Tag: lessons learned

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Keep Betting on Yourself.

15 years ago, I quit my job at a TV station, moved to Biloxi, Mississippi, set up a basic website, and started publishing stories about the five-year anniversary of Hurricane Katrina. I was my own reporter, editor, photographer, publicist, IT team — I did it all. The end result was a fellowship, which led to more reporting in Springfield, Missouri, and then that led to my gig at BuzzFeed.

I bet on myself, and I certainly wouldn’t be where I am today if I don’t make that bet.

But not all bets are big. Inbox Collective was barely a few weeks old when I went to a journalism conference in New Orleans in September 2019. I told my wife that I wanted to host a happy hour for readers of my newsletter. I didn’t have any idea how many people would show up or even if any would show up — but my bet was that if I met some people, something good would come from it.

50 people RSVPed. A few no-showed, a few brought an extra friend. I ended up spending about $400 on drinks. (Thanks to everyone who bought happy hour beers and not full-priced cocktails!)

But most importantly: I landed five clients from that one happy hour.

Anytime I feel stuck, I try to remind myself: Keep betting on yourself. Place small bets, and place big ones. It’s worked before; it may work again.

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I took that photo in 2010 in Pass Christian, Mississippi. It’s of a bust of W. Dayton Robinson, whose $2 million donation helped City Hall expand after Katrina.

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I Don’t Always Have the Answer.

At least once a week, a reader asks me a question, and my reply is: “To be honest: This is one of those questions that’s so far outside my wheelhouse that I’m not sure my advice is worth listening to!”

People are sometimes surprised to hear me say that. I do run an entire business around giving advice for newsletter operators, and I’ve been working in this space for a dozen years.

But the most important thing I’ve learned through my consulting practice is that it’s OK to say, “I don’t know!” No need to pretend I have all the answers.

And if you’re the kind of person asking the question, you should also feel free to ignore my advice entirely! I am frequently wrong, even when I have strong convictions about my answers!

So much of building any newsletter or any business is knowing when to follow and when to find your own way. (And yes, the teams that tend to build the best stuff in the long run do a bit of the former but often more of the latter!)

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I couldn’t quite find the right art for this, so I had to draw something myself using the only art tool I’m qualified to use: MS Paint. (Or, in this case, a free online replica version of MS Paint.)

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Small, Baby Goals.

I published this interview today with Alisha Ramos. She founded a newsletter called Girls’ Night In that grew to 180,000 subscribers and $2 million per year in revenue — and then she decided to downsize and start over as a one-person operation. I’ve been thinking a lot about her story — how she realized that what she’d built wasn’t working anymore for her and that she needed to start over. In an age where it feels like everyone is about being as big as possible, Alisha’s story is a reminder that it’s OK to build something that fits with your life — even if that’s something small.

And I especially loved this one thing Alisha told me at the end of our conversations:

I’m at this phase where I’m very content with where I’m at and what I have, and not having the drive or the desire to grow, grow, grow is actually nice. I have small, baby goals this year.

It’s such a wonderful way to think about things. Not everything has to be big. Sometimes, a few small, baby goals are all you really need.

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That’s a screenshot from Alisha’s wonderful newsletter, Downtime.

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Stay Right Here.

As silver DeLorean, like the one seen in “Back to the Future,” as photographed from behind.

I keep thinking about this line from poet Andrea Gibson in their book, “You Better Be Lightning”:

Regret is a time machine to the past
Worry is a time machine to the future

I’m as guilty as any of having my head somewhere else. Sometimes that means thinking about mistakes I’ve made or things I could have done better. Sometimes that means spending too much time thinking about all the stuff I have to do in the weeks and months ahead.

Gibson’s lines are a reminder: Wherever your feet are, keep your head there. There’s work to do right here, right now. That’s where your mind needs to be, too.

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Feels like the only appropriate photo for a post like this is of a DeLorean. That photo comes via Unsplash.

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You Ain’t Hamlet.

This interview with Jason Alexander, of “Seinfeld” fame, popped up in my feed the other day, and I think it’s worth watching in full. In it, he says:

I went to Boston University as a theater major, and because William Shatner was my muse, I wanted a dramatic career. I really thought I was going to play some of the great classical roles and be a dramatic actor. Sure, I hadn’t done much comedy. I’d done some musicals, so there was that, but I hadn’t done much comedy. And the summer second semester of my sophomore year, I had a professor named James Spruill at Boston. He was the only black member of the faculty. He was a guy who had come up in the ‘60s with street theater — theater is to change the minds of the masses, affect change. He brought me into his office for my my semester consultation, and he had this great basso kind of James Earl Jones voice, and he sat back, and he just kind of nodded his head and looked at me for a minute. He went, “I know that your heart and soul is Hamlet, and you would be a profound Hamlet. You will never play Hamlet, so you best get good at Falstaff.”

And he basically said, look, look in the mirror. You are 5’6’’. You are 20 to 25 pounds overweight, and you are losing your hair. You have a large performing persona. If you want a a commercially successful career, you’re going to be a comedian, and you’re not embracing it, you’re not looking at it, you’re not doing it.

Had he not said to me, “You ain’t Hamlet, man,” I would have finished that school and gone into the professional world thinking, ”Here’s Jason Alexander and the Iceman cometh. It’s what everybody is waiting for.”

And I would have been wrong.

It’s such a wonderful reminder: We all need someone in our lives who’ll be truly honest with us. Sometimes, we need that person to lift us up. Sometimes, we need them to keep on the right path. But all we need those voices we can trust, and if you find someone who can do that, you owe it to yourself to listen to them. They’ve got something worth hearing, even if it’s not what you want to hear at that moment.

