The App That Never Launched
In January, I was absolutely convinced I’d cracked the code on habit tracking. Not another generic app, but something that would use behavioral psychology to actually help people stick to their goals. I spent four months building what I thought was going to be my breakthrough project. The interface was clean, the gamification was subtle but effective, and I’d even figured out how to sync data across devices without making users create yet another account.
The beta testers were polite. Too polite. They said things like “interesting approach” and “I can see the potential.” When I pressed for specifics about what wasn’t working, they gave me feature requests instead of honest feedback about the fundamental problem: nobody actually wanted what I’d built. I’d solved a problem that existed mainly in my head, created for an audience of people exactly like me who were already obsessed with optimization.
I kept the code repository. Sometimes I still look at it, not with nostalgia but with genuine curiosity about where exactly I went wrong. The technical execution was solid. The user research, in retrospect, was almost entirely theoretical. I’d read studies about habit formation and user engagement, but I’d never actually sat with someone while they tried to build a new habit using existing tools. I’d built in isolation, and it showed.
The hardest part wasn’t losing the time I’d invested. It was realizing how much I’d been avoiding the uncomfortable work of talking to real users because I was afraid they might not want what I was excited to build. That fear of invalidation led me to build something that was, ultimately, invalid anyway.
The Course That Taught Me Nothing
June brought what I thought would be a pivot toward something more sustainable: creating an online course about project management for creative freelancers. The market research looked promising. I had the expertise. I’d even pre-sold a few spots to gauge interest. Everything pointed toward this being the smart, logical next move after the app debacle.
I recorded forty-three videos over two months. Each one felt like pulling teeth. I kept telling myself it was normal to feel disconnected from the material, that enthusiasm would come once I saw students engaging with the content. I created worksheets and templates and even designed a private community space where students could share their progress.
The first cohort launched in September with twelve students. Within three weeks, half had stopped showing up to the weekly calls. The ones who stayed were polite and engaged, but I could tell something fundamental was missing. The content was useful enough, but it lacked any spark of genuine excitement. I was teaching things I knew intellectually but hadn’t internalized emotionally.
By October, I’d refunded everyone and shut down the course. The students were understanding, almost relieved. One told me she could sense that my heart wasn’t in it, and while the information was valuable, she’d rather learn from someone who was genuinely passionate about the subject. She wasn’t wrong. I’d chosen the topic because it seemed commercially viable, not because it lit me up inside.
The Newsletter That Nobody Missed
The newsletter felt like the safest bet. Low stakes, direct connection with readers, minimal technical overhead. I’d been writing sporadically for years and had a modest but engaged following. Converting that into a regular newsletter with premium subscription tiers seemed like the natural evolution of my online presence.
For six months, I published every Tuesday and Friday. The content was solid, occasionally even insightful. I covered productivity systems, creative process deep-dives, and behind-the-scenes looks at various projects. The free subscriber count grew slowly but steadily. The paid tier, however, remained stubbornly small.
The real wake-up call came when I took a two-week break in November. I’d been feeling burned out and decided to pause publication while I recharged. When I came back, exactly three people had asked where I’d been. Three. Out of nearly eight hundred subscribers. The silence wasn’t malicious or personal, but it was telling. I’d been creating content that was nice to have rather than essential to anyone’s week.
I kept publishing through December, but something had shifted. I could feel myself going through the motions, hitting publish not because I had something important to share but because Tuesday and Friday demanded content. The newsletter had become a treadmill that nobody particularly cared if I stepped off of.
What Failure Actually Teaches You
The conventional wisdom about failure is that it teaches you resilience, adaptability, and perseverance. That’s true but incomplete. What failure really teaches you is specificity. Not “I need to work harder” but “I need to validate demand before building features.” Not “I should be more passionate” but “I need to distinguish between topics I find intellectually interesting and work that genuinely energizes me.”
Each of these projects failed differently, but they all shared a common thread: I was optimizing for the wrong metrics. With the app, I optimized for technical elegance instead of user validation. With the course, I optimized for market opportunity instead of personal alignment. With the newsletter, I optimized for consistency instead of necessity.
The other thing failure teaches you is patience with the messy middle of figuring things out. I used to think that successful people had some special insight that let them skip past the trial and error phase. Now I suspect they just get comfortable with longer cycles of experimentation. They’re willing to fail at a higher level of sophistication.
There’s also something oddly liberating about accumulating a decent collection of well-documented failures. It makes you less precious about new ideas and more willing to test them quickly and cheaply. When you’ve already proven you can survive building the wrong thing, the stakes of any individual experiment feel more manageable.
The Experiments Still Running
I’m not done failing, obviously. Right now I’m working on a project that might be completely wrong for reasons I can’t see yet. It’s a tool for helping small teams document their decision-making processes, born from my own frustration with forgetting why we made certain choices six months ago. I’m being more careful about validation this time, but careful doesn’t guarantee correct.
The difference is that I’m keeping better notes about what I’m assuming and why. I’m talking to potential users earlier and more often, even when those conversations are uncomfortable. I’m trying to distinguish between the part of me that wants this tool to exist and the part that thinks other people need it.
Maybe this one will work. Maybe it’ll join the archive of noble attempts that taught me something important about building things people actually want. Either way, I’ll write about it honestly, including the parts that don’t fit neatly into a “lessons learned” framework.
What projects have you shelved this year? I’m genuinely curious about the things that didn’t work out, the assumptions that turned out to be wrong, the gaps between what you thought you were building and what you actually built. The internet has plenty of success stories, but there’s something valuable in the archives of our almost-solutions too.
