From Side Projects to Scaling Up: Lessons I’m Carrying Forward

🧠 Context / Why I Did This

For the past few months, I’ve been building Steadfast — a personal productivity app that’s been equal parts fun, frustrating, and eye-opening. Like most of my projects, it started with a scratch-your-own-itch idea and quickly grew into something with real users, feedback loops, and a backlog longer than I expected.

At the same time, I’ve been stepping into a new season in my career — one that’s going to mean more responsibility, bigger projects, and more people depending on me to get things right.

As different as those two worlds seem — a personal app side project and leading complex, high-stakes work — the lessons are surprisingly similar.

⚙️ Building Steadfast (and What It Taught Me)

When you’re working on something small and self-funded, you make every trade-off count:

• Every feature has a cost — time, complexity, or tech debt.
• Shipping beats perfection — the sooner users touch it, the sooner you know if you’re on the right track.
• Simplicity is an asset — if it’s hard for you to maintain, it’s going to be impossible to scale.

I’ve had to be deliberate about what goes into Steadfast. Does this feature solve a problem people actually have? Is it worth the maintenance burden? Will it slow me down when I need to pivot?

You can explore more about how Steadfast works here.

Those same questions matter in bigger environments — the difference is the numbers are larger and the stakes are higher.

🔐 Applying It in the Next Chapter

In my new role, I won’t be the one committing the code every day, but the trade-offs don’t go away. If anything, they get more layered:

• Dependencies multiply — decisions in one system ripple into three others.
• Stakeholder expectations matter as much as technical feasibility — success isn’t just “it works,” it’s “it works for the people who need it.”
• The cost of rework grows fast — get the design wrong early, and you’re spending weeks, not hours, to fix it.

The habits I’ve built through side projects — questioning scope, valuing feedback early, and aiming for maintainability — translate almost one-for-one.

🧠 Lessons Learned

Whether you’re building a personal app in your spare time or steering a large-scale project, the fundamentals are the same:

• Start small, validate fast.
• Be honest about trade-offs.
• Keep complexity in check — it’s harder to untangle later.

Steadfast reminded me that good software is less about grand launches and more about the quiet, consistent work of making it better every day. With bigger challenges ahead in my day job, I’m glad these lessons have been tested and proven in the small before I bring them to the big stage.

If you want to see the principles in action, Steadfast is where I’ve been testing and refining them — be sure to sign up for updates on its full launch.