
11/30/2025 - Research in psychology tells us that enjoyment is necessary for overall psychological well-being, but it is not sufficient. We can be happy and enjoy ourselves, but lack a larger sense of purpose and meaning. Our states of happiness also don't mean that we're meaningfully connected to others or that we live lives of physical energy and vitality. When I conducted a research project to identify the psychological characteristics of successful traders/portfolio managers, one factor stood out: entrepreneurialism. Successful traders find happiness and meaning and energy and connection to others through building their businesses.
How well are you building your trading business? Are you doing what great entrepreneurs do?
If your trading business was someone's actual business startup, would you invest in that business?
If you ran an actual startup business with the same effort, planning, and execution as you run your trading, how likely would you be to succeed?
In the long run, we're most likely to enjoy trading for the same reason that we enjoy a relationship: because we're building something meaningful.
Great trading requires an investment in ourselves.
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11/30/2025 - Suppose I continually focused on all people who are wealthier than me, all people who are more famous than me, all children who are more successful than my kids, and all women who are better looking than my wife. Every day, I would reinforce the sense that I am lacking. Life would be miserable. So much of enjoying life and living it to the fullest is accepting and appreciating what we have--and making the very most of it.
This is very important and relevant to our development as traders. The goal is not a perfectionistic one; we don't focus on every move that we don't catch. Rather, we focus on what we do well and where our talents and skills lie and make the most out of those. I am a trader, not a longer-term investor. I trade the stock market, not commodities or fixed income instruments. I excel in trading the morning hours in the U.S., not trading every minute of every day the exchanges are open.
As noted below, perfectionism is a destroyer of our trading psychology. Acceptance and appreciation, coupled with targeted efforts at growth, create fulfillment--and that fuels our further development. Nothing is more important than exploring, exploring, exploring and discovering what you're truly good at and what is meaningful to you. Before we can ever achieve a degree of greatness, we have to become great at self-understanding. We become what we repeatedly do. We internalize what we repeatedly feel. Focusing on our strengths makes us ever stronger.
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11/28/2025 - I worked with a portfolio manager who put on his initial positions with a pretty wide stop level and a pretty wide target. He saw a good opportunity with good risk/reward and didn't want to be perfectionistic about getting the absolute best price. Once the initial position was on, he told me he hoped it went against him so that he could add at better levels. As long as the trade didn't stop him out and nothing happened in the world that made him question his view, he treated adverse price movement as opportunity. He actually looked forward to the market moving against him.
Conversely, he established a first target to take profits before his positions hit his primary target. By taking profits at the first level, he ensured his position would be profitable overall. Further, once he hit his first target, he raised his stop to breakeven. How he managed his trade was how he managed his psychology. He enjoyed trading because he maximized the
consistency of his profitability rather than being a perfectionist about P/L. And while his position was doing its thing? He was already talking with the other traders he valued and generating the next promising idea. Instead of staring at screens, he was engaged in the enjoyable pursuit of creativity.
How we trade shapes our psychology--
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11/27/2025 - What is the most destructive emotion in trading? What destroys the joy of our progress and turns normal, expectable losses into catastrophes? I would argue that the most destructive approach we can take to trading is perfectionism. Once we adopt a perfectionistic mindset, we cannot enjoy trading. Good enough is never good enough. Progress is never perfect. Even our wins don't bring celebration, because we always could have won more.
Where does this perfectionism come from? It's a great example of how one of our strengths (in this case achievement motivation) becomes a weakness when taken to an extreme. When we so push for achievement that we cannot stop and appreciate our progress, we create a toxic psychological environment for trading.
It's great to strive for improvement; it's equally important to celebrate our progress. Indeed, celebrating what we've done well is the best way of providing fuel for the quest to improve further. If trading is not enjoyable, we quickly run out of fuel.
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11/26/2025 - When we adopted Nomi Lyn (chocolate point Siamese cat), our first priority was to integrate her with our three other cats. As you can see above, she's bonded well with Molly Ruth (white khao manee) and Ares Payton (reverse black tabby). Her bonding with Shay Gil has taken a bit longer, as I recently pointed out, because of Shay's difficult experiences in a rescue shelter. Providing an environment where they can all flourish is tremendously personally rewarding.Let's say I felt the need to have each of the cats enter cat shows and win awards. All of a sudden, I have to control their access to one another, structure their time to teach them routines, and make sure that one of them doesn't get the others sick. In short order, I would no longer treasure my time with the cats. Instead of enjoying them as an end in itself, now they become means to my ends. For me, that ruins the experience.
Similarly, I enjoy writing. The joy of writing is learning about a subject and then using the writing as a way of thinking out loud, making connections, and deepening that learning. If I were to suddenly prioritize how popular my writing was to become--how many books I would sell, how many hits my posts would get--that would change what and how I write. I would no longer enjoy the experience. Writing would become a means to an external end, not a end in itself.
Trading is more challenging in many ways because we *do* pursue trading for the end of making money. Yes, it can be enjoyable, but it's different from treasuring the time with our cats or our children. Ultimately it *is* a means to an end. And that can spoil the experience for those who treasure the quality of our experience.
Every so often, I'll add something new to my trading: a different time frame, a new indicator, a different market instrument. When I add the new element, I reduce my size to the point where P/L absolutely doesn't matter. Then I see if I enjoy the new perspective; if it leads to fresh insights. By taking P/L out of the equation, I can see if the trading is a rewarding activity in other ways. If it is, I know it's worth including in the repertoire.
Growing the trading repertoire is like growing the cat family. Trading is most likely to be rewarding--emotionally and financially--if we make it personally rewarding.