Things I learned this year

Adventures on the independent path

This is the last edition of the year for The Rebooting. Thanks so much for reading this year. I’m now a little over two years into this project, which both feels like a long time and also like I only got started. I’m going to do a brief review of some things I’ve learned this year on that front, as I figure out how to balance growing with making something I want to make.

Quick reminder: Come to “The Sustainable Journalism Imperative,” an in-person event I’m putting on with Outbrain at the Consumer Electronics Show in Las Vegas. We’re going to have a discussion of the need for advertiser support for local journalism with GroupM chief innovation officer Krystal Olivieri and other industry leaders, along with lunch. The event is on Thursday, Jan. 6, at 11:30am local time.

Things I’ve learned this year

Getting something new off the ground is a mix of excitement and frustration. Anytime there’s an up, you can be assured it won’t last. Of course, there’s reassurance that the opposite also holds true. We all have a tendency to overrate the short term and not appreciate the long term. I’ve always found that with any form of growth. We always expect more short term progress, yet we underappreciate overall growth through the inevitable peaks and troughs. Here’s some things I’ve learned.

Simplification is leverage. The biggest challenge I’ve found in doing The Rebooting as a solo endeavor is the sheer number of things that need to be juggled, a particular challenge for someone who isn’t a natural multitasker or particularly organized. The only way out of that is to ignore things. One of the good parts of Substack is being able to ignore all the platform decisions and inevitable troubleshooting of building your site. There is an obvious cost advantage, but I think the bigger one is simply not thinking about it. I liked what Morning Brew CEO Austin Rief said on a recent episode of the My First Million podcast about Morning Brew’s early days. They boiled down what they needed to do as simply “write, grow, sell.”

Realize there are no shortcuts. Anytime I’ve been injured running, I tend to believe there’s one stretch or massage that will miraculously heal the injury. Never turns out that way. Building from scratch takes patience and perseverance. We tend to lionize the “overnight” success stories that typically took longer than billed, found a temporary growth hacking seam, or at the very least are outliers. For the rest of us, making something new is a slog defined by incremental progress, mixed with setbacks, followed by more incremental progress. I start with the assumption anything I want to accomplish will end up taking twice as long, and be twice as hard as I thought. Sets expectations. And it will be imperfect. One of the main challenges of editorial people starting a business is the need to accept the inevitable rough parts of early products. People tend to be forgiving — thanks for that.

Solo will only take you so far. Unless you’re going to go all in on being a Substacker with a pure subs model, the solo creator is mostly a myth. Nobody can do it all. That means building a support team to make up for your own deficiencies. My plan was to expand The Rebooting this year already with new verticals. That didn’t happen. I realized it will just take longer with an independent path and relying on cash flow rather than raising capital to fund expansion. If this way takes longer, it takes longer. I’m now working with Paul Turcotte to build out a real sales engine. I don’t think I’m bad at sales – we’re all in sales, after all – but I also don’t have the expertise in packaging together successful programs that someone like Paul has. It’s been great to have someone to work with to solve problems. And, since Paul is based in Miami Beach, I think I can plausibly write off trips there. If there’s one aspect of this project I’ve found surprising, it’s how challenging it can be to work by yourself most times. It’s one reason I’ve found adding the People vs Algorithms podcast rewarding. (You should check it out.) Working with smart people like Troy and Alex is rewarding.

Ask for help. This might be a Gen X thing, but the idea of asking people for help with something is somewhat foreign. Maybe it’s because we were all left to our own devices for most of our childhoods. One of the most gratifying parts of doing this is how helpful people have been along the way – and understanding of the inevitable errors and screwups that are part of the building process. The most valuable resource is having a network of people you can ask for help. The flip side of that is making time and being available to others. The only real career advice I feel qualified to give to others is to avoid being overly strategic and transactional in your relationships. It’s a waste of mental energy, and you’ll probably end up in a far better position if you try your best to be genuine and not just think of yourself all the time.

But go your own way. I haven’t had a boss since October 2020. This has been nice, but not for the reasons I expected. Taking an independent path is, like most things, a tradeoff. There are so many downsides and risks to taking an independent path. Until a few weeks ago, I had no revenue commitments at all going into 2023. That can be scary. You need to trust that if you put in the work, things will inevitably work out, as they are now. (You should get in touch to discuss how we can work together in 2023, btw.) The upside is the autonomy. Like it or not, you have to make it happen. You can make what you want and choose the path that is right for you.

Year-end Recommendations

In what I hope will be an annual tradition, I joined my former colleague Mike Shields on his Next in Marketing podcast. Mike and I have known each other for a good 15+ years — I still regularly remind him of the time he took me to Starbucks to tell me he was leaving Digiday — so it makes for an interesting podcast dynamic, hopefully good. One of the issues we talk about is how digital media has failed to create lasting brands. I want to be optimistic on this front, but the track record isn’t great.

For year-end predictions in ad tech, Scott Messer has a good rundown of what the pivot from the growth to efficiency will mean for publishers. One piece of good news amid an uncertain 2023: It’s nearly assuredly not going to be the year of mobile.

A new year is a good time to contemplate what the next big thing will be. The candidacies of crypto and the metaverse flagged in 2022, but artificial intelligence came on strong. This wide-ranging roundup has a lot of good thoughts from the tech world, but my favorite is Scott Belsky’s view that 2023 will be a time for resetting expectations created during boom times.

We tackled the year-ahead thematically in a couple of episodes of the People vs Algorithms podcast. In one episode, I discussed with Troy Young and Alex Schleifer what to expect from artificial intelligence and we spent another focused on how platforms will face a far different environment. Check the episodes out on Apple or Spotify.

For the news industry, Nieman Lab’s roundup of predictions for the year ahead is good to check out. There’s some usual gloom and doom in there, but I liked Bloomberg’s Julia Beizer’s take that the news industry will continue its shift to being audience focused to build sturdier business models.

The new year means turning the page. Packy McCormick at Not Boring has a nice essay on both the freedom and the panic that a blank page induces. Anyone who writes often can agree with this metaphor.

Thanks again for reading The Rebooting. I know it’s cliche in these end-of-the-year posts, but I truly appreciate it, and the support from all the great partners I’ve had this year on the sponsorship front. Have a wonderful holidays.