Celebrating milestones: an important leadership practice

Published by Peter on

A lot of highly successful and highly productive people don’t put enough emphasis on celebrating milestones. In this week’s post, I’m going to celebrate a few of my own.

If you read to the end, you’ll see why this is important and why it isn’t just pure self-indulgence.

100 blog posts

Last week I published my 100th weekly blog post. That means that this is #101, and in three weeks I will have completed two years of posting new weekly content.

It started with a post about why I was quitting my job. At the time, I knew I wanted to post here regularly, but I hadn’t committed myself to any particular schedule or content type. It was just a vague notion. Two years later, here we are.

Every post is original. Every post is that week’s thought. Some have been better than others. It’s a lot of work. It takes a lot of time. Is it worth the effort?

This week, in this “celebrating milestones” post, I say that yes, it absolutely is worth the effort. A hundred weeks in a row of any activity is worth celebrating. I am not going to be my own Debbie Downer right now by talking about analytics, metrics, client acquisition, or anything else.

This is post #101. That’s enough for today.

First panel moderation at SFWC

After 15 years volunteering with the San Francisco Writers Conference, this year I moderated a panel for the first time.

All through my career I’ve moderated and spoken on panels, facilitated group discussions, and taught classes. So public speaking is nothing new for me.

“Ladies and gentlemen of the jury…”
(I’m just pointing out where the printed handouts are.)

What was new was that even though I’ve done my 10,000 hours several times over, I finally feel that I’m an expert with knowledge, wisdom, and perspective to share on topics of value to the this conference’s attendees.

Not because I’ve learned so much in the past year, but because I’ve stepped out and done so much more in the past year.

I launched my own publishing imprint. Taught two classes on self-publishing. Designed and published a new style of book using tools I hadn’t used before. My partner and I are very close to publishing another book together. And we’ve also spun up a multi-author collaborative project we’re incredibly excited about.

This panel is more than just one session well executed. It is also a representation of so much more personal and professional growth.

So it’s worth pausing, in the spirit of celebrating milestones.

500 NYT crossword puzzles solved in a row

I do the NYT crossword every day now. I’ve gotten to the point where the Monday puzzle takes less than 15 minutes. When I got to 50 in a row, I challenged myself to get to 100. Then I challenged myself to make it to a full year. Then I just kept going.

Sunday’s puzzle was my 500th solve in a row. I mean, so what? It’s a game. What’s the good of it, really?

I’m celebrating milestones, though, and this is a milestone, so it’s being celebrated. Even though it’s pretty pointless in the big picture.

Today: under 9 minutes.

Why bother celebrating milestones?

I was talking with a client this morning who suffers from a similar affliction as I do: momentum often outpaces intent.

What does that mean? We set out with a goal in mind, and by the time we achieve it, we have such momentum that we can’t do anything but look ahead to the next task, the next goal.

We forget to honor our original intention. We forget about celebrating milestones as we fly past them at full speed. Momentum outpaces intent.

The result is that I can fall into a headspace where I feel like I’m constantly behind schedule. Even though I’m the one setting the schedule, and in fact I may be way ahead of my original intent.

So as we fly by the milestone, we may acknowledge it with a “hooray, but…” As in, “hooray for me for doing that, but there’s so much more to do.”

The “hooray” gets lost behind the “but.” Over time, that can become a difficult thing for high achievers, but it’s even harder for the people they lead.

Celebrating milestones is especially important for high-achievement leaders

I remember a time when one of the members of my team called me a Debbie Downer. Right there in a team meeting. In front of my whole team.

It surprised me, but she was right.

Peter is giving a thumbs-down like Debbie Downer, not celebrating milestones

Here I was, thinking of myself as measured and balanced, but I was so focused on not losing momentum that I was failing to give everyone on my team the much-deserved recognition and much-needed respite of a celebratory moment.

They didn’t need a party, or a paid vacation, or a trophy. They just needed me to pause for a minute and reflect on the success we’d had.

Instead of motivating them to greater things by keeping momentum high, my “hooray, but” attitude was bringing them down and exhausting everyone around me. In truth, it was exhausting me, too.

I think I’m good at recognizing individuals and the value they bring, but I’m less good at recognizing milestones as they’re achieved. It’s something I need to continuously pay attention to.

And I think a lot of highly effective, high-capacity, high-achieving leaders need to be aware of it in themselves, too. You may be exhausting your team rather than motivating them if you aren’t properly celebrating milestones.

I can help.

I work with top executives and middle managers to improve their leadership skills, their workplace culture, and the effectiveness of their teams. Also, I help individuals identify and achieve their personal goals. Would you like to become more aware, be more effective, be more empowered, and feel fully prepared for your next steps?

Let’s talk.

You can help.

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Stay super smart and well informed.

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Categories: Leadership


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