Why a Week of Mojitos, Water Polo, and a Pair of Reading Glasses Made Me Rethink AI at Work

This week, I took some overdue time off to fully enjoy sunny days with my family at an all-inclusive resort—think water polo, volleyball, and maybe one (or three) too many mojitos. While relaxing by the pool (reading glasses now required—thanks, aging!), I dove into “What’s Your Dream?” by Simon Squibb. The book’s core message stuck with me: it’s not always about having big ambitions, but realizing when comfort is quietly killing our dreams. Two steps from Simon’s book really resonated: • Step 3: “I don’t need it.” How many times have we settled because things seem “fine”? • Step 5: “I don’t know how.” Whether it’s financial planning, launching a project, or learning a new skill, this one gets me every time. Here’s where technology, and AI in particular, is changing the game for me. I now have a digital “dream team” of AI agents helping with finance, HR, marketing, and even tech support—giving me more time for both business and my loved ones. AI isn’t just about efficiency; it’s about making space for what (and who) matters most. That’s why I’m passionate about bringing AI to small and medium businesses—to help everyone get more out of both work and life.

Let’s set the scene: I was “OOO” (out of office) in the classiest way possible—by the pool, under the sun, basking in the glorious laziness that only an all-inclusive resort can provide. Between intense games of water polo (Olympic dreams still alive), questionable volleyball sets, and a few too many mojitos, I finally cracked open a book: “What’s Your Dream?” by Simon Squibb. Honestly, I was living my best life—unless you count realizing I now need reading glasses after decades of perfect vision. (A classic case of “Aging: 1, Me: 0.”)

The book is a breezy, practical guide on finding your dream—or, as Squibb puts it, not accidentally assassinating it along the way. Out of respect for spoilers (and also because I haven’t quite finished—blame the mojitos), I won’t drop all seven steps here. But let’s talk about a couple that hit me right in the sandcastle.

Step 3: “I Don’t Need It” — AKA The Comfort Zone Trap

Like many folks, I once believed, “Why dream big when things are… fine?” I have a job, life is good, why rock the floating raft? But Squibb points out that comfort can quickly morph into complacency. Why disrupt our sturdy little boats? Because, as it turns out, the risk isn’t in trying; it’s in never trying at all.

Step 5: “I Don’t Know How” — Familiar Territory, Anyone?

The next classic excuse: “But I don’t know how!” Guilty as charged. Whether it’s balancing finances, finding time, or finally launching that moonshot app idea, this step trips up most dreamers. I’ve been there—and bought the T-shirt.

But here’s where the story takes a digital twist. See, lately, I’ve been employing a little AI magic. I’ve set up my own digital dream team: a virtual Financial Manager, an HR brain, a marketing wizard, and even a few tech-savvy bots. Basically, I handed off my biggest “I don’t know how” headaches to artificial intelligence. (And they won’t even ask for a raise.)

That’s what excites me most about AI, especially for small and medium businesses. With the right set of AI-powered sidekicks, you can do way more with the same effort. That’s not just office productivity jargon—that is real freedom. Freedom for entrepreneurs. For families. For anyone who wants poolside mojitos without worrying about dropping the ball (or the volleyball).

AI isn’t here to replace us. It’s here so we can spend more time with the people we love—and maybe even finish that book, glasses on, with a smile.

So, what’s your dream? And more importantly, are you ready to let AI help you chase it—between volleyball sets and sips of mojito?

Got your own stories about how tech lets you live your best life? Share them below—extra points for poolside tales and cocktail recommendations!