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Advice / Career Paths / Career Change

10 Steps for Making a Successful Career Change After 40

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Christine O’Neill was 48 years old when she turned her life upside down. Leaving behind a career in medicine and hospital leadership, she set out on her own to start an executive coaching practice.

Like so many considering midlife career changes, O’Neill dealt with a fear of failure and the negative opinions of others trying to stop her from taking what they saw as too big a risk. By the time most people reach 40, they’re settled into their careers and a way of life that’s become familiar, which makes considering a career change all the more daunting.

“We become comfortable with our income, our work title and status, and our physical trappings of success. Starting something new means risking all of that, and humans are hardwired for safety and stability,” O’Neill says.

But if burnout or a lack of fulfillment have become everyday burdens in your career, or if there’s a dream you’ve wanted to chase your entire life, taking that risk may feel worth it. It was for O’Neill.

Now she and two other career coaches have some advice for anyone looking to make a similar change after 40.

Define Your Why

“I believe that the most important thing is to understand why you are making this decision,” says Sherry Ellis, an entrepreneur and author who owns SBE Consulting, a business consulting firm where she often helps women make midlife career changes. “The what and how should be discussed only after you are sure this is something you want to do.”

Everyone hits ruts in their career. Is that what this is for you? Or is there something else out there you truly believe will make you happier in the long run?

You can start by sitting down and making a pros and cons list about your job and digging into more specific questions. What do you like? What do you hate? What is currently pushing you over the edge to want a change—are you bored of the work? Sick of the people you work with? Chafing at a bad management style? Do you simply want to do what you do at another organization or do you want to make a bigger change?

This exercise can help you identify what it is you need to be happy—the “why” that is driving you forward in making this change. And that’s what you should return to as the challenges of this career change arise—because there will always be challenges.

Be Prepared for Negativity

“A midlife career pivot requires courage and a certain degree of faith,” O’Neill says. “Not only are you facing your own fears and uncertainties, but many people will impose their belief systems on you.”

She says that people are often uncomfortable with others making big life changes because it holds up a mirror to their own life choices and fears about the future.

“I was really surprised by the number of people who seemed angry with me for having the audacity to make a change they didn’t feel was possible for themselves,” O’Neill says. Because she had spent a lot of time redefining her life purpose and her core values, she was able to push past the naysayers, even as she sometimes battled her own fears over whether or not she’d be able to support herself.

For anyone who may be considering making a similar leap, start with “the deathbed exercise,” as O’Neill calls it: “Imagine you are at the end of a long life and are reflecting back on how you spent your time. What will you regret not having done? Great insight and epiphanies often emerge.”

Let Go of Fear

There are usually three main fears that hold people back from making big career transitions, according to Babita Spinelli, a licensed psychotherapist, certified coach, and founder of Opening the Doors Psychotherapy who works primarily with individuals and couples in the space of life transitions, including career changes. Those fears are:

  • The fear of not being able to maintain current financial responsibilities
  • The fear of failure
  • The fear of what others will think

Many people in the over-40 set have families to take care of and financial commitments, like mortgages and car payments. They’ve also often reached the peaks of their careers, having spent years striving toward that goal. Walking away after finally achieving what you’ve spent so much of your life working toward can be incredibly difficult—especially if doing so comes with a large pay cut and no guarantees of success.

“Look at fears or self-limiting beliefs, work on how to address financial obstacles, and benchmark others who have made similar transitions,” Spinelli says. You can prepare yourself for success by identifying potential roadblocks and thinking about how you might overcome them before you have to—and this planning will help you address your fears and move past them.

If it’s money you’re worried about, how can you insulate yourself from financial stress? Maybe you spend the next six months staying in your current position, putting as much money into savings as possible. Or are there ways you can cut expenses and live more frugally while you transition into your new career? If the possibility of failure is what’s on your mind, seek out other career changers to learn from their successes and missteps and maybe even ask if they would be willing to mentor you.

The most important thing, Spinelli says, is refusing to let the fear win. “It is never too late to make a career change. Doing what gives you meaning and what you are passionate about will lead you to being happier, more fulfilled,” she says. “Trust yourself and the journey.”

Lay the Groundwork With Your Support System

There are enough challenges ahead without also dealing with the fallout of a blindsided support system. “Discuss your desire to change careers with everyone whom it will impact,” Ellis says. “Not just financial impact, but all aspects of life.” That might include your spouse, your children, your parents, and anyone you hope to rely on during the transition period. These discussions are important so that everyone can be on the same page and prepared for the changes to come.

Connect and Learn

There may be part of you that wants to leave your current career in a blaze of glory, walking out Jerry Maguire style with your head held high. But in most cases, you’re going to be better off if you gather a lot of information—and make a plan—first.

In order to learn as much as possible about what your future career might entail, Ellis suggests talking to people who are already working in the field or specific role you’re interested in. She says you should make sure to ask questions about the nonfinancial aspects of the career, such as time away from home and family, stress levels, and the work-life balance you can expect to find. “You want to make sure that this career change will fit into your ‘why.’”

If you don’t personally know anyone working in the career field you hope to transition into, you can make those connections via LinkedIn. Just make sure you’re respecting the time of anyone you reach out to, and that you express gratitude for any advice they may be willing to give.

