Dan Oshinsky | danoshinsky.com

12/30/201512/07/2019

Opportunities vs. Possibilities.

These are two words that people often use interchangeably:

One is “opportunities.”

One is “possibilities.”

As you get older, you learn that there’s a big difference between the two.

Opportunities are the concrete choices you have to make. They come in the form of job offers or acceptance letters from a school. There’s nothing theoretical about them. When you’re presented with an opportunity, you have to make a choice.

Possibilities, on the other hand, are just dreams. Could I move to Bolivia one day and become a goat farmer? Could I quit my job, move to Thailand, and teach ex-pats how to surf? Could I become president of a big company? Sure, anything is possible!

To put it another way: Opportunities are the things that can happen, and possibilities are the things that could happen.

But here’s where it gets important: When you’re young, it’s all possibility. You’ve got dreams and ambition, but not a lot of hard choices that need to be made. As you get older, the scale starts to shift. You’re no longer thinking about what could happen because you have choices that you actually have to make. You’re setting down, you’re starting a family, and you’re thinking about the opportunities that actually exist for you at this moment.

If you’re lucky, when you’re young, you can turn a dream into real work. You’re not tied down by anything — a job, a significant other, a family, a mortgage. That freedom gives you the ability to try something crazy. That’s what Stry.us was for me — a crazy dream that I actually made happen. But as you get older, the windows of possibility start to close. You still try to stay ambitious and idealistic, but you also start to become more practical. You start to make hard choices because you have to, not because you want to.

There’s a difference between “What will you do?” and “What can you do?” So when you’re young, and everything’s still on the table, take advantage of it. Those doors might not stay open for long.

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That photo of the open road was taken by Jon Ottosson, and published on Unsplash.

12/21/201504/11/2016

Encouragers Make The Best Bosses.

I just finished Jason Gay’s excellent book of advice, “Little Victories”, and in the chapter about work, he touches on something I’ve been thinking about a lot:

“The best bosses share a common characteristic: they are encouragers. It’s easy to be an ass-kicker, to find holes in someone’s professional ability, but good bosses see a flicker of something and just let it barge out the front door.”

Two parts of that quote really spoke to me. The first was the “flicker of something.” In my career, I’ve had a few dozen of those ideas. I’ve had some big, crazy ideas, and I’ve written my fair share of memos trying to prove that my ideas could become a piece of great work. Many of my ideas were outlandish and were justifiably ignored. A handful were too good to ignore. But then there’s this strange middle ground of ideas: ideas that with the right team and a bit of work could become something great, but that could also be dismissed outright.

Which is where the type of boss comes in — because they’ll be the ones that decide which types of work get done. Like Gay wrote, some bosses are “encouragers.” To that, I’ll add the (obvious) second category: “discouragers.”

Encouragers tend to react with support to your ideas. When you’ve got a great idea, they’ll get the resources, talent, and money to make those ideas into great work. But when they hear a half-baked idea, they’ll give you the space and time to turn it into a really good idea. They’ll ask questions to try to draw out the idea. They’ll suggest that you talk with co-workers who might be able to help the idea along, or they’ll pass along a good article or book that might get the idea moving. They’ll give you the benefit of the doubt. Encouragers try to turn a decent idea into a great idea, and a great idea into great work. When you try something and fail, encouragers back you up, share the blame, and don’t let it affect future work.

Discouragers tend to react with skepticism to your ideas. They’ll generally get behind your great ideas, but when it comes to anything less, they’ll try to pick holes in your idea. They’re critics. They’ll ask questions that are intended to find the faults in your pitch. Whatever your idea, you’ll have to prove it and maybe even debate it. You will not get the benefit of the doubt. Every idea has to stand on its own. Discouragers hear a half-baked idea and work to keep it from becoming a fully-baked flop. When you try something and fail, you will take the blame.

I think every boss needs be a bit of an encourager and a discourager — the perfect mix is probably 80/20, with a heavy lean towards encouragement. There certainly are times when it’s important to set boundaries and to say “no.” And when an encourager says “no,” that comes with some credibility, because “no” isn’t their default setting.

In general, I prefer to work with encouragers. When you’ve got a “C+” idea, it’s nice to know that you have a boss and a team that’ll work to turn it into an “A” idea. Working with a discourager is harder. It can feel like you have to reestablish trust with your boss every single day. Sometimes, you shy away pitching anything but your absolute best because you’re afraid of the debate that might come.

