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.

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.

Test, Don’t Copy.

silver scissors on a pink background

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.

Things Always Change.

a photo of a green stoplight next to a red left turn arrow at dusk

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.

Change is inevitable. Be prepared.

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Life is full of mixed signals. That photo of stoplights comes via Ian Anderson and Unsplash.

It Never Gets Easier.

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.

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That photo of a boulder comes via Callum Parker for Unsplash.

Invest in What’s Next.

A bronze bull sculpture stands proudly on Wall Street, representing the resilience and power of the financial markets. This iconic symbol serves as a reminder of the bullish optimism that drives the world of finance.

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.

And so I’m starting to make investments in what’s next: Dinners, writing, workshops, partnerships.

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.

Busy vs. Occupied.

I was talking with a friend the other day, and he told me that something was annoying him. He’d been talking to his parents, who are both retired. He’d asked if they could help him with this big task, but they said they couldn’t — they were too busy.

“I don’t get it,” he told me. “They’re having lunch or dinner out every day, they’re playing pickleball, they have volunteer projects. That’s all stuff they’re choosing to do! But I’ve got work and family stuff. I’m the one who’s really busy!”

They’re not busy, I told him — just occupied. (Too occupied to take on this one task, unfortunately for him.) But it’s easy to confuse “busy” and “occupied.”

And it reminded me of something I used to do — or, if I’m being fully honest, that I occasionally still do — when I want to feel busy. I’d collect a bunch of small tasks and put them on my to-do list. And I’d cross them off. At the end of the day, I’d feel like I’d accomplished something — look at all the tasks I’d completed!

But then I’d look at the bottom of the list, and there would be one big task still on my list. It’d been the one thing I had to accomplish, and I hadn’t even started it. Deep down, I knew that I was only taking on all these other tasks to try to make myself feel better about avoiding the big task.

But occupied and busy aren’t the same thing. And sometimes, you have to stop what you’re doing and just do the work.

Might as well do it now.

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A pickleball photo seemed appropriate for this post. That one was taken by Patrick Hodskins for Unsplash.

The Hardest Questions to Answer.

That's sunrise over Puerto Rico in May 2023. Birds fly through the sky as the sun comes up

Sometimes, the simplest questions are the hardest to answer.

What does success look like?

What do I want to do next?

Is now the right time to try something big?

Do I know enough to start?

Am I ready for whatever’s next?

These are questions that are going to take time to answer. But they’re also worth putting in the work to answer.

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I was thinking about a few of these questions while watching sunrise over Puerto Rico this morning. Not a bad place to think about big questions.

Get the First Win.

This is a photo of white golf balls and red, white, and blue golf tees on a driving range.

I went to the driving range once and found myself next to a couple that was playing golf for the first time. They had an instructor with them, and within the first minutes of the lesson, he was walking them through the complex biomechanics of the swing. He was telling them that there were more than three dozen different parts of the swing, all of which had to work together. He was giving them tips from professional golfers. He was getting into the mental side of the game.

In the hour alongside them, I didn’t see either of them swing the club a single time. The entire lesson was on golf theory.

And I remember thinking: These people will never come back and try to play again — because they never had that first win.

Golf can be a frustrating game, and yes, a really good swing is a complex thing, but the reason you come back is because of the feeling that happens when you hit a really good shot. That feeling — the sound off of the club, the whoosh of the ball in the air, seeing the ball fly — is what every golfer chases. You come back to try to recreate that feeling, over and over again. Those first-time golfers weren’t going to hit a drive 250 yards or experience a perfect wedge shot, but they never even got the chance to try.

With anything you’re doing for the first time, you’re chasing that first win.

Maybe that first win is the first time someone compliments your work.

Maybe it’s the first dollar you make.

Maybe it’s the first time a lesson starts to click.

The goal is to get that first win as soon as you can. Because once you’ve gotten that first win, you’ve experienced a taste of what the work is for — and can decide whether you want to come back for more.

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That’s a photo of golf balls and tees at a driving range. It was taken by Robert Ruggiero for Unsplash.

Change Can Be the Right Thing.

This is a photo of me, ready for takeoff back to New York

When I first started Inbox Collective, I thought most of my job would involve projects and travel.

I’d do an audit for a newsroom, then travel to their office to lead a workshop. I’d take the lead on a big project, where I’d get into a client’s email platform to build something for them. I’d do talks in person. I’d speak at conferences in front of big rooms.

And the job changed when the pandemic hit. I wasn’t traveling for work anymore, which meant more calls and presentations on Zoom. A lot of friends told me they hated Zoom — I found that I loved it. I could actually work with more teams and help a lot more people since I wasn’t spending all my time on planes. I could work with newsrooms and writers in far-off parts of the world, and do so on my schedule.

And at the same time, I started to realize that I didn’t love project work. It took up a lot of time and was full of frustration — exactly the stuff that made me want to go solo in the first place.

So the job changed. I shifted towards the work I liked most: Coaching, writing, and IRL work that involves lots of 1-to-1 time. I took on some audits, but only occasionally. I farmed out work that I wasn’t enthusiastic about to other consultants or agencies.

This week, I traveled to LA for work for an on-site with a client and a Dine & Deliver dinner. I was in LA for 36 hours. I landed just before 2 a.m. in California. I got home the next day after midnight.

And I loved the work I did on site, but it was a reminder of how happy I am with the job I’ve created for myself. It’s definitely not the job I thought I’d have four years ago.

It’s better.

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That’s me on the flight back from LA. I might not have been smiling if I’d realized that I’d get home at 12:30 a.m.