Keep It Simple For As Long As You Can.

Here's a photo of a golfer. Not to overcomplicate things, but he could probably use a little more rotation here in the backswing.

There’s a famous quote from golfer Arnold Palmer about the sport: “Golf is deceptively simple and endlessly complicated.” Arnie’s absolutely right about golf: It doesn’t seem all that complicated until you really start to get into the sport. There are how many different ways to swing a club? To chip? Even to grip a club? The objective is simple — get the ball in the hole in as few strokes as possible — but the ways to achieve that goal are limitless.

The same is true with so much of the work we do. I had a conversation this week with one of my clients about the daily newsletter they want to launch. The goal with their newsletter is simple: Give readers a quick daily update to catch up on the day’s news. But the ways to deliver that to readers are endless. Do they want to have it come from a single writer or from a generic voice? Do they want to send it in the morning, afternoon, or evening? Should they focus on bringing readers stories in the inbox or requiring them to click out? How many stories should they include? What kinds of stories would make sense to include? I’d go on, but you get the idea: A single newsletter will end up being the result of dozens of different questions.

But what I’d tell you if you were learning to play golf or learning how to launch a newsletter: Keep it simple for as long as you can. It’s easy to overcomplicate things at the start. As you learn more, you’re going to want to try more advanced tactics. Save all of that for another day — and just focus on starting with the basics for now.

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That photo of a golfer comes via Matt Aylward and Unsplash.

Be Your Own Biggest Fan.

It’s not all going to go right. You’re going to make mistakes, and you’re going to do things that you wish you could undo.

And when things go wrong, it’s easy to be your own biggest critic. It’s easy to get down on yourself.

But give yourself permission to make mistakes. When things go wrong, try to pick yourself up. Remind yourself that everyone makes mistakes, and that nobody is going to do the right thing every time. Try to cheer yourself on, and push yourself to do better next time — because you know what you’re capable of, and you know that you can show the world how good you can be.

Whatever happened, happened. Now go be your own biggest fan. 

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That image of two people celebrating is about stock footage as it gets. It’s by Priscilla Du Preez for Unsplash.

Just Ask.

Back in July, I created a fundraiser for my Google Doc, Not a Newsletter, and asked my readers to donate to The Marshall Project. I wasn’t sure how much money we’d raise.

In the first 24 hours, we raised $1,000. In a month, we raised more than $3,300.

I’m thrilled, and so, so grateful.

It’s a reminder for me: Put the work out into the world, and see what happens. You don’t know what will happen until you ask.

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A big thank you to Givebutter, which made this fundraiser possible. I’d absolutely use their platform again.

The Only Time Is Now.

The truth is, I almost didn’t leave The New Yorker when I did.

I knew that I wanted to start Inbox Collective. I knew there was a market for my services. I knew that I had an opportunity to help the journalism world.

But I wasn’t sure if the timing was right.

Sally was in nursing school. She was 18 months in, with a year of classes left. She’d graduate in Spring 2020. And my thought was simple: Sally still had a few semesters of tuition left to pay, we were a one-income household, and if Inbox Collective didn’t work, we’d be a no-income household. Leaving my job to start a consultancy was a gamble, and the safe move was to wait until Sally had graduated and gotten a job — sometime in the summer of 2020.

But Sally convinced me to take the leap anyway. She reminded me that I had momentum and a clear opportunity. There was something else, too, something we talked about a lot at the time: The window for me do this was open, and we weren’t sure how long it would stay open. There was risk in leaving my job to start something new, but also risk if I waited too long and the window closed.

Now looking back, if I’d waited, I don’t think I’d ever have left to start Inbox Collective. Taking the leap to start a business is tough enough during good times, but during a recession and a pandemic? There’s no way.

It’s a reminder that when you’ve got something you’re excited about, and something you feel ready to take on, the only time to try it is now. If you wait, the window might close, and you might miss out on that opportunity forever.

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That’s a photo of me giving a talk in Sydney last year — one of many pretty amazing experiences that I couldn’t have had without taking the leap.

Just Go.

Colonel Sandurz: Driver, prepare to move out.

Dark Helmet: What are you preparing? You’re always preparing! Just go.

Colonel Sandurz: Just go.

About a decade ago, I went to a Startup Weekend event for the first time. The idea was simple: Over the course of a weekend, some people with big ideas would attempt to start up a company. They’d get access to mentors, investors, and resources — and by the end of the weekend, if things went well, they’d be well on their way to being able to start a new business.

On the first day, anyone who had a startup idea came to the front of the room to pitch their idea. I remember one pitch — I believe it was an idea for a new app. The guy pitching the idea told the group that he’d been doing research for five years, reading everything he could on the subject, and having conversations with leaders in the space.

The organizers of the event asked: So, in those five years, what have you done with that knowledge? What have you launched or made so far?

