For difficult decisions, ask the simple question: "What does right look like?" and then do that. This framework simplifies complexity. While doing the right thing can be harder or more expensive in the short term, it consistently leads to better outcomes in the long run.

Every path—being broke, rich, an employee, or an entrepreneur—involves suffering. Since difficulty is an unavoidable fixed cost of living, you should stop trying to find a path without it. Instead, choose the path that offers the outcome or reward you value most, as the cost is the same.

When facing a major career choice, use this heuristic: assume the best-case outcome is guaranteed, but the timeline will be drastically longer. This forces an honest evaluation of whether you genuinely enjoy the daily process, or if you are only motivated by a quick, external reward.

Steve Levitt's randomized experiment found that people struggling with a major life decision who were prompted by a coin flip to make a change were happier months later. This suggests we systematically underestimate the benefits of change and should default to it when facing a difficult choice.

Coming from an investment CEO, this is highly counterintuitive. Hobson advises against making significant life choices, like changing jobs, based solely on money. Taking a slightly higher-paying job at a company or with a boss you don't love often leads to misery, making the financial gain a poor trade-off for overall life satisfaction.

A psychology experiment revealed that people forced to commit to a choice became happier with it over time because the brain rationalizes the decision, effectively manufacturing happiness. In contrast, keeping options open leads to second-guessing and dissatisfaction. Decisiveness is a key to happiness.

Instead of trying to evaluate every option to find the absolute best ("maximizing"), set clear "good enough" criteria. Once an option meets them, choose it and move on. This practice, called satisficing, leads to greater happiness and less regret.

Life's default settings, like expected career paths, are powerful. To change course, you can't be tentative; you must reject the default with full force. Half-measures fail because the gravitational pull of the default is too strong to overcome accidentally.

When deciding whether to leave a stable job to start Amazon, Jeff Bezos asked which choice he would regret more at age 80. People are far more haunted by the opportunities they didn't take than the ones they took that failed. This is a powerful mental model for making bold career leaps.