It Never Gets Easier.

skiier going off the jump

There’s this lie that we tell ourselves when things are complicated and hard: “Once I get through this stretch, things are going to get easier.”

I’ve told myself this more times than I can count. Dan, if you can just finish this task… if you can just get through this month… if you can just take care of this deadline — it’s going to get easier from there.

But that’s not really how this works.

It’s OK that things can be hard. Things can be hard because you’re trying to learn new skills or taking on new challenges. Things can be hard because you’re in a new role or a new job. Things can be hard because you’re pushing yourself to get better. Things can be hard because life gets in the way — you’ve got more responsibility or more people to care for than you did when you were younger.

Every so often, I have to remind myself: Things are never going to be quite as easy as they are right now. Work — and life — tends to get more complex over time.

But you’re going to find a way to push through and keep doing the work. You’ve done it before, and you’ll do it again in the months and years to come. Things never get easier, but you’re also getting smarter and savvier, and building the team to help you take on these challenges. You’ll be able to take on tomorrow’s obstacles as they come.

So enjoy this moment, right now. Yes, things seem overwhelming some days. But these challenges and obstacles will beget new ones. One day, you’ll look back on these moments and tell yourself: What I would give to merely have those types of problems today.

It’s not getting easier, but that’s OK. You’ll be able to take these challenges head on anyway.

———

That photo of a skiier going off a jump comes via Unsplash and Maarten Duineveld.

One Day Chicken, Next Day Feathers.

A few weeks at the PGA Championship, I watched as Garrick Higgo — a 22-year-old South African — teed off on Sunday at 7:40 a.m. That’s what happens when you’re eleven shots over par, as Higgo was after three rounds. (For the non-golfers out there: The pros typically shoot several shots under par.) He’d had a tough tournament, and I was mostly watching because, well, it was something to do while eating breakfast on a Sunday. I watched Higgo for a little while, and it was clear that he could play — it just hadn’t been his week. He hit several shots close to the flag, and seemed to play freely without the pressure of having to worry about winning the tournament. The announcers mentioned that Gary Player, a retired South African golfer and winner of nine major championships, was a mentor of his. (Not bad when your mentor’s in the Hall of Fame.) That Sunday was Higgo’s best round of the entire event: He shot a 69, good for three shots under par. The PGA Championship was his first-ever PGA Tour event.

I remember watching and thinking: Here’s a pro golfer — he’d never played on the PGA Tour, but he’d won several events in Europe — who clearly could play. In his previous four pro events, he’d finished in the top ten all four times, and won two of them. But even a pro sometimes can’t seem to find his swing.

Anyone can have a bad day, or a bad weekend, even if you work hard and have all the talent in the world. As a friend from the midwest once put it, folksily: “One day chicken, next day feathers.” Bad days happen.

Still, you keep moving forward. The PGA Championship was Higgo’s first-ever PGA Tour event. But I imagine Gary Player told him after the tournament: Pick up your head, kid. If you do the work, and keep competing, you never know when you’ll break through.

Turns out he didn’t have to wait long. A month ago, in his first PGA Tour event, he finished in 64th place, fourteen shots behind the champion. Today, in his second PGA Tour event, Higgo won the whole thing — and the $1.3 million grand prize that came with it.

I suppose there’s another fowl-friendly quote that my midwestern friend would’ve used for an occasion like this: Winner winner, chicken dinner.

Create an Imperfect World. Then Improve It.

Here's a photo of several books

The New Yorker did an interview with John Swartzwelder, one of the most prolific writers in the history of “The Simpsons,” and a man who is legendary for his privacy. (The New Yorker described him as “reclusive, mysterious, almost mythical.”) The interview’s fascinating and funny, but I particularly enjoyed this part:

How much time and attention did you spend on these scripts? Another “Simpsons” writer once compared your scripts to finely tuned machines—if the wrong person mucked with them, the whole thing could blow up.

All of my time and all of my attention. It’s the only way I know how to write, darn it. But I do have a trick that makes things easier for me. Since writing is very hard and rewriting is comparatively easy and rather fun, I always write my scripts all the way through as fast as I can, the first day, if possible, putting in crap jokes and pattern dialogue—“Homer, I don’t want you to do that.” “Then I won’t do it.” Then the next day, when I get up, the script’s been written. It’s lousy, but it’s a script. The hard part is done. It’s like a crappy little elf has snuck into my office and badly done all my work for me, and then left with a tip of his crappy hat. All I have to do from that point on is fix it. So I’ve taken a very hard job, writing, and turned it into an easy one, rewriting, overnight. I advise all writers to do their scripts and other writing this way. And be sure to send me a small royalty every time you do it.

