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.
I ask myself this a few times a quarter when projects start to pile up: I’ve got a lots of things to tackle. Where should I start?
And the truth is: You can start anywhere — as long as you start.
I know I can find myself paralyzed by all those choices. Instead of getting stuff done, I end up worrying about all the stuff I have to get done. (And then I find myself with a lot less time to actually do the things I need to do!)
Don’t worry about finding the perfect starting place. The end result is far more important than where you start.
Start somewhere, and go from there.
———
That’s a photo of an American Airlines jet taking off, with pink flowers blurred in the foreground and the moon behind. It was taken by Sachin Amjhad for Unsplash.
I read this line in a New Yorker article, and I haven’t stopped thinking about it since: “They never miss an opportunity to miss an opportunity.”
There have been so many times when I’ve showed up for something without knowing exactly what I might get out it. I didn’t want to miss out on something, even if I wasn’t sure what it was! When you show up, you don’t always stumble into something good — but sometimes, you do. (Case in point: My MLK Day story.)
Point is: There are certain opportunities that only come along when you take the time to show up. Don’t miss the opportunity to miss an opportunity. Just show up and see what presents itself.
———
That’s a photo of a departures board with flights from Singapore’s airport to destinations around Asia. It seemed as appropriate a photo for the “show up” message as any. It was taken by Benjamin Wong for Unsplash.
It’s been a busy week. We went to a wedding last weekend and are going to another in 48 hours. I’ve got some new clients starting this month, a few talks coming up, and generally just a lot of work happening. It’s a ton for a small business like mine — and of course, having a 1-year-old at home adds a whole lot to your plate.
So I really could’ve done without coming home on Sunday night to find that the garage door opener wasn’t working. it was just one thing too much for me to handle — the classic straw that broke the camel’s back.
I got myself twisted in knots for a few minutes about the garage door opener. I procrastinated for a day and got myself more angry about it. Really? Now this? And then I stopped spinning my wheels and decided to fix just the one thing.
I went to YouTube (bless you, YouTube), and found a tutorial. Two minutes later, I’d fixed the garage door. (Turns out it was a super simple fix. I literally just had to push a button.)
I still have a mountain of work to do. But just getting that one tiny task completed felt like a victory. I did this one thing — I can do the rest.
I didn’t need to do it all. I just needed to take care of that one thing.
Last night, we went down to Sundance to see a few singer-songwriters from Nashville — Trannie Anderson, Josh Jenkins, and Matt Jenkins — perform on stage as part of a series of concerts with Nashville’s famed Bluebird Cafe. Together, the three of them have written songs played by some of the biggest artists in country music: Lainey Wilson, Walker Hayes, Keith Urban.
But as they told stories about their work, one thing came up over and over again: It takes an awful lot of writing songs just to get one song on an album. The Jenkins brothers told a story about writing a song for an artist, who passed on it — before deciding to record it several years later. Anderson told a story about working a job as a dog walker for a famous country musician who ended up recording one of her songs almost a decade later. All of the artists on stage said that they might have to write a 100 or more songs just get one that’s worthy of being recorded. (And there’s still no guarantee that the song will end up on an album!)
Sure, there are overnight success stories out there, but to me, the night was a reminder that it usually takes a lot of work, a lot of patience, and a lot of rejection to get to where you want to go.
———
I took that photo during the show. The stage at Sundance is absolutely spectacular — it’s built into the hill, with just a little backlight against the dark night sky. If you get a chance to go there for a concert, you should.
I have all sorts of to-do lists. I’ve got a list of ideas — “somedays,” I call them — that I want to try. I’ve got notes written down on yellow legal pads and in various Google Docs. I know I won’t act on many of these ideas.
I never worry about running out of ideas, but I know that sometimes, I forget about a really good idea. So it’s helpful to keep coming back to these lists to look through things. What am I still excited about? What could I work on as part of another project? Often, I find a chestnut in one of these docs — but I have to make sure to make time to review and give each of the ideas some thought. I don’t want to let anything slip through the cracks.
———
That photo of a small notepad and wooden pencil on top of a wood table, was taken by Michaela St for Unsplash.
On a call today, a client asked me an interesting question. “A few people unsubscribe every time we send an email,” they said. “Is that normal, or is that something that happens just to us?”
The good news, I told them, is that it happens to everyone. I used to write a newsletter called This Week in Cats, which had a 60%+ open rate — at a time in which being above 40% was rare — and we saw unsubscribes every week. (I still have no idea what those readers thought they were getting into.) If that newsletter lost readers every week, then every newsletter will lose readers.
But the bigger thing: I’m glad they had the courage to ask the question. Building something new can be a lonely business. It takes guts to be willing to ask: Is this normal? Or am I going through something that nobody else goes through?
