I recently attended a high school reunion. This was not the typical high school reunion, which is attended only by alumni from your graduating year. I attended a private all-male boarding school in the Berkshires of western Massachusetts, which operated from 1926 until 1971, after which time it closed.

So, reunions for this school include any surviving alumni from any year during the time the school was open. This most recent 2023 reunion included alumni ranging from the graduating year of 1948 until 1971.

As you can imagine, nearly all of the attendees are now retired from their careers. But not everyone. As I chatted with a number of alumni I found that among those not fully retired there were two distinct categories of workers.

There were those who continued working at their primary careers, but at a more reduced or dialed-down level, meaning they were not putting in the same amount of time or handling the same degrees of stress as when they were full time employees.

Then there were those who desired to continue working, but at some type of work which was either very different or tangentially related to their former employment. This latter category is sometimes referred to as an encore career.

One of the great benefits of both our current labor force and our prolonged healthy lives relative to previous generations is that we have an option of pursuing an encore career. Establishing one, however, brings a new set of challenges that an older individual needs to be prepared to confront.

Just because you present yourself as an experienced and reliable resource with a long track record of accomplishments does not mean you will automatically be seen as a shoo-in for the new gig. In fact, the case most often seems to be that your age decreases your chances of being accepted. This requires that initiating an encore career be done systematically and attentively.

To begin with do not shy away from being old, but instead embrace it and spin your advanced age as a positive. You have gained a lot of work experience, solved many problems, and built an in-depth skillset.

Emphasizing your general tenacity, dependability, and trustworthiness can go a long way to gaining stakeholder and customer trust, which in many cases is as important or more critical than expertise alone. People who will need your services or who will want to join with you in delivering services want the comfort of someone they can rely on. Gaining that trust early on is crucial.

Another key to attaining trust is to highlight connections between your past successes and what you are promising to deliver in your new role. There will be overlaps in type, quality, or circumstances linking accomplishments previously achieved with intended future benefits you propose to supply.

One way to identify and credibly discuss these junctures is to prepare responses to some of the toughest questions you could get in an interview or from prospective customers during a vetting process. If needed, gain assistance from trusted contacts who can be skilled in playing the skeptic forcing you to justify your claims.

Through rehearsal, anticipate the concerns from others whose trust and support you will need to succeed in your encore career and heighten your authenticity by eliciting how your past performance has prepared you for future challenges.

Also, throughout the longevity of your career you have hopefully cultivated and maintained relationships with work related individuals which span generations. Being able to depend on younger professionals who can vouch for your excellence can go a long way in polishing your new brand.

Show others that you are not just a monument to legacy ways of operating, but that your instincts and inclination are toward continuous learning and improvements with an attitude of welcoming new problems to solve. Demonstrate how you are still passionate about the work you want to do, even at this late stage in life.