How To Change Careers At 30, 40, 50, and Beyond

W&D Podcast

Laura Ingalls Wilder published her first book at 65.
Julia Child wrote her first cookbook at 50.
Ernestine Sheperd became a bodybuilder at 56.
Martha Stewart redefined the lifestyle industry at 41, years after starting her catering company.
Vera Wang started her wedding dress company at 40.
Samuel Jackson was 46 and a recovering addict before he starred in Pulp Fiction.
Ray Kroc bought his first McDonalds at 50.

In the era of overnight billionaires like Kylie Jenner and Mark Zuckerberg, it’s hard to not feel like we missed the memo. While we were busy trying to figure out how to apply for health insurance, these kids were building empires. And while we can’t get enough of their stories, the obvious is left out of the narrative.

From privileged upbringing and the genetic lottery, there are plenty of practical reasons to go easy on the comparison game when confronted with yet another 30 under 30 list. We don’t begin our lives on the same starting block, not by a long shot, but that doesn’t mean we won’t reach the finish line.

Accepting we’re not racing others helps. What’s even more powerful is realizing we’re not racing TIME, we’re challenging ourselves to change our relationship with work. While our journeys won’t look like the stories we read in magazines, it doesn’t mean they can’t be any less remarkable.

In fact, I think we could agree that the people who find their own definition of success are an even purer source of inspiration. Because if that list above tells you anything, it is that you are never too old to bet on yourself.

Why make the change now?

Perhaps you’ve found success and are craving something different. Perhaps you realize you found yourself in a career that doesn’t align with your values? Perhaps you realize it is time to stop putting off that big idea you’ve been mulling over and just go for it. Realizations like these happen when you’re ready to see and accept them. Don’t beat yourself up for not making “better choices” in your 20s because really, you were doing your best. The important thing is you see clearly you want to change something now, and that’s all that matters. What’s happening right now.

What to expect once you make the leap

Alright. Now down to brass tacks. Where to start? Accepting the path will be difficult and you’ll be wrestling with a few or all of the doubts listed below as you make a commitment towards making a career change.

It will require belief in yourself and a willingness to be uncomfortable. It will require forgiveness when you make a mistake, and the strength to pick yourself back up again. Let’s look at the five biggest internal struggles you’re facing and how to respond when they pop up.

Doubt #1: It is too late to change your career.

Truth: Do the math. If you’re planning to retire at 65 and you’re 42, you have 20+ years in a new field, which is plenty of time to make a name for yourself. Remember, your skill set may not be applicable to a career change but you’re not starting from scratch. In fact, you’re probably feeling an increase in confidence given how much you’ve already experienced in the workforce.

Doubt #2: Other people will think I’m crazy.

Truth: What other people think is none of your business. How can you know their opinion about your personal decisions are not clouded with their own resentment and fear of the future? If we lived by what other people think we should do, we would never be able to advocate for what we really NEED and want because that’s just not how humans work. When someone shares an opinion, we must always remember it is seeped in their own experiences. You’ll never get an opinion that isn’t clouded in self-judgment, even from the most well-intentioned friend. You’re the only one who can really know what’s right for you.

Doubt #3: It’s the wrong choice.

Truth: Now that we understand it is our choice and ours alone, we have to own the result! Yes, there is risk here. But what is the risk of NOT making a change? Can you live with the life you’ve been living? Who will you be if you don’t’ make a change? What will NOT making a change do for your mind, your mood, your relationships? Take inventory of how not making this change compares to the risk associated with making a shift.

Doubt #4: Change is hard.

Truth: No doubt, it will be harder to make changes, and in order to move through them we will have to accept the discomfort as part of the process. Think about the difficulty associated with change as proof of progress. When we work out to change our body, we use some sort of pain as a measure of doing the work right, so why wouldn’t we invite a little bit of discomfort as proof we’re really growing and stretching out of our comfort zones? When we learn to change our relationship with discomfort it can become much more tolerable.

Doubt #5: You don’t deserve it.

Truth: Everyone deserves a second chance and you must believe that in order to allow yourself the grace to accept that your younger self was doing their best to find the right career for you. There is no way you could have the hindsight you have now. Forgive yourself for selecting that college degree, for taking that job. Forgive your parents for not pushing you to go for that top tier college. Forgive your parents for not being able to afford to send you to college. What is in the past is in the past, and it is a reality we cannot change. What we can do is give ourselves permission to learn from our past experiences to make new choices in the present. There is no way of knowing what the future will hold, but today we get to make our own choices.

