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How often should you re-balance your portfolio?

I've actually never done it.   I simply move some %'s around for my contributions.   eg, Right now, I'm putting a bit more in international as they are being beaten up a bit and putting a little less % in the reit's.  But i've never actually redistributed out any of my gains.
How often do you do it?  And did you do it in your 30's and 40s?
Re-balancing can help you buy low and sell high over time. Re-balance too little and your mix will drift, and you will not see the "buy low / sell high benefit".  Re-balance too frequently and you will also see little benefit.
Some people re-balance on the basis of time. Say, once a quarter or once a year.  And doing it annually can be pretty easy to follow if you do it at the same time each year (birthday. year-end, etc.)
In my own account, I re-balance based on triggers I have set.  I have an overall dollar target for equities (which I escalate with CPI over time). And within equities, I have sub-categories that add up to the total.  So, for each sub-category, there is then a dollar target and a tolerance.  If the actual dollars move up enough,  I then re-balance by selling a little to bring the total for the sub-category back to target.  If the actual dollars move down enough, I then re-balance by buying a little to bring the total for the sub-category back to target.
I determined the tolerances I use based on past history over varying time periods, trying to choose trigger points that would have done the best over time (made the most money). I also wanted the triggers to be relatively stable, so that if the trigger was a little off, it would not change the results dramatically. I specifically decided to use tolerances no lower than 5% and no higher than 30%.  I based the re-balancing trigger points solely on prices, as I generally do not automatically reinvest dividends.  For the S&P500 the tolerance is +/-25%.
Note that I re-balance based on a DOLLAR target rather than a PERCENTAGE target. I  prefer the dollar target approach, because when prices go down, I do not mind owning a higher percentage of a given asset.  When they go up, I do not mind owning a lower percentage.  As an (extreme?) example, say I have $50 in equities and $50 in cash and then equities fall 50% to $25.  Re- balancing on a percentage basis gives $37.5 equities plus $37.5 cash.  Re-balancing to dollars give $50 in equities and $25 in cash (i.e., 67/33 vs 50/50).
I believe I started re-balancing essentially this way maybe 5-10 years before retirement. When you are just starting out, account balances are relatively low, and it really does not make much difference.  Better just to keep accumulating equities when you are starting out.
Short answer; when I feel I should. At my age (69) I generally think I should be 60% equities, but I've never been there. I look at the gross allocations and then reference sector allocations. When something gets out of whack, like financials did for me the past few years, I pare that sector back, but not to a fault. When financials hit 30% of portfolio, I sold a little BRKB and MA (boo, hoo!) and bought some boring bond funds and built up cash. When my investment in Bio/Health lagged, at the same time, I put some of that finance sector money there ) XBI ); When real estate was near zero, I bought a rental property in Sacramento (up 20+% now).

Result? 2 years later, still 27% financials, but I LIKE V and BRK-B, the bulk of that 'excess.' And regret I sold the MA 

Thus, total portfolio is 57% US, 13% foreign stock, 24% bonds.  Not scientific or prescribed by time, but seems to work.
Only when I add new funds to my account - I sometimes use the new funds to effectively re-balance the ratios of my various ETF holdings.  But I have never adjusted existing holdings for re-balancing purposes.
No. I've never done it. Why sell a winning horse?

New money can cover the re-distribution if want to remain invested.

I don't know about the rest but I didn't even have any investments to re-balance in my 30s... I'm still in my 40s.
Recently retired so I do it once a year.Did not when I was younger .The gurus all say when young you should be 80-100 % in equities when young.I always was 60/40 or 55/45 and that helped me sleep at night and served me well during the downturns in the market
If you are in a few diversified funds, e.g. ITOT or VT and a catch-all bond fund; then balancing is a minor issue.  If you are a mature sector investor with allocations placed every where (as I currently am); then re-balancing is performed twice per year at my convenience.
How often do I re-balance? Never. I also despise any automated re-balancing that some suggest.

If I was inclined to do it manually, it would be annual. And then I would have to ask myself "what is the measuring stick for this process?" Some think you should re-balance by sector weighting. Because I don't build my portfolio to mirror any index, I would have a hard time finding a way to "re-balance"my holdings.

Re-balancing generally means I have to sell winners to buy something else. My buy/sell decisions are more carefully crafted than that. That isn't to say that I ignore sector-related trends. I bought more technology, health care and energy when others thought they were a bad investment. I do that with the cash flow from my rich dividend-income stream.
Generally, I have seen it as busy work. I try to keep growth stocks in taxable accounts and income stocks and bonds in non-taxable accounts. Any rebalancing in taxable accounts can bring cap gains tax into play.
I never rebalance...

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