Starting Over in Midlife

Samantha Stein
4 min readFeb 22, 2024


(image by Samantha Stein)

Changing careers midlife used to be unthinkable. People spent the first part of their lives building a career, excelling at what they do, and gaining expertise in their jobs. They then spent the time until retirement enjoying the fruits of that labor. However, as people live longer than they did decades ago, second and even third careers begin to make more sense. In the US, more than 108 million people are 50 or older. There is a growing population of people who expect to live–and thrive–for at least another 25 or 30 years. This has meant that the idea of a 40-year work life has expanded to 60 years, thus shifting the idea of what it means to work over the course of one’s lifetime.

In addition to a longer life, there are other reasons second and third careers are becoming increasingly common. After years in the same field, some people seek a career more aligned with their passions, values, or interests. Some people desire to take on more challenges and learn new skills, while others might be seeking better pay, benefits or job security. Many seek careers with more flexible schedules, while others find that technological advancements have made some jobs obsolete while creating new opportunities in other fields. Educational resources are more accessible and there is growing societal acceptance of career changes. Finally, midlife may provide the financial stability, experience, and confidence to pursue different avenues, or life events outside of our control may prompt job seeking that better fits current life circumstances.

All of that said, there are many challenges for people changing careers in midlife. Some of them include:

  • Financial security. Midlife career changers often have more financial obligations than younger workers.
  • Skills and qualifications. Shifting to a new career might require schooling or certifications as well as up-to-date technological skills
  • Professional identity. Leaving behind a career, network, and recognition can be psychologically challenging. Becoming a beginner again can be hard after having experienced accomplishment.
  • Risk tolerance. As people age they become more risk-averse. Starting over can be daunting.
  • Networking and Cultural fit. Fitting into a new environment is not always easy, nor is building a new professional network.
  • Health concerns. Physical demands of certain jobs may be more challenging for older workers, and health insurance coverage may play a more significant role.
  • Age bias. Despite legal protections (and the benefit experience can bring), ageism in hiring practices and work settings is still a reality in many industries.

Despite these challenges, many people successfully navigate midlife career changes, often finding more fulfilling work in the process. If you are considering this kind of change, there can be a few helpful things to keep in mind:

  1. Identify what success means to you at this point in life. This will be important as you navigate this “next career” and may alleviate the pressure you felt while embarking on your first as a younger person.
  2. What is important to you regarding your time? Remote and hybrid approaches are increasingly common and may affect your thinking. Also think about the finances of your move and what your budget would be.
  3. What am I passionate about? This is often something that is not so far away from what you’ve already been doing. Having a role at work where you train others can lead to a job more focussed on teaching, for example. This will also help you construct a resume, bringing out the experience you already have. Take the time to assess your skills, strengths, and passions.
  4. Consider “trying on” a new career by taking courses, joining associations, or shadowing someone doing what you’d like to do.
  5. Do your homework on what the day-to-day is like. Talk to friends, colleagues, or reach out to people who are actually doing the job. Consider developing a relationship with someone who might be a mentor as you embark in a new world.
  6. Consider getting training in new technology trends and other skills that might be important in your new career.
  7. Don’t be afraid to negotiate salary, benefits, and work schedule.
  8. Try to stay focussed on the excitement of learning something new and mastering new skills, rather than the awkwardness of making mistakes or feeling you don’t know what you’re doing. Be as compassionate towards yourself as you might be for anyone learning something new.

Finally, unfortunately, although things are starting to change, ageism is still very present in the workplace and society as a whole. One study shows only eight percent of corporations include age in their diversity, equity, and inclusion policies. Many accounting and law firms still have mandatory retirement ages, pushing out highly skilled and experienced employees. Be aware of words in job descriptions like “digital native” and “high energy” that may imply a bias against those who are older. Identify companies that use algorithms to weed out age based on experience. Try to get in front of a senior executive who does the hiring. It can also pay to be upfront–telling the company how long you plan to stay and that you’d like to build a succession plan. Most importantly, showcase your value and experience.

For those fifty or older who want to embark on a new direction, there are many different sectors and industries to consider. Middle age can be the perfect time to explore, because of the experience, knowledge, contacts, and resources you’ve accrued. There are challenges to starting over in midlife, no doubt, and it can take patience, determination, and a focused strategy. But the effort can be well worth your while as you embrace a new chapter in your professional life.



Samantha Stein

I’m a writer, photographer, and psychologist who (monthly) explores self, relationships, and mental health in an ever-changing world.