How close did you come to retiring only to see your gains disappear

TLDR: I use a system that's just based on math, so there's no emotional decision-making. The math says to buy more or sell and take profits from quarter-to-quarter. The TACO and NACHO trades have been amazing.

The system I use is designed to improve on simple dollar-cost averaging by using value-cost averaging: adding more after underperformance, adding less or selling after outperformance, and maintaining a disciplined stock/bond rebalancing framework. In many historical periods, especially volatile ones, that kind of system can outperform simple DCA or passive buy-and-hold with the same contributions. But the advantage is not guaranteed in every period, and the comparison depends heavily on the benchmark, time horizon, leverage level, and whether you measure absolute or risk-adjusted returns. I have been fortunate in that it's worked exceedingly well for me, especially over the past 10 years. I retired when I turned 53 with more than I ever thought I'd have. I do use leveraged funds, though, which is something that a lot of people are scared to do.

No, but only because the vast majority of my money is in an IRA so it’s not subject to capital gains. I know people who do, yes, and if you do it long enough you eventually have longer-held shares to avoid short term gains. You may even choose to forgo following the exact plan for a year to avoid short term gains. Totally up to you.

JasonKelly.com