[jldugger]

Two tools: an annual budget spreadsheet and GNUCash.

The annual budget spreadsheet has a tab for every year, and every December I duplicate the tab and adjust for the coming year. It focuses on cash inflows (salary, equity grants, dividends) and outflows (expenses, taxes, investments). This is what I use to verify I can afford to max out 401ks and similar, as well as gifts/charity and maybe the occasional major purchase.

The other half of this equation is GNUCash. If the spreadsheet is a strategic plan, this is the tool I use to tactically manage cash flows and track assets on the ground. There are accounts for the typical double entry categories: income, expense, asset, liability, equity. It tracks in multiple currencies, including ticker symbols and custom currencies, and tracks conversion rates between symbols and my default currency. I have a variety of recurring transactions programmed in and created 90 days in advance, which is useful when paired with the 'minimum future balance' column -- if transferring money now would result in a future balance going negative (perhaps between a paycheck and rent being due or a CC being paid off), I can adjust.

What I don't yet have is a portfolio management layer. I have a few ideas in that space, but it gets complicated quickly with taxes.