Comparing your portfolio to market indices like the S&P 500 might seem like the right way to measure success, but it's actually a distraction from what truly matters. Here's the problem: the definition of "the market" constantly shifts based on whatever's performing best at the moment. Over the last decade, it's been U.S. stocks. Before that, Canadian stocks led the way. This moving target makes for a poor benchmark because unless your goals, timeline, and risk tolerance perfectly match that shifting definition, the comparison tells you very little about your actual progress. The only benchmark that counts is whether you're on track to meet your personal financial goals—like retiring when you want to, funding the experiences that matter most, and having the flexibility to enjoy life without financial stress. This is what we call tracking error regret: that uneasy feeling that you're "falling behind" when your portfolio doesn't mirror an index or match your neighbor's success story. When you chase someone else's scorecard, you risk making changes that feel smart in the moment but work against your long-term plan. Remember, you can beat an index but still fail to meet your financial goals. The real question isn't how you're doing compared to the market—it's whether your money is helping you live the life you've planned for.