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.


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.


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.

Setting Four Types of Goals: Audience, Financial, Learning, and Leadership.

goal setting

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.


That artwork comes via Katerina Limpitsouni and Undraw.

The Four Obstacles: Time, Money, Stress, Failure

here's a talk I gave in Sydney in 2019

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.


At top, that’s a photo taken of me giving a talk in 2019.

So What Are You Going to Do About It?

I keep having this conversation over and over with friends.

They’ll tell me:

I’m frustrated with the way things are going at work.

I’m frustrated with the state of the world.

I’m frustrated with the way things are in my community.

To which I’ll say: We all get frustrated, and that’s OK. But the real challenge is finding a way to turn those frustrations into fuel, to turn angst into action.

So you’re frustrated by work. What’s the next step here? You could try to build stronger relationships with key players in your office, launch new projects, or take initiative to try to slowly make your office a better, more productive place.

So you’re frustrated by the state of the world. What do you plan to do next? You could donate your time or money to causes you care about. You could read or learn more about actions you could take to make a dent in the universe. You could rally your friends and family to get involved, too.

So you’re frustrated by things happening on your block. How do you want to get involved? Volunteer, or run for something in your community. Find the people or the organizations making change, and join them.

It’s normal to be frustrated, but don’t get stuck in your frustrations. Take a step back and ask yourself: What am I going to do about it?

And then get to work.


As always, the stock footage at top — this, of the gorgeous Boca do Inferno cliffs in Portugal — come via Unsplash and photographer Rodrigo Kugnharski.