Tag: keep going

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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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You Can Do More Now.

We went on a hike this weekend. It was only four miles, but it took four hours — we started at about 8,000 feet, then went more than 1,000 feet up a mountain, all while I carried a two-year-old in a carrier on my back.

And as we went up, I kept thinking: There’s no way I could have done this last year.

Last year, we did some hikes around Utah, but rarely more than an hour at any one time. We just got too tired to do any more than that.

But the more we hiked, the stronger and more capable we’ve gotten. We can hike stuff now that would’ve been impossible not all that long ago.

All that work opened up new doors, new possibilities.

Keep going.

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That‘s the view near the top on our hike at Alta. Looking down, you can see another ski mountain, Brighton, in the distance.

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Make Time For It.

Last summer, I set a weird business goal for the year ahead: I wanted to try to play golf or go skiing at least 50 times over the course of the calendar year, starting September 1st.

And you might be thinking, “Dan, that’s not a business goal! That sounds like a personal thing!” But for me, it represented an evolution of my business. I love doing this work because it gives me flexibility to do the things that I love outside of work. But if I’m not actually doing the stuff that I love, it means I’m taking on too much with Inbox Collective.

So it’s the end of the summer, and it’s been a year. How’d I do?

This year I hit 25 days of skiing, and 22 days of golf.

(I tracked everything in a Google Sheet, if you’re curious.)

Yes, I came a little short: 47 days, not 50. But I’m still so happy with that number — it’s more skiing and golf than I’ve ever done in a single year! Plus, I’ve got a kid (who isn’t quite old enough to go skiing or play golf with me, though he did come out a few times to help “drive” the golf cart), so maybe in a year or two, getting to 50 days will be easier.

It’s not easy to make time for big things like this — even once a week was a challenge! But getting so close to the goal means I’m on the right track.

Here’s to more time outside of work, more time for yourself, and more time doing the things that you love.

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That’s Sally and I at lunch at Alta on a spring ski day. Nothing quite like skiing on a Monday instead of working!

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Never Better Than Now.

I remember when my dad turned 40. They threw a big birthday party, and friends gifted him this giant inflatable cane. Everyone at the party signed it. It sat in his office for a long time, and I every time I visited dad at work, I remember reading the inscriptions and names on the cane. There were a lot of jokes about my dad officially reaching old age, and I couldn’t disagree.

To a kid, 40 felt like 100.

But I’m 38 now, and looking up at 40 feels strange. I certainly don’t feel 100; I feel a lot closer to the starting line than the finish.

I also know that I don’t know when the finish line arrives.

I’m trying to remind myself that there’s never a right time to do the big stuff. Sometimes I try to tell myself that the timing will be better just a few months down the road, even though I know that’s not true. If you want to do something, you should do it now. Next year, next month, next week — none of this is guaranteed.

There’s never been a better time than right now.

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I took that photo alongside the harbor in Copenhagen one morning a few weeks ago. I was sitting there, watching the sun rise on a beautiful morning, and thinking about the fact that I do something that lets me travel to such beautiful places and work with such interesting people. I know how lucky I am.

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Kick Over Rocks.

I stumbled upon this story the other day about the CEO of Pittsburgh’s airport, Christina Cassotis. I’ve got a soft spot for Pittsburgh — my wife’s from there, we got married there, and about once a year, we fly through there to visit my mother-in-law. The Pittsburgh airport’s a bit dated. It was built to be a hub for US Airways, but now that airline no longer exists, and the airport they have doesn’t really fit with what the city needs.

So I was fascinated to read this story in Pittsburgh Magazine about Cassotis, an executive who, by all accounts, is doing great things to rebuild and modernize the airport. (The rebuild of the airport will cost $1.7 billion, per one account.)

This was my favorite section from that Pittsburgh Magazine article:

“You don’t know how things work around here,” someone yelled after she instituted Uber pickup at the airport soon after she was hired. “Who do you think you are? You think you just come in here and change things?”

“Yeah, I actually do,” Cassotis replied. “That’s my job. My job is literally to kick over rocks. We have to do things differently if we’re going to get different results.”

I absolutely love that mentality. Sometimes, you need leaders who can guide you through a series of slow, steady changes. Sometimes, you need a leader who can recognize when things have been broken for a long time and really roll up their sleeves.

Never be afraid to kick over those rocks.

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That’s a photo I took at Pittsburgh International Airport back in 2019. When you’re walking to the train to take you to baggage claim, you used to have to walk past two statues of legendary figures in western Pennsylvania history. One is George Washington. The other is former Steeler Franco Harris. I always loved that in Pittsburgh, these two men were given statues right next to each other, and no one seemed to think it was odd that our nation’s first President and a guy who played fullback in the NFL were given equal weight.

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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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An Idea for Your Ideas.

A few years ago, I created a text doc where I drop in my ideas. Whenever I have an interesting conversation or come up with a big question, I add it to the doc. It might be a few words or a sentence — just enough for me to know what I was thinking about when I revisit the doc later on.

And then I’ll come back to the doc every week or so. Some of the ideas turn into blog posts or new products. Some turn into nothing. (Not every idea is a good idea!)

I’ve always got more ideas than I can actually take on. There’s always new stuff for me to work on later.

So create your own doc with ideas. It can be a text doc, a notebook, a series of voice memos on your phone. You never know which ones might turn into something great.

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That photo of a series of lights comes via Unsplash and photographer Jean-Philippe Delberghe.

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A Trick for Prioritization.

a yellow legal bad with sections for NEED and LIKE written out.

Here’s little trick I like to use when I’ve got way too many tasks on my to-do list and can’t figure out what to prioritize.

Open up a spreadsheet and type out all the tasks you’ve got on your list. Then create three columns, and put these headers at the top:

• What you NEED to do this quarter
• What you WANT to do this quarter
• What you’d LIKE to do this quarter

NEED is the stuff that 100% absolutely must get done.

WANT is the next bucket of tasks you’re most excited about.

LIKE are things you’re interested in… but you can’t quite make a priority.

I know I’m guilty of focusing on stuff that isn’t in those “Need” or “Want” buckets. Sometimes, just seeing everything laid out like this helps me refocus on what’s most important.

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That’s a sketch that Canva’s AI tool created for me. It’s a decent example of what this exercise might look like if you did it on a yellow legal pad.

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Inches, Not Miles.

Something I’ve been telling my teams a lot lately: Growth comes in inches, not miles.

I’m seven years into running my business, and more than a dozen years into working my field, and it feels like I’m just starting to get to a place where I can do the work I’m most excited about.

Everyone wants to move quickly, but the good stuff takes time.

You don’t always move as fast as you want to. Celebrate the little wins. Take the inches when you can.

They all add up.

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That’s a a phot of a biker pedaling forward on a bike path, surrounded by green grass and blooming trees. It comes via Unsplash.

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Don’t Overthink This.

a brown chair, a white table, a simple fern, up against a white wall.

90% of my advice to clients is boils down to three words:

“Don’t overthink this.”

People get into their heads when it comes to tweaking their strategy or tactics. They get caught up thinking that there are a series of three-dimensional chess moves that will fix what’s wrong.

But usually, the fixes are simpler than that: Your positioning is unclear. You’re not targeting the right audience. You’re doing too many things at once.

My job is often to tell teams: You’re overthinking things! Let’s simplify and get back to the core of what you do well.

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That’s not the fanciest desk set up in the world, but it’d work just fine? Why? It’s so darn simple. Thanks to Unsplash for the photo.

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