So It’s Come To This: I’m Launching The Dan Oshinsky Quarterly Newsletter.

It’s a funny thing to admit, at least for a guy who’s been working in email since 2012, but: I don’t have a newsletter. I spend all day thinking about email and building email — not to mention replying to email — and for a long time, the idea of having to send one more email just seemed like too much.

But I’ve started to change my thinking on this. Thanks goes to some friends who’ve been sending occasional email updates: pals like Sean and Sapna, and industry folks I admire, like Robin Sloan.

So in 2019, I’m going to give this a try. Sign up, and every few months, you’ll get an email from me. I’ll feature some posts from this blog, recommend a thing or two, and ramble a little about “House Hunters.” (Sally and I watch a shocking amount of HGTV, and it’s time we discussed that.)

Anyway, you can sign up here:

No One Knows What Happens Next.

There’s a famous “Today” show clip, from 1994, about e-mail. You’ve probably seen it. Bryant Gumbel and Katie Couric are sitting on a couch, trying to figure out how to correctly read an email address, but get tripped up by the @ sign. (“That little mark with the ‘a’ and the ring around it” is how Gumbel describes it.) And then Gumbel adds the kicker: “What is Internet, anyway?”

That clip turns 25 this year. So does this New Yorker story — one that paints an equally fascinating picture of the internet in 1994, but from a very different perspective. The story is “E-Mail from Bill” — Bill, as in Gates — and it’s a profile of the Microsoft founder. Some of the passages in the piece are eerily prescient. For instance:

But all Gates’ influence and success are small potatoes compared with the influence he could have and with the opportunity that now lies before him. The computer, which in twenty-five years has evolved from a room-size mainframe into a laptop device, appears to be turning into a new kind of machine. The new machine will be a communications device that connects people to the information highway. It will penetrate far beyond the fifteen per cent of American households that now own a computer, and it will control, or absorb, other communications machines now in people’s homes: the phone, the fax, the television. It will sit in the living room, not in the study. The problem of getting people to feel comfortable with such a powerful machine will be partly solved by putting it inside one of the most unobtrusive objects in the house: the set-top converter, which is the featureless black box on top of a cableconnected TV set (the one the cat likes to sit on if the VCR is occupied).

Think about that: Computers did eventually come to most American homes. The computer did eventually absorb the phone, fax (!), and TV — and then kept going.  Today, even refrigerators and cars can be connected devices. In 1994, this prediction was spot on: The big opportunity ahead was figuring out how to power all of our devices.

Here’s another section:

At Microsoft’s main office, in Redmond, a suburb of Seattle, I saw a demo of an early version of the company’s operating software for the information-highway machine, in which the user points at the TV screen with a remote control, clicks onto icons, and selects from menus. I heard a lot about “intelligent agents,” which will at first be animated characters that occasionally appear in the corner of your TV screen and inform you, for example, that President Aristide is on “Meet the Press,” because they know you’re interested in Haitian politics, but will eventually be out there on the information highway, filtering the torrent of information roaring along it, picking out books or articles or movies for you, or receiving messages from individuals. As the agents become steadily more intelligent, they will begin to replace more and more of the functions of human intelligent agents: stockbrokers, postal workers, travel agents, librarians, editors, reporters.

Again: That’s basically right! It describes a web-based TV service (TiVo, Roku, Apple TV), 1.0 versions of what became digital assistants (Siri, Alexa), and the decline of several careers (travel agents, in particular).

OK, here’s another, from John Seabrook, who wrote the piece:

When I was ten, I would sit around with my friends watching it snow, and someone would say, “I wonder what the deepest snowfall ever was,” or something like that, and someone else would say, “Yeah, it would be cool to know that.” It seemed that there should be this giant, all-knowing brain, which could answer that kind of question.

We were just a few years away from putting a name to that all-knowing brain: Google.

Last one:

In twenty years what now takes a year of computing will take fifteen minutes. We have no idea what we are going to do with this power, but it will exist whether we want it to or not.

You could lift that sentence, exactly as written, and place it in a 2019 story about Elon Musk or quantum computing, and it would be just as true as it was 25 years ago.

You should read the whole piece. There are so many unusual moments that only make sense now that we know what happened next. It refers to AOL as “an information service.” It discusses an anti-trust suit that helped give Google a chance to grow — even though the web browser at the heart of the eventual decision (Internet Explorer) did not exist in 1994. It quotes a leader in the tech industry who says that an introvert like Gates “is not the kind of person you want building the social network of the future.” Even Gates himself, when asked about the legacy of leaders such as Steve Jobs, says, “I don’t think any of us will merit an entry in a history book.”

