Podcast

1. What should I think about before making a mid-career switch after years in my current role?

Ensure your mid-career switch is strategic—not impulsive!

Before you tap into any change in your current role, pause and reflect. Grasp the reason—what is it that you miss right now in your current role? More fulfillment, better work-life balance, a bigger challenge, or a fresher environment. Moreover, what do you expect from your next role? Is it flexibility, creativity, purpose, or something else?

It’s always smart to avoid a knee-jerk reaction and plan before you proceed. Reflect on your values, consider alternatives, and strategize a mind map. Choose a path that aligns with your long-term goals instead of opting an impulsive decision. This helps in making a change that aligns your career path, rather than making just another ‘escape’ and regret later. Because the right move isn’t just about leaving—it’s about arriving somewhere that feels right.

So, how can you strategize?

• Jot down 5 challenges you’re facing at work—and 5 things you want from your next role.
• Dig deeper into your industry. What’s changing? What’s trending?
• Make sure you’re surrounded by growth opportunities—not stuck in a dead zone.
• If your current job is making you compromise on your values or stalling your growth, it might be time to move on.
• If the issues aren’t deal-breakers, talk them through with mentors or teammates. Sometimes, clarity is just one conversation away.

Let’s dig into a real-world case study.

Kathleen Hogan: From Tech Executive to Microsoft’s HR Chief

From business and tech roles, Kathleen moved into Chief People Officer at Microsoft which was a bold mid-career move in her 40s.

And was she ready to lead with empathy after being in tech for years?

Yes, and she proved everyone wrong when she led Microsoft’s cultural transformation and played a contributory role in establishing Microsoft as a premium tech company.

Let’s glance through her dedication to make her mid-career switch an impactful decision:

• She played a key role in embedding Microsoft’s “growth mindset” culture, in 2014—a core driver of its turnaround under Satya Nadella.
• Microsoft was named Glassdoor Best Place to Work multiple times under her HR leadership.
• Recognized in Forbes’ Top 50 Most Powerful Women in Tech and Business Insider’s Most Innovative HR Leaders.
• Led initiatives that improved diversity hiring, employee engagement, and built a resilient remote culture during the pandemic.

2. How can I overcome the fear of a midlife career change in a new field after years of experience in my current role?

The fear of starting over with midlife career change is real—and totally normal.

But do you know what’s the truth is? A mid-career switch doesn’t wipe out your experience. It’s like hitting export—not hitting delete! Skills you earn like communication, leadership, and problem-solving translocate really well, even if your old job and your new dream lie on opposite corners of the world.

The fear of starting over gradually fades as you build more knowledge and skills. With more confidence picking up with more industry insights, you’ll have a clear path ahead of you. What is required of you is to counter the fear with learning, key updates, latest insights, and in the end, the confidence that makes you, you!

So, how to gain that confidence along the path?

• Start enrolling in short courses to advance your skills and have a tight grasp over your technical competency—it’s the core of confidence, shooing away the fear.
• Join industry events that will provide more opportunities to connect with experts in your field.
• Catch up with peers with deep insights into the industry you are targeting. Take notes and practice what’s trending and what’s fruitful.
• Practice the attitude of ‘It’s okay.’ Yes, understand that if it works out, well and good, if it doesn’t–it’s okay, once again.

Ready for a really inspiring case?

Shantanu Narayen: Adobe’s CEO After a Mid-Career Change

Shantanu Narayen began his career in engineering and tech product management while working for Apple and Silicon Graphics. At Adobe, he started in a technical role before making a significant mid-career switch into leadership. In 2007, he became CEO of Adobe, during a time when the company was facing immense challenges in adapting to digital transformation.

Under Narayen’s leadership, Adobe shifted from box software to a cloud-based subscription model, revolutionizing its business model and leading to a dramatic increase in revenue. Adobe’s market cap soared from $26 billion to $300+ billion under his leadership.

The Takeaway? A mid-career switch isn’t just about changing jobs—it’s about driving massive transformation. Narayen leveraged his background and leadership to guide Adobe through one of the most successful business pivots in tech history.

