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? 

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15 Comments

  1. Charmaine Ng | Architecture & Lifestyle Blog

    I think Claire seems to be in a great place now! No doubt the many jobs she’s had have given her tons of experience in different fields. I, too, did not figure out my path until later on in the game and actually switched careers from an architect to a writer. It’s fine to take your time to figure things out. 🙂

    Charmaine Ng | Architecture & Lifestyle Blog
    http://charmainenyw.com

    Reply
    • Claire

      Thanks Charmaine for your lovely message! You’re right that I do feel in a much better place. I haven’t got it all figured out – but I’m definitely moving forward in the right direction. I do feel that I got a lot of (good) experience from all the jobs I did. I love that you switched careers – I’m a big believer that it’s not too late, and we can always change course, no matter how challenging it might seem (to ourselves, or others!) Well done on your transition, and all the best with your writing – your blog is fab! Claire

      Reply
  2. Anonymous

    I can so relate to Claire, especially in the past five years since graduating from college. I got a degree in anthropology and linguistics, which I loooooved studying, but neither of those topics led to a clear cut career path. Since graduating I’ve worked in multiple restaurants, worked as a transcriber for deaf and hard of hearing students, worked in sales for a bike touring company, worked at a non-profit, taught yoga, and worked in production for a commercial film company. And just last week, I started school for massage therapy! While I’ve felt a little aimless at times, and I see many of my peers working their way up the ladder in their careers, I honestly wouldn’t change anything about what I’ve done. I think the variety of experiences has been really good for my personal growth, and I know that I’ll never settle for a job that doesn’t leave me feeling personally fulfilled.

    Reply
    • Claire

      Hello Anonymous and YES, I totally hear you on the degree! Some degrees lead to a career, and some you just do for the love of it (and there’s nothing wrong with that). Haha – I have to say that when I read your list of jobs, I thought “Oh that all sounds really fun!” Some people just aren’t meant to work in one job their whole life. Good luck with massage school! To be honest, a lot of people climb the career ladder in order to earn enough to take time off and enjoy life/live the life they want… but if we can do that WHILE we’re working, why not?! Good for you – sounds like you have a great attitude towards your career path and experiences, and I love your wish to keep doing work that makes you feel personally fulfilled. Best of luck with your next career(s)/whatever comes next! 🙂

      Reply
  3. K

    Hi Claire, I’m curious what training program you selected for life coaching? I’m interested in it myself, but I’ve been having a hard time sorting through which schools are really worth the money. I would love to hear about your experience and if you’ve decided to pursue the ICF certification or not. Thanks!

    Reply
    • Claire

      Hi K, of course, happy to help… I went through Erickson College in Vancouver. I knew I wanted to attend a course in-person rather than online, and Erickson was recommended to me. I looked at the other options in Vancouver and Erickson seemed like a good fit. It can be tough to find a school – but don’t lose too much sleep over it. The big schools generally provide very similar things. I actually wrote an article here about getting into life coaching , which I hope helps: https://www.thefivepercent.net/blog/so-you-want-to-be-a-life-coach. For now I’ve decided not to pursue the ICF certification (for many reasons – ping me an email through my website if you’d like more info!), but I’m open to it in the future. Good luck on your journey! 🙂

      Reply
  4. Britt

    Hi Claire! I’m curious what your MBTI is! I’m guessing that you are something along the lines of an INFP?

    Reply
    • Claire

      Hi Britt, yes pretty darn close! I’m ENFP 🙂

      Reply
  5. Kamina

    Claire – I too used to despair of the fact that I couldn’t stay in one job or stick to a career path. I had so many options and interests that I couldn’t commit to building my skills in one area, and ended up feeling like a failure who couldn’t hold down normal employment even though I was supposedly talented and smart. It really messed with my head.

    About a year ago I was expressing my determination to get serious about my career when my husband said something that really changed the way I view myself. He said, you’re not a person who’s designed to have a traditional career. You’re always improving and changing. Why don’t you just stop trying to do one thing and embrace the fact that you’re always going to be trying different things? Why don’t you let yourself be multi-talented or multi-disciplinary?

    That was SO INCREDIBLY FREEING! Since I made ‘evolve’ my word for 2017 and stopped trying to have a career, my career has taken off! I stopped working for an employer and now support myself full-time through a mixture of random pursuits. I’m currently freelancing as a website copywriter, ghostwriting a book, and running a blog/consulting business that helps people transition to plant-based eating, through which I just launched an ebook about vegan meal planning and nutrition basics. (Note: I have no qualifications and very little formal experience in any of these areas.) I’m also writing songs and exploring how to record an album. A year ago I wouldn’t have ‘allowed’ myself to follow any of those curiosities because I would have felt like I was getting distracted from whatever my career focus was supposed to be. So I totally relate! And I’m really encouraged to read the story of a fellow sufferer of career ADD. Let’s embrace it and make it our strength!

    Reply
    • Claire

      Hi Kamina, thanks for your comment, which I loved reading. Yes – I always felt like I had SO many options and interests! (And yes again – it’s nothing to do with being smart.) I LOVE what your husband said to you! What great, caring advice. I love the idea of letting ourselves be multi-talented or multi-disciplinary. Evolve is an awesome word for the year – so freeing and beautiful! And yes, so funny how things come to you when you stop looking for them.

