top of page

3 challenges common in midlife career change and how to overcome them

Why is it hard to change careers the older you get?  

If you have asked this question before, you’re not alone. It is common for professionals in their 40s, 50s, and even 60s to long for a career change. This desire can stem from burnout, a lack of passion for the work, or changes in financial need. Switching careers can be an explorative and rewarding journey, ending in a satisfying and fulfilling outcome. Yet the process often raises short-term difficulties and fears. These fears are entirely understandable. After all, you have spent years building your skill set, establishing yourself within your niche, and reaching financial security. The prospect of switching careers can seem unsettling, even unimaginable. But why?

Changing careers means you might face financial uncertainty, confusion about skills alignment, and age bias. So, how can you transition careers with more confidence and stability?

Let’s consider a few key strategies as you contemplate a career pivot.

Common Challenges During Midlife Career Transition

1. Financial Security

Transitioning to a new career calls for careful planning and preparation. Many professionals struggle with career transition because they wonder how they’ll be able to support themselves and their families. Why does this challenge come up?

Career transitions lead to various unplanned circumstances that can cause financial instability, such as:

  • Extended period(s) of job search and unemployment 

  • Investment in training and certification courses

  • Low-paying temporary roles (underemployment)

  • Accepting ill-matched positions (mismatched employment)

Not every gap in employment can be planned; however, if you know you’ll be making a career move, financial stability helps ease the stress and uncertainty of career change. It may also offer a higher chance of longer-term success in your new role.

Here are a few tips on how you can make plans for your finances:

Create a Budget 

A detailed financial plan must start with a budget. Creating a budget prepares you for any unexpected occurrences. It also gets you in the frame of mind to brainstorm cost-saving strategies.


You begin to ask yourself: “What are the things I can save money on?” and “Do I really need that ___________ (e.g., high-priced morning coffee)?” 

Creating a budget also prompts you to review your recurring bills and research affordable alternative expenses.

These little measures don’t seem like much, but in the long run, they can shave layers off your monthly expenses.

Find Another Income Source

In 2024, it was estimated that 39% of people in the US have some type of side hustle. The gig economy is alive and well and shows no signs of dissipating.

If you don’t have a side hustle and you find yourself desiring a career change, it might be prime time to consider starting one. 

Types of popular side hustles include: 

  • Virtual Assistant

  • Ride Hailing

  • Food Delivery

  • Home Rental 

  • Blog Writing

  • Online Tutoring

Adding a side hustle to your current job or as a way to fill the void during a career transition delivers many benefits, one of them being to reduce the financial burden of a career transition.

Prep an Emergency Fund

As I mentioned, not every career change is planned.

But most of the clients I work with have been contemplating a career change for months, even years. Their decision to make a career pivot is not a surprise, so the financial implications, if any, shouldn’t be as well. 

An emergency fund helps avoid complications that may arise from financial constraints caused by gaps in employment. If you know you’ll be making a career transition, start planning months before you execute. 

Sound financial planning, such as having an emergency fund, increases mental well-being. Having financial peace of mind will offer more mental (and physical) freedom to execute the career exploration process. 

Whether you use it or not, it’s best to have it as a source of reassurance when you embark on your career change journey.

2. Relevant Skills and Experience

In today's ever-changing job market, looking for a career change is extremely common. In fact, the Bureau of Labor Statistics reports individuals have an average of 12.4 jobs during their lifetime. That is a lot of change! 


Although your most valuable skills are the ones that transfer from role to role, a new career may require a different skill set and experience. To overcome any gaps as you move from your current to new career, highlighting your transferable skills and invest in necessary training. Here are a couple of helpful ways to set yourself apart:

Highlight your Transferable Skills

So, what exactly are transferable skills? Transferable skills are skills you already have that are ‘portable,’ meaning you can adapt them to fit your prospective job role. 

Most skills are applicable across occupations, no matter how different they may be. Any let’s face it, if you’ve been working for years, chances are you already have many of the skills you need.

