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Having a Second Career

But I Thought That You Wanted to Retire!

Transition into Retirement

Retirement can come as a shock.  One day you’re doing what you’ve been doing for most of your working life – getting up on a weekday morning, commuting to the office/jobsite, and spending most of the day doing what you have to do to earn a living.

Then one day you wake up and realize that everything has changed.  The routine that you’ve gotten used to over the past 40-50 years is gone.  You sink into your favorite chair, and while sipping on your morning cup of coffee you start to contemplate your new situation.  What do I do today, and for that matter the other days that I now own and are mine to design to my liking?

Certain careers greatly facilitate the transition into retirement.  If you’re in the professional services industry (attorney, accountant, doctor, barber, etc) or a small business owner, you can gradually cut back on your work hours.  This gives you more time-off for vacation, travel, and family while still maintaining proficiency in your profession and retaining an income stream.  For the rest of us, the transition is more difficult.

Pursuing a Second Career

For a wide variety of reasons, many people who leave their “regular” job are not quite ready for “full retirement”.  They:

  • Enjoy the challenge of work;
  • Feel the need to share their experience and knowledge;
  • Feel obliged to “give back” to society;
  • Perceive an unfilled need in their community (e.g. volunteer work, community service, or politics) that they believe they can address;
  • Like feeling important, being a part of a major cause or involved in something significant; or
  • Need or desire extra income to meet their retirement expense or achieve a certain lifestyle.

An optimal approach to starting a new career is to gradually begin while still working in your regular job.  By this I mean that you should start using your free time to explore other things that you’d like to do to broaden your experiences, challenge your abilities and provide enjoyment.  Perhaps you can take on volunteer, consulting, or other part-time work while still on the job.

Whether you have the time and ambition to begin pursuing new opportunities pre-retirement, or whether you have to wait until that moment in the chair drinking your morning coffee, you need to decide soon whether a new career is on your horizon.  If this is what you want to do, the sooner you begin the better.  Right after you leave your job, you have the best network of contacts and are used to a regular work routine.  Plus your skill set may be at its peak.

Volunteer vs Salaried Work

There are many alternative ways to pursue working in retirement, the easiest of which is volunteer activities.  Whatever your skills are, there are always more volunteer opportunities than available human resources to address them.  Opportunities exist for those who prefer consulting, teaching, analyzing, managing, or performing physical labor.  Check with your church, community or various organizations to find out what’s available within your particular area of expertise.

Finding salaried work could pose a greater challenge.  You’re now considered by many as “too old” and having “outdated” skills.  This is particularly a problem at this time because many younger employees, some just freshly out of college with current technical skills, are unemployed and competing for open positions.

However, due to an aging population and the major contributions being made by seniors, I believe that we are finally starting to appreciate the benefits of life experience.  This, coupled with the fact that your extensive experience may be available for a greatly discounted (post retirement) price, may make you a more attractive candidate.

Updated Resume & Approach

If you are interested in pursuing a post-retirement job search, you need to do it differently than you did in your “prior life”.  By this I mean that sending out 100 copies of your three-page resume to the HR departments of the large employers in town may not be the best approach.  However, the one thing that hasn’t changed much is “networking”.  Always begin jour job search by contacting fellow employees, friends, former bosses and suppliers/customers that you used to work with.

The other thing to consider is the idea of being “over qualified”.  While technically and legally there is no such thing as over-qualified, the idea still exists in the minds of many employers.  Partly compensate for this by drastically shrinking your resume and de-emphasizing your many-years of extensive experience.  Just focus on the areas and variety of expertise.  Then post this resume on Facebook, LinkedIn and other online social media sites.  Also, use this resume in structuring input and applying at internet-posted job search sites such as,, etc.

The Job Interview

There's a good likelihood that you haven't interviewed for a job in many years.  For this reason it's important to brush up on the interviewing skills that you once had, those that helped you achieve a diversified and progressive career.  Don't just show up for the interview unprepared, assuming that your extensive knowledge and experience will dazzle the interviewer.

Find the company's website and familiarize yourself with their products, mission, strategy and management.  Based on this information and the specific job that you're interviewing for, prepare a list of questions for the interviewer that shows your interest and provides more of a two-way conversation.  Be sure to demonstrate your ability to address the company's needs and make specific contributions.

Learning New Skills

Finally, if you want to maximize your opportunities while broadening your knowledge, continue to develop new skills.  These could extend your targeted job range or allow you to compete better within your primary area.  Particularly, it’s important for you to keep up with the latest technologies – computers, cell phones, etc.

Post-retirement skill development can take the following forms:

  • College courses,
  • Licensing/certification programs,
  • Lifelong learning programs/courses,
  • Volunteering for work in an unfamiliar area,
  • Reading and self-study, and
  • Trying new tools/techniques (e.g. website development, computer games, etc.).


Regardless of whether you choose to pursue a second career or volunteer work, or are content to just enjoy leisure activities, it’s important that you don’t allow yourself to become too complacent.  You need to keep your brain challenged and active in retirement.  It keeps you feeling alert, young and interesting.