Are You Still Curious?

I’ve been running Inbox Collective for almost eight years. Before that, I spent seven years in email roles at the New Yorker and BuzzFeed. Spending 15 combined years in a single space — certainly one as niche as email — is an awfully long time.

A friend asked me the other day: Do I think I’ll work in this space forever?

I told them: I’ll keep doing this as long as I stay curious about it.

Something I love about my job is that I keep learning new things. Clients challenge me every week with questions I don’t know the answer to. I still love finding the right answers.

But I imagine that one day, the curiosity won’t be there. (It would be easy to get complacent and lean on answers that worked a decade ago — even if they don’t work anymore.) And when that happens, that’ll be the sign that it’s time to move on.

Until then, as long as I stay curious, I’m excited to keep working in a space I really love.

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That’s a photo of me taken back in 2017 at an email conference in Brisbane, Australia. Tough to believe that I’ve worked nearly a decade in this space since that photo was taken!

Get a New Game Plan.

A person draws a series of wireframes using a pen and paper.

The kiddo’s been going through some sleep issues lately. It’s been tough — for him, of course, but also for us. We usually put him down around 7 or 7:30, and then we get some time at the end of the day for ourselves: To read, to watch something on TV, to clean up, to make lunches for the next day. A few hours to reset really matters.

But with the sleep issues, it’s been harder. Instead of a quick bedtime, it’s been stretched to a period of sometimes a couple of hours at the end of the night. I find myself getting mad at him for not going down, even though I know it’s not his fault.

So we’re asking for help and hiring a sleep consultant to help us figure out what to do.

The hard part with a situation like this is: I have no game plan right now. We’ve long had a great routine at bedtime, but it’s not working anymore. We need someone to help us put together a new strategy.

When I have a game plan, I feel empowered. Every night isn’t perfect, but I know how and why things work. All of us, from time to time, need a new structure to get everything back on track.

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That photo of a person drawing a wireframe comes via Kelly Sikkema and Unsplash.

You Still Have to Put in the Work.

I have been doing the consulting thing since 2019. I have done more calls, more audits, more interviews, than I ever could have imagined. Sometimes, I think that I’ve done so much of this work that I’ve seen it all — that there’s nothing left to learn.

Every time I start to think that, I stumble onto a new problem, a new challenge, or a new opportunity, and I realize I don’t know how to do this just yet. No matter how far I go with Inbox Collective, there is always more work to put in, new things to learn, and lots to be curious about.

Sometimes, people ask me if I think I’ll do this job forever. I doubt it. One day, I’m sure I’ll find that I’m not interested anymore in putting in that work, asking that extra question, or trying to learn that new thing. That’ll be the sign that it’s time.

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That photo of three men washing windows in Singapore comes via a photographer named Victor and Unsplash. It doesn’t have much to do with this post. I just liked the photo.

Perspective is Everything.

A week ago, something pretty remarkable happened in the golf world that, if you’re not a die-hard golf fan, you almost certainly missed.

Shane Lowry, a former major winner, led the Cognizant Classic by three strokes with three holes to play on Sunday. And then, on back-to-back holes, he hit shots into the water. He went from being a near-certain tournament winner to finishing second.

A few days later, I was listening to “The Tony Kornheiser Podcast,” when Steve Sands, a golf commentator, told this story about chatting with Lowry after the tournament:

He told me a cute story on Tuesday. He said, “We’re headed home, we’re getting to the house, and everybody realizes how upset Dad is and how upset I am. Nobody’s saying anything, and my 9-year-old daughter looks at me and says, ‘Daddy, what’s wrong with second?’”

When we get lost in the details of our work, sometimes we need an outside voice to reset things. We need someone to ask us: “Why does this really matter?” An outside perspective can reset things when you get too inside your own world.

As for Lowry: Yes, it was a tough way to lose the tournament. But he still won $726,400 for finishing in second place.

To which I’d say: There doesn’t seem to be much wrong with that.

Make It As Hard As You Want To.

I was driving home last weekend, through Emigration Canyon. On a weekend, there are tons of cyclists and runners on that road — people literally biking and running up a mountain. It’s impressive to see.

But then I saw something I’d never seen before: Two men, on unicycles, riding up the mountain.

Going up that road — it involves more than 1,000 feet of elevation change — is hard enough on a bike or on two feet. But on a unicycle?

And so I got home and went to YouTube, and there were all sorts of videos of people doing even more incredible things on unicycles there. They’re doing on two wheels what I wouldn’t dare do on one.

It was a reminder for me: You get to decide what challenges you take on. And with those challenges, you get to decide if you want to do things on easy mode or hard mode.

What’s right for someone else isn’t what right for you.

(And heck, I know mountain unicycling isn’t right for me!)

Embrace the Imperfection.

Brandi stands center stage underneath the spotlight, behind her red lights and her face projected on a giant screen inside a red ring.

There are days when I’m really excited about the future of AI, and days when I get a little scared about the possibility that AI’s going to take over everything.