Prep Work

Now that we’ve gone through some of the internal hurdles you’ll need to face, here are a couple of practical steps you can take if you are serious about making a big change in your career:

Figure out what you want to do—— and take the time to really figure that out. There are certain jobs that work well for midlife career changes, including business management, personal training, massage therapy, dental assistants, executive assistants, project management, consulting, freelancing, etc. More than likely if you’ve been working for a decade or so, you’ll have a strong set of skill sets that work for just about any job. I would write down what you like about your current career and what you excel at and then see which ones are applicable to a job that interests you.

Invest in a new skill. There are plenty of ways to invest in learning in 2019. Getting a sense of what is involved with making the career change first will help you feel more confident in making the switch. There will be a learning curve (remember discomfort is good!) but you’ll quickly be able to sense if you’re moving in the right direction. Personal example: I looked into going to medical school when I was 25 and took one calculus course and said… no thanks. I think it saved me a ton of time and agony in making the wrong choice and instead, I invested more time in Wit & Delight and how I could help others through the platform. At the time I felt designing liquor bottles wasn’t aligned with the type of work I wanted to put into the world. Becoming a doctor was a response to that feeling, but the solution looked a lot different when I began to look at how my skills aligned with the types of careers changes available.

Ageism is a THING and given it is widely underreported, approach your resume differently. Include only your most recent work, and consider not including your graduation dates if you feel the position you’re applying for is more entry-level. It also helps to look for companies whose teams show age diversity. Or go in with your age as a selling point and really drive home what you have to offer given your wisdom and experiences. There are career shifts where lots of experience are a huge benefit, like consulting, course work, coaching, etc. So lean into ALL that experience when going in that direction.

Give yourself time. It is going to take time for you to make the change. Don’t feel as if you need to know exactly what you’re doing after a few months of knowing you need to make the shift. It’s a big decision, and given it’s helpful to learn a few new skills before making the leap, it helps calm your mind to know the change won’t happen overnight.

Decide what success looks like on this new career path. A question I get a lot is, what if I don’t succeed? And I ask, what is your definition of success? Who would you be with this new job? Most often the person realizes that the desire to shift their career in a new direction has little to do with monetary forms of “success” and a fundamental need to have a passion for the work they are doing. As we grow up and get to know ourselves on a deeper level, all the time and effort we spend away from the people we love becomes a harder pill to swallow. So, pursuing a career that aligns with work you feel good about doing becomes the new definition of success. Success becomes about going to be bed at night at peace with the decisions you’ve made, the person you are, and the work you’re doing.

I really believe the kind of freedom we’re talking about today is worth the risk. Defining success for yourself and taking control over the way you spend your time making a living has little to do with money; it’s the kind of confidence and freedom no one can take away from you. So don’t listen to the nay-sayers, listen to what you need, look at where your strengths lie, forgive yourself for past mistakes, and give yourself a pat on the back for being brave and advocating for your future. It’s not selfish, you deserve it, and you’re never too old to pursue your dreams.

Want to listen to more on this topic? Check out The Wit & Delight Podcast!


BY Kate Arends - March 11, 2019

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March 11, 2019 1:32 pm

Such an encouragin text and really good points and tips! As someone who has switched from one industry to another more than once I know this to be really good and valid advice.
What I’m taking from this text is the reassurance that age really doesn’t define what sorts of careers we can or cannot have anymore. I just turned 30 so I have no worries anytime soon if I choose to change my career path once again 🙂

Teresa | Outlandish Blog

March 12, 2019 10:14 am
Reply to  Teresa

Im glad you found it helpful Teresa!!

March 12, 2019 4:33 am

This is really uplifting to read! Overcoming doubts can be so hard, no matter the age. So even though I am still in my twenties, I feel I can take away some valuable lessons from these insights and the idea that you can reinvent your life at any point.

March 12, 2019 10:13 am
Reply to  Lizzy

I’m glad you found it helpful!!

March 15, 2019 1:47 am

Love the line about this not being a race against others or TIME. In my mid-30s, I’m getting better at unlearning the destructive habit of comparing my achievements with the timeline of others’ success. Part of it is just being mindful when I’m consuming social media, reading those “30 under 30” lists, and hearing podcast interviews that feature wildly successful creatives/entrepreneurs. It can certainly be inspiring, but the moment it starts to feel like a comparison game, I know I need to turn down the volume.

March 16, 2019 2:02 am

Thank you so much for sharing recipes.Great blog!!!

June 12, 2019 2:39 am

This is so inspiring and motivating, and I’m sure it’s never too late. My cousin is 45, she worked as a college teacher, but she always was crazy about technology. She decided to completely change her life in 43, and now she works as augmented reality developer at this company – She is happy, she is doing what she really loves. And it’s never too late, for anything.

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