Michael Levitz
January 26, 2025
I’d love to see a scientist analyze what’s going on in marketers' minds as we press “Schedule or Send” on a newsletter. So many decisions, big and small, collide in that moment. It’s an amazing rush of excitement, doubt, leap of faith, and an ever-growing mental checklist of everything that has ever gone wrong or almost gone wrong in the past.
Did I feature the right content? Make it relevant for my audience? Nail the subject line? A/B test the right thing? Triple-check all the links (after I had already triple-checked them but then made a couple more changes). And double-check all the settings?
As I procrastinated in my favorite way - watching smart people talk about things I don’t understand on YouTube - I came across author Daniel Pink talking about his new book, The Power of Regret. This stopped me, mainly because I was looking for an excuse to stop:
Treat regret as facts, as information, as signal, as data.
Successful newsletters balance delivering on what works and keeping things fresh. If your newsletter becomes predictable and formulaic, your audience might tune out - there’s no new value for them. Stray too far from why they joined in the first place, also tune out - this isn’t what they signed up for.
When talking to marketers about their newsletters, experimentation is one of the hardest things. There is pressure to keep the metrics steadily moving up. Any tick downward is a real risk. It’s lost engagement and lost revenue. And it just looks bad on us. If an experiment fails, we might never give it another chance, even if there is a great idea in there.
That feeling of regret, it turns out, can be a great way to identify the experiments that matter most.
We probably made a hundred decisions yesterday, and today we don't remember most of them. But there are decisions and indecisions we do remember, and they still bug us. That's pretty strong signal. Listen to this signal. There's a lot of evidence that regret can help us become better problem-solvers and strategize better.
As good as your last newsletter was - now you've got to do it again. And again. And now you've made your job harder because you naturally want the next one to be better than the last one.
I show up in my office every day at 8:30 and write. Then I do it the next day, and the next, and the next. I even do it on the days when I don't feel like it, especially on those days. It's like the famous Dr. J quote: Being a professional is doing what you love, even on the days you don't feel like doing it.
Maintaining publishing frequency, continually raising the bar for our audience, and impacting business results - we don't have the luxury of picking two. We need to make all three true all the time.
Pink found that people everywhere had the same four types of regret: foundation, boldness, moral, and connection. I'm thinking of these as my new secret dashboard view in Klaviyo.
Foundation regrets tell us when we're skipping the basics. Did we skip the proofreading? Rush the research? These regrets remind us that great newsletters are built on consistent, fundamental work.
Boldness regrets signal the experiments we should have tried. That edgy subject line we pulled back from, that hot take we softened. These are pointing us toward our next breakthrough.
Moral regrets keep us honest with our audience. Are we living in their world and delivering value through their eyes?
Connection regrets show us where we're missing human moments. That reader email we didn't answer. That community discussion we didn't nurture. These twinges of guilt are showing us where to deepen relationships.
The secret to better newsletters isn't avoiding regret - it's learning to read the signals our regrets send. It's a natural filter for bubbling up what's most important to us.
So, as I hover over that send button, feeling all my doubts and second-guesses, I'll try to remember: I'm not just sending this newsletter; I'm finding what matters for the next one.
Michael Levitz is the co-founder of Forecast.ing, a content prediction platform that helps marketers identify high-performing topics using data science and game theory. He previously led content strategy for global brands like Pampers, Samsung, and Verizon during his time as a Managing Director at R/GA. Michael co-hosts the AI content marketing podcast Forecast.ing the Brief, and his insights have been featured in Forbes, Inc., and TheStreet. Connect with him on LinkedIn.
