Make the game winnable by setting clear freedom numbers

A billion is not a plan. Neither is “someday.” You make money winnable by defining levels you can reach: Security, Independence, and Freedom. Security is your needs covered without worry. Independence adds some wants and breathing room. Freedom is work-optional, with your lifestyle chosen, not forced.

Grab a notepad and price your real life. Kitchen-table math beats fantasy spreadsheets. What does Security cost monthly for you? Independence? Freedom? Annualize those numbers and add taxes and a cushion. One client thought they needed an impossibly large lump sum. When we priced their Security level honestly, it required far less than their guess. A small micro-anecdote: they wrote “Paid groceries” on a sticky note and put it on the fridge after realizing their investments already covered food.

Translate costs into a portfolio target using a conservative withdrawal rate, then factor in any reliable income. Suddenly the target isn’t a mountain range, it’s a series of trail markers. I might be wrong, but most procrastination comes from fuzzy goals, not lack of discipline.

Now plan backward. What’s a 12‑month milestone? A 36‑month one? What savings rate and investment mix make those likely? Automate to those numbers and review twice a year. You’re not chasing a myth, you’re walking toward visible markers.

Choose three clear levels for your life—Security, Independence, and Freedom—and write what each looks like. Price them with your actual monthly costs, then annualize and add taxes and a little buffer. Translate each annual cost into a portfolio number using a 3%–4% withdrawal rate, minus any reliable income you expect. Finally, set 12‑ and 36‑month milestones that roll up to those targets and automate your savings and investments toward them. Put the numbers where you can see them so your brain believes the path. Do the Security level pricing on paper tonight.