With encouragers vs. discouragers, it’s not just about positivity vs. negativity. It’s about support vs. discouragement. It’s about knowing that you have a team behind you, and that you don’t need to prove and reprove yourself.

Jason Gay’s not wrong: The best bosses are encouragers.

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That photo of horses traveling together comes via Unsplash and photographer Susan Yin. There’s a metaphor there somewhere about teams traveling together, maybe? (OK, that’s a stretch. But you get the idea.)

12/17/201502/14/2019

I Started At BuzzFeed Three Years Ago Today, And This Is What Happened.

Today is my three-year anniversary at BuzzFeed. I remember my first day vividly. My then-boss, Dao Nguyen, was out sick. So Chris Johanesen, our head of product, welcomed me and showed me to my desk. “You know what you’re supposed to do, right?” he asked.

I most certainly did not.

I had built out Stry.us and launched Tools For Reporters. I had launched newsletters with both of those projects, and I had enough experience to know that newsletters could work at scale. But I didn’t know how to launch a project at this level. I didn’t know how to grow it, or even what I was looking for in a team. I wasn’t even sure if I would last long enough at BuzzFeed to hire a team!

And now on my three-year anniversary, I’m looking back with amazement at a few incredible facts:

-On Sunday, BuzzFeed newsletters drove its 100 millionth click to BuzzFeed.com. ONE HUNDRED MILLION CLICKS.

-In the chart at the top of this post, the giant blue hockey stick of a line is traffic to the site on a month-by-month basis. How did we even do that?

-To put everything in perspective: The week I started, our five automated newsletters were driving 14,000 clicks a week. We’ve grown from those five newsletters to a dozen core newsletters, plus another 10 automated newsletters (like this) and original newsletters in four other countries on four different continents. Pretty good!

-When I started, we had fewer than 20,000 subscriptions across our newsletters. Now, we’ve got more than 2 million subscriptions across our lists. (And we’ve got plenty of room to grow!)

-The team’s grown from me to a team of four in New York, plus another half dozen BuzzFeeders around the world who pitch in to write newsletters in three different languages every week.

-Our newsletters used to be automated, and almost unreadable on your phone. Now every newsletter is written by a human, and they’re all responsively designed.

How’d we achieve all this? By testing out lots of weird ideas (This Week In Cats, anyone?) and spending a lot of time looking at the data and trying to figure out where it was pointing us. By being super clear in our mission: to send newsletters that were always useful and delightful. And by seeking out great people who could bring the ideas, energy, and work to take newsletters to amazing places.

Thanks to everyone who’s been a part of growing newsletters into such an tremendous program at BuzzFeed. Here’s to what we’ve accomplished — and to everything we’ll learn between now and our billionth click. (Hey, we’re 10% of the way there already!)

12/11/2015

Thanks, Ken.

Fantastic tribute to a pioneer… https://t.co/K9ECOzZFVc pic.twitter.com/XjQkr6FX0b

— Dave Preston (@davpresto) December 7, 2015

Everything I learned about listening, I learned from Ken Beatrice.

I know that name probably doesn’t ring a bell for you. I grew up in the D.C. suburbs, and in my house, we didn’t listen to rock or pop or any kind of music on the radio — just sports talk. And that meant that I listened to a LOT of Ken Beatrice, a local sports talk legend, almost every night as I was finishing up my homework. He had this huge Boston accent, and before bringing on a caller, he’d always say, “You’re next!” In that accent of his, it came out more like “YAW NEXT!”

Beatrice died this week — he was 72 — and I’ve read some wonderful stories about him from colleagues and listeners. Many are about that distinctive voice, or his showmanship on the air. Those stories got me thinking about why I loved his show so much in the first place.

What I remember most — besides the accent, of course — was the way he carried himself on air. Things are different now on talk radio: There’s a lot of yelling, and a lot of big opinions. It wasn’t like that on Beatrice’s show. He did something different.

He actually listened.

Right after the YAW NEXT!, he’d tee up the next caller, and…. let the caller talk! If you had a big rant about the Redskins, he’d give you airtime to vent. If you had a few questions, he’d let you ask them. And if you were really crossing a line, he’d tell you — and sometimes talk over you — but rarely cut you off entirely. It was unlike anything I’d ever heard on the radio. Callers knew Beatrice would be (mostly) patient with them, and fair in his responses. I remember calls that made me uncomfortable — and I’m sure Beatrice felt the same way, sometimes — but as a listener, I knew he’d treat every caller with a certain respect. (FWIW, most of those uncomfortable calls came from Dallas Cowboys fans.) I think back now and remember his show as a space where you could hear opinions that wouldn’t get the time of day on any other show.