But on Tuesday, I went into Salt Lake to see Brandi Carlile play. She did this thing in the middle of the show where she asked the crowd for requests. I thought they might have been plants, but no: She’s been doing it at every show.

And seeing something like that — the crowd screaming out their favorite songs; the artists trying to figure out, in real time, what guitars they needed to play and what key the song was in — was such an amazing thing. I loved seeing Brandi try to pick out a fan in a crowd of thousands, hoping that she actually remembered the song this fan wanted her to sing. I loved the band talking through, on a hot mic, how they wanted to handle these songs acoustic — who’d play what part, how they’d play the intro or the ending.

AI can be a bit of a know-it-all. Ask it for the idea chicken dish or a strategy to sell widgets, and it’ll spit out an answer in seconds. It’s often right, too.

But there’s something special — something so human — about seeing something happen in real time. Watching Brandi and her band on stage reminded me that some of my favorite moments are the ones that aren’t quite perfect. They’re messy, they’re unexpected, they sometimes go wrong.

I don’t think AI will ever be able to make moments like that.

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I took that photo from way in the upper deck at Delta Center.

Figure Out Your Vacation Work Strategy.

A laptop is open with a to-do list, while the Atlantic Ocean sits in the background.

When I first started Inbox Collective, I tried taking vacation the way I had when I had a traditional 9-to-5. I turned on the out-of-office reply, closed the laptop, and ignored emails until I got back.

I returned from vacation to a pile of unread emails and tasks. I spent days trying to catch up.

What I learned was that at my 9-to-5, there were other people who could pick up the slack and answer questions while I was on vacation. But now I was my own boss. It was just me — if I didn’t reply, no one did.

So now I take a little time, every day, to deal with tasks. Urgent stuff gets handled that day — not as fast as it would if I was at work, but usually done within 24 hours. Less urgent stuff gets tackled when I have the time. Some stuff gets put off until I’m back at my desk — no big deal.

But by spending an hour or two every day on work, I make sure I don’t come back to that big pile of tasks.

Is that strategy for everyone? Absolutely not. Some people like doing a little work on vacation. Some people would rather throw their laptop in the ocean than answer an email while OOO.

The only important thing is to figure out what works for you.

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I took that photo of my laptop a few years while on vacation in Florida.

You Can Make Time For It — If You Want To.

Ben hikes through a shady section of a dirt hiking trail in Utah.

A funny thing I’ve noticed lately: I’ll be chatting with a friend and mention something that I was able to make time for — going skiing, spending time with the kiddo, reading books. And they’ll say, “Oh, I wish I had time for something like that!”

But when you probe a little deeper, you find that they often do have the time. We’ve all met people who are willing to wake up at 6 so they can squeeze in a workout before work, but who can’t seem to find the time to cook dinner.

And I get it: We’re all busy, and there’s never enough time for everything. But if there’s something you really value, there’s often a way to make space for it.

For me, one of those things is getting outside. I was feeling a little sluggish the other day, and I had a break between calls. I sat down, ate some lunch, and watched crappy TV on the couch for an hour. Weirdly, lying down on the couch didn’t particularly help with that sluggishness!

And as I went downstairs to go on my calls, I found myself asking: Why didn’t I get outside for a 20-minute walk to clear my head?

Yes, I’m busy. No, I don’t have time for everything. And no, I don’t need to fill every minute of the day with something.

But I have 20 minutes for a walk. I have time to read before bed. I can move things around so I can do the stuff I want.

I do have the the time if I want it.

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That’s a photo I took last summer of the kiddo and I on a little hike together here in the mountains.

Great Ideas Come From Weird Places.

I’m reading Susan Morrison’s wonderful biography of Lorne Michaels, called “Lorne,” and this little story about Michaels and Paul Simon immediately caught my eye:

Michaels’s few off-hours that summer were spent in the studio where Simon was recording Still Crazy After All These Years, and he added, to his growing trove of showbiz stories, the one about how his friend Paul took the title of his song “Mother and Child Reunion” from the name of a chicken-and-egg dish on a Chinese menu.

An iconic song, titled thanks to the name of a menu item at a Chinese restaurant?

Yeah, great ideas can truly come from anywhere.

A New Rule for 2026.

A road splits into two in a dark forest. There's snow covering the road and snow on the trees.

Here’s something I’m trying to stick to this year:

I’ll get these pitches in my inbox for something that seems interesting. Not incredible, but interesting, and I’ll say yes. Maybe it’s a potential client that I’m vaguely interested in working with or a brand that wants me to demo their product. I’m not totally sold, but hey, it seems interesting enough, and I’ll say yes to the call.

And then Sunday night, as I prep for the week ahead, I’ll see that meeting pop up on my cal, and I’ll go, “Why did I say yes to this again?”

I’m getting better about saying no to certain things, but I know I need to be even pickier. It’s a waste of their time and mine if I’m not 100% in before booking the call.

If I’m not incredibly excited to meet, the answer needs to be, “Sorry, I don’t think this is a good fit for me.”

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That photo of a fork in the road comes via Oliver Roos and Unsplash.