Six honest questions. Net worth alone doesn't pick the right way in - what you understand, what's at stake right now, and who shares the money story all matter too.
Question 1 · fundamentals
Do you know roughly where every dollar of your monthly income goes?
The actual numbers, not just the categories. Within ~10%.
Question 2 · fundamentals
How comfortable are you with the basics - compound returns, withdrawal rates, asset allocation?
Could you explain them to a friend without Googling?
Question 3 · wealth
How much investable net worth have you actually built? (excluding your primary home)
Compare against your essential annual spend to make this concrete.
Question 4 · stakes
Is a big money decision on the table in the next year?
A vesting cliff, a sale, an exit, a sabbatical, a career pivot - anything expensive to get wrong.
Question 5 · partner
Are you in a partnership where money is shared (joint accounts, shared expenses, shared future)?