In a similar situation to OP, financially ok - the numbers say I am good to go, but after having worked for so long (and some time between jobs to realize the downside of not getting paid on a regular schedule) I have come to depend on a paycheck every 2 weeks.
Not getting a bi-weekly paycheck held me back from even thinking about making the leap - so I created some "buckets" at Vanguard and other fund companies to have my dividends/cap gains deposited into a cash MM account.
The plan is take 2 withdrawals per month from this account to simulate a paycheck - This gives me a warm and fuzzy feeling on the 1st and 15th and more importantly helps me stay within budget and not overspend accidentally.
Once I am comfortable with my expenses I can adjust the amount up or down for each "paycheck" - If my expenses are lower I plan to re-invest the excess back into the market - which is what I do now.
The above plan has lowered my anxiety considerably and I plan on making the leap next year (fingers crossed)
Goodluck to you!
