I'm going to go ahead and answer your question: I don't know if there's room for a product that grows with you, but I don't think such products are feasible. I

I'm going to go ahead and answer your question: I don't know if there's room for a product that grows with you, but I don't think such products are feasible. I worked with a large personal finance software company at a time when they were enraptured with re-use. They had visions of doing things like sharing contact and project management modules across customer relationship management (CRM) and invoicing applications. I had a large stake in making sure they thought through these issues clearly, as the very form of the product I was leading the creation of was at stake. We think about an invoice or a project or a task or a contact as something that's fairly self-evident, but they're not. More precisely, an application needs to create a model of these things, and that model is a useful simplification. It is likely that "a product that grows with you" is one that fundamentally changes the model of the entities that your product works with. So, for example, a simple invoicing tool might have a client or a customer field, and that works in let's say ninety-five percent of the cases, but for some people, they want a full-on contact manager where you need to know that an invoice is for ABC Co., that the client contact is John Smith, that invoices should be sent to payables@abcco.example.com. Pretty soon you're going down the contact management slash engagement business process analysis rabbit hole. And going down that rabbit hole is fine, but you're never going to be able to create 1. a simple, novice-friendly view of that industrial strength application that 2. stores data in a way that is semantically correct so that 3. when the user decides to upgrade from Invoicr Lite to Invoicr Enterprise Platinum their data isn't a nightmarish state. This is one of the reasons why it took Windows user experience so long to approach anything even remotely as pleasant as the Mac: Windows had to support a much — let us say out of politeness — richer model computing than the Mac did. The Mac user was never exposed to certain details — like whether your filesystem was "really" hierarchical (the original Mac didn't have this feature) — but instead shown a simplified view of the world that Apple and developers had the freedom (and obligation) to implement by any means necessary.