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.
Here’s little trick I like to use when I’ve got way too many tasks on my to-do list and can’t figure out what to prioritize.
Open up a spreadsheet and type out all the tasks you’ve got on your list. Then create three columns, and put these headers at the top:
• What you NEED to do this quarter • What you WANT to do this quarter • What you’d LIKE to do this quarter
NEED is the stuff that 100% absolutely must get done.
WANT is the next bucket of tasks you’re most excited about.
LIKE are things you’re interested in… but you can’t quite make a priority.
I know I’m guilty of focusing on stuff that isn’t in those “Need” or “Want” buckets. Sometimes, just seeing everything laid out like this helps me refocus on what’s most important.
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That’s a sketch that Canva’s AI tool created for me. It’s a decent example of what this exercise might look like if you did it on a yellow legal pad.
90% of my advice to clients is boils down to three words:
“Don’t overthink this.”
People get into their heads when it comes to tweaking their strategy or tactics. They get caught up thinking that there are a series of three-dimensional chess moves that will fix what’s wrong.
But usually, the fixes are simpler than that: Your positioning is unclear. You’re not targeting the right audience. You’re doing too many things at once.
My job is often to tell teams: You’re overthinking things! Let’s simplify and get back to the core of what you do well.
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That’s not the fanciest desk set up in the world, but it’d work just fine? Why? It’s so darn simple. Thanks to Unsplash for the photo.
This interview with Jason Alexander, of “Seinfeld” fame, popped up in my feed the other day, and I think it’s worth watching in full. In it, he says:
I went to Boston University as a theater major, and because William Shatner was my muse, I wanted a dramatic career. I really thought I was going to play some of the great classical roles and be a dramatic actor. Sure, I hadn’t done much comedy. I’d done some musicals, so there was that, but I hadn’t done much comedy. And the summer second semester of my sophomore year, I had a professor named James Spruill at Boston. He was the only black member of the faculty. He was a guy who had come up in the ‘60s with street theater — theater is to change the minds of the masses, affect change. He brought me into his office for my my semester consultation, and he had this great basso kind of James Earl Jones voice, and he sat back, and he just kind of nodded his head and looked at me for a minute. He went, “I know that your heart and soul is Hamlet, and you would be a profound Hamlet. You will never play Hamlet, so you best get good at Falstaff.”
And he basically said, look, look in the mirror. You are 5’6’’. You are 20 to 25 pounds overweight, and you are losing your hair. You have a large performing persona. If you want a a commercially successful career, you’re going to be a comedian, and you’re not embracing it, you’re not looking at it, you’re not doing it.
Had he not said to me, “You ain’t Hamlet, man,” I would have finished that school and gone into the professional world thinking, ”Here’s Jason Alexander and the Iceman cometh. It’s what everybody is waiting for.”
And I would have been wrong.
It’s such a wonderful reminder: We all need someone in our lives who’ll be truly honest with us. Sometimes, we need that person to lift us up. Sometimes, we need them to keep on the right path. But all we need those voices we can trust, and if you find someone who can do that, you owe it to yourself to listen to them. They’ve got something worth hearing, even if it’s not what you want to hear at that moment.
I bought this piece of art today at the Farmer’s Market downtown. It’s a big piece of wood, probably about five feet long, and on it is a carving of the mountains here in Utah. This week, I’ll hang it behind my desk.
But the memorable thing for me wasn’t the purchase of the art — it was walking it to the car.
Now, you’d think that a guy my height (I’m about 6’4’’) carrying a five-foot-long piece of wood might get noticed while walking down the street. I’m hard to miss! And yet: In that short walk, I cannot tell you how many people nearly walked directly into me.
Look, I’m as guilty as any of being distracted by my phone. But today was a nice reminder: The stuff directly in front of you might be pretty important. (Walking into me or that piece of art would’ve been a less-than-fun experience for someone.) It’s easy to miss things happening in our world, but we shouldn’t be missing the obvious stuff that’s literally right in front of our faces.
So look up every once in a while — hopefully to pay attention to what’s happening in your world, but at the very least, because you might be about to walk into a tall guy carrying a big piece of art.
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I don’t have a photo of the art, but here’s a photo that Olivia Hutcherson took for Unsplash of downtown Park City in 2018 at the Farmer’s Market, with small white booths lining the street and red flowers in the foreground.
Couldn’t I sell courses? Couldn’t I write a book? Couldn’t I give more talks? Couldn’t I charge more for each speaking engagement?
And then I have to take a few steps back to acknowledge what I’ve actually done.
I’ve built an audience, I’ve built a business. I’ve created, from nothing, the best paying and most flexible job I’ve ever had. I’ll take more time off this year than I’ve taken since college. I’m in a position where I get to pick and choose what projects I take on and who I work with.
I’m proud of the success I’ve had. Success should be enough — do I need to be excessively successful? Do I really need to do more?
