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True Story: I’ve Had 35+ Jobs (And I’m only 35 years old)

Have you had lots of jobs? If you have, you're not alone. Click through for career tips and work advice from someone who finally found a career she loves after trying 35+ jobs!

Tell us a bit about yourself!

Hello! I’m Claire and I’m 35 years old. I’m originally from London, England, but moved to Vancouver, Canada five years ago.

I’m trained as a life coach, and am currently setting up my business as an accountability coach (supporting and cheering people on via email with their projects: setting up a business or side hustle, achieving personal goals, writing a book, etc…) For fun I like to travel, swim and run. I’m also obsessed with stationery!  

Could you give us a bullet point summary of 15 of your 35+ jobs?

I’d be happy to!

  1. Assistant at pottery workshop
  2. Cashier at grocery store chain
  3. Delivering IKEA catalogues
  4. Working in a jam factory
  5. Communications Assistant, ELLE HQ, Paris
  6. Editor at Bloomsbury Publishing (publishers of Harry Potter)
  7. Parliamentary and Events Officer, UK Disability Rights Commission
  8. PA to Director at UK Charity Commission
  9. Fundraising team at National Deaf Children’s Society
  10. Events Planner at law firm
  11. Events Manager planning fundraising gala at Big Sisters, BC
  12. Event Assistant at interior design exhibition
  13. “Extra” (background actor): The Flash, Arrow, Supergirl, The 100, Okja movie and others
  14. Admin Assistant for wedding planner
  15. Usher at local theatre

Growing up, how did you think about your career? 

When I was little, I wanted to own a candy store (so I could eat the candy), or be a newsreader (I thought someone else wrote the news for them!).

When I was about 10, we had to give a talk in class about what job we wanted to do when we grew up. I remember feeling panicked – I had no idea. In the end, I said I wanted to be a lawyer, just to have something to talk about!  

My parents have very structured, “standard” jobs: my mum’s a teacher and my dad’s a realtor. They’ve had the same jobs their whole life… they find my career path very unusual!

My mum loves her job; it’s a real vocation. She couldn’t help with my career dilemma, as she always knew she wanted to be a teacher. My dad’s job is stressful at times, but there’s no way he could work for anyone else – he’s a born entrepreneur (and I’m now heading down the same route!)

When you entered University what did you major in? What did you say when career counselors asked you about your plans? 

I studied French and Russian at university. I love speaking and learning languages, so it was an easy decision. I don’t remember talking to a career counsellor at university… back then you were expected to figure it out on your own! There was a careers centre, but I remember just feeling overwhelmed in it.

The problem was that languages didn’t narrow down my choices – they opened them up. I knew I didn’t want to be an interpreter, translator, or teacher… but that left many other options! Languages are useful in so many industries that I felt lost and confused when I graduated.

What did your professional life look like after college?

It can best be described as “bouncing around”! I love reading, so I thought publishing might be my thing. I worked for two publishing companies, but never felt like I “fit”. I volunteer regularly and wanted to do work that made a difference, so I thought working at a not-for-profit might be my thing. I contracted for a few charities, but became ground down by the lack of money and resources available.

A friend put me forward for a job at her boyfriend’s law firm working as an events planner – and I loved it! I gained tons of confidence, which enabled me to take the leap to move abroad (a long-time dream of mine). There I worked in a few more roles before deciding to tackle the issue once and for all… until I finally found my purpose 🙂  

How did the people in your life react to your career path? 

My friends were supportive, but couldn’t understand my situation. I remember feeling embarrassed by my career path/choices. Why did I keep leaving jobs? Why couldn’t I stick in one job? What was wrong with me?! My friends knew what they wanted to do and had steady jobs.

Some of them have worked for one company their whole life. My family despaired of me! My uncle tried to get me a job in a financial institution (my fear). My parents didn’t know what to do with me. I felt confused, alone, and like a failure.

The thing I’ve learned now is that I’m not necessarily flighty, but I need variety, flexibility and independence – I get very down without it.

[Funnily enough, many of my peers are now having a career crisis, but feel trapped or unable to leave as they’ve been in their jobs for so long!]

Have you ever taken one of those career predictor tests or worked with a career counselor?

I’ve taken many career predictor tests, but didn’t find them that helpful. I saw a great career counsellor a few years ago (who suggested life coaching to me).

Personality tests were also helpful, especially Myers-Briggs. It says that my type may have many jobs and seem directionless, because we need to live in line with our values. Hearing that gave me hope, and made me feel like I wasn’t a failure!

What does your professional life look like now? Do you think you’ll still be doing this in 5-10 years?

I currently work two part-time jobs while I set up my business. I love the flexibility this brings. With my business, I can’t believe I get paid to do something that feels natural and brings me so much joy.

It’s really cool to see my clients make progress on their goals and dreams – I just had a client who sold her first place at her retreat, which was awesome. I certainly hope I’ll still be doing this in 5 or 10 years! (without the part-time jobs 🙂

I’m striving to create a work environment that complements my dream lifestyle – the ability to travel and work when I want, on what I want, doing work that helps people and moves them forward.   

What tools/resources/books/websites helped you navigate all this?

Live Your Legend was my main resource (their TED talk, blog, and courses). It was key to me figuring out my passion/purpose. I’m so grateful for their work. I read What Colour is Your Parachute and How to Find Fulfilling Work – which helped to explain why I kept moving from job to job.

And I did a lot of self-reflection. I like to question things, so I would ask myself: what did I enjoy about this job? What is my ideal job environment? I kept asking questions and taking notes on what made me happy or what were my deal-breakers.


What’s one thing you’ve learned from this that ANY of us could apply to our lives, regardless of our employment status? 

It’s okay to be you, and be individual. So what if you’re different? You will find your tribe/thing, and it doesn’t matter how long it takes. For some people, it might be clear from the outset. For others, it takes more time. This is totally fine!

Also, don’t worry about the people who seem to have it all figured out. They have their own struggles to work through – or they might hit their own block at some point in the future. Be you. Be curious! Be proud of your skills and strengths, and know that there is a career (or partner, etc.) somewhere that needs what you offer.

Thanks so much for sharing your story, Claire! Can any of you empathize? Do you have any questions for Claire? 

P.S. Are you required to find  + follow your calling? 

Welcome to Yes & Yes!

Want to spend your time, money, and energy on purpose? I'll show you how.

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