When Safe Choices Fail, Choose What You Love
Created at: October 6, 2025
You can fail at what you don't want, so you might as well take a chance on doing what you love. — Elizabeth Gilbert
The Myth of Safety
At the heart of the line is the observation that so-called safe choices are not immune to failure. Jim Carrey’s 2014 commencement address at Maharishi University offers a stark example: his father chose a secure accounting career yet was laid off, leaving the family struggling. Safety, in other words, can be a mirage. Given that risk is unavoidable, the question shifts from "Will I fail?" to "What is worth failing for?" That pivot sets the stage for reevaluating avoidance itself.
The Price of Avoidance
Avoidance may feel prudent, but it carries a stealthy price: regret. Bronnie Ware’s The Top Five Regrets of the Dying (2012) records the recurring lament, "I wish I’d had the courage to live a life true to myself." Behavioral science explains why we overpay for safety. Prospect theory (Kahneman and Tversky, 1979) shows we fear losses more than we value equivalent gains, nudging us toward small, safe choices. Yet when safety later fails, we suffer twice—losing both the outcome and the meaning we postponed.
Failure as Feedback
Once we accept uncertainty, failure becomes feedback rather than verdict. Carol Dweck’s Mindset (2006) shows that a growth mindset turns setbacks into information about strategies, not identity. Nassim Nicholas Taleb’s Antifragile (2012) goes further: systems can gain from disorder when experiments are frequent and losses are capped. In this light, taking chances on what you love is not recklessness; it is structured learning.
Loving the Process
However, perseverance requires more than tactics; it needs affection for the work. Elizabeth Gilbert’s Big Magic (2015) counsels replacing grandiose passion with steady curiosity—showing up daily because the process itself nourishes you. When outcomes wobble, love of the craft steadies attention. That devotion not only sustains effort but also compounds skill, naturally improving the odds of future success.
Small Bets, Real Options
To translate conviction into action, shrink the risk through small bets. Entrepreneurship research on effectuation (Sarasvathy, 2001) recommends the affordable loss principle: invest only what you can afford to lose while testing real demand. Side projects, pilot offerings, and time-boxed experiments create real options—you keep upside while limiting downside. Each iteration then informs the next, knitting courage with prudence.
Security Through Skills and Community
Courage scales best with capability and community. Building career capital—rare and valuable skills that increase autonomy (Cal Newport, 2012)—creates a portable safety net independent of any single employer. Meanwhile, mentors and peer circles supply honest feedback and encouragement, reducing the psychological cost of risk. With skills and support in place, daring choices become measured steps.
A Courageous Default
In the end, the quote flips the default. Since you can fail at what you don’t want, let meaning—not mere probability—decide where you spend your finite courage. By treating failure as data, loving the process, and advancing via small, supported bets, you honor the only guarantee you truly control: the integrity of how you spend your life.