Estimate your annual income for the rest of your career (with realistic assumptions on promotions, raises to compensate inflation and a bit more, change of job

Estimate your annual income for the rest of your career (with realistic assumptions on promotions, raises to compensate inflation and a bit more, change of jobs...). Add the pension contribution of your employer (if any); discount back with appropriate nominal investment rate (if you included inflation raises in the first place, otherwise you need to net that). This is the value of your career. Now the difficult part: how much annual income are you willing to sacrifice to get free time and being able to do all the things you want to do? You can do it on an annual basis or % basis of the total. You should also project forward your estimated expenses, to double check that you don't value your free time so much that you would not have enough money to pay the rent: if you end up in this situation, move to a cheaper country and redo the calcs. And maybe add a safety factor, for some peace of mind: as somebody else posted, shares or bonds may not do well every year. EDIT: this approach assumes you maintain your current (and foreseeable) quality of life in terms of disposable income.