Be brave enough to ask. You might find that what you’re going through is a lot more common than you think.
———
That’s a photo of an early edition of This Week in Cats, featuring that week’s cat of the week — a cat, with a white belly and brown and black striped fur, sitting upright and looking surprisingly sad.
Jon Stewart did this great interview the other day with Matthew Belloni on “The Town” podcast, and this part really stuck with me:
Jon Stewart: Post-mortem is the gift to the gods in terms of improving content and really anything.
Matthew Belloni: So Tuesday morning, it’s, “What did we do right? What did we do wrong? Did this land? Did this not?”
Jon Stewart: It‘s Monday night, and it has to be an agnostic process. It’s not a blame process. It’s always a constructive, like, “How do you feel that worked out?” You always have to be self-examining, reflective of the process, little things, because it’s the only thing that keeps you on top of it.
It’s a lesson I think more of us could apply to our work.
Running an end-of-the-year campaign? Make sure you put time on the calendar the week after the campaign ends to review everything and document lessons for next time.
Launching a new newsletter? Set up check-ins on the calendar every few months to make sure you’re meeting your goals and want to continue investing in that newsletter.
Building a new business? Make sure you hold quarterly reviews to track what’s what working, what isn’t, and what you want to do next.
It’s not enough to put the work out into the world. You also have to make space to review, reflect, and iterate.
———
That photo of Jon Stewart accepting a Peabody Award on stage in 2005 — he’s in a black suit with a dark tie and is behind a podium with a gold replica of the award — comes via the Peabody Awards and a Creative Commons license.
Every year, I spend a few days with friends who also have their own solo businesses. The offsite, as I’ve come to know it, started with just one friend. It’s grown to a group of four — each of us with our own unique perspective on how to build a great business.
Last night, I gave a presentation to the group, where I walked through a few ideas for the future of Inbox Collective. Some were small ideas that I wanted suggestions about; one was a major moonshot for the business, something that would radically change the course of the business. I wasn’t sure if I was ready to do something so big, something that might take Inbox Collective from a one-person operation into a pretty sizable business. But I wanted to know what they thought.
And I loved that the group had a unified response to that last idea: We love the idea as a business — but we’re not sure we love it for you.
It’s exactly what I’d been thinking, so to hear three friends immediately come to the same conclusion was heartening. Their hesitancy gave me confidence that I was already on the right track. Some ideas, even if they’re interesting, are worth saying “no” to.
Today, one of my friends here on the offsite tried to offer an apology. “I hope we weren’t too harsh about that last idea,” he said. I waved him off. I told him: I presented the idea because I wanted to know what you three honestly thought about it, and the fact that you all were so skeptical of the idea — and skeptical because you felt it didn’t line up with my current priorities and needs — told me everything I needed to know.
I wanted the feedback, good or bad. I’m glad I’ve got a group in my corner who can point me away from the ideas that don’t make sense for me.
A few years ago, I saw Adam Sandler perform live. He was recording what would become his first comedy special in decades, and honestly, I wasn’t sure what I was in for.
What I was in for, it turned out, was something both funny and unpolished.
Sandler’s set, which he’d trim down to about 70 minutes for TV, ran nearly two hours. He performed original songs and some stand-up material. Some bits worked; others didn’t. The cameras rolled the whole time.
What I discovered later was that this was Sandler’s creative process. He does the same thing with movies: He records lots of takes, lots of different ways, and then figures out which is the funniest once he gets to the editing bay. The goal when he’s recording is to capture all sorts of options — he’ll figure out what works later on.
That’s not a bad way to approach your work. Some things become hits, and others flop. You don’t really know which is which when you’re making it. You can’t always see around corners.
So instead of hoping that your first idea will be the right one, try doing a bit more than you expect. Leave yourself some alternatives. If something doesn’t work, that’s OK. You’ll have a Plan B already waiting for you.
Here’s a little trick I use to decide if I actually want to work on a project:
Let’s say I’ve got an idea, and I get really excited about it. I buy a domain for the website for the project, and start jotting down notes. I’m convinced that this is my next big idea!
The next step’s been a game changer for me: I go and add a note to my to-do list — one month in the future. I remind myself to revisit the idea then.
And then I do nothing — at least for 30 days.
Often, a month later, I look at the idea and go: Why was I so excited about this? That’s not a bad thing, I think — I’ve just saved myself a bunch of time and effort on an idea I wasn’t all that excited about!
But if I’m still excited about the idea a month later, that’s how I know it’s worth the investment, and that’s when I actually start to work on it.
———
I like to use Domainr to come up with domain names. But I don’t think yournextnewsletteridea.com is my next project!
