When I was preparing to retire, I debated at what point to start taking Social Security payments. I did a calculation that showed if I opted to start taking payments upon retirement I would receive a total of "X" dollars in the first few years that I wouldn't receive if I postponed receiving payments for those few years. Of course, by postponing my payments for those years, my monthly payment, once it started, would be larger. However, according to my calculation, if I postponed starting to receive payments, it would take "Y" years of these larger, later, payments to equal the money I didn't take in the first few years of retirement. I don't remember the numbers, but "Y" was a big number of years before I caught up with the money I would receive in the first few years if I started payments early. I opted to start receiving SS payments as soon as I retired, opting for present money rather than increased future money. Now that the "Y" years have come and gone, I regret not postponing starting my SS payments. If I had, I would be money ahead now and in the future.
When I retired I got a financial advisor. he lost half my retirement money in 2008. I took over handling my own money in 2010 and am doing much better and am close to recovering the half I lost. yes the stock market has been better, but there is no substitute for paying attention to your own money.