Everyday Run State: Pro Edition

Recently, ConnectWise sent me a knapsack (or Backpack, if you prefer) as part of their Champions program. It’s a program where you get rewarded for educating and advocating users about ConnectWise - I submit my YouTube videos there.

On the surface, it’s a small thing - people get free stuff all the time! Swag is everywhere, and not usually that good.

However, this was a legit, excellent quality freebie that hit close to my heart. If you’ve ever been asked “If you were in Top Gun, what would your call sign be?” mine has always been Knapsack. Not because it sounds cool, because it doesn’t, but because it’s accurate.

I am almost always wearing a knapsack. I pride myself on always being prepared, always having extras of everything, right at arms reach. It’s a little dorky, but so am I.

The fact that it’s ConnectWise represents something else to me as well. I’ve spent the last five years getting very deep into the PSA/Manage system, becoming a laser-focused specialist.

One ecosystem. One set of operational problems. And there’s something incredibly rewarding about knowing a tool well enough to understand how it behaves at scale, across different maturity levels, and under real-world pressure.

Generalist vs. Specialist. The Ongoing Tension

In our industry, it’s very easy to become a generalist.

Clients pull you in different directions. New tools pop up constantly. There’s always one more thing you could learn or offer. And there’s nothing wrong with having breadth. In many cases, it’s necessary.

But at some point, I think you have to decide where you want to go deep.

For me, specializing on just one platform has been a deliberate choice. I enjoy the depth. I enjoy understanding not just how something works, but why it breaks, when it breaks, and what decisions made early on determine whether it scales cleanly or painfully.

That depth means when I work with clients early in their ConnectWise journey, I’m not just solving today’s problem. I’m building a foundation that I know can support them a year, three years, or five years down the road. I’ve seen it work at scale. I’ve seen it fail at scale. That context matters.

Why This Matters for Businesses Right Now

I see the same pattern emerging across MSPs and technology services more broadly.

For a long time, being a generalist worked. Supporting everyone, doing a bit of everything, saying yes often. But we’re seeing a clear shift toward specialization.

Providers who focus on legal firms.
Providers who truly understand healthcare workflows and compliance.
A focus on a specific market, partnering with an association, or really getting deep into one geographical area.

That focus allows you to:

• Serve existing clients at a deeper level

• Anticipate your client’s needs, since they are all going through similar issues

• Build stronger, longer-lasting relationships

• Develop repeatable processes instead of one-off solutions

A Thought to Sit With This Week

If you’re feeling stretched, pulled in too many directions, or unsure which opportunities to say yes to, ask yourself:

Where does depth create more value than breadth for us right now?

Not forever. Not for every client. Just right now.

Because whether it’s a consultant, an MSP, or a product offering, clarity of focus tends to compound. And when you’re known for something specific, the right work finds you more easily.

Sometimes, the knapsack isn’t about carrying more. It’s about having exactly what you need, and only what you need, right at your fingertips.

What are you focusing in on 2026?