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If you anticipate the end of your professional career within the next ten years, you will need a more structured phase-out plan than previous generations.

What is new: The share of the workforce entering the final 10 years of their careers now needs to consider the transformational impact of AI on the roles they can pursue, as official retirement ages creep up.

Why it matters: Few plan for the last 10 years of their career with the same energy as their first 10 professional years.

💪 Strengths to leverage: At this stage of your career, you have one or several of the following strengths to leverage:

• > 10,000 days of professional experience, or up to 8 areas of expertise with the 10,000 hours required for each.
• Human-native communication skills, for a world where human skills differentiate us from AI agents and robots
• Understanding contexts over long time horizons, where you can put new opportunities into historical perspectives for pattern recognition.
• Diverse experience spanning a variety of roles across individual contributor and management roles.
• Representing a generation that grew up with strong work ethics.

These skills are attractive to combine with the hunger, digital-native mindset, and new technology skills that youth bring. To frame your own 10-year plan, explore the following questions.

⌛️⏰ The whole 9 yards or checking out early: A mix of retirement laws, unspoken rules, and personal preferences defines the end of your career. The flexibility varies depending on your profession and the savings you have set aside.

Many can and want to work the whole 9 yards, and with retirement ages varying among individuals. With 60 being the new 40, your target retirement ages can extend by 5, if not 10, years beyond what your parents aimed for.

Checking out early can result from careful career planning or from circumstances beyond your control, often with two different outcomes for your time in retirement.

🌎🏠 Open to move, or stay where you are: Early in our career, moving to a new job or for a new role was commonplace, especially in large multinational companies with operations in many countries and locations within a country.

Our family and support situation late in our career set boundaries. Caring for the generation ahead and enjoying time with grandchildren shapes an optimal life. You might also have settled into a “forever home” with a strong social network of friends.

The decision to be open to moving or staying affects your options for the next 10 years.

👥👤Management vs. Individual contributor: At the tail end of a long professional career, you have likely enjoyed roles both as a manager and as an individual contributor. Your experience in both types of roles aligns with available opportunities.

A long management career makes you attractive in roles on similar or lower management levels than your peak, where your experience makes you a safe bet. You will be selected based on what you already know and can manage, rather than the development potential that guides the selection of young and coming managers.

In individual contributor roles, you can lead cross-functional teams without direct staff responsibilities or support young and upcoming managers in reverse-mentoring setups. This approach is attractive if you have built up extensive knowledge of a market or industry in a company with a prosperous future.

💡😅 Inspiration or perspiration: Working smarter or working hard is a crucial choice. A choice guided by how much time you work already, and what you consider a suitable work-life balance going forward.

Working smarter means focusing the energy you have to where you can make a meaningful impact. It is realistic to assume you work fewer hours than you did at your peak of grinding or effort. You are more attractive when you keep the energy up for fewer hours rather than working too many hours at a lower intensity.

Doing more with less is probably not for you at this stage. Doing more essential jobs with less, or doing better with less, are important distinctions worth considering. A late step on that journey can be to work fewer days or fewer hours per day—a strategy that maximizes Inspiration over perspiration as your key contribution.

🤹 👨‍🏫 Executive vs. Board roles: Executives face the choice of staying operative or pivoting to board roles.

Operative roles are demanding, with all focus on one company. The thrill and pressure are as intense as earlier in your career, if not more so, in reading. Company policies on the maximum age for stepping into an executive role can be a limiting factor at this stage, as well as unspoken rules on when to retire from an executive role.

Board roles allow you to leverage your vast experience and contribute with perspectives and insights rather than hours. The limited time commitment required per position will enable you to combine work for multiple companies. Getting to your first board role is hard, but adding roles once you have a brand and training as a board member is easier.

📝 Succession planning vs. selling your company: Entrepreneurs face additional elements in the choice. They need to plan for their own role as well as their company.

Succession planning is in play when you have willing and able candidates in the family, or talent in the company that you have groomed to take over one day. Finding the timing for when you step aside and your selected candidates are mature enough to make the big step. A transition where a soft approach, where you remain in the company and/or the board, is likelier than a hard exit.

When your exit is about selling the company, you face very different considerations. You want to time the sale to a good market, when earnings and valuations are peaking. The ownership structure is an additional consideration, where the desires of partners or family members can differ from yours. Expect golden handcuffs and performance clauses for the years immediately after the sale to be in play.

Both approaches require a clear exit strategy that takes multiple years to execute.

🪪 Employed or being your own: Employees face different challenges than entrepreneurs. Some might favor a shift from being employed to being their own. Others may prefer to remain employees throughout their careers.

Employees benefit from shorter exit cycles than entrepreneurs. The time from firm plans and decision to execution does not involve lengthy preparation or golden handcuff situations. There might be opportunities to reduce your work time below the standard five-day workweek. Some companies buy out older employees when their skills or interest in reskilling don’t fit with the business’s future needs.

The option to be your own is less about building a business to sell later and more about creating a sustainable revenue stream. Hence, the returns you can generate from operations are your strategy priority, rather than building assets.

The final aspect to consider is making a change decision or letting it happen to you. By waiting too long, you expose yourself to the latter, which can substantially reduce your attractiveness for re-employment, and transitioning to your own might be your only option.

💵 Accelerate savings or enjoy spending: Your financial strength defines the retirement age and lifestyle you can aim for.

With too low retirement savings, you can either increase savings or accelerate paying off real estate loans during your last ten years.

You might be fortunate to possess more capital than you need. A situation allowing you to buy a second home, or spend existing capital on a more expensive lifestyle at the tail end of your career.

This episode came to life on multiple train trips in Italy from Rome to Salerno, Florence, and Venice, after some profound reflections.