Don’t Overthink It.

This morning, I had an idea for a friend, but I wasn’t sure how to tell them. I started thinking about how I’d present the idea to them. In my head, I started writing the email to them — how I’d say hi, maybe share a story or two from the weekend, then get into the idea, couch the idea with a few different caveats just in case they didn’t like it, and then close with a “lemme know!” kind of thing at the end. I spent the better part of breakfast thinking about that email, writing and rewriting it in my head.

I can overthink things sometimes, and this was one case. It was a simple idea, not all that controversial. It didn’t need a whole email. In fact, I realized, it didn’t need an email at all — a text would do the trick.

So that got me out of the rut. I picked up my phone, and fired off the text. Two sentences, and it was done. If my friend wants to follow up, they can. If they want to talk about it on the phone, they can. But I spent 20 minutes this morning overthinking an email I didn’t even send, and then 20 seconds sending a text instead. I wish I could have those other 19 minutes and 40 seconds back.

Send the email, send the text, make the decision — and move on. You’re too busy to waste time overthinking something as small as this.

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When you search “overthinkingon Unsplash, that photo by Nathan Dumlao pops up.

When Will Then Be Now?

This is the second in a semi-occasional series of Spaceballs-inspired blog posts.

Lord Dark Helmet: What the hell am I looking at? When does this happen in the movie?
Col. Sandurz: Now. You’re looking at now, sir. Everything that happens now is happening now.
Lord Dark Helmet: What happened to then?
Col. Sandurz: We passed it.
Lord Dark Helmet: When?
Col. Sandurz: Just now. We’re in now now.
Lord Dark Helmet: Go back to then!
Col. Sandurz: When?
Lord Dark Helmet: Now!
Col. Sandurz: Now?
Lord Dark Helmet: Now!
Col. Sandurz: I can’t!
Lord Dark Helmet: Why?
Col. Sandurz: We missed it!
Lord Dark Helmet: When?
Col. Sandurz: Just now!
Lord Dark Helmet: When will then be now?
Col. Sandurz: Soon.

When you’re building something new, it’s hard to be patient. You’ve got a great idea, and you’ve got some momentum, and it feels like you’ve got all the potential in the world. You want to fast forward to the ending — when the work is done, and everyone gets to see your genius idea become something real.

But when it comes to the work, there is no fast-forward button. There are no shortcuts. The work still needs to be done. Networks still need to be built. The team needs to be assembled. Hours need to be put in.

The future you want needs to be made, piece by piece, and day by day. I promise: Then will be now — and sooner then you think. But you’re in now, now. It’s time to start putting in the work.

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

The Bad Idea Notebook.

I have a lot of ideas — and most of them, frankly, are bad. But having bad ideas is OK — as long as you develop a filter to decide which ideas are worth working on, and which ideas should move to the scrapheap.

I know I’m not along in having bad ideas. I read a story recently about Dr. Seuss, and learned that he was full of bad ideas, too!

In 1939, at the age of thirty-five, Theodor Seuss Geisel was tinkering with an invention that was doomed to failure. Geisel had published a few books under the name Dr. Seuss, but he was hoping that a device he had patented, the Infantograph, would be a money-maker at the techno-utopian New York World’s Fair, which was opening that year. “If you were to marry the person you are with,” the banner that Geisel designed for his pavilion asked, “what would your children look like? Come in and have your INFANTOGRAPH taken!” In the tent, a couple would sit side by side; a double-lensed camera would blend their features together, then plop a composite mug shot atop an image of a baby’s body. “It was a wonderful idea,” Geisel insisted, but, as a feat of engineering, it was more of an evocation of outlandish, off-kilter Seussian machinery than it was a functional prototype. After much fiddling, he scrapped his plans, admitting, “All the babies tended to look like William Randolph Hearst.”

Knowing when to kill your bad ideas is crucial. I run a lot of my ideas through the Shower Test to see if they’re sticky enough. But I’ve also started doing a new thing: Writing my bad ideas down in what I’ve been calling my Bad Idea Notebook.

The Bad Idea Notebook is what it sounds like: a small notebook full of truly terrible ideas. There are ideas for products, for TV shows, and startups in there — all ideas worthy of the scrap heap. Every time I have a quarter-baked idea , it goes into the Bad Idea Notebook.