But what I find most incredible is this: it’s a 12,000-word story that does not use the word “internet” once. (The word that Gates and others use, repeatedly, is “information highway.”) It helps to be able to see around corners, to know what’s coming up ahead — Gates clearly could. But no one knew exactly what would happen next, or even what they’d call it when whatever’s next arrived. In 1994, AOL was an experiment, Google was a dream, the hosts of one of America’s most-watched TV shows had no idea what email was, and Bill Gates wasn’t calling the internet “the internet” yet. Remember that. There are times when you’ll feel like you have no idea what’s happening, or what you’re supposed to do next, but you’re not alone. No one knows — we are all just figuring this out as we go along.

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That photo of Bill Gates is by Thomas Hawk and is used here thanks to a Creative Commons license.

A Wish For The Year Ahead.

As we wrap up 2018, and look towards the new year, I wanted to say:

In 2019, I wish you good luck, and good timing. (You won’t go very far with the right idea at the wrong time.) I wish you amazing co-workers and teammates, and the resources you need to do great work.

But above all: I wish you the courage to push yourself in 2019. Test new ideas. Ask tough questions. Do things that scare you or make you uncomfortable. Let’s make 2019 a year of amazing growth.

Cheers.

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That very New Year’s-y photo is by Nora Schlesinger, on Unsplash.

Here’s a Limited-Time Opportunity, Just For Readers of the Blog.

I’m lucky to have had the opportunity to talk to some journalism classes this year. I’ll talk about my career and my experiences, and answer questions as best I can about how they can set themselves up for success after college. (Yes, you should take that extra class in creative writing or photography! No, your GPA won’t matter — at least not after you get that first job.) Lately, I’ve been trying to drive home the importance of building a great online portfolio to showcase your work, and I’ve been adding an offer: Take some time to work on your portfolio, and then send me what you have. I’ll give it a look and help you make it better.

A great website isn’t the reason you’re going to get a job. But it might make the difference between getting the initial interview, or not. I know that as a hiring manager, if I see a poor portfolio, or even a free Wix site, I might have second thoughts about a candidate for a digital job.

It’s the end of the year, and it’s the season for giving back. So between now and the end of 2018, I’m extending the offer to you, too. If you’re reading this, and you want some advice with your portfolio or your resume, send me an email. I’m happy to take 20 minutes and give you the feedback you need. I hope it helps!

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That image at top, Personal CV/Resume, by Daniela S Nassetti, is used here thanks to a Creative Commons license.

Here, Read This: My Year Of 101 Rejections.

Here’s a fantastic story from Emily Winter about a reach goal she set in 2018: To apply for more opportunities, even if it meant getting rejected 100 times. She writes:

In pursuit of 100 rejections, I put myself forward for opportunities I’d previously thought were for smarter, funnier, cooler people. And sometimes I wasn’t rejected. I wrote for new publications, got a joke-writing gig on my favorite comedian’s radio show and interviewed guests on my podcast who I’d thought wouldn’t waste their time on me. At a stand-up show this fall, a peer told me the thing every comedian wants to hear: “I see your name everywhere! You’re killing it!”

Read her entire piece here.

The Show Goes On Because It’s 11:30.

“The show doesn’t go on because it’s ready; it goes on because it’s eleven-thirty.”

That’s what Lorne Michaels, creator and producer of “Saturday Night Live,” said about “SNL.” As Tina Fey explained a few years ago:

This is something Lorne has said often about “Saturday Night Live,” but it’s a great lesson in not being too precious about your writing. You have to try your hardest to be at the top of your game and improve every joke until the last possible second, but then you have to let it go.

I remember reading those words back when “Bossypants” came out in 2011, and they stuck with me. In 2012, I decided to make a commitment to this blog, which I’d first started in 2008, but hadn’t written for regularly. I decided I wanted to write three times a week for the blog — and somehow, despite everything I was doing with Stry.us that year, I somehow stuck to it. Then I went through a lull — just a handful of posts per month. In 2015, I made myself re-commit to writing one post a week, and have stuck with that pace ever since.

I’ll admit: Many of my blog posts aren’t great. (In fact, they’re mostly bad!) But it’s something I always do. The work happens, and then I move on. Writing for this blog has taught me so much about how to do the work even when I’m in a creative rut.

Lorne and Tina are right: Don’t be too precious with your work. Your work isn’t going to be perfect. Some of it will suck. But the show goes on at 11:30 — just get it done.