3. What emotional roadblocks should I expect with a midlife career change, and how can I manage them?

Emotions are meant to flow—let them!

Yes, emotional roadblocks are part of mid-career switch. Tackle them smartly. These emotional doubts tend to come in the form of self-doubt, imposter syndrome, and the fear of failure.

If you think, “Am I even qualified for this?” or “What if I fail,” you are under the process of progress and these feelings are natural. So, what’s the best strategy? Acknowledge them! Don’t let them dictate your decisions. Implement incremental actions, celebrate small wins, and surround yourself with a supportive community— mentors, friends, or colleagues who believe in you.

The discomfort you face today will be the confidence you’ll have tomorrow. So, embrace them and acknowledge them as a part of the growth process.

Break emotional barriers with these power moves:

• Practice mindfulness to acknowledge your present state and understand it completely.
• Don’t escape discomfort. This might rather sound harsh but it’s important. Embrace it and navigate through it to build resilience.
• Connect with teams and collaborative professionals. Have a peep into their working style, philosophies, and expectations.
• Relax and enjoy the transition. Any change seems burdening and regretful in the beginning but mostly it turns out to be a useful step later.

Let’s learn about Pat Wadors who reinvented through vulnerability.

A seasoned HR leader, Pat Wadors held senior roles at LinkedIn and ServiceNow. But her successful career could not prevent emotional burnout and self-doubt which emerged while shifting roles and industries in her 40s and 50s.

Some of the emotional roadblocks she faced were:

• Fear of Irrelevancy- Younger talent rose fast, giving her concerns about her skills’ relevancy.
• Identity Loss- Leaving her legacy and influence behind disturbed her peaceful state and evoked vulnerability.
• Imposter Syndrome- Fast-paced and tech-heavy environments invoked a feeling of self-doubt and she often thought “Do I belong here?”

How did she manage?

• Owned her emotional struggles. She acknowledged them and looked above them.
• Reframed the meaning of growth by leaning into mentoring to stay fresh and keep learning.
• Stayed Mission-Driven and built inclusive, human-centered cultures.

Want to know the real mantra to tackle midlife career change? Read our insightful busting it all for you!

4. How can I maintain a positive mindset during a midlife career change when I’ve made the switch, but things still feel uncertain or slow to take off?

Career transitions are a marathon, not a sprint!

It may tempt to throw in the towel when results don’t show up within a couple of days. But you probably know that instant success is a myth. Outcomes other than microwaving popcorn don’t happen with a blink.

So, what’s the solution? Have patience! While recognition and satisfaction are important in the new job role, journey also matters. Till the time, learn new skills, meet the right people, gain hands-on experience, and build a strong foundation for a career that lasts and speaks for itself.

In the end, it’s not just about landing a new role right away—it’s about setting yourself up to thrive in it.

Maintain a positive mindset with these moves.

• Count your learnings—mastering a new skill every day is no less than a recognition.
• Remember, you’ve just started. Expecting satisfaction too soon after the switch can hinder the learning process.
• Remind yourself of your achievements. Navigate through your past rewards—don’t stomp over them.
• Chant the mantra often—Slow progress is still progress! Track it and celebrate the small wins.
• Kill the pessimism. Pause and take a moment to recognize how far you’ve come and tomorrow you’ll go farther. If you doubt, can it go wrong? It can go right as well!

Leena’s Flair for uncertainty: From HR to Global CEO

From starting in engineering, moving into HR at Unilever, to rising as CHRO, she switched boldly, becoming Global CEO of Chanel, with no prior fashion experience.

Her mantra to fight back with uncertainty?

• Focused on her core values- executing people-first leadership.
• Embraced change. Treated it as growth, not disruption.
• Trusting her journey by trusting the process and her own will.

So, what do you learn from her fight?

Stay grounded once you make that midlife career change switch. In the end, trust your skillset and stay curious.

