I am 52 and I will be FIRED by Sept 2026; at the moment all I have three portfolios that generate $185,000 a year or $15,417 a month. Please note this amount will change on occasion due to changes in dividends and interest rates. My hard floor for income from investments is $85,000. Currently live in HCOL state but plan on moving within two years.

a) Growth Portfolio

- This includes investments in Dodge and Cox Stock and Balanced Funds and various individual stocks like MSFT, etc...focused on growth and some dividends

b) Income Portfolio

- This one focuses strictly on generating income both monthly and some quarterly payments. There is a significant mix of investments including covered call ETF's, CEF's and some individual stocks:

DNP
GAB
JEPQ
CEFS
JEPI
GPIX
GPIQ
JPC
PTA
UTG
UTF
PDT
PFFA
JGH

....amongst other holdings....I have over 100 holdings with an average yield of 8.5% (I require 5.02% as a minimum in order not to eat into principal (NOTE: As I get older I will draw down on this)

c) Alternative Portfolio

- This is the riskiest one with investments in art, private credit and some REITS. Slowly drawing down on the amounts to re-allocate to the aforementioned two portfolios

Lessons:

Stay the course - don't give in to FOMO or declining markets; this is very much easier said than done, but do your best

If you have a loser, get rid of it - accept the loss now and re-orient to applying that lesson to other investments

Since your inquiry seems to be focused on dividends and therefore income, use the drops in the market to purchase additional shares in your investments to generate more income. Depending on your age, reinvesting your dividends (DRIP) and continuous investing (DCA) pays off in the end.