That’s interesting. So create an imperfect world and then improve it?

That’s the way I do it.

I absolutely love this idea. And the most interesting thing for me is, it’s actually the second time I’ve heard this idea this month!

The other time? On the podcast “Two Writers Slinging Yang,” as shared by award-winning food writer Alan Richman. He told host Jeff Pearlman:

I would sit down with my notes in front of me and whatever’s in my head, and I would write a first draft, and I would make sure it was much longer than the story was going to be. I would write maybe three or four thousand words, just off the top of my head, just spewing it out and typing it, and I knew that was not going to be the story. But that gets everything out of my head. By doing that, I would say, “Oh, this is important.” I would start to see what I had in my head and what would make the story… I always wrote a first draft as fast as I could until I got everything out of my head and on paper. And then I would write the second draft, and that’s when I’d start to write.

Someone once said all writing is re-writing, and that’s what I believe in. I re-write and re-write.

Here are two very different writers: A comedy writer, and a writer of long food feature stories for GQ. But they both know their strengths — they’re good at re-writing! — and have built their creative process around that strength. When you’re a writer, you’re judged on your output, not your process. Who cares how you get there? All that matters is that you get there.

Whatever it is you do, play to your strengths. Figure out what you like doing most, and see if there’s a way to build your process around that.

———

That photo of old books comes via Unsplash and photographer Patrick Tomasso.

I Don’t Have All The Answers. But I Do Have A Few Questions.

here I am giving a talk back in 2019 in Sydney.

Last week, a friend was giving a presentation for work, and asked if she could include a slide with a few email tips she’d learned from me. At the top of the slide was an explanation of who I was.

“Here’s some advice from Dan Oshinsky,” she’d written, ”newsletter guru.”

I cringed.

The truth is, I’m not a guru, or an expert, or any of the other titles that people throw around. I’ve seen a lot in my time in this space, and shared a lot with others. But the thing I like most about my job isn’t that I get to share what I’ve learned with my clients.

It’s that I get to keep learning.

Often, as I get to work with a client, we’ll realize that there are things they want to try that I don’t have the answers for. And to me, that’s the most exciting part of the job — the chance to learn something completely new!

So we’ll start asking a few questions. We’ll dig into the issue. I might even reach out to others who’ve tried something similar, just to get their perspective.

And then we’ll start to test and learn. We’ll keep asking questions until we get some answers — even if they’re not the answers we expected.

I know that I don’t have all the answers. But I have a lot of the questions to help me figure out how to get the answers that me and my clients need.

———

That’s a photo of me giving a talk at an event in Sydney in 2019.

Slowing Things Down.

turtle

Time’s moved in a strange way during the pandemic. In the early days, the weeks seemed to draw out for ages. But an odd thing’s been happening lately: Time’s seemed to be moving much more quickly. It’s like I’ve accidentally sped up a podcast — from 1x speed to 1.2x speed, a change small enough that I didn’t really notice it at first. Over the past few weeks, though, it became pretty clear that something had changed. On Tuesdays or Wednesdays, I’d start thinking, “The week’s almost over, and I haven’t accomplished enough!” The time between certain monthly tasks seemed to shrink. Everything just seemed to be moving a little faster.

I’ve got a thought as to why this might be happening. I’m reading Tom Vanderbilt’s “Beginners,” in which he talks about why it’s so important to keep learning, especially as we get older. In one chapter, he learns how to juggle, and writes:

The more things you have to pay attention to, the faster time seems to move. But as you get better, you learn what to pay attention to. You have a better sense of what to expect. Suddenly, you’re not thinking about the balls at all. You’re just tracking a pattern in the air. You have all sorts of spare attention. You can carry on a conversation while you juggle. Time seems more unoccupied, and thus slower.

As I started to think back on the past few weeks, it hit me: Something actually has changed this spring. I’m working on a few big projects unlike any I’ve tackled before. I’m — apologies, but it’s the right phrase here — juggling also sorts of new work and tasks, and with so many new things to keep track of, I’m much more aware of everything that needs to get done.

