"Am I doing okay with money?" is actually two separate questions wearing one disguise, and conflating them causes a lot of unnecessary confusion. Cash flow asks: am I living within my means this specific month? Net worth asks: is my overall financial position improving over time? They can move in completely different directions, and you need to track both.
Here's how they can diverge. You might have a fantastic cash-flow month — income comfortably exceeding expenses, money left over — while your net worth barely moves, because that leftover money just sat in a low-interest account doing very little. Or you might have a tight cash-flow month, spending close to your full income, while your net worth still climbs nicely because a chunk of that spending was actually a loan principal payment, quietly shifting you from debt to equity.
Why both views matter together: cash flow tells you whether this month's habits are sustainable — are you spending more than you earn, which is a clear warning sign regardless of your net worth. Net worth tells you whether your overall trajectory, built from months and years of those habits, is actually heading somewhere good. A good month on its own doesn't guarantee a growing position, and a growing position doesn't mean every individual month felt comfortable.
The practical habit: check your cash flow every month — income versus expenses, are you in the black. Check your net worth less often, perhaps quarterly — assets versus liabilities, is the overall trend rising. Together, they give you the full picture neither one alone can provide.