or the next year or the next decade, and start to make moves to invest in things that will help you in whatever comes next.
Maybe that means starting to have conversations with others who operate in the space you want to move into.
Maybe that means finding ways to level up your skills in a certain area.
Maybe that means making a little time to work on the ideas you have.
Maybe that means launching something small to start to carve out your niche.
Maybe that means finding partners to work on these ideas.
Whatever’s next is coming. Time to make your investments now.
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That’s the eye of the famous bull on Wall Street. This post isn’t about that type of investing, but it still seemed like a nice fit for this blog post. The photo was taken by Redd F for Unsplash.