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That illustration at top (of one of Dan Aykroyd’s most famous sketches), is titled ”SNL 40th Anniversary,” was created by James Gilleard, and is used here thanks to a Creative Commons license.

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.

Beware The Silver Bullet Metric.

A few years ago, I wrote about one of the best pieces of advice I got from my old boss, Dao Nguyen:

I’ve learned a lot from Dao over the years. But one sentence in there really drives home Dao’s biggest message: “Anyone who just optimizes to one metric is going to eventually have a problem.”

What we’ve learned with newsletters is that there is no “silver bullet” metric. If you try to optimize your email for open rate, you’ll try to game the system with headlines that entice subscribers to click. (Case in point: “You’re Fired.”) But if you overpromise and underdeliver, you’ll lose subscribers in the long run. If you try to optimize for clicks, you’ll use bold colors and buttons. It’ll work well at first — but readers will learn to tune them out. There are dozens of other metrics out there for email. And what Dao’s taught me is true: If you focus all of your energy on a single metric, in the long run, you’ll fail.

What I’ve recently learned is that there’s actually a law that explains exactly this! It’s called Goodhart’s Law, and it has one key rule: “When a measure becomes a target, it ceases to be a good measure.” Or as NPR’s Planet Money put it in a fantastic recent episode: “Be careful what you measure because your employees are going to make it happen.” They may break some rules to hit their assigned goal. They may actually make things worse, from a big picture perspective, to reach their target. But Goodhart’s Law suggests that if they have that silver bullet metric in mind, they will find a way to hit it.

Listen to the whole “Planet Money” episode — it’s a fantastic look into how things can go wrong at the office.

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That photo, of an old GE voltmeter, comes via Thomas Kelley and Unsplash.

I Am 31 Years Old. This Is What I Believe.

I am 31 years old, but I know I’m not too old to try something new. It was a year ago, right around Thanksgiving, when Sally made an incredibly brave choice: After nearly a decade in social work, she decided she wanted to go back to school to pursue a new career in nursing. We talked about the sacrifices she’d have to make to become a nurse, the work she’d have to put in. But we both knew: If she didn’t do this now, she might never get the chance again.

In January, Sally started taking classes at a community college in the city. It hasn’t been easy. There was a stretch those first few weeks where she’d come home every other night in tears. “Can I do this?” she’d ask me. “Should I drop this class?” But she always kept at it. I’ve watched her grow at school: making new friends, forming study groups, going to office hours and study halls, and taking notes until her hands hurt. She’s made more than 6,000 flash cards this year — I’ve got the Amazon order history to prove it. But my greatest joy has been those nights when Sally’s asked me to stay up late to stay with her to study, and I’ve asked her about something on one of those note cards, and her face lights up. “Oh my God, so this is so cool…” she’ll say, and then talk for five minutes straight about the human heart or the periodic table or a concept she learned in bio. I’ve known Sally for six years, and we’ve been married for two, but I didn’t know that the woman I married was this hard-working, this tough, this smart. I do now.

A few weeks ago, Sally got into nursing school. She starts in January. I’m so proud of her — of the work she’s put in, of the dream she’s still chasing, of this idea that with a nursing degree and a social work background, she can do even more to help her patients. I know how lucky I am to be married to someone who has the courage to do this.  She’s an absolute wonder, and she’s going to be an amazing nurse.

Over the past year, there are certain things I’ve come to believe hold true. I know that my beliefs will continue to change. I know that I will change.

But here, at 31, is what I believe:

You can learn something from everyone. You just have to ask the right questions.

There are going to be moments when you look at former classmates or colleagues and think that they’re ahead of you in their careers. Remember these words: You are not behind. There is no timeline but yours.

Your plan can be complex. But your goal should be simple.

Leadership means being willing to accept blame, even when it’s not your fault, and doling out praise to others, even when you deserve the credit.

If you’re reading, you’re learning. Read more.

New York City can be such a frustrating place to live. But once a month, it still does something that makes me go, “I can’t imagine living anywhere else.”

The staff at LaGuardia Community College deserves so much credit for Sally’s success this year. I’ve been so impressed with the resources — in particular, the study halls for several classes, and the library — that they have for their students. I’ll always be thankful for the support they gave Sally — she couldn’t have done this without them.

Wedding hashtags are out. 2019 will be the year of the shared iCloud wedding album.

It’s O.K. to believe.

Be kind. The world needs more of 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.

And one last thing: This year was incredible in so many ways. I got to launch some new products at work. I got to see some of my favorite people in the world get married. I got to drink champagne out of the Stanley Cup. I got to watch my wife take an incredible step in her career. I am so lucky, and thankful, for all of this.