But don’t stop there, Ellis says. “Do your research. Gather information about potential salaries, training, job outlook, etc.” Do you need further education? What kinds of companies are hiring and where are they located? The more you know, the easier it’ll be to set your expectations and make a plan.

Dip Your Toes In

When possible, Ellis says you should also try to test out your new career, either on a part-time or volunteer basis. If you’re interested in becoming an elementary school teacher, for instance, you could try volunteering at a nonprofit that offers homework help after school. Or if you’re a salesperson trying to transition into marketing, see if you can volunteer to help with publicity efforts and other marketing needs for an alumni association initiative or event.

“Depending on your chosen career, you may be able to do it at night or on the weekends to see if it's something you want to do full-time,” Ellis says. “Sometimes, just doing something else part-time may be the answer for you.”

The point is to walk before you run, making sure this is truly the right fit for you before throwing yourself completely in—while also adding some more relevant experience to your resume.

Focus on Your Transferable Skills

“The ‘sunk cost fallacy’ trips people up,” O’Neill says. “We’ve invested so much time and money in our current career that we don’t want to throw it all away.”

But she explains it’s important to recognize you’re not actually throwing anything away. “All of that education and professional experience probably translates well into a different career,” she says. “For instance, I use the clinical and leadership skills I honed as a medical professional and hospital leader every day as a self-employed executive coach.”

Spend some time looking at job descriptions in the field you’re hoping to transition into. What skills are hiring managers in that field looking for? Compare those skills to the ones you use in your current role as well as all the ones you’ve held in the past to identify your transferable skills. And remember, you’re allowed to think beyond the obvious.

For instance, let’s say you want to transition into a marketing role, but you’ve never officially been in a marketing position. That’s OK. Think about the communication skills you’ve had to use in your current role and how those might translate. Perhaps you’re that person coming to marketing from a sales background and have years of experience collaborating with marketing folks on collateral to present to prospects, interacting with current and potential clients, and using data to convince potential customers you can help them address their needs. Those are all skills that would help you succeed in marketing.

Anyone in their 40s who’s been working for a couple of decades likely has a host of skills they’ve never bothered to write out on their resume before. You just have to keep an open mind and figure out which of those skills would serve you well in a different type of role. Try to remember that nothing in your career history is a waste. It all holds value and will be part of what helps make you more successful in your new career path.

Revamp Your Resume

Once you’ve identified your transferable skills, you can recreate your resume to highlight what you bring to the table. You might want to consider using a hybrid or combination resume, which allows you to list your most relevant skills near the top of the page. You might also consider including a resume summary to give you a chance to tell your career change story in a succinct way before you list your work experience. In some cases, career changers will opt for a functional resume, which is organized around your skills rather than the jobs you’ve had, but beware that this may be a turnoff for recruiters and hiring managers.

Because ageism is unfortunately still a challenge to overcome in the workforce, you’ll also want to age-proof your resume by ensuring it follows all the most current best practices, replacing mentions of outdated software, deleting dates you received degrees or certifications, and removing job positions that you held more than fifteen years ago (unless, of course, you have experience from earlier in your career that’s extremely relevant to the new role or field you’re pursuing).

Sell Yourself in Your Cover Letters and Interviews

As a career changer, your cover letter is an opportunity to position yourself as a strong candidate even if you haven’t taken the most linear path. Write a letter that briefly explains your career change, but mostly focuses on how your past career experience has prepared you for this new field. Don’t apologize for or overexplain the experience you don’t have—focus on what does make you a great fit, not what doesn’t.

Read more: 5 Steps to Writing a Cover Letter as a Career Changer (With Samples!)

When thees time comes for interviews, you’ll have an even better chance to confidently talk about how your career change is actually an asset to the role you’re applying for. Prepare yourself and get yourself comfortable telling your story by practicing with peers and friends now. And most of all, be ready to share your passion and excitement for this new career—your enthusiasm could be one of your biggest selling points.

Get Help

Making a career change can be a trying and scary experience at any age, but perhaps especially after 40, when so many of your peers are committed to staying the course. You may have come to feel like no one around you can really relate to the choices you’re making, or maybe you just need a sounding board as you consider your next steps. That’s where a therapist or career coach could come in handy.

“Working with a therapist can help clarify what it is about your current situation that isn’t working so that you don’t simply repeat old patterns. And a therapist or life or career coach can support you on your journey toward the less known,” O’Neill says.

If consulting with a therapist or career coach feels out of reach, she recommends two books to anyone exploring a midlife career change: The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level by Gay Hendricks and Essentialism: The Disciplined Pursuit of Less by Greg McKeown. These were the titles she says helped her redefine her own concept of success and prepare for the leap she was about to take.

You might also want to check out Get a Life, Not a Job: Do What You Love and Let Your Talents Work for You by Paula Caligiuri, Switchers: How Smart Professionals Change Careers—and Seize Success by Dawn Graham, and Strategize to WIN: The New Way to Start out, Step up, or Start Over in Your Career by Carla Harris.

As for how she feels about that leap today, O’Neill says she only has one regret: “I wish I hadn’t worried so much about what other people would think about me leaving my ‘successful’ career. I’ve never felt happier or more fulfilled professionally.”

It’s never too late for you to achieve the same.