5. How can I deal with the uncertainty of a mid-career change and make peace with it?

Uncertainty is certain—that’s the irony of a midlife career change. But guess what? It’s totally normal. When you make your own mid-career switch, you have no idea what’s next. And yes, it unnerves—but do you have a way out? No! The cards are played. You have to be patient, and guess what? It will turn out to be great and oddly exciting.

Growing, doing something bold, or challenging your horizons—they all bring uncertainty and that’s the nature of it. So instead of panicking, focus on what you can control—your effort, your mindset, your next best step.

What we know is that nobody has it all figured out (some are just better at pretending).

Turn your uncertainty into self-confidence with these strategic strides:

• The initial phases of midlife career change are always unnerving, creating a sense of doom if it doesn’t work out. Let them pass.
• Let’s be logical. What causes you to develop the fear of uncertainty? Lacking skills? No prior experience? Work on skills that minimize the uncertainty and boost the certainty of it to work out. Learn, learn and learn.
• What even if it doesn’t work out? You have already gained years of experience until now. Stay patient and embrace!

A peek into Bozoma Saint John’s Reinvention Through Uncertainty

Bozoma Saint John had an influential marketing career—spanning her tenure at PepsiCo, Apple Music, Uber, and eventually the CMO of Netflix. Known for her boldness, creativity, and unapologetic presence, she left Netflix in 2022 after just 2 years without announcing a next move.

Why so?

When Boz was 45+, she chose uncertainty over plans. Announced no next big gig. Gave no clear “why!” Later she shared that she grieved for the loss of her husband and prioritized her personal healing over professional upgrade.

So, what did she do?

She dived into the unknown fearlessly, wrote a memoir (The Urgent Life), spoke about loss, and pivoted into a more mission-driven space.

She, today, is one of the most sought speakers for in-depth reinvention.

Yes, her path wasn’t linear—but it was authentic.

Your learning?

Uncertainty is the proving ground that you can conquer with one step at a time till you know the next move. It isn’t about knowing the next 10 steps. It’s about owning the next one-simple as that!

6. How do I stop fearing failure when considering a career change?

Failures are not the end of the world—They are just plot twists!

Almost everyone faces failures during their mid-career switch. Anshuman Tiwari, explains, “Even I faceplanted a few times jumping into HR but turned out to be learning in the end.” Failures build character and a strong foundation for an established career.

But how can you fold them up and slip them back into your pockets?

Don’t bring on the high-stakes drama. Take them as learning steps. Don’t focus on the failure—instead zoom in to learn the causes for it. Remember, the instant you learn the lesson it tries to teach you; it will stop occurring.

Laszlo’s blunt answer to fear of failures:

If Laszlo Bock, the mind behind the revolutionized Google’s People Practices was concerned about the resistance to his approach of data rigor into HR, Google wouldn’t have been ranked among the best places to work. He did it with analytics, transparency, empathy, and of course, bypassing the failure overwhelm!

Every setback is a tool for learning and improvement, and you’ll find yourself growing stronger with every step.

Need to break failures down? Here’s the plan:

• Failures are not setbacks but learning opportunities. Divide them into smaller chunks and you’ll figure it all out.
• Plan it. Break your midlife career change into small progressive steps. Don’t dive into vast challenges all at once—accept one at a time.
• Talk to mentors. Absorb their invaluable insights that may help you. Let them know, you’re a beginner.
• Keep minimal expectations from yourself initially. Unreasonably high expectations lead to impatience and bad decisions.

7. How do I build confidence in a new field when I feel like a total beginner?

A beginner needs learning—learning builds confidence!

Starting as a beginner feels like I’m underconfident. But hey, that’s not permanent. With constant learning from online courses, attending workshops, reading blogs, and people who already know their stuff, self-doubt fades soon. Also, you may want to volunteer for small projects or part-time work to get your hands on some real-time experience. Also, don’t underestimate the power of a mentor. A person who’s already walked the path and earned some real-world experience can help you avoid petty mistakes.

