Ok let's address all three questions.
Is it wise to buy at historical highs?
Well if there is a number of tailwinds that lead you to the conclusion that the stock will continue to rally, then yes. But also look at the potential headwinds. At some point you must make the decision to either buy a ticket for the roller coaster and jump on, or just sit at the ticket booth and watch, interviewing people who are on the ride and either regret your decision not to buy a ticket, or rejoice in your decision to stay on the sidelines.
Have I brought at historical highs?
Yes, most recently $NVIDIA Corp(NVDA)$. And to date I have no regrets. I brought at $1.08, not many, but now it's over $1.30 in under two weeks or so. Do I regret not buying more? No, whenever I start a new position in a stock I always take a very small position. I wright down all my assumptions and keep checking them, if they hold true, I will add to my position as the stock goes up because my DCA, will remain lower than the current price. If the stock goes down I may buy more also to lower my DCA.
Have I made money buying at historical highs?
Yes, in fact I have never not made money. But a caveat to this is, I rarely buy at historical highs, unless I have total conviction that the stock will continue to roar. In fact, if I'm seriously a believer, especially if I've owned it for over a year, and see it moving up and I sell some on new highs and buy it back on drops, provided I still feel my facts still support its growth. this way I lock in profits.
But let's flip the coin for a sec. What about buying on historical lows? Much less success there, I brought $Pfizer(PFE)$ For eg at its low, then it went lower, so I brought more, it went lower, and lower, still brought more. It recovered a little, in the end I sold at a 28% loss. But used that money that I split over 3 other stocks that have all performed well, and easily covered that loss. Pfizer is up a bit now, but I would still be loosing on it. And I'm winning by not holding on to a stock that has a mixed future.
$ZIM Integrated Shipping Services Ltd.(ZIM)$ Was another one, I did ok on that, brought on lows, then it went to the basement, so I brought At historic lows, and it recovered quite a bit. In the end I was up 14%, but let's cut to the chase... Lessons learned.
With the very odd exception, going forward, I'm not into buying on historic highs or historic lows. The time spent researching, and checking that research, let alone making decisions on whether to buy more, sell more. Well it's just not worth it. Better to stick with more consistently sound stocks in my portfolio. No thinking required, they just deliver monthly, quarterly, annually. And have done it for decades. $Snap-on(SNA)$ $Visa(V)$ Are two examples, but there are plenty more
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