Where there’s a will…

…there’s a way, right? That’s what they say.

It’s been a little while since I’ve added to the site.  Summertime, kids out of school—and a major shift in our household.  My son is heading off to study aerospace science (with a focus on flight!), and my youngest is about to start high school.  When did I become old?

I spend a lot of time working—usually online early, and out late more often than I’d like.  Working from home helps, but it still makes for long, tiring days.  And sometimes, honestly, it’s hard to figure out what to do next.  It’s hard to see what the next step is.

Keeping up with technology is no small feat.  It can feel daunting.  That old saying, “you can’t teach an old dog new tricks?”  Turns out, you can.  It just takes a little more time—and a willingness to adjust.  That’s really the key: understanding that change is real, inevitable, and necessary.

Which brings me to what’s been on my mind lately:
Why is it that the “old school” crowd has such a hard time letting go?

We’re living through an incredibly exciting era in tech. The cloud—AWS, Azure, Google—keeps expanding. The ways to learn, grow, and automate are increasing by the day. Cloud adoption enables flexibility, faster adaptation to change, and in many cases, simpler disaster recovery.  And yet… so many people (especially those around my age) cling to legacy approaches. Those systems from 2005? They’re not built for 2025.

On-prem infrastructure is no longer the center of the universe. Most companies today are remote-first or hybrid. They use Azure, Entra, and Microsoft 365. So why tether these modern workflows to outdated systems? Why not leverage the automation and intelligence the cloud provides instead of fighting it?

I’ll admit, I can be stubborn. Pretty sure if you dropped me on my head, I’d bounce—and it wouldn’t do much damage. But I can look at what’s available and say, “Hey, this is interesting. This could help.” So I learn something new, I bring forward a proposal with evidence, and what happens?

A giant wall. Brick.  With an iron door.  A little slit opens.  I expect someone to ask for the password.

Instead, I hear: “That’s not how we’ve always done it.”

And yeah—I get it.  Change can be scary.  It forces us to think differently.  But it also opens doors.  New tools, better efficiency, improved security.  That’s how you grow.  That’s how your company evolves.

I hear this story over and over again:

“We’ve always done it this way.”

“We’ll look at that later.”

Then I hear from the folks trying to drive change, exhausted:
“All we’re doing is doubling the amount of work because we’re trying to do things two ways.”

What’s the point in buying a full-featured platform if all you use it for is saving a few Word docs and Excel sheets?  Why pay for a top-tier security suite if you don’t build the processes to actually use it?

A Microsoft E5 license—at $50+/user—covers productivity, identity, compliance, and security.  Why bolt on five extra tools when the one you’re already paying for does the job?  I just don’t understand.  Sometimes I feel like I spend more time convincing people to give modern tools a chance than I do actually implementing them. 

And look—I’m a GenX guy. We went from Pong to PS5. We remember the days of loading Oregon Trail off a 5.25″ floppy and printing our school reports to a dot matrix printer. My first computer was an HP 8088 XT with a magical Turbo button that took it from 1MHz to 4MHz. At 4MHz? That Sopwith Camel game was impossible.

We’ve seen massive change.  We embraced it.

So why is it that when it comes to the systems running our businesses we’re suddenly afraid to move forward?

Not all change is good. But change is constant. It deserves thoughtful discussion—not knee-jerk rejection. We owe it to ourselves, our teams, and our customers to embrace the changes that help us grow stronger, smarter, and more secure.

So here’s my challenge:

Look at your world.
Find one change that matters to you.
Pick it up.
Plant the seed.
See what grows.

If I can keep learning, anyone can.
Harness the change.
Keep improving.
Work toward the future.
Let go of the past.

That’s how we build something better.

Leave a comment