Highlights:

• Harvard social scientist Arthur Brooks argues that treating life like a startup leads to greater meaning and success.

• Risk-taking, when approached strategically, can unlock fulfillment across career, financial, and personal domains.

• Fear of regret often prevents individuals from making bold moves, but smaller “micro-risks” can build confidence.

Your future success and well-being may hinge less on security and more on your willingness to embrace uncertainty. That is the central argument of Arthur Brooks, Harvard University professor and social scientist, who in his new book The Happiness Files urges people to think like entrepreneurs. For Brooks, living a meaningful life requires adopting the mindset of a startup founder: calculated risks, strategic experimentation, and courage in the face of uncertainty.

Rethinking Risk as a Pathway to Growth

Entrepreneurs understand that launching a business is inherently risky, with failure rates often exceeding 50%. Yet, Brooks notes, the same qualities that drive entrepreneurial ventures—courage, confidence, and resilience—can also apply to personal and professional life. Whether it is changing careers, purchasing a home, or committing to a long-term relationship, he argues that carefully managed risks provide opportunities for growth and reward that far outweigh the comfort of avoidance.

This perspective challenges the conventional narrative that success is found in stability. Instead, Brooks emphasizes that a willingness to take appropriate risks creates momentum, pushing individuals beyond stagnation and closer to fulfillment. Much like investors balancing portfolios, people can weigh potential downsides against outsized gains, making decisions that align with long-term aspirations rather than short-term fears.

The Psychology of Fear and Regret

One of the greatest barriers to risk-taking, Brooks explains, is the human tendency to anticipate regret. Research in behavioral economics supports his observation: people often overestimate the pain of potential failure and underestimate their capacity to recover. This mental “time-travel” leads to risk avoidance, even when the probability of success is significant.

The irony, Brooks suggests, is that regret from inaction often lingers longer than regret from failed attempts. In this sense, fear of making the wrong decision can quietly erode happiness by keeping individuals from pursuing meaningful challenges. By reframing risk as a disciplined choice rather than reckless behavior, Brooks argues, people can dismantle these psychological barriers.

Building Confidence Through Small Steps

For those unaccustomed to bold moves, Brooks and workplace experts recommend experimenting with incremental challenges, or “micro-risks.” These could be as modest as initiating conversation with a new colleague or volunteering for a difficult project. Such exercises help build confidence in navigating discomfort, creating a foundation for larger, life-altering decisions.

Importantly, Brooks underscores that risk-taking should never be impulsive. Instead, it requires deliberate planning and thoughtful scenario analysis—much like an entrepreneur assessing market conditions before launch. In this framework, the act of committing to a risk, regardless of outcome, becomes a source of satisfaction. It signals agency, resilience, and a willingness to shape one’s future.

What May Lie Ahead

Brooks’s thesis resonates in a global economy where volatility is increasingly the norm and resilience is prized. For professionals in both Israel and the United States, the lesson is clear: success in modern life may depend on embracing uncertainty with strategy rather than retreating from it. As the boundaries between work, personal growth, and financial security continue to blur, the ability to take calculated risks could become one of the defining skills of the next generation.