Entrepreneurial failure is more common than many realize, but it doesn’t always mean the end of an entrepreneurial career. In fact, for many, it’s just one chapter in a longer story of persistence, adaptation, and growth. Yet, not all failed entrepreneurs make a comeback. Some retreat into wage employment; others reemerge stronger. What explains these diverging paths?

This question is especially important in the context of family businesses, where the entrepreneurial journey is often entwined with family legacies, intergenerational aspirations, and emotionally complex dynamics. This study sheds light on the factors that influence whether an entrepreneur returns to business after failure—offering insights that are both theoretically rich and practically relevant.

What We Studied

The research team—Massimo Baù, Philipp Sieger, Kimberly Eddleston, and Francesco Chirico—adopted a developmental career perspective to understand reentry behavior. They argued that an individual’s career is not static but evolves across life stages (early, mid, late), each characterized by shifting priorities, motivations, and emotional landscapes.

Using a large-scale longitudinal dataset from Statistics Sweden, the researchers tracked 4,761 Swedish entrepreneurs whose ventures failed between 2000 and 2004. These individuals were followed until 2008 to determine whether they:

• Reentered entrepreneurship (started a new venture), or
• Transitioned into wage employment.

They analyzed how age at failure, gender, and whether the failed venture was co-owned influenced the likelihood of reentry. Advanced statistical methods (Cox proportional hazards model) ensured robust findings across time.

Key Insights

1. Age Matters—But Not in a Straight Line

The study found a cubic relationship—shaped like an inverted sideways "S"—between age and the likelihood of reentry.

• Early Career (under 40): The younger the entrepreneur, the more likely they are to reenter. Failure is seen as part of learning, and there’s less stigma or emotional baggage.
• Mid-Career (40–50): Reentry drops significantly. This is a period of reflection and recalibration. Many face growing family responsibilities, financial pressure, and existential doubts about their career paths.
• Late Career (50+): A resurgence in reentry is observed. Older entrepreneurs tend to reframe failure positively, focus on meaningful work, and possess more resources and self-knowledge. Entrepreneurship can also be seen as a fulfilling path post-retirement.

This nuanced pattern helps explain the inconsistent results of prior research on age and entrepreneurial behavior.

2. Gender: Different Timelines, Different Pressures

While men generally followed the cubic pattern described above, women's likelihood of reentry increased steadily with age, flattening slightly in late career but not declining. This suggests:

• Women’s entrepreneurial motivations often peak later in life, potentially due to shifts in family responsibilities (e.g., children growing up).
• Career confidence grows with experience, making reentry more appealing over time.
• Emotional processing of failure differs: Women tend to internalize setbacks more deeply but also grow stronger through recovery.

Interestingly, women in their late 30s and 40s were just as likely as men to reenter entrepreneurship, challenging the stereotype that men are inherently more "resilient" entrepreneurs.

3. The Role of Co-Ownership: A Double-Edged Sword

Entrepreneurs who failed in co-owned ventures showed different reentry patterns compared to those who were sole owners:

• Early Career: Co-ownership softens the blow of failure. Blame is shared, and young entrepreneurs are more likely to attribute setbacks to team dynamics rather than personal inadequacy. This encourages a return to entrepreneurship.
• Mid-Career: Here, co-ownership backfires. Entrepreneurs feel deeper regret and guilt, possibly tied to disrupting shared ventures and personal relationships. This emotional toll suppresses reentry.
• Late Career: The effect flips again. Older entrepreneurs with co-ownership experience tend to blame others (more so than themselves), use self-protective emotional strategies, and focus on legacy and fulfillment. This facilitates reentry.

Takeaways

1. Understand the Career Stage Lens

Entrepreneurial support programs should be tailored by life stage:

• Young adults benefit from low-stigma learning environments and second chances.
• Mid-career professionals need psychological support and flexible options.
• Late-career individuals require purpose-driven pathways and intergenerational mentoring roles.

2. Gender-Sensitive Policy and Practice

Women’s entrepreneurial trajectories often diverge from men’s due to social, familial, and emotional contexts. Support systems—especially in family businesses—should:

• Provide mentorship opportunities tailored for mid-career women.
• Recognize and celebrate late-blooming entrepreneurs.

3. Consider the Psychological Impact of Co-Ownership

Family businesses should reflect on how team structures influence failure and recovery. Involving family or external partners in ventures can shape how entrepreneurs process setbacks and whether they try again.

Impact

This study offers a dynamic view of entrepreneurship as a lifelong, evolving journey—especially relevant for family businesses, where personal identity, legacy, and business continuity intersect. It also underscores the importance of contextual resilience—how the “when,” “who,” and “how” of entrepreneurship matter just as much as the “what.”

By integrating career theory, gender studies, and entrepreneurial behavior, this research helps family enterprises and policymakers design better interventions to support second chances, promote inclusivity, and manage succession more effectively.

Recommendations

For Family Business Leaders

• Encourage open conversations about failure as part of growth.
• Recognize that readiness to lead or start anew may come later for some family members.
• Use co-ownership strategically, but be mindful of its emotional consequences.

For Policymakers and Educators

• Design entrepreneurship training with differentiated tracks for early-, mid-, and late-career individuals.
• Provide targeted support for women’s reentry, particularly after midlife transitions.
• Consider psychological and social dimensions, not just economic ones, in entrepreneurship recovery programs.

For Entrepreneurs

• Don’t rush to define your path after failure. Your readiness depends on where you are in life.
• Reflect on whether going solo or building a team suits your recovery and growth.
• Use age and experience to your advantage—there is no "best" time, only the right time for you.

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