And sometimes, when I get really excited about an idea, I’ll pop open that notebook and scroll through my list of terrible ideas. It’s a reminder for me: Yes, Dan, you’re excited about this idea right now — but just remember, 70 percent of your ideas are truly terrible. Give it some time, mull over the idea a bit. Think through what it would really take — time, team, money, work — to put this idea into motion.

Often, a few minutes later, having started to think more clearly through things, I’ll realize a few flaws in the idea — and pop open my Bad Idea Notebook to add a new entry. I have lots of ideas, and lots of work already in the mix. The next idea — a better one, often — typically comes around soon enough.

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That photo comes via Unsplash and AP x 90.

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.”

Keep on Learning.

It’s been a decade since I graduated from college. I thought that when I graduated — after all those years in school — that the learning would stop there.

Turns out, that was just the start.

As you go through your career, you’re always going to be working to learn new things, and discovering new ways to learn them. You’ll find that you can:

Ask something to learn something.

Make something to learn something.

Meet someone to learn something.

Whatever you do, keep learning. There’s always going to be more to learn.

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That illustration is by Katerina Limpitsouni for unDraw.

Make Time for You.

If you’re the bride or groom at a wedding — or if you’re just the host of a big party — here’s something I’ve learned: You have to make time to eat.

Sure, you spent a lot of money on the food at your party. You did a tasting. You thought carefully about what you wanted to serve. You were really excited to actually eat that one dish on the big day!

And then the big day comes, and you don’t eat. It’s your party, which means that every guest knows you, and every guest wants to come over and chat. It doesn’t leave you much time to actually eat.

The secret is: You have to make time to eat. You need to carve out time for it, separate from the party. (On our wedding day, Sally and I took 20 minutes after our ceremony to go into a private room to eat dinner, just the two of us. It was one of the best decisions we made all weekend.)

The same thing holds true for taking a managerial role at a company. There are going to be big, ambitious projects you want to take on — that you suddenly won’t have time for. You’ll have 1-on-1s, stand-ups, big meetings, calls, etc. Your time at work becomes your team’s time. Your week will be filled with meetings, and the stuff you want to do will end up getting pushed off to another day.

The challenge is figuring out how you want to make time for yourself and for the things you care about. At Stry.us, I made the mornings my time — anything between 6 and 9 was my time to write, plan out strategy, or work out. I’ve seen co-workers carve out big chunks of their week, adding two-hour blocks on their calendar where meetings can’t be scheduled and work can get done. Or maybe you want to limit your meetings to certain days — no 1-on-1s, let’s say, on Mondays, so you can get ahead on your tasks and projects for the week ahead.

Whatever you do, just remember: You have to make time for these things. Don’t be the person who didn’t get to enjoy the ice cream sundae bar at their own wedding — and don’t be the manager who never gets to work on their favorite projects because they couldn’t find a spare moment for it.

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That illustration is by Katerina Limpitsouni for unDraw.

The Opposite of Division Isn’t Unity. It’s Collaboration.

A few months ago, Sally and I saw Dar Williams play in the city. Dar’s a wonderful musician (“One of America’s very best singer-songwriters,” The New Yorker once wrote, but what do they know?), and she’s had a fascinating career. She’s performed solo and in groups, championed environmental causes, and even wrote a book about rebuilding small towns in America.

When we saw her, she talked a little about what she learned from the book. She said, and I’m paraphrasing here: I’ve been to a lot of towns across this country. I know our country is divided. But the opposite of division isn’t unity — it’s collaboration.

Dar was talking about political division in this country, but I’ve been thinking a lot about that quote in the context of the modern workplace. So many offices seek to present a united front — a “we’re all on the same page” mentality. But it’s not enough to know what else other teams are working on. The best work comes from getting incredibly smart people in the same room, asking great questions, and looking to discover new things from one another. Or, as Dar once put it: “Where does magic come from? / I think magic’s in the learning.”

That’s where the best stuff happens: When teams aren’t just working in parallel, but start working together. That’s where you go beyond being aligned on goals, and start building something truly special.

The Plan Can Be Complicated. The Metrics Can Be Complex. The Goals Can Be Ambitious. The Mission Should Be Simple.

Go ahead and write that memo. Make that deck. Put together an ambitious plan, with lots of specific goals, and multiple ways to measure success.

But don’t lose sight of the ultimate mission. So many big plans get derailed because teams don’t know what they’re actually trying to achieve. Your organization may exist to inform or serve your community, or to better connect groups of people, or to make life simpler for your users. Think about your office for a moment: What’s your larger purpose? It sounds cheesy, but every organization should have a mission statement, and everything you do should be in service of that mission.

