Dan Oshinsky | danoshinsky.com

07/20/201504/11/2016

Let’s Make Yesterday Count.

When I first started working, there were really only two types of days: good days, and bad days.

But over time, those two categories spawned a whole new set of days. There were good days that were slow, and good days that were fast; good days where a dozen great things all seemed to happen at once; good days where it felt like months of work paid off on the same day.

But there were plenty more good days where nothing obviously good happened — where no big work seemed to get done, but that still definitely qualified as a good day.

Those are actually some of my favorite days, but they’re hard to recognize in the moment. They’re the days where you’re doing lots of work to set up another day. For me, that might mean working with someone on my team to brainstorm a big new idea, or building out the tech back-end for a project. It could even be a day where I’m working on spreadsheets or other monotonous work that just has to get done.

It’s that kind of work that frees you up to do the exciting stuff another day, like launching a project or hiring a new member of the team. Those are the days when you lay out the framework. The next day, or the day after that, you’ll start building something big on top of it.

So when I get to those exciting days down the road, I try to remind myself to make those yesterdays count. I’ll tell myself: You’ve already put in the hard work. Now make something awesome with all of it.

Great work is built on a whole lot of yesterdays. When a big work day arrives, take a moment to appreciate how many good days you’ve already put in to get to a day like this. And then go out and do the work to make those yesterdays count.

———

There’s probably a symbolic meaning to that photo, but I mostly picked it for this post because it looks cool. (Hey, not everything has to have a deeper meaning!) It’s by Thomas Brault for Unsplash.

07/06/201507/05/2015

What Does The Modern News Media And Whaling Have To Do With One Another?

I’m taking the week off, and spending it up in Nantucket. I love it up here: the days are simple, and there isn’t internet or TV at the house. (I’m making a quick exception to log online for this post.)

The island is an interesting case in reinvention. A few hundred years ago, this was the whaling capital of the world. Today, the big industry is tourism. Aside from the Whaling Museum downtown, and a few extra copies of “Moby Dick” at local bookstores, you wouldn’t have any idea that life on Nantucket was so radically different in the 1700s and 1800s.

But something caught my eye this week in the local paper, the Inky Mirror. (Back in the day, I used to write for the Inky’s rival, the Indy. They like their newspaper abbreviations up here.) Every week, they publish an excerpt from the paper back in the day. The full excerpt is at the top of this post, but I wanted to highlight a snippet. It’s from the Inky 150 years ago, and it depicts an island on the verge of a huge transition:

“But the whale fishery is gone; gone beyond hope of revival. And if we truly love our island home, and would retain its already reduced population, we must introduce new branches of industry.”

The general theme of it seems familiar to me: Good news to report on the new industry in town, followed by a warning that said industry might not actually work, followed by a reminder that the old industry is long gone, and total reinvention could be necessary.

Why so familiar? Because… that’s the formula for nearly every report on the state of the news industry over the past 10 years! There’s always the good news (“We’re making more money via digital advertising than last year”), following by the big warning (“But this pales in comparison to ad revenues from 20 years ago”), followed by the requisite announcement (“We still need to make much more money to be sustainable in the long run.”).

I know how things turned out on Nantucket, even though I’m not sure islanders would’ve believed it 150 years ago. (“You’re telling me that this postage-sized stamp of scrub brush 30 miles off Cape Cod is going to be a tourist destination? And everyone’s going to wear cranberry-red pants? Really???”) How things turn out for the news industry, I’m not sure. But it’s not hard to alter that Inky warning for the news media of 2015:

“But print advertising is gone; gone beyond hope of revival. And if we truly love journalism, and would retain its already reduced influence, we must introduce new branches of revenue and distribution.”

Anyway, check back to this blog in 2165, and I’ll probably have an update then on how things turn out. (Hopefully sooner.)

06/26/201504/10/2022

There’s One Little Problem With That Famous Wayne Gretzky Quote About Pucks.

