I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
In 2011, I got the chance to participate in a small startup competition in D.C. to talk about Stry.us. The next day, I got an email from a woman named Tiffany Shackelford, then the Executive Director of Association of Alternative Newsweeklies. She wanted to know if I’d be interested in speaking at the annual AAN conference.
I hadn’t met Tiffany at the event, but she saw something the night before that piqued her interest.
At first, I didn’t know what to make of her offer. I was 24, and I’d never spoken at a journalism conference before. Still, Tiffany thought there might be a place for me on the AAN stage.
I couldn’t make the event that year, but Tiffany promised she’d be in touch again. Sure enough, the next year, I got another note from Tiffany: Would I be interested in pitching a talk for that year’s event?
That’s how in June 2012, at the AAN conference in Detroit, I led a talk about responsive design for newsrooms.
Since, I’ve been lucky to speak at events all over the world. But Tiffany was the very first to give me a shot, and for that, I’ve always been grateful.
Tiffany died this week — she’s one of the more than 300,000 Americans who have died from COVID-19. Reading remembrances from other journalists about her, it became clear: What Tiffany did for me, she also did for countless other journalists. There are a lot of us in the journalism world who are better off because Tiffany was in it.
Thanks for everything you’ve done, Tiffany. I’ll do my best to use my platform to give others that first shot, just like the chance you gave me.
As we wrap up 2020, and look towards the new year, I wanted to say a few words:
So many of us are hoping that when the calendar flips to January, we’ll slowly begin to move towards a more normal world. As I look through my Instagram feed, nearly every day, I see another photo of a friend receiving their first shot of the COVID-19 vaccine. That alone is reason for optimism.
But no matter what 2021 brings, I wish for you to think back upon this year as a reminder: of how connected we can be, when we choose to be; of how kind we can be, when we choose to be; of how giving we can be, when we choose to be; of how engaged we can be, when we choose to be.
2021 will be an opportunity, too, to choose to work for a better world, in whatever ways you can. There is no returning to the lives we had before this virus, but together, we can build a world that is different, exciting, and far more just. I wish for you the courage to choose that future.
In this new year, I wish you and your loved ones good health, and I wish you the optimism to believe that brighter days lie still ahead.
An unusual thing has happened in the second half of 2020 for my consultancy: I’ve started turning away work.
When I started this business, if a client approached me and I thought it was a good fit, I almost always said “yes” to the work. Even as I took on additional clients, I kept saying “yes,” since I still had a manageable workload.
But as 2020’s progressed, and I’ve learned more about what each client needs, and how time-intensive some of these projects are, I’ve gotten more selective about saying “yes”. I know that saying “yes” to a project I don’t have the time for is even worse than saying “no” — because it keeps the client from finding another partner to take on the work they need done.
I hate saying “no.” My default position is “yes” — I like trying to find solutions, and I like trying to help. I especially hate saying “no” to exciting projects. But sometimes, “no” is the right answer.
And even when I say “no,” I try to be transparent about why I’ve said so, and when I might be able to work with this client. A few clients have asked if they can sign on to start working with me a few months down the road, and we’ve set up a schedule that works for everyone. A lot of these are businesses that have been around for years or decades — turns out that waiting another 60 or 90 days to get started isn’t that big of a deal.
Other times, I’ll recognize that the client needs help ASAP, and I’ll pass along the lead to another consultant or freelancer who I think can help. If I can direct them to a good partner to take on the work, that’s still a fantastic outcome.
I know as the business grows, I’ll have to be even more selective about what I say “yes” to. Taking on new clients? Launching new products? Hiring staff for Inbox Collective? These aren’t questions I can easily say “yes” to. I need to continue to be honest with my partners — and myself — about what I can truly do, and do well.
Every year, I set a goal: Write one thing per week here on the blog. This post is no. 50 — which means I’m right on track, despite everything that’s happened this year.
