About Michael

Founder, Executive Coach and Consultant at C5 Executive Strategies.

Focused on helping leaders at all stages of their careers who constantly ask themselves, "What's Next?".

I am also a former Town Manager with over a decade of experience in that seat. Prior to that I was a musician (guitarist/vocalist).

Those roles may seem completely different. The through-line in all of them is vision and creativity. I like to leave communities, organizations, and people different than when I first encounter them...and hopefully for the better.

Failure found me pretty early in life, and I worked really hard to lift myself up from hard times in order to be successful. I had a lot of help with that, too. It took me a long time to realize that other people's successes gave me a lot more joy and hope than my own.

I enjoy writing, teaching, thinking, and conversations. Also, I like to build and make things. But I've found more success surrounding myself with "doers" than anything I've done.

Read the longer story ↓

The longer story

If there is a through-line in my life so far, it's that I'm a creator.

At first, it was in the traditional sense. As a musician. Writing songs. Improvising guitar solos. I liked to create things that other people found beautiful. But what I really liked to create was emotions.

And as much as I loved that, what I really loved, what made me feel electric, was creating something with a band. Those experiences where the connection and chemistry create moments that go beyond description. In musical terms, you have all found the pocket. It's the closest thing to true bliss I've experienced. If you're a musician, you know what I'm talking about.

So it's understandable that people who know me from that time period scratch their heads at the fact that my professional career has been defined by successfully leading a town for over ten years. They hear "Town Manager" and ask what the heck is that. After you spend some time reciting the job description, the usual response is, "Oh...so kind of like a Mayor".

They think politics. Or even worse, bureaucracy. (Maybe that's not worse.)

I always saw it as an opportunity to create.

I remember when I was interviewed for Town Manager, one of the Board members referred to me as a "numbers guy" and asked how I was going to broaden my view.

If you've ever been introduced by the one thing you're good at, you know how that sits.

But I never saw finances as the be all end all. The finances were an instrument - like a guitar. Because I couldn't build what I wanted to build without the capital to do it. And I learned very early that the decision makers controlled the money.

So I found a town filled with people who wanted to build the same type of community that I saw in my head (There's an important lesson in that by the way). They just never were able to get it off the plans and into reality. And I believe that there was a part of that community that didn't feel like they were worth the investment to make it happen. Otherwise, they would have done it.

If you're an entrepreneur, you probably know that feeling. Having a vision of something and seeing it before other people can see it. And then finding out that the hard part is getting everybody else to see what you're seeing is possible.

So I found my calling for the next ten years; blending inspiration with creativity to build a community that required them to make an investment that was both measurable and reasonable with a belief in themselves that they were worth making that investment.

And we did it. For a little town that didn't spend much, we found a way to leverage every dollar to create amazing things. Converted a rusted, institutional-green metal bridge spanning a waterfall into a beautiful gateway to downtown that has become the backdrop of hundreds if not thousands of photos celebrating engagements, weddings, and senior years.

We worked with the private sector to reinvent a downtown that was crumbling, tired, and disconnected into a town center that people go to so they can meet their neighbors and friends from other communities.

We built a lot. And we celebrated what we built by celebrating together.

If you've ever celebrated with a team, company, or community you helped build, you know the sensation of this is hard to communicate.

And pretty soon, people outside that little town started to take notice and wonder what was happening. And many wanted what we had. They either moved to town to take part in it, or they replicated what we did in their own communities.

As we accomplished what we set out to do, the recognition for what we did as a community started pouring in. In the spring of 2026 the Boston Globe Magazine named Ashland the top spot to live west of Boston in its price range. What they wrote about wasn't the bond rating or the balance sheet. It was the Corner Spot; a town-owned lot nobody had a use for, that we turned into the place where the open mics and the festivals happen.

And once we pretty much realized the vision that was in my mind, I found myself getting a bit restless.

You may be familiar with that feeling. That voice in the back of your head saying "What am I going to accomplish next".

There was only one problem.

I was comfortable. I was established. And the hardest part of all...I finally felt like I created a place where I could belong. That's a hard thing to walk away from.

So I spent most of my last year there asking myself how I could leave and be safe, instead of how to stay and be happy.

So with some encouragement, I left to try to create that next vision.

It took me most of a year to hear that I had been asking the wrong question. If you're comfortable, established, and quietly restless, there's a good chance you're asking one too.

Nobody could have handed me mine. But someone could have helped me find it faster.

See what the work added up to →

If some of this sounds familiar, I'd enjoy hearing your story.