There’s a Wayne Gretzky quote that’s been repeated in a thousand PowerPoint presentations, and I’ll repeat it here: “Skate to where the puck is going, not where it has been.” It’s a wonderful thought: Instead of chasing what’s already happened, try to get a step ahead! And hey: Wayne Gretzky once scored 92 goals in an 80-game season, so he must know something about success.

But there’s a flip side to Gretzky’s mantra, and I think it’s just as interesting: Everyone’s trying to skate to where the puck is going, and when they make their move, they usually move in packs.

If you’ve ever seen “Trading Places,” you know what I’m talking about. There’s the famous scene at the end where the Dukes try to corner the market, and everyone else starts following their lead. The other brokers don’t know why the Dukes are doing what they’re doing — they’re just chasing them blindly in hopes that there’s money to be made.

I haven’t been around for very long, but I’ve seen enough to know this: That kind of scene happens all the time. When one big player in an industry makes a move, a bunch of smaller ones often go chasing after them — even if they don’t quite understand why. Most aren’t trying to find the puck; they’re just watching bigger players for clues, and hoping they can beat the giants to the right spot.

And when you have this sort of movement in packs, with everyone trying to be first to the next big thing, it’s incredibly hard to stand out. There are too many competitors.

I’ve always taken a different approach: Watch where everyone’s moving, and then go where they aren’t. Some of the best stuff I’ve worked on (longform journalism, email marketing, responsive design) were spaces that didn’t have any buzz when I got into them. In time, they were all tapped as “the next big thing.”

Not everything I’ve done has turned out quite that well. (I started Stry.us as a replacement to the Associated Press. That, uh, didn’t quite work out.) But it’s been a pretty good policy: When you’re a little fish, don’t go swimming into big ponds. Ignore the hottest trends. Ignore what the experts are saying.

To bring it back to Gretzky: Find pockets of space where you can work, and if you do things right, the puck might even come your way.

———

That hockey photo comes via Flickr’s Nicole Yeary.

06/19/201507/13/2020

The Window Is Open.

When I was about 3 years old, I used to walk around my house pretending to play guitar on this red plastic pan. By middle school, I’d walk around school breaking into the occasional air guitar. By high school, family friends would grab my mom and ask, “Why doesn’t Dan actually take guitar lessons?” And she never had a good answer for them.

When I got to college, though, I had this realization: If there was ever a time to learn to play guitar, it was right then. My freshman year, I made friends with a guy on my floor who played. He needed roommates for the next semester. I agreed to move into his place under one condition: He teach me how to play.

College happened to be an amazing time to learn a new skill. I had a LOT of free time, and I spent much of it the next 3 years learning how to play. It was just a matter of recognizing that the moment was right to learn a brand new skill — and then putting in a ton of work to learn that skill.

The same thing happened when I realized that I was ready to start Stry.us. The same thing happened when I realized that I was ready to move to New York. I recognized that the window of opportunity was opening, and I had to have the guts to go ahead and take my chance before the window closed.

There are ways to know when the window is opening for you. Sometimes it’ll be obvious: a friend will extend an invitation to do something, and you’ll recognize that you’ve got a chance to do something special right now. Sometimes, it opens when you’re frustrated with what you’re working on, or when an idea nags at you for weeks. Sometimes, there’s no sign — you just know.

But if the window opens, take your shot. It doesn’t always stay open very long.

———

That photo has nothing to do with the window of opportunity — I just like it :-) It comes from Mikael Kristenson on Unsplash.

06/08/201506/07/2015

A Note To My High School Self, 10 Years Later.

me at 18

10 years ago this month, I graduated from high school. (It’s only been 10? It feels like more.) But as I look back on 2005 — an age of flip phones, buddy lists, printing out Google Maps before road trips, limited text messaging plans, no Facebook, and a whole host of stuff that had absolutely nothing to do with the internet — I’m thinking about what it would be like to be 18 all over again. If I could go back, I’d have a few words of advice for myself, among them:

-Learn how to work hard and how to build good habits. It’ll make all the difference.