The blog is always a bit of time capsule, and that’s especially true this year. Looking back, it’s easy to see the fear (and uncertainty) of the early days of this pandemic; the excitement (and uncertainty) when I hit a year of Inbox Collective; the optimism (and uncertainty) as I started to look forward to 2021. (If anything, it was certainly a year of uncertainty.) But if I had to pick just five blog posts I’m most proud of this year, I’d start here:
When I was younger, working as part of a larger newsroom, I had a bad habit: I always wanted to win.
This wasn’t about getting big projects done on behalf of my team. These were moments when I got hung up on some petty issue, decided someone was in my way, and that I needed to show them not just that I was right, but how right I was.
Why? Stubbornness, mostly. These were fights over tiny issues only I’d noticed. I wasn’t fighting over worthy causes — I’d found a few molehills, and decided to defend them like mountaintops.
But as I’ve gotten older — and in particular, ever since I started running my own business — I’ve learned that I need to give up on most of these fights. It helps to have a great support system that I can turn to when I’m feeling stubborn to remind me to ease up and move on. But it’s also just a matter of time: I can’t afford to waste time on these trivial issues. (I mean this literally: I bill by the hour. Losing a few hours over a silly fight is a money-losing cause.)
When I start to get stuck on one of these fights, I try to find the path of least resistance. Is there an easy way out? Is there an alternative solution? Is there a way for me to communicate clearly and quickly what needs to get done so we can all move on? I try to find the path, and then I get back to work.
At the end of the day, the work is more important than being right. It does you no good to go looking for the fight. Find the way forward, and keep moving on to bigger things.
It’s easy to spend your week putting out fires. You wake up on a Monday morning, ready for a big week of work ahead. You’re going to take on some significant projects this week, and really get some stuff done.
Then the requests start coming in:
• Something’s wrong, and it needs to be fixed ASAP.
• A manager emails with requests that require immediate attention.
• A colleague needs help on a project that has to launch in mere hours.
• A key tool breaks, and it’s all hands on deck to make things right.
The week goes on like that: Urgent project after urgent project, until you look up on a Friday and realize that you never got the chance to do the work you promised yourself you would do.
Don’t let the urgent drown out the important. Make sure you block out time for the big, focused work. Otherwise, it’s too easy to go through the week putting out fires without ever actually getting to the work you really want to do.
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That photo of Jersey City at sunset comes via Uvi D on Unsplash.There’s no real reason why I chose that photo for this post — I just thought it looked nice.
I’m 33 years old, and I’m starting to appreciate the little decisions each of us makes in life.
I’ll take you back to March. I had a busy spring lined up: I’d be traveling to nine cities in 12 weeks. Berlin, Sao Paulo, St. Louis — it was all happening. I’d been following the news about the novel coronavirus fairly closely, but I wasn’t too worried. The World Health Organization kept saying this wasn’t a pandemic (really, this happened!), and only a handful of people had tested positive in the United States. I flew to Boston for work (the first cases there would be reported hours after I left), and then to Austin, where I gave my first-ever remote talk. (I didn’t know it’d be the first of 20+ digital events I’d speak at this year.) I visited friends, and even attended a concert. (Indoors! At a crowded Austin bar! No masks!)
And then on March 11, I took off on a flight from Austin, and landed in a world I didn’t recognize.
It’s 2 hours and 10 minutes from Austin to Atlanta, but that’s the longest flight I’ll ever take. I watched on the in-flight TVs as the NBA postponed its season, the President shut down travel to Europe, and Tom Hanks announced that he’d been diagnosed with COVID-19. I landed in Atlanta and knew that everything had changed.
So I flew home.
Well, not right away. I actually — and I cannot believe I did this — first flew to a conference, in South Carolina. I stayed about three hours at the event, never sat down, and spent most of it on the phone with friends trying to figure out if New York was about to close the airports.
Then I flew home.
Sally and I spent the weekend trying to figure out what to do next. At that point, it was pretty clear to us that:
1.) Things were very bad in Europe.
2.) Things were likely to get very bad in New York.
3.) We were both about to start working fully remotely, indefinitely, from a one-bedroom apartment. (So much for all that travel I’d planned!)
