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10/17/202310/17/2023

Don’t Assume. Prove It.

a no. 2 pencil works through math homework on a white sheet of paper

There are things you know. These are things you’re certain of — you’ve got data, you’ve got proof. These are things that are absolutely true.

And then there are things you think you know.

Assumptions are dangerous. They start out as ideas that your team kicks around, maybe based on something you heard at a conference or something you read online. They’re based on casual conversations or hearsay. With time, those assumptions can easily turn into things you believe. And if you don’t take the time to prove them out, they will quickly turn into universal truths.

These assumptions might be right or wrong — you don’t know yet — but you can’t let them guide your thinking. You can’t let these untruths or half-truths or maybe-truths influence your long-term decision-making process. You can’t confuse them with things that are actually, provably true.

One bad assumption can lead to a whole slew of bad decisions.

So be willing to challenge your assumptions. Prove them out. See what’s actually true and what’s not. Then you can make the best decisions for you, moving forward, with the proof you need.

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That photo of math homework comes via Unsplash and photographer Chris Liverani.

10/07/202310/07/2023

10,000 Tiny Puzzle Pieces.

a stack of hundreds of colorful puzzle pieces

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.

10/04/202310/04/2023

I Figured One Thing Out Today.

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.

For today, that might be enough.

10/01/202310/01/2023

Apologize, and Move On.

Shit happens when you’re doing the work.

Work doesn’t get done, or doesn’t get done as well as you expect. Mistakes get made.

Don’t dwell on those errors. Own up to your mistake, apologize directly to those that were affected — and then be willing to move on past it.

It happened, and you admitted your error. Don’t let one mistake lead to another.

You’re onto the next.

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Those neon arrows come via Unsplash and photographer Charlota Blunarova.

09/17/202309/17/2023

Be Brave Enough to Ask For Help.

a bright sky over the Sixth & I synagogue in Washington, D.C.

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.

09/09/202309/09/2023

People Remember The Little Things.

On a Delta flight today, the flight attendant stopped by my row. “Mr. Oshinsky,” she said. “We wanted to thank you for your loyalty.” And then she handed me the note above.

“Aww, that’s nice,” I thought.

A few minutes later, the flight attendant stopped at the row in front of me and handed another passenger a similar handwritten note.

“Aww, that’s so kind,” she said.

And then I saw the flight attendant do the same for someone else a few rows ahead of me, and then for the passenger sitting beside me. All gave a big smile after reading it.

The notes were a tiny gesture — but the fact that someone took the time to hand write a few words of thanks felt meaningful. Had I gotten that exact same message in a marketing email from Delta, it probably would’ve felt far less powerful. The medium — a hand-written note — changed everything.

Those little things get remembered. Those little gestures often feel extra meaningful.

Sometimes, it’s a small act of kindness. Sometimes, it’s someone taking the time to make sure you feel seen and heard.

Whatever you do, do the big things well. But don’t forget about the little moments, too.

09/03/2023

Only the Prepared Can Be Spontaneous.

Daddy walking his baby in a stroller in front of one of Stockholm's emblematic creamy façades in Södermalm.

One funny lesson from parenthood: In order to be spontaneous with the baby, we’ve learned we first have to be prepared.

Whenever we get home from being out with the baby, the first thing we do is prep the stroller to go out again. We’ll restock the diaper bag with new diapers and wipes. We’ll make sure all the stuff we need to feed the baby is clean and ready to go. We’ll add a fresh outfit to his bag if he wore the last one we’d packed.

Why? Because we want to be able to be spontaneous. We want to be able to meet friends out for a last-minute drink. We want to be able to go for a long walk in the park. We want to be able to stay out a little longer than we expected with the baby.

But that starts by being prepared. Imagine being out and about and wanting to do something spur-of-the-moment — but realizing that you’ve left a few key things at home? You’re probably not staying out — you’re heading home right away, and probably not heading back out.

I always want to be a more spontaneous person. But having a baby’s reminded me: The only way to be truly spontaneous is to be prepared for anything.

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That photo of a stroller — which, I’ll note, doesn’t seem to have anything packed underneath — comes via José Jóvena and Unsplash.

08/30/2023

It Goes So Fast.

I’ve been listening to Mary Louise Kelly’s book, “It. Goes. So. Fast”, while taking my newborn son on walks around my neighborhood. It’s a book about a parent’s journey during her son’s senior year of high school, which makes for quite the contrast from my day-to-day. It’s tough to imagine my son graduating from high school — something that should happen in the year 2041! — but I know the years will go by fast.

It’s certainly been my experience so far. To be a parent to a newborn is to live on a schedule completely untethered from normal time. There are no clocks on newborn time; we operate hour to hour. There have been a lot of 4 a.m. feedings, and a lot of late nights. Time isn’t something we obey anymore — it just kind of happens while you’re busy with the baby.

But to operate on newborn time is to also live in the moment, as much as you can. The baby will never be this small again. They’ll never smell the way a newborn smells, or smile the way a newborn smiles. There is no going back; there are no do-overs.

And it’s an amazing reminder: Be present. Pay attention. Celebrate the moment.

It will be gone soon, and fast.

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That image of cars blurring past on the highway comes via Jake Givens and Unsplash.

08/23/202308/23/2023

What Do You Need When You Start?

The first Inbox Collective website was six Google Slides, with a few details about my work and contact information.

Four years ago this week, I left The New Yorker to launch Inbox Collective. I kept things simple at the start.

I launched Not a Newsletter as a Google Doc so I wouldn’t have to build a website. It was enough to start.

I set up my email list with TinyLetter, not something more sophisticated, so I could launch faster. It was enough to start.

I set up my company’s website as a set of Google Slides, again so I could get something live as quickly as I could. It was enough to start.

I didn’t spend money on a logo or business cards. I realized: Why would I need those on Day 1? I just needed enough to start.

Four years later, a lot has changed. I’ve switched email platforms (twice, actually), built a real website, and brought on freelancers and contractors to help with some Inbox Collective work. I still don’t have a logo or business cards, though — maybe one day, but that day isn’t today.

The question for you is, and always should be: What do you need when you start? Figure out the stuff that’s worth spending time and money on right away. The rest can come later — or, as the work progresses, you may find you might never need it at all.

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Above, the original Inbox Collective “website” was just a public set of Google Slides.

08/15/202308/15/2023

Test, Don’t Copy.

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.

Use it as the starting place for a test.

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.

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That photo of scissors comes via Edz Norton for Unsplash.