By Michael Herbert

Friday, Jan. 16, 2026, marked ten years as Ashland's Town Manager. Most managers move on after three to five years. I stayed.

Not because I couldn't leave. Because staying taught me things leaving never would.

Ten years gives you a vantage point. You see patterns you couldn't see in year two. You watch projects that felt urgent become memories. You realize how much you didn't know when you thought you knew everything.

Here's what a decade in one place actually taught me - and most of it isn't about municipal management at all.

1. I grossly overestimated what I could do in one year and underestimated what I could do in ten.

Early on, I had plans. Big ones. I thought I could transform things quickly if I just worked hard enough and smart enough and hired people that had the same kind of ethos.

I was wrong.

The projects that matter most - the ones that actually transform a community - take years. It also takes belief. Underground utilities downtown. The Arboretum. A comprehensive plan shaped by hundreds of conversations. You can't rush a decade. You can’t transform inertia into action overnight. And you can't see what's possible in year one.

But if you stay? If you're patient? You look up one day and realize we've built something together that I couldn't have imagined when I started. My role was to hold the vision and create the conditions. The building happened because of the people who showed up.

Any leader who stays long enough in one seat learns this: the long game is the only game.

2. The dumber I got, the wiser I became.

In year one, I had answers. Lots of them. I was smart, capable, ready to prove it.

Somewhere along the way, I stopped knowing so much. I started asking more questions. I got comfortable saying "I don't know" and "tell me more" and "what do you think?"

A department head told me recently that they feel more support now. Not because I'm solving more problems - because I'm not rushing to solve them at all. And yet I’m somehow more present.

The less I knew, the more I learned. The less I spoke, the more I heard.

Leaders across every sector eventually face this: your expertise can become a wall. Getting "dumber" - letting go of the need to be the smartest person in the room - is what actually makes you wise.

3. I started understanding that two people could be right at the same time.

This might sound simple. It isn't.

Year one: someone's right, someone's wrong. My job is to figure out which.

Year ten: Two people can both be right. The resident AND the department head AND the Select Board member can all have legitimate perspectives that are true from where they stand.

That shift changed everything. How I listen. How I decide. How I hold conflict. I stopped being an arbiter of truth and started being a container for complexity.

Maybe this is more maturity than leadership. But the ability to hold different perspectives at once - without rushing to resolve the tension - has been a game changer.

4. Trying NOT to run in and fix things is harder than running in and fixing them.

As mentioned before, I don’t run in to fix things as much anymore. But it’s hard. My instinct is to help. Someone has a problem, I want to solve it. That's what leaders do, right?

Wrong.

The hardest discipline I've learned is staying out of it while still being present. Letting people struggle. Letting them figure it out. Trusting that they don't need me to rescue them. We had a meeting recently where a couple of member of a department started sharing some old grievances. As opposed to jumping in and shutting it down, I sat there silent, letting it play out. Eventually, they worked it out on their own and had the gratification of figuring out how to resolve their differences on their own.

Almost always, their breakthrough happens right when they're about to give up. They just needed space to find their own answer.

It allows me to get things done a lot more elegantly now. Not because I do more - because I know more of what doesn't need my hands on it.

5. Doing the job “right” means working all the time. Doing the job “well” means taking time to rest.

This one is a big work in progress. But here’s a secret…there's a difference between “right” and “well”.

"Right" is being responsive. Never dropping a ball. Always available. Working nights and weekends because the work is never done.

"Well" is showing up whole. Being present, not just productive. Protecting your capacity so you can sustain this for the long haul.

You can do the job "right" and burn out in five years. You can only do it "well" if you learn sustainability.

That took me longer to learn than I'd like to admit.

6. I used to care about being seen as a leader. Now I'm more concerned with others being seen as leaders.

Year one: look at me.

Year ten: look at them.

I don't need to be the one with the answers or the ideas or the credit all the time. What I want now is to watch the people I've developed step into their own.

The spirit of the team you build outlasts every initiative. The leaders you develop are your actual legacy.

Yes, this one, too, is a work in progress. But that shift - from ego to service - might be the most important one I've made.

7. The things that were important to me in year 1 are vastly different than the things that are important to me in year 10.

Year one: proving myself, building things, being seen as competent, making my mark.

Year ten: knowing myself, developing others, trying to rest, staying by choice.

I thought this job was about the town - projects, budgets, services, outcomes.

Turns out it was also about me. Who I was becoming. What was getting exposed. What I had to confront.

The job didn't change. I did.

8. Process became just as important as product.

For years, I measured success by outcomes. Projects completed. Budgets passed. Problems solved.

Somewhere along the way, I started noticing the how. Not just what we built, but how we built it. Not just what we decided, but how we got there.

There's beauty in the process itself…in the conversations, the setbacks, the slow accumulation of trust and understanding. I used to rush past all that to get to the result.

Now I know: the process is where the real work happens.

9. Managing people is more about managing yourself than anything.

This is the one underneath all the others.

Every challenge I faced as a leader - the conflicts, the crises, the impossible decisions - ultimately came back to me and the person I was. My need to be right. My need to fix. My need to be seen. My patterns. My triggers. My exhaustion.

The town runs better when I run better.

All my relationships taught me the most important relationship is the one I have with myself.

Leaders who don't learn this eventually hit a wall. I know because I hit it...1-star: Would Not Recommend.

10. A couple of these last ten years made me old.

I don't mean that metaphorically.

Some years changed my perspective. Made me more wise. I can hold complexity now in ways I couldn't before. I don't need to be right. I can sit with uncertainty better.

But a couple of years burdened me with grief. Months of carrying weight that aged me. I'm not the same person I was.

Some of that is good. Some of it is just heavy.

Both things are true.

Closing:

Here's the paradox I didn't expect: I became a better Town Manager when I stopped needing to be one.

No, that doesn’t mean I am leaving tomorrow. But, somewhere in the last year, staying stopped being about what I'd lose if I left. I'm here now by choice, not by need. And that freedom - that lightness - lets me hold the role differently.

Ten years in one place will teach you things that moving on never would. Not about the job. About yourself.

Ten years is long enough that you can't hide behind the learning curve anymore. The role reveals who you actually are - your strengths, your edges, your tendencies. And eventually, you have a choice: keep growing, or move on.

I stayed. And I'm grateful for everything staying taught me.