Overcome Self-Doubt: Small Bets to Your Dream Career

Many skilled executives grapple with ambition-stifling self doubt. Take Taylor, for example—a strategy executive at Climate Tech who has successfully led multiple successful investments and partnerships within a social enterprise focused on climate change. However, despite her achievements, Taylor feels an unsettling self-doubt about starting her own impact fund. This internal struggle can paralyze talented individuals like her, preventing them from pursuing their dream careers and realizing their full potential. Common self-doubting beliefs include: • feelings of inadequacy. Executives like Taylor believe they lack the necessary experience, wins, or credentials to succeed in a transition to a fund manager, undermining their ability to pursue their dreams and magnify their impact. • a belief their vision just isn’t possible. For instance, Taylor hopes to pursue a thesis based in strategic long-term climate investing strategies. However, the prevalence of short-term focused funds in the news and her immediate network leads her to question the viability of her dream.

As a result, the belief that extensive preparation is required may lead to procrastination. In Taylor’s case, she might might delay taking action for years, if not decades, waiting until she feels fully prepared. Or she might create challenging preconditions that might stop her from starting at all. Take for instance, her belief that substantial independent wealth is required to comfortably engage in investments that align with long-term investment goals at odds with her understanding of the industry. These cautious approaches can result in missed opportunities—whether they’re once-in-a-lifetime market opportunities, unique skill-building experiences, or constant psychological tension between current actions and true aspirations. In contrast, the three “small bets” outlined below aim to empower individuals like Taylor to confront self-doubt and confidently invest in themselves. By refining their aspirations and challenging preconceived notions, executives like Taylor may uncover that their true dreams differ from initial expectations, leading to unexpected opportunities, impactful innovations, and a more authentic path to fulfillment.

Self doubt often stems from perceived skill gaps that hinder career advancement. Many professionals conduct informal or intuitive self-assessments that can be biased and inaccurate—leading to skewed perceptions of capabilities that reinforce feelings of inadequacy. To combat this challenge, it’s essential to conduct a thorough self-assessment to identify current skills and how they align with career aspirations. Seeking feedback from mentors or professionals in the desired roles or fields can provide an accurate understanding of one's strengths and areas for improvement. To implement this strategy successfully: 1. Audit: Conduct a formal skills and resources audit with a trusted mentor doing your dream job. 2. Goals: Set measurable goals to address gaps and use your unequal strengths. 3. Roadmap: Draft and refine a roadmap to not just improve these skills but get to your ultimate goal with your mentor and other advocates.

One significant barrier many professionals face is the belief that they must develop every skill independently before pursuing their goals. This mindset can lead to inefficiencies and missed opportunities. Instead, consider whether you can “buy” or “partner” your way to an effective solution. For example, rather than spending years building expertise in areas like product or operations, Taylor could consider partnering with individuals or organizations that already possess these skills, accelerating her journey toward launching her fund and realizing her vision.

To implement this strategy effectively: 1. Prioritize: Find gaps in your audit based on strategic criteria for partnership. For instance, prioritize skills that you lack interest in developing or those with a high opportunity cost (i.e., forces you to curtail deepening your unequal advantage).

2. Partner: Identify potential partners or vendors within your network or industry who have complementary skills. 3. Test: Start with a small project to assess fit and how strong their skill truly is.

Taylor's dream of launching an impact fund focused on strategic long-term climate investing strategies seemed at odds with the current market landscape. Many funds she encountered through news or her immediate network prioritized short-term gains, leading her to doubt the viability of her vision. To address this problem, Taylor considered three strategies: 1. Hypothesize: Draft a perspective relevant to your industry and your vision, like an investment thesis aligning with long-term value creation, supported by environmental analysis, case studies, and data. 2. Explore: Your initial hypothesis likely revealed names of people, communities, and organizations where your target might live. Start attending events, learning from experts, and building relationships by understanding your niche's biggest unmet needs. 3. Add value: Eventually, you’ll start narrowing down which communities are your best fit and start investing into a handful. A good way to do that is to contribute: Consider publishing articles solving your niche’s unmet needs on a niche blog. Or volunteer your time by serving on a board of a relevant association. Where possible, partner with existing thought leaders to build credibility, test your vision with your target market, and refine it as you learn more about the biggest unmet needs in the field. 4. Activate: As you get to data saturation and perhaps even strong “pre commitments,” consider stronger tests to validate your hypothesis. Negative feedback here can reveal large risky assumptions, accelerating your learning. For instance, raise a small round to validate your investment thesis further and activate LP leads, starting with a pilot fund or co-investment opportunities to demonstrate the viability of the long-term strategy.

In conclusion, while self-doubt often appears as a formidable barrier, it can also serve as a catalyst for growth and evolution in one's career journey. By reframing self-doubt as a signal for areas of potential development, professionals like Taylor can transform these challenges into opportunities for self-improvement and innovation. The strategies above, however, don’t advocate for wishful thinking. They suggest taking multiple "small bets" to overcome self-doubt and gather high-quality evidence to guide personal and professional growth. This process of confronting and working through uncertainties often leads to a more refined and authentic vision of one's dream career. It's through the courage to face doubts and pursue proactive growth that individuals can uncover paths they may not have initially envisioned, leading to more fulfilling and impactful careers. I encourage readers to share their experiences of how they've transformed self-doubt into opportunities for growth in their careers.