A few years ago, he did an interview about his old show, and here I’ll cite a transcription from Dan Steinberg at the Washington Post:

“You know, what gets me is, some shows are based on being nasty to callers,” he said a few moments later. “That’s like if I invite you to my house for dinner. You show up with a bottle of wine under your arm, and I slam the door in your face. Next time I invite you to dinner, are you going to come? You’re certainly not going to bring any wine. And that’s all. Everybody deserves dignity and respect.”

Dignity, respect, and a few minutes to give people a chance to share their voices. I’m glad I got the chance to listen in.

11/30/201507/04/2020

Another Word About Failure.

Three years ago, I wrote a thing about failure. Much to my surprise, it still holds up pretty well! I wrote:

There is a phrase I use a lot. I overuse it. A lot of my friends do, too.

The word is “fail.” ….

But sometimes, when we just wrap all that in into that one word — fail — we lose a sense of what we’re really trying to say. …

So if I’ve told you, “It’s okay to fail” or “Go fail fast,” I’m sorry. I can say it better.

This year, be willing to do difficult things. Be willing to go on adventures where you don’t know the outcome. Be willing to persevere.

Most of all: Be willing to do great work.

The idea of “failing fast and failing often” has spread even further since I wrote about it back in 2012. And looking back on that first post, I realized: I never got around to defining what failure is!

Here’s the thing: Anyone who tells you they like to “fail fast and fail often” has probably not truly failed in their life. Maybe they’ve goofed up on a project. Maybe they fucked up an assignment.

That isn’t failure.

When you take on work that really matters to you, and you truly fail, you feel like absolute shit. Failure gnaws at you. It keeps you up at night. It makes you question every decision you’ve made along the way.

When you fail while doing something meaningful, it sucks the life out of you. And that kind of failure takes weeks or months — or even years! — out of you.

The people who advocate “failing fast and failing often” are people who really mean to say: It’s OK to screw up! It’s OK to suck at your work! And they’re not wrong — it is OK to make little mistakes along the way.

But that’s not failure. Failure is the roadblock that keeps you from going one step further with your work. Failure sends you onto a detour from which you don’t completely return. And in the long run, that’s also OK — failure is something that can shift you onto a completely different track, and maybe that’s a path where you can do great work and succeed.

Anyone can screw up. But to fail, deal with that failure, and somehow pick yourself back up and start again? That’s a different thing altogether.

———

That photo at top comes via Flickr user Sister72.

11/25/201511/23/2019

I Am 28 Years Old. This Is What I Believe.

the entire family

I am 28 years old, and everything is about to change — again. That’s what happens when things start to seem settled in your life. You meet a girl, and she’s amazing. You move in together. You’re in a job you like, and you’ve been doing it well for a long time. (Well, “long” as far as internet standards go.) Things are good!

And then you look at the calendar year ahead and realize: You have 11 weddings to go to next year. Eleven! And one of them is yours! Your friends are having kids and buying homes. You drive through the suburbs and think, Having more space might not be so bad!

It hasn’t all happened yet. But it’s happening. By the time I write the 2016 version of this post, things could be very, very different.

For now, though, there’s 28, and it’s been an incredible year. 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 28, is what I believe:

The hardest part of the work isn’t getting it going — it’s keeping it going, week after week, year after year.

End results matter, but the routines and processes you use to get there are so much more important. Master those, and the results you want will come more often than not.

When you stop feeling like a little like an impostor at work, that means it’s probably time to take on a brand new challenge. You should always have something to prove.

There are so many big, weird ideas I want to try. I’m just waiting for the right teams and the right time to try them with.

Inbox Zero is too hard. Shoot for, like, Inbox Twelve. It’s more do-able.

The no. 1 secret to wedding-related sanity: Stay the hell off Pinterest.

Travel reveals who you really are when things get stressful. So if you’re dating someone, and you’re thinking about popping the question, and you haven’t taken a big trip, well: Maybe it’s time to see how much a round trip for two to Thailand costs.

I don’t know what happens at my alma mater next, but I do know this: We stood up for Michael Sam. We stood up for Jonathan Butler. We can stand up for a whole lot more, Mizzou.