Basic skills such as problem-solving, project management, quick thinking, writing skills, and time management can be transferred from your last role to your new career path. Every organization wants to hire an employee who has strong communication skills. 

For instance, if you’ve been a senior project manager in the construction industry, your ability to manage budgets, delegate tasks, and work through complicated projects makes you highly valuable for project management roles in a variety of fields. 

So, how can you identify which skills to transfer into your new career? 

To begin, make a list of responses to the following questions:

  • What are your day-to-day responsibilities in your current role, and which skills do they involve? 

  • What are your significant accomplishments? Which skills helped you achieve them? 

  • What skills does your target career require? Do these skills overlap with your current job responsibilities?

  • How can you reframe your current and past experiences to highlight your transferable skills using keywords that align with the expectations of your target career?

There are also computer-based assessments that can offer insights into your transferable skills, helping figure out which ones to highlight and which one’s you might need to brush up on for that next role. 

Finally, a career coach can assist you in identifying your transferable skills, framing your experience for your resume and cover letter, articulating the value of these skills in various contexts, and helping you navigate the interview process.

Have a Gap in Skill? Seek Necessary Training 

In this digital world, the ability to obtain and learn new information is easier than ever before.

Platforms like Coursera, Udemy, and LinkedIn Learning provide courses anyone can take to upgrade their knowledge and even get a certificate. Colleges like Harvard, MIT and Google offer free certificate courses as well. 

If the courses you’re looking for aren’t on the free list and that’s what’s standing between you and your next professional move, apply some of that emergency fund towards necessary learning or save up to get the required education. Research the courses and platforms that offer flexible and affordable programs you can tailor to your needs.

Note: In some cases, a career change may require additional schooling, such as an advanced degree or diploma. It is important to consult with a career coach and other experts if your change points to this option, as the financial investment is usually greater. It’s great to invest in education later in your career, but with so many learning options, and so many avenues for growth, you want to ensure the investment pays off! 

3. Age discrimination 

In recent years, the employment rate of older professionals has fallen drastically. Ageism has made it increasingly more challenging to maintain employment and even harder to change careers. Research suggests older job applicants with years of experience are three times less likely to be offered employment when compared to younger applicants with almost no experience.

This discrimination can be discouraging for senior-level employees who plan to switch careers. Even when employed, older applicants receive less than ideal treatment and might be overlooked for leadership roles because of age bias. The challenge, as the article states, is that “Ageism is one of the most common and socially accepted forms of discrimination.”

Change Your Mindset

However, reports of agism aren’t all doom and gloom. Many companies welcome, even seek out seasoned workers. In fact, there are many industry sectors that rely on the knowledge and skill-level of senior-level employees.

Pew research reports that workers ages 75 and older are the fastest-growing age group in the workforce, more than quadrupling in size since 1964, many choosing what economics call ‘bridge jobs,’ positions with less stress, reduced hours, and higher working satisfaction.

Surround yourself with friends and colleagues who support your career change and understand the value you offer to an employer. These individuals can increase your motivation and confidence.

Educate Yourself

Whether looking for another full-time role, or searching for your bridge job, changing careers can be a long, complicated journey, and no one should have to navigate it alone.

The good news is, you don’t have to. Career and executive coaching is on the rise. But first, ask yourself, why exactly do I need coaching, what challenges do I need to overcome, and what coach is the right match for my needs at this time. 

  • Understand your rights!

  • Research Facebook and LinkedIn support communities and join them.

  • Help dispel the myths associated with the aging workforce. Educate yourself, talk to your colleagues, and use social media to spread the word that agism is bias and should not be tolerated.

You can also reach out to a mentor or career coach to connect you with other professionals who have successfully transitioned careers. This is a quick way to learn how others have coped with career transition struggles like ageism.


Changing careers can be a tremendous milestone in one's professional life - a change that can be daunting and exciting.

With solid financial footing, a strong understanding of your transferable skills, and an understanding of the workplace landscape, your chances of success during career transition increase significantly.

Eliciting the support of friends, family, your professional community, and a career coach can secure your transitional success!

97 views0 comments


bottom of page