You can build it. Should you?

I've spent my career helping people build software. This is a series of letters about what happens when the tools for building change faster than the principles behind building. Each one is a reminder that while the technology changes quickly, the questions that matter often stay the same. -- Dear past Jenna, The thing that drew you to tech in the first place, that it's always changing, is the thing that will keep you here. Tools change (sometimes for the better and sometimes not) almost weekly. People who never consider themselves technical, much less a developer, will build apps in an afternoon with this new programming language called English. Products will go from idea to deployed before you finish your first cup of coffee (you have a toddler now, so you rarely get the full cup before it goes cold anyways). "I don't know how to code" or "I'm not technical" is no longer a barrier to building. And that's exciting, given you've focused nearly your entire career helping others build software. But we can't confuse the ability to build with the wisdom to build. One of the most valuable habits you've developed over the last two decades is asking a simple question: "Should we build it?" For most of your career, "Can we build it?" was a hard question. Time, budget, complexity, maybe the tech wasn't there yet. But those constraints were usually temporary. With enough people, time, and money, just about anything is possible. But the real questions were always: Should we build this? Is this the best use of our time? Does this solve a problem our customers actually need solved, or does it create new problems? What are we choosing not to build? Those questions haven't changed, but the environment around them has. Today, almost anyone can build software. Between tools like Lovable, Bolt, Replit, Claude Code, Codex, and whatever's next, the barrier to building software is lower than it's ever been. Now the question "Can we build it?" is too easy to answer. It's almost always ye