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.

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

Now’s No Time to Stop.

At the start of the year, I had a revenue goal in mind for Inbox Collective. Revenue isn’t the only metric that matters to me, but it’s certainly an important measuring stick for a consultancy like mine.

This week, I broke my revenue goal for 2020 — with two months to go in the year.

But I’ve still had this odd feeling all week. Work is good, I’m as busy as ever, and thrilled about the clients I’m working with. I just hit a big goal, despite all of the obstacles that 2020’s thrown my way!

And yet, there’s this nagging fear: What if this all goes away? What if the business hits a rough patch? What if my clients leave?

What I’m recognizing is this sense of paranoia that I’ve seen in several founders I look up to. It’s a sense that you can’t get complacent, even when business is good. I know I have to keep learning and keep creating new ways to help my community. I know I need to think about new revenue streams. I know I have to start thinking about big choices for 2021 — where I might expand my work, and ways for me to better serve the clients I have.

I feel like I can see around the corner to what’s coming next, and I’m excited about what lies ahead. But I’m still nervous. None of this is guaranteed, and I know I have to keep working to move this business forward. I still have a lot more to learn.

Yes, I’m taking some time to celebrate the little victories — that’s so important! — but I can’t get too comfortable just yet. There’s so much more work to do, and it’s up to me to keep moving.

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That stock photo — of a motorcycle going through the mud, which, honestly, doesn’t have anything to do with this post — comes via Gabriel Sanchez and Unsplash.

Here’s to Another Year.

I left The New Yorker a year ago today. Leaving a place as special as that to start a consulting business is a true leap, and I’m lucky to have had so many amazing people supporting me on this journey.

To everyone who offered words of encouragement, advice, introductions; to everyone who shared my Google Doc with their friends; to every client who believed in me and decided to take a chance to work with a one-man newsletter operation:

Thank you.

And, of course, to Sally, for encouraging me to take the leap. I could not have done this without her.

Here’s to an amazing, unexpected, unforgettable first year. And here’s to wherever the road leads next.

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Thanks again to Wesley Verhoeve, who took the headshots on my site. They’ve been republished here with his permission.

Introducing Inbox Collective, a New Email Consultancy.

In a few weeks, I’m leaving my job as the Director of Newsletters at The New Yorker.

Why would I leave a dream job, you might be wondering?

Well, I’m opening up a little consultancy to help brands with email.

I’ve been working in this space since 2012, when I became the first Newsletter Editor at BuzzFeed. When I first started working in email, it was hard to find anyone in the news space who had expertise in email. Now, most news organizations and brands are investing in it.

But there’s still more work to be done! Ever since I started Not a Newsletter back in January, I’ve been getting notes from readers, telling me about their email goals and aspirations. So many of them have told me that they need help with all parts of their email program — from content strategy to growth, from monetization to deliverability.

And at some point, I realized: The work I’m doing with Not a Newsletter isn’t enough. I can do even more to help this community.

So I’m starting up a consultancy. It’s called Inbox Collective, and it’s here to help news organizations, non-profits, and other brands grow audiences, build relationships, and get results via email.

Interested in working with me? You can read more here.