Iron Sharpens Iron Series: Jayson Dubin, Boss

If you are new to the Iron Sharpens Iron Series, I urge you to check out the inaugural post to learn more about what the series is all about.

Iron sharpens iron, and the people in my life sharpen me. They make me better. They make me more than I can be alone. And this series is about interactions I’ve had that make me better, that change my perspective, and that challenge me to grow. 

This is all about interactions that have left a lasting impression on me. No matter how small, or short the interaction, if it leaves an impression worth sharing, it will live in this series.

Jayson Dubin

Jayson is the CEO of Playwire, and the only person I’ve been willing to agree to call my “boss” since I stopped working as a traditional employee nearly two years ago.

The Sharpening of Iron

I was lucky enough to start working with Jayson as a contractor early in 2021. Over the course of our first few months working together, I had the distinct pleasure of working on a case study that had me interviewing one of the most inspiring women I’ve ever met, Lisa Tortolani of ABCya.

Her case study interview already had me on the verge of tears (you’ll see why if you read it), and then she shared how her relationship with Jayson, and the entire Playwire team, played such a pivotal role in a very painful time in her life.

If I didn’t already love the Playwire team (hint: I did), man was I sold after that. Here was a company, and a leadership team, that really put people first. As in: they didn’t just say it, they meant it. They didn’t just talk the talk, they walked the walk. 

Now that I’m finally done with the lead-in, let’s get to what this post is really about… Sorry, I can be kind of a sucker when it comes to the emotional stuff.

After a few months of working together, with this heart-wrenching, beautiful story already fixed firmly in my head, Jayson made an off-hand comment during one of our meetings. It could have been a joke, it could have meant nothing. I still remember it word for word: “What’s it going to take to get you here full time?”

And apparently this is Jayson’s style, as I’m not remotely the first person to join Playwire in this manner. I guess he has a good eye 😆.

That little comment that could have been a joke planted a seed that never left the back of mind. Much like the Princess and the Pea, he planted an idea that, no matter how many mattresses I tried to stack on top of it, wouldn’t quite leave me alone.

And then, other signs began to arise telling me it was time for a change, like this little gem from one of my favorite authors appearing magically in my feed:

I finally decided that it was time to reconsider what I’d always thought was the right path for me; I realized I couldn’t keep ignoring the pea.

Jayson had seen in me what I’d never quite been able to see in myself. And (as long as I don’t drive him completely insane next year), I’m pretty sure he was right. So now I find myself taking a step I never thought I’d take, stepping up to do something that, while challenging, is exactly right.

So, thank you Jayson, for believing in me (and for the future you have of putting up with me). I can’t wait to jump in!