Now, individual teams are going to to have their own objectives, and will be using several different metrics to measure up against those goals. (At a news organization, like where I work, the editorial, sales, and HR teams all have very different goals, and we’re setting new goals a few times per year.) But where organizations get in trouble is when their teams lose sight of that overarching mission. Teams often make decisions — taking on a new opportunity to make a bit more money, or to add a few more users, or to partner with a third party — that ultimately compromises their ability to serve that larger mission.

Just remember: The plan can be complicated, the way you measure it may complex, and the goals of individual teams may be ambitious. But everything you do needs to be service of that ultimate mission.

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That photo comes via Stephen Dawson for Unsplash.

Do More of What You Do Uniquely Well.

What are you good at? Think about it for a moment. What skills do you bring to the table? What are your best qualities or habits?

Then think about your team at work. What is your team best at? What are your collective strengths?

Lastly, think about your entire workplace. What is your organization great at? What do you do well?

Give yourself a second, and really think about your strengths.

Now think about your weaknesses. Think about yourself, your team, and your organization. What do you do poorly? What do you need to improve on?

Now let’s consider one more thing: If you had an opportunity to improve one of these things — to double down on your strengths, or to better your weaknesses — which would you choose?

Many would choose to improve their weaknesses. That’s natural. People tend to focus on their own faults — I’m not good enough, I’m not smart enough, I’m not talented enough — and would love to have the chance to improve.

But my advice would be to do just the opposite: Do more of the things you already do uniquely well. Take the things you’re good at and truly master them.

Imagine for a second that you’re a Major League Baseball pitcher, pitching for a National League team. In the NL, pitchers have to hit, too, and even the best-hitting pitchers are, by any other standard, bad hitters. (Madison Bumgartner, one of the best-hitting pitchers ever, has a career .183 batting average.) Let’s say it’s the start of the offseason. You’ve got a few months to improve as a baseball player before the new season rolls around. So what would you do: Work on your hitting, and try to become a passable (but still poor) hitter? Or would you work on adding new pitches and becoming a dominant pitcher? The answer is easy: You’d work on your pitching. Baseball teams don’t need good-hitting pitchers — they need great-pitching pitchers.

It’s rare to find a true jack-of-all-trades. Most people specialize in just a few things — and that’s OK!

I started thinking about all of this a few weeks ago, when I was talking with a group of news organizations. Many of them were thinking about launching new newsletters, and trying to decide what to focus on. So I asked: What do you do uniquely well? What’s something you do that your fans fans already love? Many of them talked about their coverage of local news or sports or culture — the areas of expertise that their readers, listeners, and viewers rely on them for. That’s where to focus your attention, I told them. Invest in products to serve those audiences, and give them more of the things they already depend on you for.

There’s a great Steve Martin quote: “Be so good they can’t ignore you.” He’s right. Be so good they have to hire you. Be so good that your fans have to pay to get more of what you do. Identify your strengths — and work hard to get even better at the things you do well.

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I took that photo of San Antonio Missions pitcher Simón Castro — who later went on to pitch for the White Sox, Rockies, and As — back in 2010.

How I Set a Simple Goal for 2019.

That's a perfect push-up

At the end of last year, I wrote about three types of goals to set in the new year: Learning goals, personal goals, and fitness goals. I wrote:

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.

I’ve tried to put that idea into practice in 2019, starting with a simple fitness goal: Doing 10 push-ups, every day.

I don’t like doing push-ups. At the gym, I always felt self-conscious when I got down to do a push-up. I felt like the people around me would judge: Did he just get tired from a few push-ups? Is that all he can do?

So I set a truly simple goal: 10 push-ups, every day. It doesn’t seem like a lot, but it adds up. If I stick to this goal, I’ll do over 3,500 push-ups in 2019. I’d bet that’s more push-ups than I’ve done in the rest of my life — combined!

And I’ve discovered: I actually don’t mind doing push-ups! After a few weeks of my daily push-up routine, I feel more confident when I do them at the gym. In the morning, if I need a jolt of energy before I leave for work, I might drop and do 10. Often, I’ll add an extra set, since 10 push-ups isn’t that hard anymore.

It’s a simple goal, and a small goal. But by committing to the task every single day, it’s going to build to something that, by year’s end, I can be proud of.

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That photo of a perfect push-up, by Sgt. Justin A. Moeller of the U.S. Army, is re-used here thanks to a Creative Commons license.