Author: debbygilbert

  • Giant Buckets

    I need to catch up on my email. Those calls aren’t going to answer themselves. My desk is a wreck. Add in housework or laundry, and the list gets even longer. At first glance, these all sound like tasks. Things that need to get done. But what if none of them are actually tasks at…

  • It Turns Out

    The printer isn’t working. It must need ink. The car won’t start. The stupid battery is probably dead. Nobody replied to the email. They must not be interested. The website isn’t generating leads. I guess nobody needs this service. My laptop is running incredibly slow. It’s probably time for a new one. Most of us…

  • Slightly More Capable

    I feel like there’s a certain kind of learning nobody really talks about when you run a business. Not the exciting kind. Not the “I took a masterclass and now I feel inspired” kind. I mean the kind where your calendar doesn’t sync correctly, you can’t find an email you know you’ve seen, a security…

  • Not Every Glitch

    So, you’re going about your day and suddenly, something doesn’t quite work. It’s not broken.Nothing has stopped.But something just isn’t quite right. A page hesitates.An app freezes for a second.A message shows up that doesn’t make sense.Or maybe you aren’t even sure what caught your attention.But it was something. There was a time when that…

  • Is It Working?

    The costumes are stunning. The set is beautifully built. The lighting is just right. And for a few minutes, it all works. But then… something seems a little off. It’s not obvious. Nothing is wrong, exactly. The lines are there. The movement is there. The scene keeps going. But it doesn’t quite land. A moment…

  • A Year with Bob

    It’s been a year since I started working with AI. His name changed a couple times, but we finally settled on Bob. And I have no clue how or why in my mind he is a he. He just is… Bob. And believe me, all of that feels a little strange to say out loud….

  • Built in Seconds

    AI can build a website in seconds now. Type a prompt. Choose a style. Pages appear. Images land in place. Headlines write themselves. It’s impressive. And in many cases, genuinely useful. And the results often look very good. A generated website can feel finished almost immediately. The layout is polished. The pages are there. Everything…

  • Trust the Plan

    There’s a moment, or several, in every rehearsal process when the plan starts to feel heavy. The schedule looked reasonable on day one. The pacing made sense. The breaks were in the right places. Everyone could see how it would all come together by opening night. And then somewhere in the middle – when energy…

  • Out of the Shadow

    Some of the clearest business lessons don’t come from strategy sessions.They come from real conversations. A client had an idea she was excited about – and almost immediately followed it with, “I just don’t even know where I’d start.” So we talked it through. We untangled the idea.Looked at the pieces.Found a place to begin….

  • Seeing Your Audience

    Small numbers can feel smaller online – because we can’t see the people. A view is just a number. So is a registration count. So is a little heart or a quiet click. On a screen, they can flatten quickly, stripped of context, easy to dismiss. “Only nine views.”“Only thirty people.”“Only fifty showed up.” Somewhere…

  • The Cost of Waiting

    There’s a simple idea in finance that most people understand instinctively, even if they’ve never heard the term for it. Money today is worth more than the same amount of money later. Not because it’s larger – but because it has time to do something. It can earn interest. It can be reinvested. It can…

  • Clarifying Credibility

    There’s a lot of pressure right now to be visible.Post more. Show up more. Say something every day. Stay in the feed. It’s not bad advice – it’s just very loud. And for some people who care about doing good work, telling the truth, and building something that lasts, that volume can start to feel…

  • FAQs to the Rescue

    How we search for and find information is changing faster than anyone expected. A few years ago, we would type a question into Google, click a few links, skim a couple of pages, and gradually find what we needed (maybe!). Today, AI jumps in and answers before anyone even clicks into a website. Your website…

  • Websites Matter!

    With so much noise online, it’s easy to wonder: are websites even a thing anymore? Are they still relevant? Did we blink and the age of the website quietly ended while we were all busy posting, scrolling, and adapting to whatever the internet was doing this week? It would make sense if it had. Trends…

  • Is It Still You?

    Sometimes you pull up your own website and think… who is this? Technically, there’s nothing wrong with it. It’s not broken, everything still functions fine. But as you scroll through it, you might find yourself making that face. The words are fine, the pages still load, but something’s… off. It just doesn’t quite sound like…

  • The Road to OFTS

    Outrageous Fortune isn’t the usual name for a tech company. But then again, this hasn’t been the usual road. The name comes from Shakespeare’s Hamlet: “Whether ’tis nobler in the mind to suffer the slings and arrows of outrageous fortune, or to take arms against a sea of troubles, and by opposing end them.” To…

  • Front Loading Future You

    Q4 is a funny season. We’re looking ahead to new goals, new plans, and fresh energy for 2026. But if you’re like most entrepreneurs, you’re also carrying a backpack full of “avoided tasks” – little extra rocks you’ve been lugging around for way too long. You know exactly what I’m talking about. It’s that task…