I Built a Journaling App to Give Me Answers

I remember the day I added AI-powered reflections to Activities Matter. I’d been logging activities for months by then, and the app had a nice pie chart showing how I split my time: work, fitness, social, mental wellbeing, travel. I could see how my balance shifted week to week. Now, I thought, the AI would analyze all this and tell me something profound.

The response came back: “You’re demonstrating a strong, healthy balance in your life. This is a great sign of intentional living and self-awareness.”

That was it. With more prompting, I got variations of “do more of X and less of Y.” Technically accurate. Completely useless.

I was baffled. I’d given it all this data. Why couldn’t it tell me anything meaningful? After a few days of frustration, I understood: the answers shouldn’t come from the AI. They should be mine.

No amount of data can make an AI know who I really am. It doesn’t have access to my thoughts, my feelings, my way of perceiving the world. All the context that makes advice meaningful. And even if it did, it won’t be living my life. Following AI-generated answers means living according to its logic, not mine.

We’re taught by search engines and now by AI that we can get any answer we want, instantly. Type a question, get a response. But learning who you are doesn’t work that way. That work is yours alone.

The Stoics had a phrase for this kind of acceptance: amor fati, loving your fate. Not fighting against what is. Not wishing things were different. I’d encountered the concept before building the app, and it’s part of why those AI suggestions felt so wrong. When I was exhausted from work, the AI essentially said “do less work.” But I loved my work. I had a great opportunity in front of me. Being tired didn’t mean I should quit. It meant I needed to find a way through the next few weeks with intention. That nuance, that understanding of what mattered to me, was something only I could provide.

So I stopped asking the app for answers. I started using it differently. Not as an oracle, but as a mirror.

Learning 1: Patterns, Not Prescriptions

The breakthrough came when I noticed something in my own data. Days when I accomplished a lot (big coding sessions on the app, great training runs) weren’t necessarily good days. That surprised me. Wasn’t productivity supposed to feel good?

I went deeper, using AI reflection not to get answers but as a thinking partner. I’d write out my thoughts and ask it questions to push my reasoning further. What emerged was a pattern about expectations. When I didn’t do much during the week, I’d load huge expectations onto the weekend. I’d try to cram in everything I’d missed. By Monday, I was disappointed and exhausted, even if I’d technically accomplished a lot.

The app didn’t solve this. It showed me the pattern. I had to do the internal work to understand what it meant and what to do about it.

That led me to clarify what I actually value. Things like mastery and novelty kept showing up in the entries that felt most alive. I started finding ways to incorporate those values throughout my week, not just on weekends.

I began living more true to myself. Not because an app prescribed it, but because it gave me the space to figure it out.

Learning 2: Intentionality Over Automation

Using the app daily has made it part of my life, like an enhanced commonplace book. Commonplace books have been around for centuries: personal collections where people copied down quotes, ideas, and observations that resonated with them. Not everything they read, just what mattered. The act of choosing was intentional because those notebooks weren’t cheap.

What makes Activities Matter “enhanced”? Every day, I rate my mood on a simple scale from -2 to 2 and reflect briefly on whether it was a good or bad day. This small ritual, combined with the activities I log, creates structured data that reveals patterns over time. I can see that reading has a positive impact on my mood. That unplanned activities on already-full days drag it down. These correlations only emerge because I’m intentionally logging what matters and taking a moment each day to reflect.

I considered adding Garmin or Apple Health integration. Automatic syncing would make logging “easier.” But then I realized that would turn the app into just another view of data I already have in three or four other places. It would remove the intentionality.

Think about your phone’s photo gallery. Because it captures every image (screenshots, receipts, random pics) it’s often a mess. We lost something when we stopped curating physical photo albums. The act of choosing what to keep is what gives a collection meaning.

When I read a book or listen to a podcast and then write it down with my thoughts at that moment, I have a clear memory of what I did and how I felt. That intentional act of adding an entry with my thoughts right then is what makes the reflection valuable. I’m not just recording that I read something. I’m capturing why it mattered, what it made me think about, how it connected to other things in my life.

The act of choosing what to log is the reflection.

Learning 3: Enough Is a Strategy

Here’s the counterintuitive one: while Activities Matter is technically a business, I’m not running it like one. And that’s made all the difference.

My day job provides impact, learning, great colleagues, and financial stability. That last part is freeing. Not thinking about money means I can build the product I actually want, rather than what might get traction or please investors.

I think about Paul Jarvis’s book Company of One. His core idea is powerful: instead of growth at all costs, you define what “enough” looks like. Maybe that’s enough income to live comfortably. Enough customers to serve them well. Enough complexity that you still enjoy the work. Then you build toward that definition of enough and resist the pressure to push beyond it.

That’s intentional living applied to business. And it’s exactly what Activities Matter is trying to help people do in their own lives. How could I preach balance while grinding 80-hour weeks? How could I talk about aligning with your values while optimizing for metrics that don’t align with mine?

I believe we’re entering an era where this approach is more viable than ever. AI changes the economics of software. You don’t need a team of fifty to build something sophisticated anymore. You can be intentionally small and still create real value for a specific audience.

Here’s the paradox: not treating it as a business has made me more consistent than I’ve been with any project in my life. I don’t push through exhausting weekends or pivot based on what might get attention. I build at a sustainable pace, week after week, because that aligns with how I want to live.

Loving What Is

These three learnings feel interconnected. They’re all about not forcing things to be what they’re “supposed” to be.

The app won’t solve your problems. That’s the design, not a flaw. You solve your problems. The app helps you see them clearly.

Automation won’t make it better. Sometimes the “inefficiency” is the point.

Business pressure won’t make it sustainable. Removing that pressure is what enabled consistency.

It’s about reflecting honestly, knowing what you value, and practicing amor fati: loving what is. Not what you wish it was. Not what you think it should be. Not what others tell you it needs to be.

I started building Activities Matter as a side project, adding features so I’d have something worth using. Somewhere along the way, I stopped building it to improve it and started using it because it genuinely helped. Now, 600 days in, I look back and barely notice how the time passed. I’m just grateful for the streak, for the learnings, for the slow accumulation of self-knowledge that no AI could have handed me.

That’s exactly how it should be.