From Grindstone to Joyride: How AI Is Making Drudgery Fun
I’ve been in business for more than 31 years, and I still love it. I enjoy the strategy, the problem-solving, the creativity, and the satisfaction of making something good for a client. What I don’t love is the grind that comes with it: administrative chores, support queues, repetitive steps, and all those little jobs that somehow take longer than they should.
Lately, something unexpected has happened. I’ve started looking forward to dealing with some of those jobs. Not because the jobs have become fascinating, but because I’ve assembled a virtual team of AI assistants that can take on much of the drudgery. My role is shifting from doing every step to deciding what needs to happen, delegating the execution, and checking the result.
The support chat I didn’t have to sit through
One of my clients needed to address a website security concern. The question involved the precise PHP version and patch level on one of my hosted sites. It’s familiar territory for me. I know how to investigate hosting configurations. But anyone who’s dealt with hosting support knows the ritual: verify your identity, explain the issue, wait, explain it again, perhaps get transferred, and wait some more.
This time, I handed the investigation to my AI hosting agent. It used the web host company’s text chat to communicate with a live support person and work toward an answer. I can’t say for absolute certain whether the person—or system—on the other side was human. What mattered was that my agent could handle the back-and-forth that would ordinarily have kept me glued to a support window for half an hour or more.
When it came back with the resolution, it even asked whether it should contact my client with the update. That’s the part that struck me. I had identified the problem and decided what needed to be done. The AI handled the tedious coordination, then returned for a decision about the client communication.
And while all of that was happening, I was brushing my teeth.
It’s a small domestic detail, but it captures the paradigm shift better than any grand prediction about artificial intelligence. The business problem was being handled without requiring me to spend part of my evening typing into a support chat window.
A domain renewal becomes a little adventure
Another example began with an unwelcome domain renewal: roughly $320 Canadian, with a two-year commitment. Ouch. Instead of simply accepting the charge or spending an afternoon comparing registrars, I asked my AI hosting agent to investigate alternatives. It identified a possible move to Cloudflare that could save me roughly $50 a year.
The transfer wasn’t entirely hands-off, nor should it have been. I had to unlock the domain and obtain the authorization code myself. I started the process one evening, got tired, and picked it up the next day while sitting in Starbucks. I supplied the authorization code and entered my credit card information personally. I wasn’t interested in handing sensitive payment details over to an agent.
Once I’d completed those human-only steps, the AI took care of the remaining transfer workflow.
That’s a useful distinction. The goal isn’t to surrender judgment, access, or control. It’s to reserve my attention for the parts that genuinely need it and let the system handle the rest. A chore that might once have sat on my list for days became something I could move forward with a few decisions.
From operator to orchestrator
None of this means AI suddenly knows my business better than I do. I’ve spent years learning how websites, hosting, marketing, and client service work. I could perform these tasks myself. That’s not the point.
The point is that I no longer have to personally perform every repetitive step to get the outcome I want.
It’s rather like having a capable team behind me—except this one is virtual. I can assign work, ask for progress, examine the results, and intervene when judgment or authorization is needed. Sometimes the agents make mistakes. Sometimes they need direction or correction. Supervision is still part of the job. But that feels very different from being trapped in the mechanics of every task.
I used to postpone certain non-billable chores simply because they were annoying. Now I sometimes catch myself looking for the next one to delegate. There’s a game-like quality to it: can we clear this obstacle quickly, correctly, and with less fuss than last time?
And the to-do list gets shorter and shorter.
The real payoff isn’t just productivity
We talk a lot about AI saving time, and it does. But time saved isn’t the whole story. There’s also frustration avoided. Mental clutter removed. Momentum restored.
When a nagging task disappears from my list, it stops occupying a corner of my mind. I can concentrate on the work I enjoy: helping clients, exploring ideas, making decisions, and building my business. I wake up feeling that I have a support team behind me, rather than a pile of administrative obligations waiting to ambush the day.
That feeling matters. A business owner’s enthusiasm is a resource, too.
Back to the joyride
The funny thing is, I haven’t stopped loving what I do. I’ve always loved being in business. What I never loved was the tedious stuff that came with it—the waiting, the chasing, the repetitive tasks, and the little jobs I’d keep putting off until tomorrow.
Now, with a team of AI assistants behind me, even those chores have become strangely enjoyable. Instead of procrastinating, I find myself looking for the next thing to tackle, just to see how easily we can get it done. My to-do list is getting shorter, my enthusiasm is getting bigger, and there’s a spring in my step that I haven’t felt in years. I’m still running the same business. I’m just having a whole lot more fun doing it. I’ve traded the grindstone for a joyride.