• by Kaila Colbin , Featured Contributor, April 18, 2025

Editor’s Note: Today we say goodbye to Kaila Colbin, a regular MediaPost columnist since -- wow! -- 2007, as she points out below.  As her longtime editor, I’ve appreciated her distinctive, big-hearted perspective on the business world and technology, most lately with a focus on adding humanity back into AI. We don’t usually allow self-promotion in commentaries, but for her farewell appearance, we’ll let her address readers directly with additional contact info.  

Kaila, we will miss you.  -- Phyllis Fine

I wrote my first article for MediaPost on July 18, 2007. It was titled, “Want Passive Revenue? Give Your Product Away.”

I was terrified readers would point out all the ways my ideas were wrong and stupid, convinced they would spot the intruder immediately.

But that didn’t happen.

I wasn’t any kind of instant success, but neither did the immune system reject me. I was just kind of… there.

So I kept going.

My schedule varied; sometimes I wrote every week, sometimes every few weeks. I wrote for Email Insider, Performance Marketing Insider, Search Insider, Media Insider. Wherever they wanted me. I became slightly less terrified. I grew the muscle and developed the grit of just doing the thing.

Every now and then, I’d write something I felt truly proud of. In 2009, I wrote a column called, “My Father’s Stroke And The Incredible Power Of Habit,” about the ways that some neural pathways get so deeply etched in our brains that they can survive even a cerebral hemorrhage. A few months later, I wrote, “Find the Kitchen: Your New Online Marketing Mantra,” a piece that holds up enough, 16 years later, for us to have republished it this past November.

In nearly 18 years, I’ve written 592 articles for MediaPost. Around 350,000 words. Maybe five books’ worth. I feel proud of that accomplishment. But mostly, I feel grateful.

My editor, Phyllis Fine, and MediaPost Chair and CEO Ken Fadner allowed me to do all that writing. They supported and encouraged me to do it.

They never told me what to say. They never tried to control the direction of my columns. They never asked why I was writing about my dad for a performance marketing blog.

That doesn’t mean they did nothing. Phyllis’s careful editing made my work better. Having a deadline and an editor pushed me to a level of commitment I would have struggled to attain on my own. It forced me to develop the muscle of having and articulating opinions. It forced me to pay attention. It forced me to think. I don’t have words for how valuable I believe that to be.

The magic of time zones meant that my columns were officially due before I went to bed on Friday. Many’s the time I sat there at midnight or one in the morning, staring blearily at the screen, praying for my half-formed idea to just f’ng finish gestating so I could go to sleep.

If I didn’t have Phyllis on the other end, waiting for my submission, I would have given up years ago. As it stands, contributing to MediaPost has been the most enduring thing I’ve ever done.

Now it’s time for me to say goodbye, and go all-in on my company, Boma. We’re using sports to inspire a world of intentional, intelligent, courageous leaders.

While I still have lots of Opinions™, they are typically less about advertising or technology and more about leadership and communication. If that’s something you’re into, please feel welcome to connect on LinkedIn or sign up for my newsletter at KailaColbin.com.

Whether or not you’re keen to stay connected, please accept my thanks. Thanks for not pointing out all the ways my ideas were wrong and stupid. Thanks for not calling me out as an intruder. Thanks for giving me the space to grow the muscle, develop the grit, do the thing.

You’ve meant more to me than you’ll ever know.