-You’re going to mess up a lot. That’s OK! You’re young! One screw-up doesn’t define you. You’ll have lots of chances to do something great. Don’t let one mistake stop you.

-You have some pretty exceptional friends. Stay in touch — they’re going to do some amazing stuff, and you’re going to want to be a part of it.

-And keep in touch with your classmates, too. They’ll be the ones running cool businesses and projects in the future. (They might even be able to get you a job.)

-It’s OK to ask for the stuff you want. If you don’t ask, you’ll never know.

–Don’t fake it ’till you make it. Just be confident in who you are and what you want, and keep working to become the person you want to be.

-Take advantage of your windows of opportunity. Once you get a real job, there are no more summer vacations. You’re never going to get a month or two off again. Enjoy it.

-You could always spend more time reading.

-You could always travel more, too.

-Surround yourself with great people. You’ll never regret making time for people you love.

-Don’t waste too much time wondering, “What should I do with my life?” You might never know, and that’s OK.

-Don’t overthink things. Just try to be happy. Life doesn’t need to be much more complicated than that.

And don’t try to skip ahead. Enjoy the moment, 18-year-old Dan. You’ve got some great stuff ahead of you.

06/01/201504/11/2016

So What Do You Want To Ask?

I’ve been lucky to meet some exceptional people in my life, and there’s something interesting that I’ve noticed about almost all of them. They have a lot of the common traits you’d expect — they work hard; they surround themselves with good people; they’re highly skilled; you get the idea. But there’s something else:

Almost every one I’ve met has asked excellent questions.

I think anyone can come up with an answer to life’s weirdest questions. But it takes a different kind of person to ask a good question. To ask a good question, you have to be curious, and you have to be genuinely invested in asking that question. (Anyone can tell when they’re being asked a question by someone who doesn’t really care about the answer.) I find that people who ask good questions tend to be detail-oriented.

To put it simply: A person who asks great questions is someone who actually wants to understand how and why the world works, instead of just taking it all at face value.

And I don’t just see it in the journalism world! Open up a biography about Warren Buffett or Sam Walton and you’ll find countless stories of men who were constantly asking questions, always probing beyond the surface for answers. (Walton’s biography, in particular, is full of stories about him going to Wal-Marts with his tape recorder in hand, spending hours asking his employees questions about the way they really worked.) Doctors, artists, bankers, coaches — I’ve met all sorts who know how to dig for answers.

I think it’s everyone could get better at — myself included! I think we’d find that there’s a lot more to learn about the people in our lives, if only we’d learn to ask.

Want to get better at asking questions? I’d recommend this quick guide to asking questions by a former investigative reporter.

———

That photo of someone searching for something — higher meaning, or probably just a bird in the woods — comes via Unsplash and photographer Caleb George.

05/27/201504/11/2016

10 Things That Will Save You So Much Trouble At The Office.

1.) Don’t send emails if you don’t have to. If you can walk over to someone’s desk and explain something, do it. If you can make a phone call, do it. Unless it’s something simple, don’t send that email. It’ll save you time in the long run.

2.) Say “Congrats!” If someone kicks ass on a project, send them a quick note. It can be three sentences. It can just be a link to their project with the words “Nice job!” in the subject line. Even a small gesture makes an impression.

3.) Be direct. Don’t sugarcoat things. Don’t bury bad news. Just be straightforward with people, especially around bad news.

4.) Set limits for work. I don’t respond to emails between 7 p.m. and 7 a.m. I set that expectation early on in my job. There are often nights I’m up working past then, but unless something’s on fire, I won’t respond until the morning. It’s all about setting your personal boundaries. Own your work — and don’t let your work own you.

5.) Be prompt. I try to respond to all texts and all emails within 24 hours. Think about how you feel when someone responds to one of your emails a week late. You don’t feel valued, right? Always try to respond promptly (not immediately, just promptly).

