09/06/2026
We asked Paul what’s harder — knowing when to buy or knowing when to sell. He immediately said selling.
Buying, he explained, is the easy part. You do your research, the price makes sense, you pull the trigger. Selling is where it gets genuinely hard, and for more reasons than most investors realize. Knowing when to let go of a winner, when to admit a thesis is broken, when to walk away — none of it is simple.
And he added a wrinkle a lot of people miss. Even buying more of a stock you already own gets hard, especially if the price has fallen since your first purchase or some bad news has come out. Now you’re second-guessing everything. Do you average down, or is the market telling you something? That’s the emotional tug-of-war that makes selling and adding so much tougher than the first buy.
Watch the full breakdown and tell us — what’s harder for you, buying or selling?