How to Change Careers After 30 Without Starting From Scratch

Feel stuck in a career that no longer lights you up—but afraid it’s too late to pivot?
You’re not alone. And more importantly—it’s not too late.

In this inspiring episode of the Thrive Careers Podcast, career coach and HR strategist Olajumoke Fatoki sits down with Katie O’Malley, Founder of (en)Courage Coaching, to bust the myth that you have to start over to make a meaningful career change after 30.

💡 Inside this episode, you’ll learn:

• Why your past experience isn’t wasted—it’s leverage
• How to shift careers after 10+ years without losing momentum
• What a career portfolio is (and why it matters more than climbing a ladder)
• How to upskill with clarity and confidence
• Why staying stuck is actually riskier than making the leap

Whether you’re in your 30s, 40s, or 50s, this episode gives you the mindset, strategy, and tools to pivot with purpose—and build a career that finally fits who you’re becoming.

📘 Free Resource:
Download the Career Clarity Playbook—your step-by-step guide to planning your pivot with confidence:
👉 https://bit.ly/CareerClarityPlaybook

🌐 Connect with Katie:

• Katie on LinkedIn
• encouragecoaching.org

🎧 Stop settling. Start building forward.
Tap play now on Spotify, Apple Podcasts, or wherever you listen—and take the first step toward your next chapter.

Transcript

Olajumoke Fatoki (00:06): Hello, hello, hello everyone! Welcome back to another inspiring episode of the Thrive Careers Podcast. I’m your host, Olajumoke Fatoki, and I’m so excited about today’s episode because it’s for everyone who’s ever thought, "It’s too late for me to pivot" or "Where am I really going with my career?" Maybe you feel stuck in a path you’ve been on for over 10 years—and guess what? Today’s conversation is here to help you change that narrative and remind you that it’s never too late to start again.

We have an incredible guest joining us—Katie O’Malley! Katie, welcome to the Thrive Careers Podcast. Please introduce yourself briefly and tell us a bit about your background.

Katie O'Malley (00:58): Absolutely! I’m so delighted to be here and have been looking forward to this conversation since our first chat. My name is Katie O'Malley, and I’m the Founder and Principal Coach at (en)Courage Coaching. Before launching my business in 2018, I was a bit of a career nomad. Instead of following a traditional career ladder, I’ve built what I call a career portfolio.

The one consistent thread through my journey has been a strong sense of altruism—wanting to make a difference in the world, positively impact my community, and support the people around me. I started my career in politics in 2004, working on Senator John Kerry’s presidential campaign. It was incredibly intense—seven days a week, 16-hour days—and after the campaign ended, I found myself unemployed, without healthcare or prospects. That’s when I realized politics wasn’t going to give me the stability I needed.

So I pivoted to the nonprofit sector, working with organizations like the Innocence Project in NYC and the AIDS Foundation of Chicago. While the work aligned with my values, living in big cities on a nonprofit salary was tough. I thought my dissatisfaction was about money, so I switched to commercial real estate, thinking, “If my friends can do it, why not me?” But if I’d talked to a career coach back then, they would’ve pointed out the misalignment in values.

From day one in that new role, I knew I’d made the wrong move. But with a Midwestern upbringing that emphasized hard work and never quitting a job without another lined up, I stuck it out for nearly four years. It took a huge toll on my mental health. When we operate outside of our strengths and values, it can lead to a real identity and mental health crisis. That’s exactly what happened to me.

In 2012, I took a medical leave of absence and realized through recovery that I wasn’t alone. Many people were struggling with work-related identity crises. That inspired me to go back to school at 30 and pursue a master’s degree in counseling, hoping to help others at the intersection of work and well-being. Unfortunately, insurance companies didn’t recognize workplace issues as valid mental health concerns, which blocked my path to licensure. Instead, I pivoted again—into coaching.

I spent the next decade working in higher ed—UT Austin, University of Chicago, Booth School of Business—supporting student career and leadership development. But I wanted these kinds of services to be accessible to everyone, not just elite institutions. So in 2018, I founded (en)Courage Coaching to do just that.

Olajumoke Fatoki (06:31): Katie, thank you for sharing that powerful journey. I love how purpose and passion thread through everything you’ve done. I’m especially excited because you’re the perfect person to help us challenge a mindset so many professionals struggle with: “I’ve been in this field for too long to make a change.”

So, to start: Why do you think this belief is so common, and how did you come to challenge it through your own work?

Katie O’Malley (07:58): It’s all about the narrative we’ve been fed. We’re told: “Pick a field when you're 18 or 19, specialize, and stay there for 40–50 years.” But the science tells us our brains don’t even finish developing until age 25. How can we be expected to choose a lifelong path before we fully know ourselves?

We get stuck thinking, “I studied this in college, I’ve worked in it for 5 years—I have to keep going.” But that’s simply not true. Unless you’re in a highly specialized role—like brain surgery—your skills are transferable. Whether they’re technical, leadership, or power skills (formerly known as soft skills), those can carry you across roles and industries.

And the job market is shifting. Many industries are moving toward skill-based hiring. Employers care less about where you’ve worked and more about what you can do. That opens up so many more options.

