Who Needs Another App?

A reluctant user, a life transition, and the surprising value of choosing the day before it chooses you.

When my former colleague first told me about Own Day, I had what I thought was a perfectly reasonable reaction:

Who needs another app?

I already had a calendar. I had Outlook. I had Teams. I had Notes. I had a phone full of apps I had downloaded with optimism and abandoned without shame or regret. Some were for fitness. A couple for tasks. One “personal operating system” which sounded like something only a consultant or a 24-year-old with a ring light could say with a straight face.

So when she told me she was working on an app to help people live more intentionally, I nodded politely and thought: good for her. Not for me.

Then life did what life does. It changed.

When structure disappears, attention goes with it

After many years at Microsoft, I accepted a voluntary retirement package. On paper, this was good news. A choice. A transition. A chance to take a breath and think about what came next.

I had imagined my final stretch would feel like a slow victory lap. A few handoffs. A few farewell coffees. A little time to clean up folders, pass along context, and maybe feel wise. Instead, as my time at work started drawing to a close, so did my attention.

I still had things to do, but my mind kept wandering. I would sit down to finish something and suddenly find myself thinking about retirement accounts, college tuition, whether I should finally fix the garage shelving, whether my daughter was calling home enough, whether I should get back in shape, whether I wanted to consult, teach, travel, coach, or finally learn how to make decent barbecue.

I wanted structure. I really did. I did not want another app.

Still, because I am a supportive former colleague and because curiosity usually gets the better of me, I signed up.

The world’s Most Reluctant User

I told her I was joining as the world’s Most Reluctant User. MRU. Put it on the dashboard.

The first thing I noticed was that Own Day did not ask me to plan my entire life. That helped. I was in no mood to create a five-year roadmap for becoming my best self. I had spent enough years in planning meetings to know that the more ambitious the deck, the less likely anyone is to open it again.

Own Day started smaller.

It asked me to choose a few areas that mattered right now. Not forever. Not as a grand declaration of identity. Just right now.

Health. Relationships. Money. Peace of mind. Joy. Growth. Giving. Gratitude.

That list got my attention.

Because those were the things running around in my head anyway. They just usually showed up as noise.

Lose ten pounds. Call my brother. Figure out what comes next. Be less distracted at dinner. Stop waking up at 3:30 a.m. thinking about RSUs. Go to the gym. Read something that is not a work memo. Be more useful to people. Be less irritable. Enjoy the fact that I have earned this phase of life instead of treating it like another problem to solve.

Own Day gave those thoughts a place to land. Well, not all of them. I was forced to choose a maximum of three focus areas, which felt mildly unreasonable until I realized that taming ambition is apparently part of the system. Also par for the course for retirees, I guess.

A sticky note for life’s important stuff

Once I identified the focus areas I was prompted to identify some foundations and priorities.

Foundations are the things that keep you steady. The basics. Walk. Stretch. Read. Drink water. Sleep better. Check in with someone. Spend ten minutes learning. Notice something good. You will not post them on LinkedIn. But when you do them consistently, life feels less wobbly.

Priorities are different. They are the few things you choose to move forward today.

That was harder for me than I expected. I set up foundations and one priority for a single focus area, then skipped through the rest of the setup until I reached Today.

Today is where you choose the foundations and priorities you want to carry into a specific day. I stared at the screen like I had been slacking off work and I had been called for a performance check in.

What are my priorities today?

At first I could think of nothing. Then, I wanted to add everything. Clean inbox. Review documents. Call financial advisor. Work out. Email former manager. Research consulting options. Fix the sprinkler. Book dentist. Read estate planning article. Watch the Mariners game without checking my phone.

Own Day asks you to stick to slim pickings. I picked three.

Walk for 30 minutes.

Call my mom.

Write down three ideas for what I want this next chapter to look like.

I wish I could say I immediately became a new man. I did not. I still checked email too much. I also added one slightly cheaty priority called “pay Visa bill,” which I am pretty sure was not the philosophical intent of the product. But that is also part of what I liked. Own Day did not scold me. It did not give me a red warning badge. It did not act disappointed.

That mattered, because my first attempt was not exactly a triumph.

I did two of the three things I had chosen. I walked. I called my mom. I even wrote down a few scattered ideas about what this next chapter might look like.

Then I forgot to update the app.

The next two days were worse. I did plenty of things, technically. I paid the Visa bill. I answered emails that no longer really required my attention. I moved a few household tasks from one mental pile to another. I stayed busy enough to avoid feeling lazy, but not focused enough to feel like anything meaningful had moved.

Without work providing the shape of the day, I found I could fill time very easily. What I was not doing was choosing it. By the third evening, I had a small but noticeable wave of existential dread, which sounds dramatic but is also one of the natural side effects of having too much time and no clear plan.

So I decided to give Own Day a more serious try. Partly because, to be honest, I knew I would eventually be asked for feedback. But also because the first day had worked better than I wanted to admit. I had walked. I had called my dad. I had written down a few thoughts I would otherwise have left floating around in my head.

There is a quote on the Today screen, and I found myself pausing on it in the morning. At first, I thought that would be too precious for me. I am a sports guy. I like box scores, not inspirational wallpaper. But the quote became a small interruption in the best way. A second to ask: what kind of day am I actually trying to have?

That is where Own Day started to make sense.

A calendar tells you where to be.

A to-do list tells you what is waiting.

Own Day asks what deserves your attention.

That is different.

The app became, in my mind, the moral equivalent of a sticky note. But not the sticky note you use for urgent tasks like “call plumber” or “send reimbursement form.” It is the sticky note for life’s important stuff.

Some days, I used it well. Some days, I checked off one thing and called it a moral victory. Some days, I ignored it until evening and then had to admit that I had drifted through the day in a fog of errands, half-work, and ESPN clips. But then, the app helped nudge me. And maybe that was the point all along. I like that the streak on Own Day is around setting intentions not completion. I used to be on Duolingo. I get streaks.

A small system for shapeless day

Own Day does not confuse intensity with progress. It does not assume every day is going to be optimized. It understands that people have families, jobs, transitions, aging parents, college kids, bad sleep, unread messages, and random Tuesdays where everything takes longer than it should.

After a couple of weeks, I realized something I did not expect going in. The app was helping in my transition.

I liked choosing foundations. I liked seeing progress at the end of the day. I also liked that it took less than a minute most mornings to set my plan for the day and even less in the evening to strike out the items I had completed. That matters. I do not need a second job managing my self-improvement software.

The best days were not the days I completed everything. The best days were the days I made one thoughtful choice I might otherwise have postponed or frankly not paid any attention to otherwise.

Eventually, I signed up as a founding member.

This was not because I became an app person. I remain suspicious of apps. I still believe most of them are tiny rectangles of good intentions and eventual guilt.

But Own Day earned a place because it helped me pay attention to the person I wanted to become. That is especially useful in a transition.

When your work identity starts to loosen, even in a good way, the days can get strangely shapeless. You may have more freedom, but less structure. More time, but less direction. More room to think, but also more room to drift.

Who needs another app? Maybe nobody. Except, perhaps, someone whose calendar is full but whose life feels a little cluttered.

Note: Some details have been changed to protect the author’s identity. The accompanying image is for representational purposes only.