Once a week, reach out to a friend you haven’t talked to in a while. Write an email. Send a text. Or (and this sounds crazy): Make an actual phone call! The 15 minutes you spend laughing and catching up might be the best 15 minutes of your week.

I still think this is the year my Washington Capitals are going to win it all.

Screw “Fake it ‘till you make it.” Don’t pretend to be someone you aren’t. Recognize your weaknesses. Be willing to say: “I don’t know — but I can find out.” There’s power in that.

I used to say, “Define your greatness, and go out and do it.” Now I see it a little differently. First, you’ve got to define what success means. Because if you don’t know how to define it, how will you know when you’ve achieved it?

Friday is my 10-year high school reunion. On the day I graduated, I had never held a smartphone before. Never even owned an iPod. Never blogged. Never tweeted. Never posted a photo or a video online. Never downloaded an app. Never started a video chat. I don’t know what the next 10 years will bring, but I know it’s going to be amazing.

And most of all: I know change is scary for some. But when I think about Sally and the things we want to do together, I’m not scared at all. I’m excited.

Bring it on.

———

In that photo at top, from left to right: Sam, Mom, Dad, Sally, and El. Love you, guys.

11/18/201504/11/2016

Why Didn’t Anyone Show Up To My Presentation?

Here’s something that happens at every office: You work hard on a big presentation. It’s got everything a great presentation needs: Actionable advice, clear takeaways, and data to back up your big points. You send out the calendar invite to a large group of co-workers — maybe an office listserv full of people who could use your advice.

Then when presentation time comes, only a fraction of the invited employees show up.

Why? What went wrong?

I’ve been thinking a lot about this problem lately. It’s something we struggle with at BuzzFeed, and something I hear echoed in conversations with friends who work in fields from media to medicine. Why aren’t people showing up for valuable presentations?

Three things are usually at play:

1) No one is holding them accountable — This is the big one. If you’re inviting people on a more personal basis — emailing 2-3 people at a time, or reaching out to folks on a 1-to-1 basis — they know that you personally want them there, and that you expect them to be there. When you reach out to a big team/group/listserv, it’s more impersonal, and people often feel like their attendance isn’t necessary. They also know that if they don’t show up, there won’t be any pushback — you won’t follow up to ask why they didn’t make time for your presentation.

2) They don’t know what’s in it for them — WIIFM isn’t just a silly acronym — it’s also an important part of any good presentation! Every time someone gets an invite to a presentation or a training, they should have an expectation for what they’ll be getting out it. If there’s nothing in it for them, why would they show up in the first place?

3) They don’t believe presentations are valuable — If you’ve been to a handful of sub-par presentations at your office, you’re less likely to think of them as valuable — and much more likely to think of them as a waste of time. And that’s a shame! A great presentation can change the way you work and give you the skills to produce amazing things. In a perfect world, people would LOVE going to presentations — they’re opportunities to make you better at the things you do every day!

So what can you do to improve your presentations? I’d start here: When you send out the calendar invite, let everyone know what they’re going to get out of your talk and why it’s so important. Follow up with people in person to make sure they understand why they should come — and create the expectation that their attendance is important. And lastly: Knock your presentation out of the park, and give them great advice that they can use!

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That photo of a presentation comes via the University of the Fraser Valley’s Flickr.

11/09/201504/11/2016

One Thing You Should Know Before You Send In Your Résumé.

Over the past three years, I’ve been lucky enough to hire a handful of really talented candidates to join my teams, first at Stry.us, and now at BuzzFeed. In the process, I’ve looked at a lot of résumés.

And here’s what I can tell you: Everyone — and I mean, EVERYONE, from entry-level candidates to experienced hires — struggles to write a good résumé. It’s understandable! This is something they don’t teach you in school. It’s tough to figure out what you should be doing with your résumé.

So here’s a way to think about it:

A résumé isn’t a listing of everything you’ve ever done. It’s not a complete catalog of all your work.

A great résumé is more like the book on your career — and as the hiring manager, I’ve picked up the story on page 60, and I’m quickly glancing through the previous pages to find out if I should keep reading or not. A great résumé shows me your career path, and makes it clear to me why the job you’re applying for is the next step along that path. Every job listing, college degree, side project, and skill listed should serve as a milestone along that path.

If I was a hiring manager at a law firm, and I was hiring a new lawyer for my team, I’d expect to see certain milestones on your résumé: A law degree, internships or jobs in the field, and maybe even a side project or a background in relevant clubs at your school (the debate club, Model UN, etc).

