In life and at work, we often get stuck persisting in unpleasant activities even when more enjoyable and equally effective alternatives exist. Research shows this happens due to “entrenchment,” where repeating an activity blocks consideration of better options and makes you more likely to keep doing it. The author’s research focuses on enhancing well-being by limiting over-persistence in these tasks and suggests solutions that include reducing repetition, dividing attention, and alternating tasks to break the cycle of entrenchment. By adopting strategies to prevent entrenchment, individuals and organizations can increase employee satisfaction and efficiency.