Why chasing what you ‘should’ want leads to regret—and how to reclaim authentic motivation

You're told all your life what a 'good choice' looks like—good job, safe relationship, stable town. Maybe you chase these goals for years, trying to qualify others’ approval or silence inner doubt. Time passes, and you find yourself restless or resentful, wondering why—despite being on paper ‘successful’—happiness is always just out of reach.

In one moment, prompted by stress or a sense of stuckness, you spend time honestly writing about the difference between what you should want and what you actually desire. The gap startles you: some 'shoulds' feel hollow, only fueling anxiety or regret. When you finally let yourself try something purely for your own reasons, even on a small scale, the excitement is visceral. A parent expresses relief skipping a traditional commitment that never felt meaningful. A university student ditches a safe but dispiriting path and tests out an internship in a creative field just for fun. Research shows intrinsic motivation—where actions align with personal values, not social approval—leads to deeper satisfaction, better learning, and, over time, resilience to setbacks. Unburdening yourself of at least one ‘should’ at a time clears space for genuine passion to take root.

Start by writing down your biggest current obligations or goals that sound like ‘I should’ statements, especially ones that keep you awake at night. Next, try flipping those statements to express your real want or need, even if it feels messy or rebellious. Reflect on which of those goals leave you energized or hollow, asking which ones you'd actually still pursue if nobody was watching. Then make a small experiment: for just a week, drop one big 'should' and replace it with something that excites you. See if your energy and enthusiasm begin to shift, and notice how your life feels when your motivation is your own.