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#65: Three lessons from this newsletter

Maryrose Milkovich Ewing
April 22, 2022
a cartoon depicting the stages of a ball being thrown to another person

Talking Big Ideas.

“A year from now you may wish you had started today.”
~ Karen Lamb

Bob and I first talked about starting a newsletter in 2019. As with many good ideas, we shot it down almost immediately. It seemed too daunting.

Maybe we could do a monthly or quarterly newsletter. Definitely not a weekly. That was too much pressure. Too much obligation.

Cut to almost two years later. During our 2020 year-end review, Bob says he wants to start a writing habit.

What better way to start writing than to promise friends, family, and (most importantly) clients that you will send them a well-written, valuable article every week?

I added a newsletter sign-up to our website that said “Coming January 2021.” A few friends and clients graciously subscribed.

We didn’t have any logistics figured out, but Bob decided on a clear theme:

One Idea. One Challenge. Once a Week.

We set specific goals:

  1. We’ll have at least 5 pieces written in the backlog before we launch.
  2. It’ll be a Monday newsletter to kick off people’s week.
  3. It’ll go out first thing in the morning (inspired by our client Matt Paprocki’s staff newsletter).
  4. We’ll finalize each piece at least two days before sending it.


We make our way through January without much progress. A handful of new people subscribe each week, so we know we’re going to have to send SOMETHING out.

The last week of January comes.

Monday passes, no newsletter. OK, maybe it’ll be a mid-week.

Wednesday passes, and still, nothing ready to send out. Well, Thursday is still technically mid-week.

Finally, Friday morning. We edit until 12:30 pm EDT and then hit the send button.

With that, this newsletter became a Friday mid-morning / lunch edition.

We didn’t meet the goals we set for ourselves. Except for the only one that mattered: We started.

Over a year later, we have almost 80 thoughtful, well-written articles to help people become better communicators and leaders.

We use these articles every day in our training. Our clients and readers share them on their own. We’ve even received praise from some of our favorite thinkers like Dan Pink, Chip Heath, and the philosopher Daniel Dennett.

Our weekly process wouldn’t win any business operations awards. (A last-minute Friday morning scramble is not unusual.) But we started. And this newsletter has created significant value for us and our clients (and hopefully for you!).

Here are three key lessons we learned as we went from zero to one:

1. Create accountability for yourself. Bob has talked about building a writing habit for as long as I’ve known him. It became a reality once he put skin in the game. Once he had 23 people on an email list expecting a weekly article from him.

2. Process is overrated. I love optimizing processes. But when you first start something, trying to maintain a strict process can be the death of it. Focus on creating value, not toeing the line.

3. *Capture interesting things you find in the wild. Bob has a unique propensity to gather and remember ideas. His writing process then becomes about synthesizing and connecting those ideas rather than thinking of them in the first place.

Once you’ve created something of value, your next challenge can be to optimize it. Hopefully, in another year we’ll be able to share those lessons.



Start now. Figure it out later.

What’s a project or idea you haven’t started because it feels too daunting? What’s one way you could make more progress on it today than you did yesterday? Do that.


*We have an early prototype of a tool for capturing ideas. If you’d like to check it out, email maryrose@theewingschool.com and let us know!

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