That's not really a question that can be answered with certainty.

Five years is fairly safe that the markets will return to/surpass previous highs. Two years will probably see us out of this bear market and most stocks should have recovered.

At this moment in time, the Fed is planning on a 75BPS (3/4%) raise in the Fed funds rate on Nov 2 and another 50BPS (1/2%) on Dec 15. As long as those rate increases occur and the Fed continues QT, the markets should be lower than today in mid-December.

In addition to raising the Fed funds rate, the Fed is also shrinking its balance sheet through Quantitative Tightening (QT), which is the opposite of QE. The Fed has been engaged in QE off and on since early 2009, buying both TBills and mortgage backed securities. For QT, the Fed is allowing their balance sheet to 'run off' ... they are allowing the assets to mature and rather than 'roll' (reinvest) them, they are shrinking their balance sheet.
It was the QE policy over the last decade that helped cause assets to rise so much; all of that money sloshing around (liquidity) the system flowed into assets. Now that the Fed (and other central banks) are doing QT, the world's money supply is shrinking and it's causing asset prices to fall.
However, it is QT that is currently starting to cause problems in the world's economy. The UK's government debt market is stressed to the point where the Bank of England (their version of the Fed) has had to go back to QE due to British inflation-linked government debt blowing out. Here's a quick article: https://www.reuters.com/markets/euro...ts-2022-10-11/
Credit Suisse is also on the verge of blowing up. https://indianexpress.com/article/ex...ahead-8190225/
Japan's also got major issues related to higher rates and QT.
So we're starting to see the first cracks in worldwide finance as countries try to tame inflation. I don't know how much worldwide financial damage the Federal Reserve will allow before they stop QT and possibly rate increases.
So far, they've been pretty resolute on killing inflation, but things are now starting to break. So that raises the question of how strong the Fed's resolve on controlling inflation is. If they blink as soon as things start breaking, we could be stuck with high inflation which could ironically also inflate asset prices.

If you're not willing to sell your investments, none of this matters. You will sit there and watch the markets rise and fall.

Since I'm parked completely in ultra short term Treasuries, I am watching inflation reports, Fed statements, etc for any major changes. But then again, almost all of my TV time is spent watching CNBC and Bloomberg. I tend to fly on weekends because there's little financial news over weekends. It's what I do - if you have no interest in doing that, you need to figure out a few great information sources that you can easily digest.
This is one of my favorites; excellent technical analysis: https://www.youtube.com/channel/UC_y...JrnMuZt33y7QYQ
One investor I follow closely is Dan Niles of Sntori Capital; he appears on CNBC on occasion. Here's one of his interviews: https://www.youtube.com/watch?v=f8ZYXGW6Um8
My personal Technical Analysis puts the S&P in the 2500 range, but I tend to be overly negative. The bottom is likely to be higher than 2500.

I personally am not bothering to try to trade anything in this market; I will wait until I think all's clear. I won't hit the bottom exactly and I sold a bit past the top. That's fine for me. I sleep easily at night.