mental do you do it?

Since this is my first post, quick background on me: I first started following Motley Fool on AOL back in the 90’s (yes, I’m that old). I even won a Fool branded golf towel and golf balls from the fun daily question contests they had back then.

I decided I finally had time to actively manage my own investments in 2017 and took a small chunk of my portfolio (about 20%) and built up a suite of 20 Foolish stocks (mostly from Rule Breakers). I tracked my performance and after the first 6-9 months of being behind the S&P (at one point by 20% – it was up 10% while I was down 10%) I “figured it out” and recovered and began crushing the market. In mid 2019, I discovered this board and began transitioning to a more active strategy (as opposed to the buy and hold philosophy of TMF) and reduced the number of stocks I own (from 20-25 to 6-12).

Over time I have gained confidence in my research, my style, and my performance and now I actively manage 70% of my money. That increase from 20% has come both from rapid appreciation and gradual reallocation from mutual funds and ETFs.

Currently, of the 9 stocks I have, the only stock I’ve been holding for more than a year is TTD. It was one of my first investments in 2017 and is a 15-bagger for me so far. Another favorite is ZM which is a 4-bagger for me in less than a year.

Thanks to all of you who contribute to this board. I have learned a lot…not only about which fish to keep, but how to fish!!! I’m happy to say my managed portfolio is up 130% YTD even though since June, it has included a significant amount of cash. This brings me to my question. I hope you don’t find it too off topic, but I believe it is something many of us may be struggling with so I would like to hear the perspective of more seasoned minds.

Between the increase in my commitments to self-investing, the appreciation I have seen, and the reduction in the number of stocks in my portfolio, the size of my new investments in stocks at times gives me vertigo. The average amount of money in any one of my holdings is about 8x what it was just 3 years ago. This is intimidating to me and a significant part of the reason why I have been sitting on so much cash the last few months. (Currently I’m at 20% cash, but it had gotten as high as 45% at one point.) I put “toes in the water” now on new stocks with more money than what used to be a fully committed position just a few years ago. I struggle to get to a full position now because it just feels like so much money to put in one company. Barring a collapse, when I exit my positions is TTD, ZM, and CRWD this will become an even bigger issue for me. These 3 companies are 45v % of my portfolio right now.

Do others struggle with these issues? I haven’t seen anyone mention it or write about and I have followed the board pretty closely for about 18 months. I would love to hear others thoughts on this and how I can handle this mental block I am struggling with. Thanks…for everything!!!


The average amount of money in any one of my holdings is about 8x what it was just 3 years ago. This is intimidating to me

This is portfolio management and actually off topic for our board. I will try to give you a quick answer but PLEASE, no further answers on the board.

It sounds as if you are doing very well with your investing. The increased amounts are the results of success. The only way to handle it is to think completely in percentages of your portfolio and not in dollar amounts. That works for me and others I know.