4.) If we had a chance to leave New York, we had to leave as soon as possible.
We started texting and calling friends, looking for advice. Some told us to stay, many suggested that we go. We leaned towards “go” — we just weren’t sure where.
I called Ryan, one of my best friends for more than 15 years. The week before, he’d texted me a photo of himself on an empty flight — he was wearing a surgical mask over his nose and mouth, and I teased him for looking like a doomsday prepper. But Ryan usually knows the right thing to do, and in this case, he’d already done it: He’d flown back from California, where he lives, to his home state of North Carolina. His family owns a house along the beach, and he’d be riding out COVID-19 from there.
He asked: Would you guys want to come down here for a few weeks? I’ve got space.
Eight hours later, we were in a rental car, headed south.
We didn’t know just how bad it would get in New York. We didn’t know that Sally would graduate from nursing school in that house — not at Yankee Stadium, with the rest of her NYU class, but on YouTube. We didn’t know that we’d spend 10 weeks with Ryan living in North Carolina.
What I do know is this: If you’re lucky, you get to have people in your life who are there for you when you absolutely need it the most. We didn’t know how much we’d need your help when you invited us down, Ryan. But we’ll always be grateful for that kindness — and for you.
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 33, is what I believe:
Fifty years ago, Mel Brooks coined this line: Hope for the best, expect the worst. That’s 2020.
We’re never going to be able to fully explain this year to our children. Our kids will look at us and say: ”So they asked people to cover their faces and stay home, whenever possible, and people just… refused?”
Part of the reason this year has been so challenging, I think, is that you can’t see where this battle is being fought. Anderson Cooper isn’t broadcasting from inside an ICU. If people could’ve seen, from the earliest days, what nurses and doctors saw inside our hospitals, I think things might have been different.
There are days when I wish I didn’t have to spend so much time on Zoom. But the truth is: Zoom allowed me to not just stay in business, but to grow it this year. To the team at Zoom: Thank you.
At the time, it seemed absurd to pack up and leave for North Carolina on just eight hours notice. Looking back, I’m surprised we even waited that long.
I remember Memorial Day in North Carolina, seeing people partying on boats, acting like COVID-19 was over, and knowing: Yeah, it’s time for us to go home.
I love my wife. But a little alone time is probably a good thing for a marriage.
Corporate jobs bring frustration. Running your own business brings stress. Every job has pressure — it’s just about the type you choose.
No one is supposed to spend this much time staring at a computer. This year reminded me of what I want, whenever life gets back to some sort of normal: A few coffees or lunches per week. A little time in the office with my clients. And maybe once a month, a work trip somewhere. That’d be more than enough.
Had ESPN made a 10-part documentary about Michael Jordan getting food poisoning in Utah, I probably would’ve watched.
Publix makes some of the best subs in America. I’m a believer.
New York City says it’s going to allow outdoor dining to continue in 2021 and beyond. Now the city should bring back the other bright spot of 2020: To-go drinks. Make it a once-a-year thing, just for the week of 4th of July. I’m not saying New York should become New Orleans — but I wouldn’t mind it for one week a year.
Your vote matters.
Sally, you were right. The Peloton was a good investment.
In retrospect, getting airline status for 2020 wasn’t quite the game-changer I thought it’d be.
I remember this moment from the summer. Sally and I had rented a car and gone to New England for a quiet weekend away. On the drive home, we decided to pick up a pizza at Frank Pepe’s in New Haven. They didn’t have outdoor seating, so we took our pie, drove to a nearby strip mall, pulled out the camping chairs, and tailgated. It was a Monday afternoon, a beautiful, sunny day, and for a few minutes, we forgot about the fact that we were eating pizza in a Palm Beach Tan parking lot. I’ll remember 2020 a lot like that: Surreal, strange, but occasionally kind of beautiful.
Of course, five minutes later, a guy in a RAV-4 pulled up next to us and started projectile vomiting out the window. I’ll probably remember 2020 a lot more like that.
