Balancing the Grind with Dan Oshinsky, Consultant at Inbox Collective

Dan Oshinsky is a Consultant at Inbox Collective, a consultancy that works with news organizations, non-profits, and brands to grow audiences via email.

1) To kick things off, could you tell us a little about your career background and current role?

I run Inbox Collective, a consultancy to help news organizations, non-profits, and brands figure out how to get more readers and make more money, all through their email strategy.

Before this, I was the Director of Newsletters at The New Yorker and BuzzFeed. I also write this giant Google Doc every month to help people in the email world. It’s called Not a Newsletter since it’s, well, not a newsletter! (There is an email alert you can sign up for if you want to be alerted when the next issue publishes.)

2) What does a day in the life look like for you? Can you take us through a recent workday?

The trickiest part about being my own boss is that there isn’t a set structure to my day. I work with clients around the world, so I’m often up early or up late to help out my teams in other parts of the world.

But on a normal day, I’ll usually have a few calls with clients to check in, and I try to block out time for hands-on project work with my teams. As someone who works in the email space, I also spend a lot of time in my inbox, both replying to emails and looking through my newsletter folder for inspiration.

I try to carve out time to sit down for dinner with my wife — getting to unwind with her is always one of the best parts of my day.

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

It does, and it’s one of the things I like most about this role. I’ve been lucky enough to travel a fair bit for work in the past year, and even when I’ve been far from home, I’ve been able to do my job.

Long before this pandemic, Zoom was a huge part of my day, and Google Docs allows me to collaborate with clients even at a distance. As long as I’ve got a laptop and an internet connection, I can do this job.

The flip side of that is that work can follow me around wherever I go. I’m often up working before 7 and up late working past 10. But when I do, it’s because I’ve made time in the middle of the day for myself.

4) What does work-life balance mean to you and how do you work to achieve that goal?

It’s a little strange: Everything blends together in a funny way. When I had a more normal office job, things were blocked out: personal time at home, work at work. That’s not really the case anymore. I work from home, and it can be a little tricky to understand where work ends and where my personal life begins.

The thing I’ve learned is that I have to block out time during my day for myself. Before this pandemic, every Sunday, I’d go through my calendar for the week ahead and reserve a daily 90-minute block to take a long walk, read, or run a few errands.

During the pandemic, that’s shifted to more stay-at-home types of breaks: Cooking, working out, or taking a few minutes to check in with loved ones. I find that if I don’t do it, I’ll just work all the way through the day, so it’s crucial that I find moments to pause.

Here’s how I know that I’m too overloaded with work: I’ll start having the oddest stress dreams, usually where the dream involves replying to client emails or being on calls with clients. When work takes over my dreams, that’s how I know I need to dial things back a little and make more time during the day for myself.

5) What do you think are some of the best habits or routines that you’ve developed over the years to help you achieve success in your life?

A few things I’ve learned about being my own boss and working from home.

Every morning, I shower and get dressed for work. Now, my work outfit is still pretty relaxed — jeans and a shirt with a collar — but it’s a nice reminder that the day’s begun.

I try to keep healthy foods in the house. If I’ve got Girl Scout cookies in the house, and if my wife’s not home, I’ll happily eat a sleeve of Thin Mints before noon. If I’ve got fruit in the house, I’ll eat that instead.

Have a designated work space. If I’m half answering emails and half watching The Price is Right on the couch, that’s not work. Get yourself a good desk, a comfortable chair, and the right equipment you need to work from home.

Turn on your Out of Office reply when you’re going to be offline for a few days. When I first started Inbox Collective, I always forgot to do this — and then clients would get frustrated that I wasn’t responding to them.

Especially when you’re working remotely, it’s so important to be transparent about your schedule — and your need to take some time off — but that Out of Office message helps establish boundaries, too.

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

Some stuff from the past year that I’ve read and absolutely loved:

• Boom Town by Sam Anderson
• Daisy Jones & The Six by Taylor Jenkins Reid
• One Day by Gene Weingarten
• Trick Mirror by Jia Tolentino

I try to read stuff that’s unrelated to work — it’s one the best ways for me to unplug.

7) What is the number one thing you do to make sure you get the most out of your day?

I’ve been a user of TeuxDeux for almost a decade now. That checklist helps me understand how productive I’m being in a given day or week, and is one of the best ways I can hold myself accountable.

8) If you could read an interview about work-life balance by anyone, who would that be?

Stephen Colbert. He seems to be able to balance a big writing staff and stressful deadlines while somehow still being a dad and having a personal life. I’d love to hear how he does it.

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

True story: It took me almost two weeks to respond to these questions about my work-life balance because things got way out of balance.

The fact that I couldn’t make time for an interview about how I make time for myself because I didn’t actually have any time was, well, a sign that I needed to do better!

Hold yourself accountable, remember that it’s OK to say “no” to things you don’t have time for, and give yourself permission to make time for yourself.

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