6.) Say “I’m sorry.” Take responsibility for your actions, and sometimes, take responsibility even when it’s not your fault. Nobody wins when you pick a fight.

7.) Be nice! Hellos and remembering names go a surprisingly long way.

8.) Don’t be a jerk! It is shockingly easy to be one — especially in an email or over Gchat. At any office, you don’t have to be liked to get stuff done — but you do have to be respected, and nobody respects the jerks in their office.

9.) Remember these rules for email: Don’t reply all to inter-office threads. Use Gmail’s Mute button liberally. And don’t be afraid to use smiley faces and exclamation points — they’re really good at communicating tone.

10.) Be someone who delivers on promises. I always seek out the people I know will deliver their work on time. There aren’t enough hours in the week to wait for other people to get their crap together. Work with people who get shit done — and be one of those people yourself.

———

That photo of a workspace comes via via Unsplash and photographer Jeff Sheldon.

05/20/201504/11/2016

What Are You Going To Do?

When someone comes to me with a problem, one of my favorite things is to listen to what they have to say and then ask six of the best words in the English language:

What are you going to do?

And oftentimes, they’ll start talking about planning or ideas, and I’ll just cut them off and rephrase the question:

No no, I asked: What are you going to DO?

Do — as in, you have to do something!

Action is good. Setting up new routines is good. Work is good.

Planning is definitely not work. Just about everyone has a secret idea for a project they think could be huge. Huge! If only they had the time, resources, connections — oh, and actually wanted to put in the work to make it happen.

Planning is not work. It’s an important step — but the only thing that counts is when you turn ideas into work.

So do this: The next time you’re stuck, ask yourself: What am I going to do? Take 10 minutes, and write down the first 10 things you can to do take a step forward today.

Then go ahead and start accomplishing those things. Every time you do one, cross it off the list.

When that list is all finished: Take 10 minutes to write the next 10 things. And then start crossing those things off.

Sound easy? Good. Now do it every day. (That’s not quite as easy, you’ll find!)

These don’t have to be big steps. Sometimes, they’re just little things that get you moving. And sometimes, even those little steps will feel like missteps. That’s OK!

The important thing is this: Moving forward is so much better than sitting there and wondering away the days, losing valuable time when you could actually be doing the work.

———

That amazing photo of a man looking over a cloudy horizon comes via Unsplash and photographer Joshua Earle.

05/12/201504/11/2016

One Little Piece Of Advice For The Class Of 2015.

Hi, there! Congrats on graduation — and welcome to the world of unemployment!

You’re probably already applying to a million jobs online, and not hearing anything back from employers. And worse: You’re living at home with your parents, and they’re going to keep asking you the big question:

Why haven’t you gotten a job yet?

At first, this won’t bother you, because none of your friends will have jobs either! But then one friend will get a real job, and then another, and then you’ll wake up one day and your parents will have slipped an LSAT prep book under your door.

This is the point at which you’ll start to think that your parents might murder you soon.

But it’s OK! You will get a job eventually. And in the meantime, here’s what I suggest:

Make a list of 50 people in your city or in your field that you admire. Don’t stop at 15 or 20. Make it all the way to 50.

Then find their email address or mailing address, and write them a note. Make it short — 5 sentences or less. Tell them that you’ve just graduated, and you admire their work, and then tell them that you want to bring coffee to them and ask 3-4 questions about how they got to where they are.

This is very important: You have to offer to bring coffee to them. People HATE leaving their office in the middle of the day if they don’t have to. But anyone can make 10 minutes if you promise to bring them free coffee and not waste their time.

So here’s what’s amazing: A lot of the people you email/write to will actually write back and take you up on your offer! You’re a recent grad, and everyone’s been in your shoes before. There are a lot of really smart, really talented, really powerful people out there who’d be happy to help you… just as long as you come to them and don’t waste their time.