Olajumoke Fatoki (10:59): I love that. And yes—“power skills” is such a better term than “soft skills”! Let’s go deeper into this idea of the career ladder versus a career portfolio. What does that shift in mindset look like, and why is it so crucial today?

Katie O’Malley (12:21): Great question. First of all, not everyone wants to climb the ladder. Some of my clients say, “I love the work I do now—I don’t want to manage a team or chase titles.” And that’s perfectly okay! We need to normalize that.

Second, the ladder itself is broken. Take women, for example: Research shows that for every 100 men promoted early in their careers, only 81 women are promoted. This inequity compounds over time. The system wasn’t designed for everyone to rise equally.

Third, the world of work is changing fast. Even if you stay in the same company, you’ll need to keep learning. So I tell clients: Whether you’re 30, 40, or 50—that age will arrive either way. Wouldn’t you rather reach it with a new set of skills, instead of staying stuck?

Your portfolio—everything you've learned, built, tried, failed at, and succeeded in—comes with you. Nothing is wasted.

Olajumoke Fatoki (18:15): That mindset shift is everything. And your own pivots—from politics to nonprofit to real estate to higher ed—are proof that reinvention is possible.

So let’s speak to the person who wants to pivot but feels like they’ll “lose everything” if they do. How can they reframe that fear?

Katie O’Malley (20:29): Start by asking: Where do others consistently see me at my best? What strengths do people compliment me on? And then ask: How do I want to spend 8–10 hours a day?

The intersection of those two questions is where new career possibilities begin. And if you’re unsure, enlist support. We were never taught how to explore careers or make pivots. That’s a gap in education systems around the world.

Also, remember—feedback from others matters. We’re often our own worst critics. In my case, people told me for years I should be a counselor. I brushed it off. But they were right.

Olajumoke Fatoki (24:44): Absolutely. And once you identify your strengths, the next step is building on them. So let’s talk about upskilling and reskilling. What practical steps would you recommend for someone who wants to future-proof their career without starting from scratch?

Katie O’Malley (25:55): First—be a lifelong learner. But also, be intentional. Time and attention are limited resources. So upskill in an area that genuinely interests you.

For example, I was curious about behavioral science and thought I’d love it. But then I hit the stats and regression models and said, “Nope.” Instead, I leaned into what came naturally—listening—and pursued my master’s in counseling. That three-year journey taught me how to truly listen.

And now, that’s one of my differentiators as a coach. So look for areas where your natural talents align with a skill that can be deepened.

Olajumoke Fatoki (29:10): That’s so powerful—and I agree, everyone should take a course in real listening! Now let’s touch on confidence. What advice do you have for mid-career professionals who want to pivot but feel unsure or unqualified?

Katie O’Malley (30:17): Confidence is tricky. Often, a big pivot means taking a step back—at least on paper. When I made my switch, my salary went back to what I earned five years earlier. But I knew that role would position me for future credibility.

Ten years later, I’ve 10x’d that salary and built a business I love. So don’t just look at short-term pay cuts—look at the long-term possibilities.

Olajumoke Fatoki (34:40): That’s such an important point—sometimes what looks like a step back is really a launch pad. Before we wrap up, do you have a favorite client story of someone who embraced the portfolio mindset?

Katie O’Malley (35:09): Yes—my client Brittany. She was a social worker during the pandemic, incredibly talented but underpaid. She believed she had to suffer to make an impact. Once we reframed her narrative and highlighted her transferable skills, she pivoted into a mission-driven startup—and tripled her salary.

It was amazing to watch. But the breakthrough only happened because she opened herself up to new possibilities.

Olajumoke Fatoki (37:29): Wow. That’s powerful. Thank you for sharing that. Now before we let you go, a little rapid-fire for fun: What do you enjoy doing when you’re not coaching?

Katie O’Malley (38:05): You’ll find me on my Peloton! I’m Courageous Kate on the leaderboard. I’m also walking my dogs or rehearsing for my upcoming TEDx Talk in Boston on June 30th—lots of Post-it notes everywhere as I memorize the script!

Olajumoke Fatoki (39:17): Amazing—congrats on the TEDx! One last question: What’s the best career advice you’ve ever received?

Katie O’Malley (39:32): A client once told me: "Take care of the clients you have. You don’t need a fancy marketing plan—just treat them like gold, and more will come." That helped me build a strong, service-focused foundation.

Olajumoke Fatoki (40:15): Beautiful advice. So as we close out, what final words do you want to leave our listeners with?

Katie O’Malley (40:30): Stay optimistic. Stay optimistic about your career, the labor market, and your ability to grow. With clarity and effort, anything is possible.

Olajumoke Fatoki (40:54): Perfectly said. Katie, thank you so much for being on the Thrive Careers Podcast. Where can people find and connect with you?

Katie O’Malley (41:21): You can visit my website: encouragecoaching.org. I’m also on Instagram and Facebook @encouragecoachchicago, and on LinkedIn at Katie O’Malley. Or email me at katie@encouragecoaching.org.

Olajumoke Fatoki (41:54): Thank you again, Katie! And to our listeners—don’t be afraid to make the change you need. You have what it takes to pivot and thrive. Until next time, keep thriving!