Founders don’t let go of their businesses easily. According to Noam Wasserman, a longtime Harvard Business School professor, four out of five entrepreneurs are forced to step down from the CEO’s post, often clinging to their firms for too long (article). This reluctance isn’t just about losing control; it’s deeply rooted in identity, purpose, and the fear of a future without the daily grind that defined them for so long.
There’s an abundance of exit planning literature advising entrepreneurs on “how” and “when” to sell their business. The advice predominantly focuses on the financial aspects like maximizing valuation, navigating legalities, succession planning, and ensuring the business thrives under new leadership. What often goes unmentioned, however, is the hidden anxiety that founders experience when they think about what comes next for them. Once the sale is finalized and the transition is complete, a more personal question looms: What will I do with my time?
For many business owners, the idea of stepping into retirement feels like stepping into a void. They don’t want to retire and sit on a beach, but the end of a business sometimes seems to present that as the only viable option. The reality is that a life of leisure does not suit everyone, especially those accustomed to the adrenaline of building and growing a business.
Redefining the Second Career
The first step for any business owner contemplating a second career is to shift their mindset. They should consider that post-exit life doesn’t have to be a single, linear path. Instead of thinking about their “next career” they can think about the next set of careers. Imagine a variety of roles that complement each other, where they can leverage their experience in different ways, from mentoring to consulting, to investing, or even starting a new venture in a different industry with trusted partners.
Test and Validate New Opportunities
This period of transition offers a valuable opportunity for business owners to reassess their skills, interests, and how they might translate to new domains. Many will have accumulated a wealth of knowledge, leadership expertise, and a robust network: assets that can greatly benefit other businesses. Here are a few ways to explore these opportunities thoroughly:
- Conduct Informational Interviews: Reach out to peers who have made similar transitions—those who have become advisors, investors, or board members. Understand the roles they play, the skills required, and the challenges they face. These conversations can reveal new possibilities and help in understanding whether a particular path might be a good fit.
- Leverage Existing Relationships: Tap into professional networks and industry groups to identify opportunities where their expertise could add significant value. For example, a former tech entrepreneur might offer invaluable insights to a mid-sized company struggling with digital transformation. Or, an Operating Partner of a PE firm may want you on their boards.
- Explore Interim Roles, Fractional or Advisory Positions: Before committing to a full-time role, consider interim positions that allow for flexibility and exploration. This could mean acting as an interim executive or joining advisory boards, where one can share expertise without the long-term commitment.
Embrace Learning and Reinvention
Exiting a business doesn’t mean leaving behind the hunger for growth and learning. In fact, it can be the perfect time to pivot toward new learning experiences. This could involve acquiring new skills, such as digital marketing, strategic foresight, governance, or even diving into an entirely new industry that has similar characteristics to the one they excelled at. Lifelong learning is a powerful way to keep the mind engaged, and it can open doors to unanticipated career paths.
Consider Purpose-Driven Work
For many founders, the next chapter is not just about financial success but also about making a meaningful impact. Purpose-driven work can take many forms such as becoming a philanthropist, supporting startups as an angel investor, or even leading a nonprofit organization. Many find fulfillment in mentoring the next generation of entrepreneurs by sharing their lessons learned and helping others avoid the pitfalls they faced.
Balance is Key: Blending the Personal with the Professional
Finally, it is crucial to balance professional engagement with personal fulfillment. After years of dedicating themselves to their businesses, entrepreneurs deserve the time to explore hobbies, travel, or spend more time with family, activities that may have taken a backseat during their first career. By embracing a multi-faceted approach to their next chapter and considering a portfolio career, business owners can enjoy a diverse and fulfilling post-exit career landscape that leverages their strengths, satisfies their ambitions, and aligns with their values.
A sale or exit of a business is not the end of a career journey but can be the beginning of a new one.