Now all you have to do is show up with coffee and make your 3-4 questions count. And then afterwards, write the person a thank you note. Don’t write an email — write a letter and mail it to them. This part is important, too.

Will this land you a job? Well… maybe not. But if you do this — if you send 50 notes, if you bring them coffee, if you don’t waste their time, if you follow up with a note — I can pretty much guarantee that you’ll meet at least a handful of people who you can build a relationship with. They’re people you can send links to or drop a note to say hi every once in a while. And they’re the kinds of people who also control a lot of the hiring at companies. Maybe they won’t be able to offer you a job today. But they’re going to be the people who — when they hear of a job in the future — might email you and give you a heads up, or even make an introduction. In the long run, that network can be a hugely valuable thing.

Good luck, Class of 2015.

———

That photo of graduation comes via Flickr’s Andrew Schwegler.

05/04/201505/04/2015

Forget About My Money. What Are You Doing To Get Me Back My Time?

When I’m traveling, it’s the inefficiencies that really kill me.

I know that travel is going to cause some headaches. There are going to be lines at security, and flight delays happen. I get that.

But it’s the little moments of inefficiency at the airport that, to me, can make flying a real pain.

For instance (and excuse the Andy Rooney rant, please):

These days at the gate, as soon as the gate agent mentions “preboarding,” everyone gets up and stands right in front of the gate. With everyone packed in up there, it takes forever to get everyone on board. But it doesn’t have to be this way! A few months ago, I flew Air Canada up to Toronto, and the agents actually told people to sit down and wait for their boarding group. With the boarding lanes clear, it was the smoothest boarding process I’ve been a part of in a long time.

It must’ve been 15 years ago that I flew Southwest for the first time. I laughed when I saw people lined up in their boarding groups, ready to board before the plane even got to the gate. Now Southwest is the model of efficiency — every person boards by a pre-assigned number — and it’s the rest of the U.S. airlines that are backwards.

And airlines: When you ask people to volunteer to check their bags at the gate, has anyone actually listened? Of course not! A decade ago, plenty of people checked bags. Now, a younger generation sees it as an enormous inconvenience. But we might be willing to change our tune — all it would take is the right incentive. 150 free airline miles for a checked bag at the gate, maybe, or a $10 voucher toward a future flight. And you’d get bags checked in advance and no extra waiting on the tarmac as flight attendants struggle to get big bags squeezed into overhead bins.

Another thing: Why is the check-in process at rental car counters so miserable? This past weekend, I waited in line for an hour to get my car. Ordinarily, I rent with Hertz, and I’m a member in their #1 Club Gold program. You enter in all your information in advance, fill out your insurance information online, and walk straight up to you car. There’s no waiting whatsoever. The whole thing is free, too — I don’t understand why anyone wouldn’t want to be a member!

But this trip, I redeemed some credit card points for my reservation, and had to wait in line. There were maybe 10 guests ahead of me, but the line barely moved. And when I got to the counter, the Hertz associate had to enter in all of my information line by line. But it doesn’t need to be so time consuming, Hertz. The airlines can check me in via a computer — why don’t you do the same? I’m betting a computerized check-in would actually explain the benefits of various opt-in programs (like pre-paying to fill up your tank) better than an employee could in person. All I really need a human for is to hand over the keys and point me towards my car. Instead, I lost an hour waiting in line, and 10 more minutes once I got to the counter. (I even had to sign a waiver declining free maps! I lost two minutes declining maps!)

Meanwhile, this past weekend, I managed to pay for a parking meter via text message. (It even texted me when my meter was up!) I got a hotel bill emailed directly to me. And even the TSA was able to streamline me straight through security. Those little efficient touch points along the way made a huge difference — but it’s the pain points we all remember.

What I’m getting to is this: Some companies work hard to return savings to a customer. But here’s something just as important: My time. And as a customer, I’m asking myself: What is your company doing to return my time to me?

Companies that work efficiently to maximize my time are the ones that exceed expectations — and they’re the ones I’m going to come back to time and again when I travel.