      Congrats on supporting yourself full-time – that’s fantastic. The work you’re doing sounds awesome – amazing what transpires when you just let it happen, hey! Most people disagree with me, but I don’t think qualifications are the be-all and end-all – and as you can testify, you don’t need to let things like that hold you back if you don’t want to. I can only imagine what an inspiration you are to people around you… (“no you don’t need a qualification necessarily… yes you CAN do many different jobs… yes it’s okay to embrace the unusual…!”)

      Haha career ADD – that totally sums it up 🙂 Thanks for sharing your story and making me realize that I’m not alone out there! I 100% agree with embracing it – it IS a strength! Good luck with the rest of your journey – it sounds like your acceptance is really moving you forward onto exciting (well-fitting) jobs/experiences. Here’s to being okay with our career-nomad leanings! 🙂

      Reply
  6. C

    This is a great post! I relate to it a lot although my situation is a bit more complicated. My question to Claire is how did you promote yourself in the different jobs to get hired?
    I find that jobs usually want you to have experience relating to the position, and so I find it challenging to market myself when I’m bouncing around the different industries. Do you have different tailored resumes and/or highlight your soft skills? Or are most of your jobs through connections/networking that hire because they already know you beforehand?

    I hope my question makes sense.. haha

    Reply
    • Claire

      Hi C, thanks for your comment! That’s a great question (and yes – made total sense). I had the same concern when I’d started my “career shuffle” and I thought it was making me un-hireable. A wise friend said to me “You can sell anything if you try hard enough”. As in: use whatever your experiences are, and SELL them to the max. E.g. say you’ve been travelling for 6 months – that’s a perfect way to show how great your financial planning is (living on and being in control of a tight budget), your organizational skills (planning trips to three countries in four days…), or adaptability and getting on with people (being asked to stay longer in a volunteer role, making long-lasting connections with people from all around the world, etc…) And then have good, specific examples for all the skills that you want to demonstrate. Fit the skills the job wants, to the skills you’ve picked up along the way.

      I do agree that jobs usually want you to have experience relating to the position, so as well as the above (selling the sh*t out of my experiences!) I would quite often volunteer, help out at a one-day event, or take a course relating to what I wanted to go into. Anything to put that particular field or industry at the top of your resume – i.e. to show that it’s the direction you’re heading in/the most important thing to you. (Even better if you can find a way to pepper it throughout your resume and in your short summary at the top.)

      And then in interviews (and in my cover letter), I’d make sure I stressed that I’d had different jobs as I wanted to get a flavour of different industries/wasn’t sure what I wanted to do etc, but now I was ready to settle down and really apply myself into one role and grow within a company. It may not be the absolute truth all the time – but people also apply for jobs when they are pregnant/wanting to start a family, or planning to go travelling in a year. You can still provide great service to a company for a year or two and then move on if necessary. People leave jobs; it’s just the way it is.

      I always use a different/tailored resume for each role or industry, for sure. It doesn’t have to be a complete overhaul – just tweaks here and there. And yes, I highlighted my soft skills too! I think soft skills can be as important to an employer as hard skills (e.g. someone who can walk into a team and get on with everyone? Someone who understands what they need to do straight away and runs with it?) Working in different roles means you’re likely flexible, get on with people, can give examples of how other companies do things, and can adapt to many different situations – and those skills are not to be sniffed at! I didn’t get many of my jobs through connections. I hope that helps… that was quite a long answer! 🙂

      I’m curious to know about your situation! What are you looking to get into, or are you not sure yet? Best of luck anyway – and feel free to reach out if you have any more questions!

      Reply
  7. Calluna

    I’m a little bit late, but basically: Yay, I’m not the only one! I had about 40 jobs prior to my mid 30s before I settled down into one. I don’t know anyone else like this; it really made a lot of people upset with me. My husband was very sweet, but even he put the kobosh on more schooling for a while after I’d gotten a BS and two vocational certifications. (Also so fun – I made the money back in the jobs afterwards…)

    I had so many jobs more because I would bore quickly after I learned enough of my job to get good at it, and loved the thrill of getting a shiny new job with a shiny new set of skills to learn. I like things to be *hard.* I often had 2-3 jobs at a time, and gigs. But back then, “gig economy” was not a thing and it was not as acceptable to switch jobs, so I had to quit when I reached the point that temp agencies told me I didn’t have a steady enough job history to temp. (HA) I usually stayed at a job for 3 mos-3 years until I learned everything, but no matter to them.

    In the end, I learned that (for me) money to live by is easy but security is hard. Now I’ve been in the same job for over ten years, incredibly. The organization is large enough that when I get bored of one job, I can ask the bosses to move me to another section or division so I can do something else, and the tasks where I work are difficult enough that I can stick in each position for longer. It’s been pretty perfect, and my supervisors have been so understanding and kind.

    It’s starting to get a little bit stale, but this is one of the few places left on Earth it seems that still offers a pension, and *oh I want that so much.* Just imagine all the “job hopping” I can do risk-free after I retire early with a pension? For now, I’m hoping I can keep it interesting long enough to hang on until I get into management, which will open up a whole new level of skills to learn and sustain me for even more years.

    Reply
  8. Ralf

    Hi Claire, I came across your post from a search as I have had too many jobs.
    I am an ENTP and 34 and have two university degrees (one was too boring;)). I have loved all my jobs, but I would like to stop changing jobs and create a solid, well-payed career. Any advice how to become just a “good & well respected broad-knowledge leader” in a field? I have realized the job needs to be varied and broad to keep me engaged…

    Thank you

    Reply
  9. Ericka B.

    Oh my goodness. This article is a lifesaver. So good to know there are others out there like me 🙂

    Reply

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