And finally, whenever we make it through this pandemic, remember: Be good to each other. Enjoy every moment. And whatever you really want to do, do it now. You never know when you’re going to get the chance to do it again.
As you’re setting goals for the new year, think about setting a few different types of goals. It’s not just about driving as much revenue as possible, or growing your audience as fast as possible. I want you to think about setting four types of goals for the new year:
1.) What is your audience goal? Set a goal for the audience you’re trying to build. Where will you build your audience? On what platforms? Then think about growth. How big do you need your audience to be for your business to be viable? How big do you think it can be?
2.) What is your financial goal? What is the minimum amount of revenue you need to hit? What do you hope to reach in the next year? And if you exceed all expectations, what numbers do you hope to hi?
3.) What is your learning goal? If you’re going to succeed in your role, you’re going to need to keep learning. So what do you hope to learn next year? Think about the skills you’d like to gain or subjects you want to master that might help take your work to the next level.
4.) What is your leadership goal? No matter what you’re doing — working within a larger company, or going solo — you’ve still got an obligation to be a leader in your community. Think about ways you can lead: Mentoring, joining an organization, sharing learnings with others. Finding spaces to lead gives you the opportunity to both give back and stay involved.
Think about the year ahead and try to set all four types of goals. Those that do — and that seek to actually achieve those goals — will do big things in the new year.
There’s a tendency at a moment like this — whether you’ve just completed an election, like we did in America this week, or whether you’ve completed a big project at work — to have a sense that things are over. You put in the work, you did the work, and now you’re done.
But the truth is: There’s always more work to do. New doors are going to open, new opportunities are going to become clear. The work is never really done.
Inbox Collective is my second attempt at starting a business — a decade ago, Stry.us was my first. I know more this time around, I’ve better organized a network of supporters around me, and this time, I’ve built an audience to support my work. I learned so much from Stry.us, and it’s put me in a far better place to succeed with Inbox Collective.
But even with all that knowledge, I’ve found that there are still obstacles in my way. I believe that these four obstacles exist for everyone who starts something — no matter how ambitious the project or how prepared the team is behind it:
Time — There’s never enough time to do all the things you want to do. In a business like mine, it’s so hard to strike the right balance between doing the work that pays the bills and building the relationships that will lead to paying work down the road. If there were twice the number of hours in the day, I still don’t think it’d be enough. It means that I need to prioritize certain work and say yes to only the things that are most important to me — even though sometimes, I have to say no to stuff I’d really love to be able to do.
Money — This was the big question when I launched: Would anyone actually pay me to do this? The answer’s been a resounding yes, and I feel so grateful for that. But now there’s pressure to keep this thing going. 2020 changed everything — no work-related travel or talks, but lots of remote projects. Could I keep that up for another year or three if I had to? So many of my 2020 projects came from meeting people at conferences and events back in 2019, and if my business stays remote for the foreseeable future, I wonder if I’ll be able to keep this going. I know I can do it, but that fear is still going to be a small weight on my shoulders. Even when things are going well, I’m always going to be looking ahead and trying to plan for what’s next.
Stress — Anytime time and money get involved, there’s going to be a certain amount of stress, too. Inbox Collective is my work, and mine alone. If it succeeds, if it fails, it’s on me. I like the pressure of it, and I’d gladly take this work — even when it’s stressful — over the frustrations of working within a larger organization. (And that might change down the road — that’s just how I feel today!) But it doesn’t change the fact that this job applies real pressure on my life, and it’s up to me to manage that stress. It’s something I’ll always have to deal with.
Failure — At the end of the day, there’s always the chance that Inbox Collective fails. I might not be able to do the work, I might lose clients, I might have to change careers or fields. Now that things are working, there’s pressure to keep this business going, and to keep learning so I can continue to grow Inbox Collective.
I don’t know what Inbox Collective will look like in a year or five. I certainly have no idea whether it’ll be around in 10 years, or beyond that. But I know that as long as I work on this, those four pressures — time, money, stress, and failure — will weigh on me. That’s just part of the job.
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At top, that’s a photo taken of me giving a talk in 2019.
