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How To Start Again After 50 With A Career Strategist

Caterina Perry on the secrets to overcoming self-doubt, unlocking new possibilities, and confidently navigating career changes at any stage of life.

The world’s oldest man just died.* John Tinniswood was 112 and lived in England. He was married for 44 years, experienced two world wars and retired at 60. That left him with 52 years to do what he wanted. His advice? “Always do the best you can, whether you’re learning something or whether you’re teaching someone.”

I love a good story about accomplishment. And when I say ‘accomplishment’, I don’t mean wealth. I mean following your dreams, creating the life you want, being able to live authentically and with the purpose and path that you know in your heart you were meant to follow.

When I found myself leaving my loved-job after over a decade, I left intentionally. My heart knew a shift in my life was coming and I closed my eyes and dived in headfirst.

I floundered.

I was scared I’d made the wrong decision.

Scared that I’d given up stability for something unknown.

And along came Caterina Perry, a career strategist who appeared in my life like manna from heaven. She knew exactly how to help me navigate this transition from a long term employee to job seeker. But what she helped with was more than just finding the next job - she helped me find my purpose.

We dug deep into all of the skills that had driven my success, and repackaged them into what my future could be based on what I wanted. While that may include another stint at a full time job, it also includes creating something on my own.

She helped me create a showcase portfolio - a brag book - to remind myself of all of the skills I have that can propel my future self into something truly special.

Leaving a long term job is a bit like leaving the military (Caterina has a ton of experience with this!) and it can be hard to readjust to ‘civilian’ life.

So I was thrilled to interview her for The Founder Mindset.

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Here are some of the highlights of our talk.

  • Mindset Matters More Than Technical Skills
    Caterina emphasized that overcoming mental barriers is often more important than technical expertise. She said, "What’s holding somebody back is not the technical skills. It’s actually the mindset." For women looking to change careers, cultivating a mindset of possibility can unlock new opportunities.

  • The Power of Personal Narrative
    Caterina introduced the idea of a "showcase portfolio" to help clients present themselves more effectively. She explained, "It tells a story more strategically than a resume can... it combines a resume and an interview rolled up into one." This portfolio allows women to showcase their achievements and tell a more complete story to potential employers.

  • Embrace Change and Failure as Growth Opportunities
    Caterina stressed the importance of reframing failure as a chance to grow. She shared, “Failure is not something that we should be afraid of. It should be something that we embrace, because without failure there is no growth.” Women can embrace challenges, knowing that each setback is a stepping stone to success.

  • Reframe Age and Career Gaps as Strengths
    Caterina spoke to the value of experience, even when facing barriers like age or career gaps. She noted, "You just need to reposition that narrative so that an employer understands... somebody who's accomplished at a certain age has... already mastered many of the emotional and social intelligence skills." She encourages women to see their years of experience as assets that make them more resilient and adaptable.

  • The Importance of Confidence and Self-Belief
    Confidence is a key ingredient in success, according to Caterina. She said, "Your success rate for getting through tough times is 100%, because you're still here." Believing in yourself, especially after setbacks, is essential to moving forward and achieving your career goals.

Caterina’s Book Pick:

Psycho-Cybernetics by Maxwell Maltz

Caterina Perry is a seasoned Career Strategist and the founder of Your Success Unlimited. (book a coffee chat with her!) With over 20 years of leadership experience, her mission is to help women navigate career transitions with both practical strategies and empowering mindset shifts. As the author of Now That the Candy’s Gone, she speaks on topics that help women overcome limiting beliefs and advance confidently in their careers, whether it’s landing a promotion or transitioning to entrepreneurship. She’s now on Substack with Career Edge

*The Guardian: World’s Oldest Man, John Tinniswood Dies Aged 112

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Salty Divas
The Founder Mindset
The Founder Mindset explores stories and tips from people who are creating purposeful lives - how they got there and why they do what they do. There may be tips and strategies - there will always be inspiration from creators, visionaries, community builders and leaders - true founders who don't let age stop them from moving the needle in their own lives.
Authors
Michelle Laurie Smith