I plan on starting at least a partial withdrawal in 2021 as I wind down my business (maybe 1/3rd of my planned spend will be earned income). Right now, plans are to put 1 year's planned spend in two high yield online accounts (1 account holds the budgeted planned spend, the other account holds my contingency/capital funds which will grow year to year assuming there is surplus). From there, I plan on moving maybe 3 month chunks of cash from my budgeted planned spend account to a checking account to pay the bills. When/if there is a capital need, plans would be to move over the cash from that account as needed. Additionally, will probably continue to use Mint to track all these expenses to make sure I am staying inside the lines. While planning for significant discretionary spending, I am sensitive to my former LBYMs thinking... and will it pull back my spending, despite the fact I know I can. At the same time, if say some big expensive fancy trip opportunity presents itself that I did not plan for that takes me above my yearly planned spend, I want to pull the trigger and avoid the fear of overspending that year. I suspect time will cure these concerns once I cross over, but what tricks/rules/systems did you put in place to 1) make sure you were not reckless in your retirement spending, and 2) made sure your did the things you know you can afford to do, even if they bump you over a particular year's spending plan. Oh, and if you are married, what changes, if any, were made to keep mama happy with her spending (my mama is somewhat of a free spender!)