Freelance After 50 Newsletter

F50 Issue #20: Five Questions to Reinvent Your Career After 50

Published about 1 month ago • 5 min read

F50 Issue #20: April 16, 2024

Working Well Beyond Retirement: Turning Your Vocation into a Second-Act Career

If you retired tomorrow, would you miss your job? And if you’ve already retired, do you wish you could keep working?

Over the past few months, we’ve shared stories from people over 50 who are enjoying fulfilling careers in their chosen field. Actors Tom Cruise and Harrison Ford are still going strong. Retired TV executive Ron Petrescue found a new freelance career in front of the camera, working as an extra actor.

And today we’re going to shine a spotlight on two more industries that work well beyond retirement — doctors and ministers!

In a recent newsletter issue titled “The Midlife Adventure,” Brian Clark discusses the concept of “career reinvention.” He says,

“Replace the word ‘retirement’ with ‘reinvention’ to better understand why a new career or your own business at midlife is the new status symbol for those seeking greater purpose and fulfillment.”

Former American Medical Association (AMA) President Gerald Harmon, MD, is one doctor who has embraced his own career reinvention. In an interview, he explains his reasons for embarking on a new chapter in his medical career instead of retiring after 35 years as a family physician and many other roles:

“I think it's the realization that I still have an opportunity to share my lived experiences with others. The term 'doctor' is derived from the Latin term meaning to carry, meaning to teach. And I really feel that I'm still able to teach, to share my lived experiences, to educate and provide guidelines, if not mentorship, for a generation of physicians in training and even practicing physicians."

Dr. Harmon suggests that other physicians who wish to continue working in their field can choose a variety of roles:

  • Apply your skills in a volunteer association.
  • Work in extended care facilities, school-based clinics, and free clinics.
  • Be a volunteer lecturer.
  • Find other ways to share your experience to build awareness and train new doctors.

Similarly, in an article titled “The best jobs for retired clergy,” Rev. Earl Thorpe, PhD, shares his insights about retirement:

"We often consider retirement the end of a person’s vocational journey. But if, as Shakespeare wrote, 'all the world is a stage,' retirement might just be the end of the first act in a clergyperson’s calling and the beginning of the second act in their life of service."

Rev. Thorpe suggests a wide variety of roles that could easily transform retirement into a freelance reinvention of a minister’s career:

  • Teaching theology or religious studies
  • Becoming a hospice, healthcare, Police and Fire Department or industrial chaplain
  • Joining non-profit organizations that do community outreach
  • Working for clients as a pastoral counselor to provide emotional and spiritual assistance
  • Becoming a spiritual career coach or a life and transition coach to help clients achieve personal and professional growth.

Now, how about you? Would you like to reinvent your career instead of choosing retirement? If so, here are five questions to ask yourself.

Five Questions to Help You Reinvent Your Career After 50

1. Do you consider your career a vocation?

The Cambridge Dictionary defines vocation as “a type of work that you feel you are suited to doing and to which you should give all your time and energy, or the feeling that a type of work suits you in this way.

The Collins Dictionary says, “If you have a vocation, you have a strong feeling that you are especially suited to do a particular job or to fulfil a particular role in life, especially one which involves helping other people.”

Is that how you feel about your job, or how you felt about it before you retired? If so, you might enjoy reinventing that career as a freelance business.

2. What do you enjoy about your industry?

Now it’s time to look closely at your chosen industry and think about all the roles and tasks involved in it. Are there some you enjoy more than others? Which ones mean the most to you and make you want to jump out of bed in the morning?

Take out a notebook, an online app, or a piece of paper and make a list of your favorite roles and tasks. See whether some of them are connected enough to become part of a new, reinvented role.

3. What do you dislike about your industry?

No matter how enjoyable a job is, there are usually some less enjoyable aspects. Make a list of all the things you dislike about your industry. Maybe they involve certain things you have to do, the schedule you have to keep, or the environment you have to work in.

Go through the list and identify which aspects can be removed from your role and which ones are necessary for the running of a business. For example, if you dislike the environment or schedule, maybe you can create a better environment with a more flexible schedule in your own home office.

If you dislike other necessary aspects, like the admin part of your work, maybe you can come up with a better system for completing it.

4. What part of your work would you like to continue doing?

In a previous Freelance After 50 newsletter issue, we discussed the concept of “ikigai,” a strong sense of purpose exemplified by the residents of Okinawa, Japan, in a Netflix documentary series called Live to 100: Secrets of the Blue Zones.

Your ikigai is the reason you get up in the morning, and it can ultimately contribute to your longevity. Looking at your list of enjoyable tasks and roles, identify which ones give you the strongest sense of purpose. Which ones would you miss if you couldn’t continue doing them?

5. How could you turn your ikigai into a freelance career?

If you’d like to turn your ikigai into a flexible, fulfilling, and financially beneficial second-act career, we have a set of questions you can use to find your niche (a specialty service and/or market that is suited to your personality, passions, proficiencies, and professional background).

These questions are part of our Niche Identification Matrix that helps you examine four elements:

  1. Personality: How will this niche mesh with my personality?
  2. Passions: Will this niche align with my passions/interests?
  3. Proficiencies: How does this niche complement my skills and experience?
  4. Profitable Niches: Will this niche expand my income potential and opportunities?

As Dr. Harmon says in the article above, “You have a wealth of experience. You have decades, typically, of experience. You have a skill set that's impossible to reproduce.” He’s talking about doctors here, but these statements could easily apply to many industries!

You have so much to offer, well beyond retirement!

Handy Tools

We’ve given you a lot to think about. If you’d like to jot down your thoughts in an online app, try Evernote. It helps you stay organized and productive in both life and work, with note-taking and project-planning features.

The free plan lets you create up to 50 notes and one notebook. If you’d like additional features, paid plans start at $17.99 per month.

Healthy Habits

If you decide to become a freelancer, it’s important to create healthy boundaries for yourself, especially if you’ve never worked from home before. We recommend focusing on five types of boundaries:

  • Time (your schedule and availability)
  • Work (what you will and won’t do)
  • Payment (your payment schedule and terms)
  • Ethics (your refusal to compromise honesty and integrity)
  • Technology (a set time period when you notify clients you’ll be unplugging from your work and devices).

If you’d like more information, check out an article titled “Practical tips for healthy work boundaries.” It explains the difference between remote-work boundaries and office-based boundaries and guides you through the process of formulating your own unique boundaries.

Often, your chosen industry is more than just a job — it’s a reason to live. Remember, we’re always here for you if you’d like to discuss your ideas and explore the possibilities!

Until next time,

Co-founders of Freelance University

431B 41st Avenue NE - Unit 94, Calgary, AB T2E 2N4
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Freelance After 50 Newsletter

Craig & Kelly Cannings, Co-founders of Freelance University

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