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It Might Not Happen Today.

A funny thing about being a parent, especially a parent of a young child in daycare, is that your entire schedule can change in a moment.

One phone call from daycare — “Hey, your son has a runny nose and a weird cough, so I think you need to pick him up” — and suddenly, there goes your week. Calls get canceled, work gets postponed. That big project you wanted to do today? It’s definitely not happening today anymore! (And maybe not next week, either.)

All of this has made me weirdly grateful for the days when things go right. There are days when things actually work out, where the work gets done and your child comes home completely healthy. Those are great days, even if this winter, it feels like there are far fewer of them than before.

Still: The mindset shift is important. I used to get mad when the work didn’t get done. Now I know it’s part of being a parent — and it’s my job to adjust how I work, adjust what I work on, and adjust my mindset. I’m a dad and a business owner. This is just how things work now, and that’s part of what I signed up for.

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That’s a photo of my son carrying a reusable bag upstairs. Why? Who knows, but parenting means a lot of unexpected moments — like my son deciding that a bag is far more fun to play with than the toys we got him.

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No Skips. No Fast-Forwarding. Be Here Now.

I had this moment yesterday where I wanted to skip ahead.

I sometimes get jealous of the parents who have a few kids who are already in elementary school. They’ve gotten through the toddler years where kids get sick every 20 minutes. (My son has RSV right now; so does everyone in his class.) They’ve gotten through sleepless nights and potty training. They can take their kids on big vacations and really do fun stuff with them.

Plus, they don’t need as much attention every day — so I could reclaim a bit of that time to get stuff done at work.

And then I thought about it some more and remembered: I don’t want to skip ahead. I don’t want to miss these moments. I hate that Ben is sick, but there are also wonderful moments these days, too. Yesterday, he climbed into my lap and gave me a huge hug — in a few years, he’ll be too big for that! (At this pace, he might be too big for that by July.) Those moments won’t last forever.

So I’m writing this to remind myself: I don’t want to hit fast-forward. I want to be here, right now, in the moments that will never happen again — big smiles and new foods and new experiences and colds and restless nights and all of that. This is part of the journey; I want to make the space to really be here for it.

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That’s a photo of Ben wearing my sunglasses around the supermarket. When I talk about not skipping ahead, I’m talking about moments like that — he’s such a silly little guy!

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A Goal for 2025.

I set a big goal for 2025 — something I’ve never set in the six years I’ve run my business.

My big goal isn’t around revenue.

It isn’t about growth.

It isn’t about launching new products.

My goal? I want to be able to ski or play golf 50 times in 2025.

To me, success isn’t about building the biggest, most profitable business. It’s about making something that brings in the revenue I need, has the impact I want, and gives me the time to do the things I love.

If I can run a business that does all three, then I must be doing something right.

Here’s to a lot more days on the mountain in 2025 — and on the links this summer.

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That’s me on the mountain at Deer Valley a few weeks ago. If you see a tall guy in a loud jacket skiing around Park City, it might be me!

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Declaring Parenting Bankruptcy.

I declared Parenting Bankruptcy last week.

What is Parenting Bankruptcy, you might ask?

Well, last week was one of those weeks where everything seemed to go wrong. My wife got strep. My son got hand, foot, and mouth disease and had to be held out of daycare. The heat broke in our house.

And the day we were set to send our son back to daycare, there was a pinkeye outbreak at his school.

It was just one of those weeks.

Sometime around Wednesday, I decided that I wasn’t going to get anything big done. I had some sizable projects that I was hoping to tackle — and it was very clear those weren’t going to happen. My only goal was to make it to the end of the week.

So I declared Parenting Bankruptcy. I cleared everything off my to-do list, and made it my only goal to get to Friday.

The hard part about parenting — at least for me, a dad with a toddler — is time management. (I’m betting that I will have a very different take on this in a decade!) When things are good, there’s a good balance between parenting and work. But when a few things go wrong, the balance gets entirely out of whack.

I’ve had tough weeks before, though I can’t recall one where I kicked all of my to-dos to the next week. This was my first time declaring Parenting Bankruptcy.

I’m sure I’ll do it again one day. This whole “being a dad” thing isn’t always easy; there will be more days and weeks like this.

But I also have to remind myself: There will be even days and weeks where things are great, where my son is an absolute joy, and where I’m so grateful that I’m a dad.

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That’s a photo of my son reading at this little table in our living room, in a far quieter and less hectic moment than the one we went through last week.

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Get a Head Start.

One little thing that’s worked for me when it comes to New Year’s Resolutions: Starting just a little bit early.

I used to do the thing that everyone does: I picked a resolution or two at the end of the year, started in January, and completely quit on it by the end of the month.

But what I discovered works a little better for me is if I start now — not in January.

Let’s say the resolution is to work out more in the new year. (In this case, this is something I genuinely want to do next year!) I know that if I try to go from 0 to 60 in January, it probably won’t stick. I need a little time to warm up to the new habit.

So instead, I’ll start now — in December. I’ll put a few workout classes on my calendar. I’ll make sure to make time during the month to use that stationary bike. And by January, I’ll already have started to slowly build that habit.

Once you’ve gotten the ball rolling, it’s so much easier to keep it moving when January comes around.

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That is 100% not me on an exercise bike, but it is a lovely black-and-white photo of someone biking from Josh Nuttall for Unsplash.

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