“If the market is cut in half three years from now, could you take it on the chin?”
That’s the question I asked my cousin Dave a few years ago when he requested investment advice. He wanted to know about different asset allocation strategies that were all heavily weighted toward stocks.
Dave is investing for years down the road, but he’s a worrier. I can talk all day long about how markets go up over the long term… or how you would have made money 93% of the time over rolling 10-year periods since 1937… or how the only time you wouldn’t have made money over 10 years was if you sold during the depths of the Great Depression or Great Recession.
But none of that matters when your portfolio is down 30% because you’re in the middle of a bear market a few years after you’ve invested.
(Note: I’m not calling for a bear market in the near future. I don’t have a crystal ball. I’m simply pointing out that bear markets happen and that one probably will occur at some point.)
So I talked to Dave about investing in Perpetual Dividend Raisers (stocks that raise their dividends every year), index funds, and actively managed mutual funds. I discussed the pros and cons of each, including managing the money himself versus turning it over to an advisor.
I encouraged Dave and his wife to have an honest conversation about what they would do if the market headed south. Otherwise, the fact that the S&P 500 has a 10-year average total return of 140% over the past 40 years will be meaningless, as they may not be able to handle the volatility.
If they are invested in the market without the proper risk tolerance and the market slides, they will no doubt sell into weakness, probably near the bottom like so many other investors.
When you hear about people who got their clocks cleaned in 2008, it’s usually because they panicked and sold. I’m not judging. The panic was understandable. We narrowly escaped financial Armageddon. (That’s not hyperbolic. The entire financial system was on the verge of collapse.)
But investors who held on were made whole fairly quickly. Even if you bought at the very top in 2007, your portfolio was back to where it started by early 2013.
It’s easy to be rational when stocks are moving higher (as they are today) and say, “I’m in it for the long term.” But like Mike Tyson accurately stated, “Everyone has a plan until they get punched in the mouth.”
If you were in the market in 2008, think back to those dark days and consider whether you could handle a repeat of that experience. If you were not invested then, imagine what it would be like if your portfolio were cut in half. Would you have time to make it up? Would you be able to sleep at night? Would you be able to take it on the chin?
If the answer to any of those questions is no, get into safer assets like bonds, CDs, and money market accounts today.
If a downturn wouldn’t have you up against the ropes, stay invested, confident in the knowledge that markets go up over the long term.
Good investing,
Marc
P.S. What’s the best financial advice you’ve ever received – or advice that you often give to your kids, grandkids, or friends? Drop it in the comments below.

I pay some for insurance. Depending on the market, right now I have QQQ 540 Puts in place. Less than 1%. Buy some, sell some. A balancing act but I sleep better buying insurance. Any thoughts?
Start investing early and dollar cost average monthly. Start with most in a managed fund, keeping 30% out. Use 10% buy gold, 15% market play. After some education, switch to a self managed account and set up your own portfolio. Education and read, read, read.
Buy stocks that pay solid dividends, watch the cash flow on those companies and be frugal in your lifestyle.
Compounding, compounding, compounding.
Great guidance! As a broker retired with 35 years of stock trading, it has been my experience that the down times must be dealt with before the big drop. Prepping investors to understand, is great guidance from you. You go, Marc.
My advice to my grandsons 19 and 21 is to start investing now on a regular basis and their Nana will match every penny they invest! It’s so interesting….my youngest grandson sends money to me regularly to invest for him and his older brother can only manage to Venmo me $25 once every couple of months. Needless to say, the younger one’s investment acct is leaps and bounds ahead of his brothers and I really must thank you for all of the great recommendations from the Oxford Club. I’ve learned so much from being a part of this group!!! Have a great day!
I like the dollar matching idea. Humm…