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Starting over

Lucy Caldicott
Lucy Caldicott
4 min read

The idea of starting over later in life can feel overwhelming.

Throughout my career, I've navigated major transitions, some through choice, others not so much. I started out in corporate marketing in financial services, moving to fundraising and leadership roles in the charity sector to local politics and now running my own consultancy. Each shift brought uncertainty and self-doubt. Each time, I worried whether I was making a terrible mistake and, in some cases, I probably was!

Some years ago I was in a stable role that paid well, with many highlights, working alongside a fantastic team, doing worthwhile work. But I constantly felt like I should be doing something else. When I'd been there for five years, I thought maybe I should try to move on. I applied for different roles and while I did well at interview, I didn't get the jobs. "Appointable number two" is a phrase I never want to hear from a recruiter ever again. My confidence was through the floor and I didn't know where to turn. Eventually I decided to take a bit of time out.

Alongside uncertainty and disappointment, career change also involves a significant identity shift. For years, you might have identified strongly with your job title or organisation. Changing careers means letting go of that established professional identity, which can be hard to do. But it was letting go of that stable job that allowed me the freedom to set out on the path that led to what I'm doing now.

I was reading up on people who changed career later in life and one who really stuck out was Maya Angelou, who is remembered as a legendary poet, memoirist, and activist. But her path to literary fame was far from direct. Before publishing her first famous book, she lived many lives: dancer, singer, actor, streetcar conductor, cook, journalist, and civil rights worker.

Her breakthrough came at age 41, when I Know Why the Caged Bird Sings was published. Its success launched her into literary history. From there she evolved again, becoming a celebrated professor, a voice of social justice, and one of the most quotable thinkers of the 20th century.

I love this quote from her:

We delight in the beauty of the butterfly, but rarely admit the changes it has gone through to achieve that beauty.

Research consistently shows that mid-career crisis is a very real phenomenon, yet it can be hard to discuss these feelings in professional settings. We're expected to project confidence and certainty at all times, especially online, so I wanted to be honest about some of my own down times.

2025 has been a year of big change for me. I started it with no idea what I'd be doing by the end of it and I was pretty low. I spent a lot of time trying to dig myself out of a gloom and thinking about what next which has led me to here. I've reinvigorated ChangeOut and am now 100% focused on working with charities and individual charity leaders. As part of this I've started the Henley Business School professional coaching course to back up my own career-based learning and broaden/deepen my offering to teams and individuals. And I've also started creating more video content which I'm really enjoying. Here's my video about career change in midlife.

I've worked with some great organisations during this year and it looks like most of them already want to work with me again next year. I've got some new projects on the horizon and I'm really excited about 2026.

Useful links 🔗

Pay and Equalities Survey 2025
ACEVO’s annual Pay and Equalities Survey is the most comprehensive breakdown of the sector’s CEO remuneration packages available.

Day of the Week 📆

Snoopy is 75

Such a huge part of my childhood. Happy birthday, Snoopy.

What am I reading? 📚

My life has no purpose, no direction, no aim, no meaning, and yet I'm happy. I can't figure it out.

Snoopy

What am I watching? 👀

Oh my goodness, Emma Thompson is tremendous in Down Cemetery Road!

What am I listening to?👂

Excellent interview with Pussy Riot's Masha Aloykhina on challenging Putin's regime and fighting for freedom of expression.

Joy-giving things 😍

I spent more time than was sensible trying to find rescue bears Benji and Balu on their bear cam. Maybe you'll have more luck!

Have a great weekend

Lucy


If it’s your first time reading this newsletter, find out more about me here.

I write this newsletter because I believe in sharing ideas that help us work towards a truly equal world, particularly in the workplace.

Share it with your friends so they can read it too 📣


ChangeOut is created by Lucy Caldicott. You can find more about my work at ChangeOut.org. If you’re looking to have a chat about culture, leadership, purpose, equity, or a facilitated team discussion about any of those things, get in touch. You can also find me on Bluesky, Instagram, and LinkedIn.

🎺🎺🎺 YouTube 🎺🎺🎺

If you like what you read and you'd like to show your appreciation in cash, you can do that here. I'd be very grateful!

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