Whenever I talk to my paid subscribers, there’s one question I consistently get asked: “Are you ever bringing back your Office Hours?” 

For those who don’t know, I used to host a live Zoom call at least two times per month. I would pick a topic for the call and then line up some guests who were experts on that topic. Here are two examples of what these calls looked like:

1. How B2B publisher Skift scaled its business by diversifying its revenue streams

2. How Starter Story ditched recurring payments and built a $1.5 million information product

Only my paid subscribers were able to attend these calls and they were incredibly participatory, meaning I would let anyone on the call interrupt me at any point to start asking their own questions to the guests. The best Office Hours calls would be attended by 30 to 40 people and we’d have upwards of a dozen people piping in with their own questions and insights. The next day I would then distribute the video recording to the entire paid list so people who weren’t able to attend could still watch it.

In many ways, these calls were extremely successful, as evidenced by the fact that I still get asked about whether I’m bringing them back. But I ended them anyway. Why?

Well, I put myself under a lot of pressure with these calls. For each one, I’d line up several guests, and I’d be extremely stressed in the lead-up to the call that these guests would have to pull out at the last minute, in which case my subscribers would show up to the call and be disappointed.

At the same time, I also felt extreme pressure to make sure that the call had lots of attendees so that these high-profile guests didn’t feel like they were wasting their time.

Ultimately, I caved to the pressure and ended Office Hours. I instead put my efforts into building out other offerings, and while I think a paid subscription to my newsletter packs a lot of value — after all, it includes a one-on-one phone call with me and an entire library of exclusive interviews with some of the world’s most successful media entrepreneurs — I still can’t help but think I killed something magical when I shuttered Office Hours.

Recently, I was having lunch with one of my paid subscribers and, surprise surprise, he asked me why I never did Office Hours anymore. I relayed to him all the reasons I just outlined above, and he looked at me like I was an idiot. “Stop putting yourself under so much pressure,” he said. “Just announce you’re hosting a live Zoom call, and people can just show up and chat with you.”

To him, the value of Office Hours had little to do with the guests I’d lined up; he really just liked the experience of hanging out with a lot of other professional content entrepreneurs who were dealing with similar challenges. He got just as much value from the random people who piped in with their own questions and insights than he did with the featured guests.

I left that lunch determined to relaunch Office Hours, and I’ve been brainstorming for the past few weeks on how to structure it. Here’s what I’m thinking:

1. About twice a month I’ll send out an email to my paid list announcing a time and a Zoom link for the upcoming Office Hours. I’ll probably still line up a guest or two, but I won’t include their names in the announcement. That way, nobody will be disappointed if they aren’t able to make it.

2. The Office Hours will be a lot less focused on featured guests or specific topics. While I might spend some of the call interviewing a guest, I’ll also spend a lot of time calling on people and asking them to talk about challenges and insights they’re facing with their own content businesses. My hope is that the call will feel like I took a really good conference panel and smashed it together with a really fun networking happy hour.

3. I’ll distribute the recorded video of the call to my email list the next day.

What do you think? Does this sound like something you’d find valuable?

No really. I want to know what you think. I’d love some feedback on this plan, and I’m also open to hearing other ideas for how to format it. You can leave your feedback in the comments section here:

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You can also reply to this email and send your feedback directly.

Lastly, if you’re not on my paid list and think it’d be really fun to attend these calls, now’s a great time to sign up for a paid subscription. Use the link below and get 20% off for your first year:

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