Should I build this myself, or just buy it?
You keep landing on "it depends" and treating that as an answer. It is not an answer. It is the absence of one, dressed up to look thoughtful. You are not lacking judgment. You have judgment. What you lack is a short list of questions you ask every time, before a sales pitch or a deadline makes the choice for you. This is fixable today. Not with more experience, and not by waiting until you feel certain. You fix it by writing down the same five questions and refusing to decide until you've answered them.
You do not need better instincts. You need five questions, asked in order, every time: What problem, exactly, am I solving? What does buying cost in money and control? What does building cost in time and people? Who maintains this in a year? Decide only after you answer all four.
What changes unlock by starting
- A written build-or-buy answer you could defend to someone else.
- A five-question checklist you reuse on every future decision like this.
- Less time spent circling the decision, more time spent acting on it.
- Fewer regretted purchases or projects because you named the real costs early.