Usually you fix more than you replace, and you almost never start over. The instinct to rip everything out and rebuild is the most expensive mistake a growing business can make. The right move is to work out which systems are genuinely holding you back, which are just annoying and which are quietly fine, then deal with them in that order.
How to tell the difference
A system is worth replacing when it is actively costing you, in lost time, in errors, or in work you cannot win because the system cannot do it. A system is worth fixing rather than replacing when it works but is clunky, or when the real problem is that two systems are not talking to each other rather than either one being bad. And a system is best left alone when it is unglamorous but doing its job, no matter how old it looks.
The hidden cost of replacing
Replacing a working system carries costs that are easy to miss: the months of disruption, the data migration that always takes longer than promised, the retraining and the risk that the new system solves yesterday's problem. None of that means never replace. It means be sure the gain is real before you commit.
Where to start
Start by listing what actually slows the business down, in plain terms, then trace each one back to its cause. Often the fix is smaller and cheaper than a full replacement. Integration between two systems rather than a new one. A process change rather than a purchase.
A Technology Discovery and Blueprint does exactly this triage for you and hands you the ordered list, so you spend money where it counts.