You don’t need a background that’s quite as specific to work at BuzzFeed, but there are milestones that should stand out. I’m looking for a relevant degree (creative writing, journalism, communications, and English lit are popular ones), and job experience that involves a combination of writing and content production. And I want to know that you’ve worked on long-term projects that require collaboration and organization. (If you’ve been a part of launching a big project, that’s a huge bonus!)

Let me put it another way: Within 60 seconds of reading your résumé, it should be glaringly, ridiculously obvious that this is the job you’ve been working towards all along.

Before you write a résumé, ask yourself this: What do you envision yourself doing in the next decade? What do you want to accomplish in that time period? And how does this next job keep on you the path towards completing all of those goals?

With those answers in mind, you can tailor your résumé around your intended path.

If you’re applying slightly different types of jobs — maybe you’re applying to work on my email team at BuzzFeed, but also applying for a writing job over at Refinery 29 — that’s OK! But your résumé shouldn’t be one-size-fits-all. Your résumé should be tailored to each specific job. It should be clear why your skill set has brought you to my door.

Because if you don’t, you may be out of luck — there’s a good chance I’ll be onto the next candidate after only 60 seconds.

———

That photo of a desk comes via Unsplash and photographer Dustin Lee.

11/04/201511/04/2015

It’s OK To Break Your Routine.

A photo posted by Dan Oshinsky (@danoshinsky) on Mar 5, 2015 at 5:27pm PST

I’ve written lovingly about routines before, and how building good habits can help you do amazing things. A good routine can keep you focused and productive. But I’ve also learned that sometimes, routines can make work feel monotonous.

So what can you do? Here’s an idea: Break your routine just a little bit.

It can be a small thing. Like last night: The work’s been good for a few straight weeks, but I was still feeling a little bit sluggish at the end of the day. Maybe it’s the changeover from daylight savings times, or may it’s just the weather. Whatever it was, I had a good day at work, but I needed a little pick-me-up.

My change? It was as simple as taking a different way home. I got off at a different subway stop, and walked past Radio City and 30 Rock. And just that little act — just a slightly different route home — was enough to throw a jolt into my day. I started thinking about how I’m coming up on three years in New York City. In fact, it was three years ago to the week that I interviewed with BuzzFeed. I remember sitting around waiting for a job offer I wasn’t even sure would come. And walking through Midtown, I had to remind myself: I made it here! I’ve built out a pretty awesome team, and some amazing products, too. I’ve been a part of building a remarkable media organization.

Just a small tweak was enough to help me snap out of it. But your little tweak could be easy, too: Grabbing coffee at a different time during the day to break your routine; grabbing a new co-worker every day for a quick walk around the block; eating lunch with different people at your office. Sometimes, even a small change is enough.

10/31/201504/11/2016

We Should All Stop Eating Those Sad Desk Lunches.

BuzzFeed’s grown a ton since I started in December 2012 — not just in prestige or influence or monthly UVs, but also in raw size. We had about 175 staffers in New York when I started. Now, we’re so big that we take up two different offices — one across the street from the other.

And we’ve seen a few unexpected side effects of that growth. Here’s one: We don’t have nearly as much space in our canteen to eat lunch in anymore.

When I started, I regularly ate lunch with co-workers from across the company. We talked about what we were working on, and interesting ideas and projects often sprung from those lunches. But as we grew, and as space became as issue, I started eating more and more lunches at my desk. Eventually, it became my daily routine.

And because I started doing the Sad Desk Lunch, everyone on my team started doing it, too.

But a few weeks ago, I noticed one team at BuzzFeed that was still actively eating together — our team focused on content distribution. They’re run by Summer, who happens to be one of our best (and friendliest) managers. I noticed them eating lunch, enjoying conversation with one another, and I realized: My team needed to follow suit.

So on the newsletter team, we’ve made a new rule: On Mondays and Wednesdays, we grab lunch, head to the canteen, and eat together for 20 minutes. It’s a time to bond as a team, and it’s an opportunity to talk about work in an informal setting. Sometimes, you need to get buy-in from team members through a formal meeting or an emailed request. But other times, over a sandwich, you can talk about an idea and actually set some work in motion, and that’s also great! Some of our best ideas — our Dude A Day newsletter, for instance — have come out of those informal lunches.

Collaboration, communication, and a sense of camaraderie. They’re all wonderful things that have come out of a simple act: Eating lunch together.

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That photo at top comes via Flickr’s Link Humans.