He said: I’ve just done research. I wasn’t ready to start yet.

And one of the organizers told him the hard truth: The knowledge you gained from all those books and all those conversations is nothing compared to what you’ll learn from actually starting something. If you’d started five years ago, you’d have so much to show for it: a functional product, lessons of success and failure, knowledge about what actually works for your app. The research and the ideas aren’t worth anything — everything valuable comes from doing the work.

And it was painful to watch as the guy at the front of the room realized: I just wasted five years of my life, and I don’t have anything to show for it.

The secret is: You know enough to start. You have enough to start. And you’re good enough to start.

So don’t overprepare. Get started as soon as you can.

Just go.

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That photo and quote at top comes from Mel Brooks’s classic spoof, Spaceballs.”

The Best Things In Life Are Free.

Believing in yourself is free.

It doesn’t cost a cent to be kind.

You don’t have to write a check to go the extra mile.

You don’t have to go to school to learn a new skill.

Connecting with an old friend costs nothing, and might mean a lot to both of you.

You can’t put a dollar value on hard work.

You can always make time for a good conversation, to offer advice, or to just listen.

There are certain things in life that are available to all of us. They don’t cost a thing, and they don’t require a fancy degree — just time, or kindness, or a little bit of effort. Make time for those things. Be good to others. Listen carefully. Challenge yourself. Work hard. Some of the best things in life are free — and entirely up to you.

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That photo at top comes via Michael Longmire for Unsplash.

Set Simple Goals For 2019.

I wrote about this in my most recent Things I Believe post, and wanted to expand on it:

Commit to making time for something simple in the year ahead. Make a goal to try the crossword every morning, or to invite friends over for a home-cooked dinner ever week, or to see live music once a month. It’s the little things that often make you the happiest.

This is the time of year when people commit to New Year’s Resolutions — which inevitably end up discarded by the time February rolls around. So instead of setting a major resolution you’ll fall short on, start smaller. Start with something that’s going to help you grow, or feel more connected to your friends or community.

There are three types of goals that are easy to aim for:

Commit to a learning goal — Pledge to make time in 2019 to learn something new. If your company has a learning & development team, make it your goal to attend one of their trainings every quarter. Choose to read more — say, a new book every month. Or you can go even smaller: In 2018, when I realized that I didn’t know enough about the archives of the magazine I work at, I pledged to read one archive New Yorker story every day. It required me to set aside 30 additional minutes a day to read, but it’s helped me learn so much about the writers who’ve shaped this publication.

Commit to a personal goal — Again, keep it small. A few years ago, I pledged to save money by bringing my lunch to work more often. (The back-of-the-envelope math: Bringing a sandwich instead of buying lunch saves me about $1,500 per year. New York lunches are expensive!) You can commit to getting coffee each week with a colleague you don’t work with that often — expand your network at work! You can commit to volunteering more, or to making time for a puzzle. (I’ve never been one for crosswords, but I made it my goal in 2018 to try to get better at them. I’m still not very good, but I can get through about Wednesday in The New York Times, thanks to regular practice.) In 2019, I’d like to try to have friends over for a home-cooked dinner at least once a month. It’s a small goal, but it might push me to try to cook more (which I always enjoy!) and to connect with old friends (always wonderful!).

Commit to a fitness goal — A few years ago, I made it my goal to run 500 miles in a year — and I didn’t come close. (I ran 70 miles in the first three months, and 57 the rest of the year.) Reach goals for exercise are especially hard to hit. Set a more reasonable goal instead: Make it your goal to try a new fitness class every month. Or do what I’m going to try in 2019: To run three races (probably in the 5k-10k range) over the course of the year. One race every four months is doable, but would still be a real achievement for me.

Most importantly: Once you’ve set your goal, find an accountability partner to hold you to it. If you have someone there to keep track of your progress and urge you on, it makes it so much easier to keep going.

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That photo of a planner comes via Estée Janssens and Unsplash.

Try It Before You Realize How Hard It Is.

When I was 17, I got an summer internship working at a paper on Nantucket. It didn’t pay much, but the paper was small — there were maybe eight of us, total, putting out a newspaper every Wednesday — and they gave me opportunities to write. For a high school junior, it was a great job.

Being young had its advantages: I was willing to say “yes” to assignments that more veteran reporters would have been wise enough to say “no” to. I pitched a weekly profile on local workers, a new police blotter column, and several big feature stories. It was a lot for one reporter to take on, but I didn’t have enough experience to know better.

But nothing really compared to something my boss, Don, pitched to me. He’d seen a weekly paper in another town that had printed an ambitious special section. They’d dispatched a handful of reporters and photographers, in shifts, to document a single day in their town, and then packaged it all together into a special section on 24 hours in the life of their city.

Don suggested that instead of having a team of reporters and photographers attempt that, I could do it alone. 24 hours, a bunch of stories and original photos — by myself.

