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The entrepreneur’s second phase: how the role changes after 60

9 March 2026
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For many entrepreneurs, their identity coincides with the company they have built.
Years of work, daily decisions, operational responsibilities and personal relationships make the business much more than an economic activity. It becomes part of their personal story.

Over time, however, the relationship with the company inevitably changes. Not because interest or energy disappears, but because the personal and professional context evolves.

After the age of 55 or 60, many entrepreneurs begin to reflect on a question that is rarely discussed but increasingly relevant: what role should they have in the future of the company.

This is what can be described as the entrepreneur’s second phase.

Entrepreneurial identity and the company: a deep connection

In many Italian SMEs, the entrepreneur and the company are almost inseparable.

Those who have founded or developed a company over several decades know every detail: customers, suppliers, production processes and market dynamics.

This close connection is one of the reasons behind the success of many family businesses. At the same time, it can become a limitation when the functioning of the company depends too heavily on the founder’s daily involvement.

When the company is viewed from the outside, for example by investors or industrial partners, the key question becomes different: how well the company can operate without the direct presence of the entrepreneur.

Understanding this dynamic does not diminish the entrepreneur’s value. Instead, it means recognizing that the value of a company should exist beyond the individual who created it.

After 60 the entrepreneurial perspective changes

During the early stages of an entrepreneurial journey, the main objective is almost always the same: growing the company.

After a certain age, the perspective often changes. The questions are no longer only about the business, but also about time, personal balance and the type of contribution one wants to make in the future.

Common reflections include:

  • the sustainability of daily operational involvement
    • the long term continuity of the company
    • the personal role in the coming years
    • the opportunity to dedicate time to new projects.

This phase does not necessarily mean leaving the company. More often it represents a transformation of the entrepreneurial role.

From operational control to strategic leadership

One of the most natural evolutions in an entrepreneur’s life is the transition from operational management to strategic leadership.

This means changing perspective:

  • less involvement in daily operations
    • greater focus on long term strategic decisions
    • participation in governance and key decisions.

Many entrepreneurs choose to remain involved as chairman, shareholder or strategic advisor, supporting a new management team or an industrial partner.

In this way it becomes possible to preserve the continuity of the company without concentrating all operational responsibilities on a single person.

The entrepreneur’s second phase is not retirement

Associating this transition with retirement is one of the most common misunderstandings.

In reality, the second entrepreneurial phase can take different forms:

  • supporting a new generation taking leadership of the company
    • working alongside a more structured management team
    • contributing to the company’s growth through governance roles
    • dedicating time to new entrepreneurial or investment projects.

The entrepreneur’s experience remains a fundamental asset, especially in strategic decisions and long term relationships.

Preparing the second entrepreneurial phase

Like every stage in the life of a company, this phase requires preparation.

Companies that navigate this transition successfully are usually those that start working on it well in advance.

Key elements include:

  • developing an autonomous management team
    • defining a clear governance structure
    • separating ownership from operational management
    • transferring key know how to the organization.

When this transition is managed gradually, it is not perceived as a disruption but as a natural evolution of the company.

A new way of being an entrepreneur

The second phase of entrepreneurship is not the end of a journey. In many cases, it is its most conscious stage.

After years of daily operational management, entrepreneurs gain the opportunity to observe the company with greater distance and perspective.

Leading no longer means doing everything personally. It means creating the conditions for the company to continue growing without depending on a single individual.

In this sense, the entrepreneur’s second phase is not only about the personal future of the founder. It is about building companies that can endure beyond the person who created them.

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