I know that over time, as I get better at these tasks, things will slow down. But I’m also trying to do what I can to slow time down on my own. I’m building breaks into my day to do more reading. I’m trying to find excuses during the week to step away from the work — after I finish this post, I’ll take a long walk down to the farmer’s market in my neighborhood. These moments are an opportunity to pause, to reset, and to prepare to jump back into the work.

———

That photo of a turtle comes via Unsplash and photographer Patti Black.

Ask Simpler Questions.

people raising their hands

When I sit down with a potential client, the first thing I do is start asking a few questions.

Often, I’ll be excited to interject a few suggestions or ideas. (“Oh, I love that you’ve tried that! You know, I’ve got a client who tried something like that last year…”) I know that if I start talking, I might ramble on for a while. So I’m always working to quiet that urge. When I give the client space to open up, I typically get the best answers from them.

Whenever possible, I try to keep my questions as simple as possible. I start with the big questions:

∙ Where do you see opportunities to improve?

∙ What do you hope to achieve with this project?

∙ What does success look like for you?

And then I start to drill down further. A question about success, for instance, might lead to other specific questions:

∙ What metrics matter to you?

∙ Where are you tracking those metrics?

∙ How much do those metrics influence the choices your team makes?

If I can ask a question in a single sentence, I do. Be direct, and give them room to reply. After that, it’s up to you to listen — and when they’re ready, ask another.

———

That photo of people raising their hands comes via photographer Edwin Andrade and Unsplash.

Brand = Trust + Time.

clocks

How do you build a great brand? It’s simple, at least in theory: By establishing trust over time.

Trust is about relationships. It’s about setting expectations for your reader, your user, or your customer, and then exceeding them. It’s about being there when they need help. It’s about doing good work that serves them well. It’s about asking questions, and listening to their answers. It’s about doing the right thing for them, and being transparent about your choices. It’s about offering them good value for their money. Trust is hard to win and easy to lose, so you have to treat your audience with respect, and hope they keep placing their trust in you.

Some might disagree, but trust can’t really be bought. It’s something that must be earned, through thousands of tiny actions, over the course of months and years. There is no shortcut to establishing trust. You can hire a spokesperson to recommend your product, ask your clients to refer their friends, or spend big on marketing. But those merely accelerate the process — they put you in position to build relationships faster. You still need to do the hard work of establishing trust with that audience, and that’s only going to be done over time.

Trust and time, trust and time. To build a brand, it’s the only way forward.

———

Those clocks come via Heather Zabriskie for Unsplash.

Do The Stuff That Doesn’t Scale.

So here’s a story: It’s September 2019, and I’m flying to New Orleans for the annual Online News Association conference. It’s my first one representing my own business. I’m not Dan from BuzzFeed or Dan from The New Yorker anymore.

I’m Dan from Inbox Collective.

I want to do something to make as many connections as I can while I’m there. All year, I’ve been doing stuff that doesn’t scale — guest posting on other blogs, doing podcast interviews, sharing my content 1-to-1 with friends in the industry. My newsletter’s growing, but I know there’s more room for growth.

So I announce that Not a Newsletter is throwing a happy hour. (Naturally, I call it Not a Happy Hour.) I invite anyone to come out — drinks are on me. I hand my credit card to the bartender and hope the bill won’t be too extravagant.

50 people showed up that day. A bunch of readers brought friends, which meant that I got a few newsletter subscribers out of it — but I also landed three new clients from that night, and got asked to give a keynote talk at a conference. (The total bar bill: About $400.)

When you’re growing an audience and building a brand, do things that don’t scale. That’s where your initial growth is going to come from.

And remember to tip your bartenders well in the process, too.

You Have to Do the Work First.

it's a long way to the top

There’s a project I’m working on right now, and I’m pretty excited about it. Sometimes, I’ll spend a few minutes thinking about the positive outcomes: What might come of the work, how others might want to get involved with it, too. I’ll daydream a little about where it might lead a few months or a few years down the road, thinking of what happens if this and that and the other thing all go right. If I really get lost in my own head, I’ll start wondering about how I’d publicize the project — the interviews I might do, the outlets that might want to cover the work.

And then I remember that every hour I waste thinking about the work instead of doing it is an hour I can’t get back. None of this can happen until I start doing the work first, and who knows where the work will actually lead me.

So: I forget about the next steps and the what ifs, and I get back to work.

———

That photo by Victor Lozano for Unsplash is a reminder: There’s a long way to go to the top.

You May Have to Say No.

stop here

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.

———

That photo of a traffic signal comes via Kai Pilger and Unsplash.