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Is a Midlife Career Change Right for You?

There's plenty to consider before calling it quits

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Table of Contents

  1. 1. A Microsoft Bigwig Branches Out
  2. 2. Letting Go of Regrets & Bad Habits
  3. 3. The Truth About Starting a Midlife Business
  4. 4. A Career Coach Finds Her Calling
  5. 5. Midlife Career Change Checklist
  6. 6. What About Retirement Benefits?
Generally, the desire to change careers midlife is not something that happens overnight.
- Claire du Preez business coach and co-founder of The Potential Program

If you’re fed up with your current job, you are not alone. In fact, according to a 2019 Bureau of Labor Statistics (BLS) news releasebaby boomers, on average, work approximately 12 jobs throughout their lifetimes. Additional BLS research from 2018 reveals that workers age 55 to 64 achieve a median tenure of 10.1 years per job post, which is 3 times that of workers age 25 to 34, at an average tenure of 2.8 years per professional position.

While the statistics seem promising for elder workers, it is not uncommon to reassess your career path once you reach your midlife point. As the saying goes, life is too short – especially when it comes to feeling stuck and unhappy in your current place of work. If you are in your 40s (or older) and are considering a new career, make sure to take the time to prepare for this life change – both mentally and financially – before making the transition.

A Microsoft Bigwig Branches Out

Stefan Weitz spent 18 years conquering different departments at Microsoft, from eCommerce platform project manager to working on the launch of the famed Bing search engine. After leaving Microsoft at age 42, and following his multiple sclerosis (MS) diagnosis, Weitz sold an eCommerce company and was left trying to figure out what to do next. “I thought hard about when I was really happiest, and it was when I was doing work with meaning – liking helping vets or schools through my various projects at Microsoft,” shares Weitz.

Enter Jetson, a seasonal probiotics supplier that was born from Weitz’s own need for the supplements to help him manage the symptoms and side effects of his MS medication. “Jetson was perfect; I know we can heal millions of Americans’ chronic health conditions through the gut because that is what I did,” explains Weitz. “But, I also recognized my enormous privilege in my access to people and resources that got me healthy – so bringing that forward to everyone became a real mission for me.”

Letting Go of Regrets & Bad Habits

At times, Weitz does feel the sting of leaving Microsoft, like “the quadrupling of the stock price after it had traded horizontally for years.” Also, he misses being able to just pick up the phone to call his former colleagues, a collection of Nobel laureates, skilled technologists, and talented business thinkers that he could once ask whatever he wanted.

Still, Weitz says that in order to thrive today, he remains cognizant of letting go of bad habits, as well as relaxing his expectations a bit. “You expect to see things go a certain way, and you begin to see all the things through that lens, which could actually harm your ability to see another version of the truth,” he explains.

The Truth About Starting a Midlife Business

For those also seeking to change career paths midlife, Weitz says to make sure you are running toward something; not away. “Clearly talking with your financial advisor and understanding what happens if your new venture goes belly-up is critical,” he says. “If you’re not comfortable with the unknown, which is more common as we age, you probably shouldn't start something new – especially in this world, where things change every hour.” 

Moreover, Weitz recommends having some younger friends to keep you "current" with both business models and technology.

A Career Coach Finds Her Calling

For many years, Claire du Preez worked in marketing and management consulting in Cape Town, South Africa, where she spent plenty of time in leadership roles, serving large teams. Consequently, this allowed her to develop a particular interest in understanding how to reveal the potential in people. 

While on this journey, du Preez says she began to experience severe burnout and started to struggle professionally. So, with the help of a coach, she made the decision to leave her job and was able to find her own calling in the coaching world. “Through this, I experienced firsthand the incredible role coaching can play in helping someone through a significant change,” she explains. “I knew I wanted to put my coaching skills to use to do the same for others.”

Today, du Preez is the co-founder of The Potential Program, which assists professionals and entrepreneurs looking to make significant life changes, from switching career paths to handling the closing of a business. “It’s not just about transitioning under that change, but learning how to leverage significant change to unlock bigger potential in your life, career, and/or business, which are all connected, at the end of the day,” explains du Preez.

Moreover, du Preez says your career is far from over at age 40. “You have so much more potential to realize.” To start, she says we need to stop looking at our careers as jobs, and examine our abilities to create value – rather than simply encompassing a skill or experience. “How can you create value?” du Preez asks.

To start, du Preez offers the following suggestions:

Learn new skills.

Work in unfamiliar industries.

Take on different types of roles.

Become entrepreneurial.

“It’s actually in our best interest to learn how to be agile, and what better way is there to do that than throwing yourself into a midlife career change and investing in your learning and growth?” she questions.

Midlife Career Change Checklist

“Generally, the desire to change careers midlife is not something that happens overnight,” shares du Preez. “It’s usually a tipping point reached after months – or even years – of really feeling that what you’re spending your time on professionally is no longer serving you in the way it once did.”

To illustrate, du Preez says it tends to start with an uncomfortable feeling that doesn’t go away. “You can’t quite put your finger on what it is, but you know you’re not happy,” she says. “You probably blame it on many other things and convince yourself it will pass.” Subsequently, du Preez says the danger of this is that you’re allowing yourself to continue down a path that can lead to resentment and burnout and/or disruptions to other parts of your life because you’re fundamentally not feeling fulfilled in the workplace.

Currently, there are plenty of resources to help you determine if a midlife career change is right for you. From Indeed job searches to networking via Shapr, there are many technological tools at your disposal.

Furthermore, du Preez offers a helpful checklist regarding the extensive process to change careers midlife. As you consider the transition, be mindful of the process that awaits you, including:

Permission and conviction – Give yourself permission to change. Oftentimes, we talk ourselves out of something before we even understand the real reward change can bring.

Interest and immersion – Before making any decisions, investigate what else you’re interested in doing in a way that gives you greater clarity around whether or not it’s really what you’re seeking.

Support – Never make a significant change alone. Coaches are trained and skilled helpers when it comes to these sorts of professional and personal journeys. A coach can help you gain clarity on whether or not to make the decision in the first place, and once you do, can support you through it.

Scenarios and plans – Entertain worst-case scenarios and plan for them. This is also the time to look at the financial implications of your career change – money is a big barrier to address, and it's sensible and necessary to plan financially, especially if the change entails launching a venture from scratch.

Learn to grieve – There is often a grieving process that accompanies any change as we leave behind one version of ourselves and move to another, and we need to both identify and deal with this grief head-on.

Trust the process – Every person’s journey is unique to them. Don’t compare yourself to somebody else. You’re dealing with a unique set of circumstances, personality traits, past experiences, and current realities that only you need to navigate. 

What About Retirement Benefits?

When it comes to reviewing your retirement benefits prior to a new job search, du Preez says you might want to consider enlisting the aid of a financial planner to ensure your portfolio is diversified enough to provide for retirement. 

“Today, it’s no longer enough to just have one retirement vehicle in an annuity or similar, which is often offered by employers,” she shares. “This benefit, from your employer, should only be one part of your future wealth creation strategy. If it’s not, then I’d advise you to get some financial planning support – before making a career change – to be sure you’re protecting your future adequately.” 

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Is a Midlife Career Change Right for You?



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