Shed the beginner’s phase with these brainy actions:

• Accumulate knowledge with certifications, workshops, and experience by volunteering and freelancing.
• Build confidence by taking initiatives. New ideas bring uncertainty, overcoming which boosts confidence.
• Seeking mentors’ advice who have made the switch can give career path guidance and help you with exact methods that helped them.

John Tarnoff’s bold moves!

John Tarnoff had an established career that spanned 40 years in the entertainment industry. At 50, his tech startup failed at 50, prompting him to reassess his career.

He earned a master’s degree in spiritual psychology and made the switch into career counseling. Once he became a career coach, he helped age defying baby boomers reinvent their professional lives.

Tarnoff developed leadership training programs while serving as Head of Show Development at DreamWorks Animation.

8. What’s the biggest lesson I should remember when making the midlife career change?

Reinvention is rarely a quick fix. It’s a process.

The biggest lesson? It requires persistence and continuous learning to reinvent yourself. Figuring out everything, all at once, is not required—the key is to adjust your strategy accordingly and stay focused on growth, rather than perfection.

It’s not the mid-career switch but the impatience that makes the risk taker fumble. The best play? It’s to let the process get completed and allow it time.

Embrace the process with these smart plays:

• Don’t panic when clarity takes a backseat. Transitions feel chaotic before they feel aligned.
• What got you here won’t get you there. Recalibrate. Reframe. Repeat.
• Perfection is a trap. Progress is fuel. Pick the one that takes you forward.
• Power isn’t in speed—it’s in patience. Let the process play out before calling it a failure.

Katarina Berg – Spotify’s Long-Haul Reinventor

What was the transition?

Berg joined Spotify when it was a growing startup. While it scaled and exploded globally, she stayed there—reinventing both her role and the People’s function.

She founded Spotify’s “band manifesto” that helped teams identify themselves as bands, working for the best experiences, and staying in sync like music bands do. It helped the company build agile HR, flatten hierarchies, and experiment with people strategies.

What is the takeaway?

Reinvention takes more than just leaving. It needs to re-evolve in place, again and again until you hit the right notes like Spotify under Katarina Berg did.

9. What are the first practical steps I should take when I’m ready to make a midlife career change?

Drafting a clear roadmap for your transition starts with assessing your current state.

Try these high-impact actions:

• Map out a roadmap to fill any knowledge gaps. Enroll in relevant certifications, seek mentors’ knowledge, gain practical experience. Begin small. Take one course or attend one event.
• To navigate the complexities in a new field, assess your current state and the skills your next field needs. Bridge the gap.
• Once you’ve gained a bit of knowledge, start networking and talking to people in your desired field.
• Build a network in your new field.

Did you know how Jeff Bezos could build an empire ‘Amazon?’

When Bezos was 30, he had a lucrative Wall Street job at D.E. Shaw, but he saw the internet boom happening. Before making the mid-career switch, he made a risk list.

• He calculated whether he could handle regret
• Drove across the country to gain diverse perspectives and pick new ideas.
• Kick started Amazon out of a garage at age 31!
• Started with a narrow niche- books and eventually made calculated expansion rather than impulsion. The rest is history.

Want to know more about mid-career switch?

What things should I consider before a mid-career switch?

Wait and reflect. What’s that you need? Is it higher pay, growth, or satisfaction at your new job. List them down and plan strategically. Avoid impulsive decisions.

How can I be more confident while making the mid-life career switch?

Invest in activities like upskilling, building networks, and staying agile. Ensure you have the necessary skills like communication and that’ll help you achieve supremacy in your next role.

How can I handle the emotional roadblocks that might come my way during a midlife career change?

Doubts like imposter syndrome, and fear of failure are common, but can go away once you acknowledge them. Build resilience and surround yourself with a strong support network.

How to fight with uncertainty during the mid-career switch?

Keep your eyes on small wins. Career change takes time and till the time it’s natural to feel uncertain. Learn continuously and track your progress. It’s a slow process.

What biggest lesson should I keep in mind while making the midlife career change?

The biggest lesson is to accept that growth occurs after discomfort. Midlife-career change isn’t a quick process. It needs patience, resilience, and time. So, stay patient.