If It Makes Your Life Easier

Let’s talk about new technology. More specifically: software.

I can’t tell you how many conversations I’ve had with business owners lately who are absolutely terrified to change software. And listen—I get it. Changing over your systems is no small thing.

I know it’s scary.

I know it’s time-consuming.

I know it often comes with a hefty price tag.

And I know that if you don’t have a thoughtful plan—especially when it comes to software and SaaS tools—you can wind up with a mess: unused subscriptions, security gaps, and tech stack confusion.

But here’s what I also know:

If there’s a piece of technology out there that will make your life easier—buy it. Period.

Not carelessly. Not impulsively. But decisively, with a clear plan and a strategic purpose.

So, how do you know if it’s time for a change?

Start by asking yourself a few key questions:

1. Is the software I have doing everything I want it to do?
And more importantly, is it easy for my team to use? If you’re constantly making workarounds or training new team members takes weeks instead of days, that’s a red flag.

2. Can my managers easily see what’s going on?
I work with companies whose systems are so siloed or cluttered that managers have to click through dozens of tickets just to get a picture of what’s happening. That’s not OK. Your technology should provide real-time visibility—at a glance.

3. Do I have to bolt on multiple tools to make it all work?
If your system requires five different add-ons just to function, it’s probably time to reevaluate. In this day and age, APIs should be open, integrations should be seamless, and platforms should be built to work together.

4. Can I get my data out if I need to?
This is a big one. If your current system locks your data in a way that makes it difficult to move, migrate, or even back up, that’s a serious limitation. Before switching, make sure you understand how data exports work—and don’t get stuck in a system that holds your info hostage.

Once you’ve asked these questions—and if the answers reveal gaps—it’s time to act.

Not next year. Not when things slow down. Now.

I used to be the CEO who tried to piece together a tech stack with duct tape and best guesses. I spent more time managing the software than I did managing my clients.

And that’s when I realized: I was doing it backwards.

If your tech is causing friction—change it.

Because here’s what happens when you get it right:

• Your productivity skyrockets.
• Your team feels empowered.
• Your managers can actually manage.
• And you? You get to work on the business, not just in it.

So if you’re sitting at a crossroads with your technology—if you’re facing that familiar rub where nothing feels smooth—it might be time to make a change. And you’re not alone.

If this letter resonates with you—and you’re in the middle of a software switch or even just thinking about one—reach out. I’d love to hear where you are, share a few lessons I’ve learned the hard way, and offer a little encouragement.

You’ve got this. And if it makes your life easier—buy it. Period.

Cheering you on,