I know the answer to those questions, but it’s hard to quiet the voice that wants to do more. I have to remind myself: I don’t need to do everything. This is more than enough.
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That’s from a talk I gave in Denver in September. It went well — but yes, I still do wonder if I could’ve done better for those who attended.
I’ve been listening to Mary Louise Kelly’s book, “It. Goes. So. Fast”, while taking my newborn son on walks around my neighborhood. It’s a book about a parent’s journey during her son’s senior year of high school, which makes for quite the contrast from my day-to-day. It’s tough to imagine my son graduating from high school — something that should happen in the year 2041! — but I know the years will go by fast.
It’s certainly been my experience so far. To be a parent to a newborn is to live on a schedule completely untethered from normal time. There are no clocks on newborn time; we operate hour to hour. There have been a lot of 4 a.m. feedings, and a lot of late nights. Time isn’t something we obey anymore — it just kind of happens while you’re busy with the baby.
But to operate on newborn time is to also live in the moment, as much as you can. The baby will never be this small again. They’ll never smell the way a newborn smells, or smile the way a newborn smiles. There is no going back; there are no do-overs.
And it’s an amazing reminder: Be present. Pay attention. Celebrate the moment.
We live in an age of copycats. When someone has success in a particular way, there’s a rush for others to copy that model.
There’s nothing wrong with learning from others. There’s no reason to make the same mistakes that others have already made. Ask good questions, listen, and learn from others. Use existing examples to make the work you do better.
But you have to find your own way, too. You have to find ways to take what you’re doing and put your own spin on it.
Only you can do what you can do. So don’t be content to copy and paste — learn from others, and find a way to make things your own.
I keep thinking about this thing I saw a few weeks ago in New York.
I was walking down the sidewalk, and as I looked ahead, I saw something I’d never seen before: A young woman was reading a book while she walked. And this wasn’t some act of passive reading — her face was buried in the book.
It was hard to miss. She almost walked directly into me — I had to slide out of the way to avoid her. (She didn’t seem to notice.)
I know people are busy. I know everyone’s trying to get the most out of their day. But not every activity is one that allows for multi-tasking.
If you truly care about something, you’ve got to make time for it. Maybe that means putting down your phone before bed and picking up a book. Maybe it means blocking out time on your calendar to read. Maybe it means subtracting something — fewer after-work drinks, more reading. Or maybe it means finding ways to responsibility multi-task. (Audiobooks are great for the commute!)
And if you’re walking through New York City, please: Walk responsibly.
By the end of January, I had my calendar for the entire year pretty much set.
I knew where I was going to give talks this year, and had the flights planned out. I knew which weddings I’d be going to. I had some vacation days penciled in.
Then Covid-19 hit here in the U.S., and all of that changed.
I used to have a nice balance of remote work and in-person work. Now, like everyone else, my work’s shifted entirely online. I’m not sure when I’ll fly next or when I’ll travel again for work.
And that’s OK! I’m lucky to be the position that I’m in. Inbox Collective is doing well, and I’ve got my hands full with work. I feel incredibly grateful for the opportunities that I have.
Still, I’m realizing how much I miss being able to look forward to the next thing: The next trip, the next birthday party, the next night out. Zoom is such a useful app, but it’s not the same as being there with friends or clients.
Here’s the closest thing I’ve found to life before Covid-19: This past weekend, my wife and I decided to get out of town for a few days. We rented a car and drove upstate. We didn’t do much — we ate, we drank, and we saw a few friends from a distance — but just knowing that we had something like that on the calendar lifted both of our moods for an entire week.
Going forward, I’m going to try to keep putting something on the calendar to look forward to. It could be small (setting aside some time to meet a friend in the park) or big (a road trip somewhere). I’m not going back to the pace I had a year ago, and that’s alright by me. Just knowing that something’s coming up is enough to keep me moving forward.
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That’s a screenshot of Flighty, the app I use to track my travel. That’s what my travel schedule looked like from March through June. (Obviously, it all changed.)
No one knows what happens next. We don’t know what things will look like in two weeks, two months, or two years. We don’t know if we’ll be working in offices again, traveling to conferences, or even sitting down at the table with loved ones. Sure, you can make a prediction about the future — but your prediction is little better than a guess.
Historically, pandemics have forced humans to break with the past and imagine their world anew. This one is no different. It is a portal, a gateway between one world and the next.
So how should you approach making a tough choice about an uncertain future? Try to think through two big questions:
What do you know right now? — Do your research. Read a lot. Talk with people you trust, and listen to what they have to say. Try to collect all the information you can about the situation.
What do you believe right now? — Trust your instincts. Think about what you need at this moment. Put all the options on the table, and make the best choice you can with the information you have.
You may not end up making the perfect choice in the long run. Again: To make the perfect choice for whatever’s next, you’re going to need to get a little bit lucky. But you do have the power to look at the current situation, ask the questions you need to ask, think through the options in front of you, and make the right choice for right now.
