Yesterday, I spent way too many hours fighting with Windows Task Scheduler. Even my trusty AI companion couldn’t figure it out, and I could practically imagine Claude staring into the void after we’d collectively exhausted the accumulated body of human knowledge and AI hallucinations we could come up with. AI doesn’t really give up although the increasing repetition and fanciful imaginations told me I was basically on my own.
The problem eventually came down to this strange combination of file permissions, the login I was using, and the fact that the pre-retrograde shadow of Venus doesn’t begin for another thirty-five or so days. I’m pretty sure planetary alignment is the most important factor behind my struggle.
I was in a full-on fist fight with Task Scheduler because my business collapsed, and the product we spent almost a year building still needs to reach the market. I’m not someone who walks away when events don’t take shape how I hoped and planned. What I seem to possess, in quantities that are sometimes useful and frequently unhealthy, is the capacity to keep pushing something forward through sheer force of will.
A few companies have expressed interest in the product, and some of them might even be willing to pay for it. That, of course, is the real test of hobby vs. business. Software can be the bees knees but it only gets to be a business when customers value the product enough to give you money for it. Before everything fell apart, we did our homework and found evidence of market fit. What we don’t have yet is investors who are willing to support that belief with their money. (I could go on here about the pervasive tech bro culture in Utah, but I will forebear.)
We like food with our meals, so I accepted consulting work that consumes most of my regular business hours. That means the product I’m building gets the fringe hours: early mornings, late nights, and whatever bits of energy remain after work, family, grief, and ordinary responsibilities get their share. I’m in a weird space where relief and grief coexist alongside opportunity and failure. I’m grateful for work that keeps home stable, and I still mourn the company I wanted to build.
That’s why I keep clicking away at the keyboard, propelled by the possibility that someday, somehow, with enough persistence, timing, luck, and planetary cooperation, I’ll be able to launch the product, find some paying customers, and convince someone that the entire undertaking wasn’t completely irrational.
Truthfully, there’s still a reasonable chance that I’m a little crazy.
I can live with that.
When I was young, I was a dreamer. I loved writing stories, and I still do. My best friend and I spent hours writing on another friend’s mother’s computer, which had Novell WordPerfect. Mind you, this was the late 1980s and early 1990s, so having the ability to perfect words on screen before wasting paper or printer ribbon felt like magic. Once we got into high school and Juno then Hotmail were a thing, we started writing a book together, passing it back and forth by email, taking turns adding chapters or editing.
My career ambitions during those years were all over the board and not really connected, much, to reality. I dreamed of becoming a writer, a zoologist, a geneticist, a chaotician, Indiana Jones, or a Ninja Turtle. Engineering was never a consideration until one Saturday afternoon when I decided and attempted to convert my parents’ cordless telephone (another new invention) into a universal garage door opener. The experiment didn’t produce either a universal garage door opener or a functioning cordless telephone. I will say this, however, it was an early indication that I might enjoy taking systems apart to see how well I could understand them, and maybe even put them back together with improvements.
I still enjoy writing. I’ve never made much money doing it unless you count June 2025 when I somehow made $238 on Medium. That was my white whale. Most months, my Medium earnings cover exactly one forty-ounce Diet Dr. Pepper refill. That, I think, is what you might call a loyalty program with extra steps.
I never became a chaotician, Indiana Jones, or Rafael (the ninja turtle, not the painter). I studied mechanical engineering and spent more than twenty-five years working in warehouses, mostly in operations. Eventually, I started a software company at either the greatest or the worst moment in history to get into software development. The jury is split 50–50 on that.
Building that company was the most fun I’ve ever had professionally. It was also crazy expensive. I assembled a team that I love and we created products that I still believe in. We built something meaningful. Then the runway ended before the next tranche of investment arrived, and I had to let everyone go.
It’s interesting. The dream that keeps me motivated now comes from the memory of what existed for a brief period of time. We built something worthwhile with people I still admire, and for a little while I got to experience the kind of company I had always wanted to work for.
The memories have become the fuel for the seemingly impossible dream. I want to finish the product we came so close to deploying, begin generating repeatable revenue, and create a path that might someday bring some of that team together again inside a healthy company. The dream is motivating enough to keep me working through exhaustion and discouragement. I’d be lying if I said there weren’t days when the whole thing feels futile. Five hours spent fighting a task scheduler is enough to make me question my own nerdhood and make futility feel… persuasive.
Those are the times when I cling to the people. I remember how much fun I had working with them, the amazing satisfaction that came from shipping something that worked, and a very real sense that we were building people, not software. Once again, I would be lying if I said I didn’t want to make a lot of money. I do, but my biggest professional dream has never been centered on what people think my company is worth. What I want professionally, more than anything, is to see that team come together again.
Don Quixote and impossible dreams both have a bad reputation. While we’re often told to “dream big,” we’re also encouraged to be realistic, pivot quickly, and stop pouring good hours after bad. That advice reflects wisdom, sometimes. There are ideas that should be abandoned. There are also ambitions that are nothing more than expensive monuments to ego.
I think I’m old enough and have enough experience to understand the difference between a living, tenable dream and a corpse I keep dragging around because letting go is too painful. At least, I hope I do. Some days I am unsure which one I’m carrying. From the inside, it’s often hard to tell. If I succeed, history will very likely judge it an achievable dream because the evidence will be there. Failure will be judged in the same light.
There are certain dreams that are worth hanging onto even if they can’t keep the lights on. They have intrinsic value that can’t be quantified on a spreadsheet, much as I love spreadsheets. A useful dream is one that keeps a person from collapsing when the world around them says they should quit.
A lesson that I’m learning now is that failing at a venture is not the same thing as being a failure.
Dreams and the benefit of hindsight can’t alter the past. They can’t pay contractors or give people their jobs back. They don’t rebuild payroll or remove the consequences of poor timing.
What they can do is motivate me to come back to my laptop day after day.
Yup. That might be irrational. Irrationality may even be part of what allows worthwhile things to survive their least promising seasons.
I’m pretty confident the product will ship this year. However, I don’t know if investors will ever arrive or if my team will come back. If they do, I don’t know if the future reunion will match the version in my brain. There’s no honest, clear way to wrap those uncertainties in a bow as some kind of gift-lesson about persistence always being rewarded.
For now, I just keep showing up during the fringe hours and continue moving the product toward daylight. Permissions, logins, Venus, or whatever other absurd obstacle appears next will be knocked into submission.
All I really know is this: the dream doesn’t need to be probable to be useful.
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