No one else on staff would have been dumb enough to agree to that. Of course, I did.

So what happened? That day, I set out with a camera, a notepad, and my RadioShack tape recorder. (It was 2004.) It was a quite the day: I interviewed people all over the island, ate lobster on the beach (for journalism! And also for my first-ever expense report!), and reported a story from a nightclub that wouldn’t legally allow me to enter their premises for another four years. At one point, in the middle of the afternoon, I stopped by the office to hand over a flash drive of photos. I remember one of my co-workers semi-jokingly announcing, “Look! He’s still alive!”

In the end, we turned my package of stories and photos into its own eight-page section of the paper. My bosses were thrilled, and so was I: By trying something that no one else was willing to try, I ended up with my own section of the paper. Not bad for a summer intern!

Naïveté was my secret weapon that summer. I wasn’t scared or nervous or overwhelmed by anything at the paper — just excited to try new things. That mentality got me all sorts of exciting opportunities. Over and over, I tried things because I didn’t know how hard they were supposed to be. Fifteen years later, I’ve learned how hard many of these things really are — but I’m still trying to push for new things anyway.

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That’s a photo I took a few years ago, flying above Nantucket.

You Can Learn Something From Everyone.

The next time you meet someone new, try this: Assume they have something they can teach you.

It could be a coffee with a new acquaintance, a big meeting at the office with several co-workers, or a casual chat at a cocktail party. No matter who they are, or what they do, make that simple assumption: They know something you don’t, but they’d be happy to tell you more about it — if only you asked!

What happens when you meet someone and you’re curious to learn more from them?

1) You ask more questions.

2) You listen more closely.

3) You end up building deeper relationships with them — and perhaps sparking the types of conversations that can lead to new ideas and initiatives.

Just that one shift in perspective — this new person has something to teach me! — can change the way you approach a conversation. It can put you in a mindset where you’re curious to learn.

I know I’m sometimes guilty of shutting myself off from conversation before one even starts. I do it for all sorts of reasons: I’m busy, I’m tired, or I’m just disinterested. Sometimes, on my worst days, I’ll sit in on a meeting and think, “I know more than these people.” That’s always a mistake — I’ve eliminated the chance of learning something right from the start.

Instead, keep that open mindset. Ask lots of questions, and be willing to challenge yourself and your own beliefs. You never know when you’re going to meet someone who might teach you something new.

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That photo of a dog with big ears — the better for listening, obviously — comes via Kyle Smith and Unsplash.

Side Project Stories: Build The Internship You Really Want.

In the spring of 2006, I was finishing up my freshman year at Mizzou, and trying to find an internship for the spring. I was too young for jobs at a big paper — they were looking for a junior or senior who they could hire soon. So I tried two different avenues: One was to apply to smaller papers back home in Washington, D.C.; the other was to try to convince an organization that didn’t have a media presence to let me create one for them.

There’s a college all-star baseball league in the D.C. area, with a team about 15 minutes from where I grew up. I shot their general manager a note, and asked if they wanted someone to “cover” the team for the summer. I’d write game stories and longer features on the team, and cut together video that we’d put on YouTube. It was a low-risk kind of ask. I wasn’t looking for housing, or even to get paid. They didn’t have anyone who did that kind of work already, so anything I contributed would be a bonus for them.

The team said yes — but so did a paper in D.C., and they were offering the chance to cover a handful of teams, including the Washington Nationals. I took the job at the paper.

But here’s a story from The Ringer about Dan D’Uva, who actually followed through on the idea of creating his own summer internship program on Cape Cod, in their famed college baseball all-star league:

In 2002, D’Uva and his New Jersey high school classmate Guy Benson came to the Cape and told the Chatham brain trust they wanted to be the team’s announcers. No team in the league had announcers. But D’Uva and Benson had an unusual sense of purpose. “They were like laser beams,” Bob Sherman, the A’s vice president, said.

D’Uva and Benson called games featuring Evan Longoria, Andrew Miller, and Todd Frazier. When D’Uva graduated from college and began his long climb through the minor leagues, he volunteered to run the Chatham internship program…. When former Chatham interns started getting jobs at MLB Network and Colbert and with various minor league teams, word got around the broadcasting factories of Syracuse and Arizona State that the Chatham job was the one to score.

D’Uva’s now the voice of the Vegas Golden Knights hockey team — logging thousands of hours on air during his high school and college years surely helped — and the broadcasting program he started in 2002 is one of the most desirable broadcasting internships in sports.

This is exactly the kind of thing an ambitious college — or high school! — student could try. Maybe there’s a minor league baseball team near you that could use a photographer to run their Instagram, or a museum in your hometown that would love to start a podcast series. Maybe you could do something part time — just a few hours on a weekend — and combine that with a summer job to help pay the bills. Be ambitious and pitch the internship you want. You might end up building something that could be great for your future career.