How my job-hopping years prepared me for self-employment

by | Aug 23, 2017 | Freelance Business & Finance

job-hoppingThis week we’ve got a guest post from the lovely Michelle Abrahall, a member of the Freelance Lifestylers group and a graphic designer, illustrator and copywriter. I loved the idea of this post she suggested, as I know quite a few freelancers have a history of job-hopping a little before settling into freelancing (myself included). 

You can also check out Michelle’s charming illustrated gifts in her Etsy shop. 

Here’s her guest post! 


job-hopping

Like many freelancers, my path to self-employment was far from smooth sailing. After leaving Uni with a degree in Illustration, I had a ‘what now’ moment that I’m sure every graduate can relate to. Caught in the Catch-22 of not having enough work experience to apply for jobs, and not being able to get a foot in the door to gain said experience, there followed a decade of job hopping that would have put Kermit to shame.

During the Decade of No Direction I did all sorts to pay the mortgage for minimum wage: split shifts at a gym that meant finishing at 10.30pm and going back in for 6am the next day, working in a card shop in a new shopping court that was as quiet as a graveyard, and being stuck in a Groundhog Day-esque loop of tidying a perfectly tidy stationery cupboard in an office full of old men.

At the time, if you’d offered the wisdom that ‘all experience is good experience’ you probably would have got a Grade 5 Paddington Hard Stare for your trouble. When you’re in job hopping hell, you don’t want to hear such platitudes. You just want a job that actually uses your skills (thank goodness for freelancing!).

But, lo and behold, looking back on my job-hopping years I can see that they did have value and have even contributed to my self-employed success.

Validation of Ambition

Many times during those uninspiring years, I wished I was the kind of person that would be happy just doing a job to pay the bills. But I wasn’t, and as a friend of mine says, sometimes dissatisfaction is the price of ambition. All that time spent not doing what I really wanted just reinforced the idea that there was a better job out there for me, even if I had to create it myself.

Customer Service

It doesn’t matter what area of business you freelance in, ultimately you are working for a customer. My various retail and hospitality positions gave me an excellent grounding in customer service, and an ability to talk to just about anyone. Dealing with both happy and disgruntled customers taught me that friendliness and politeness goes a long way, but also that some people just can’t be reasoned with!

Office Life

Administrative roles were fantastic work experience for me: even simple things like knowing how to compose an email, use a spreadsheet, update a website, and plan an event are all invaluable when you’re self-employed. Helping to run a business day to day taught me so much about how to run my own, so even though giving up a salary felt like taking the plunge, I wasn’t in completely unchartered waters.

It’s been great to look back and put a positive spin on those job-hopping years, and to feel like perhaps they weren’t the waste of time I always thought they were. Who knows if I’ll ever go back to ‘traditional employment’, but I know that if I do, I’ll have plenty of experience to fall back on!


All about Emma Cossey

I’m a long-term freelancer, mum and all round digital geek, and I’m happy to welcome you to The Freelance Lifestyle. I launched this blog in 2011, to provide freelancers with down-to-earth support, and practical advice. I wanted it to be a kind, supportive place to get tips and advice on living a great freelance life. I’ve been a pro blogger, a social media consultant, a copywriter, a teacher… but my passion is helping people just like you take the next step. So whether you want to pick up tips from the blog, listen in to the podcast, come join the Facebook group or get some more focused 1-2-1 support with my coaching, there’s something here for you.

You can find out more about Everything I do here

job-hopping

Summer Break: What Do You Want to Hear Next?

I’m taking a short summer break from the podcast while I rethink what’s next. Here’s why I’m pressing pause and how you can help shape future episodes.

job-hopping

My iPhone Podcast Recording Hack

Discover a simple iPhone podcasting hack that improves audio quality and creates transcripts using the built-in Voice Memos app on iPhone 16 and later.

job-hopping

Underpromise, Overdeliver: My Secret to Business Success

Discover why underpromising and overdelivering is one of the best habits freelancers can adopt for happier clients, less stress and stronger relationships.

job-hopping

How Much Should You Charge As A Freelancer?

Wondering how much to charge as a freelancer? Explore trusted resources for researching freelance rates, comparing prices and setting sustainable fees.

job-hopping

Freelance Realities: Not Just the Glossy Highlights

Freelancing isn’t always easy. Discover why quieter months are normal, how to build a more resilient business, and why you’re not alone if work feels harder right now.

job-hopping

Discovery Call Scams: What Freelancers Need to Watch Out For

Discovery call scams are becoming more common. Discover the warning signs, simple checks to make, and how freelancers can protect themselves.

job-hopping

Tax-Free Childcare & Summer Holiday Survival Tips for Freelancers

Tax-free childcare can make a real difference for self-employed parents. Discover practical tips for managing childcare, holiday clubs and summer work schedules.

job-hopping

How to Respond to Free Work Requests (Without Feeling Awkward)

Learn how to respond to free work requests without feeling awkward. Discover when to say no, when unpaid work might be worthwhile, and how to protect your time and value as a freelancer.

job-hopping

Tiny Ways to Outsource (Without Feeling Overwhelmed)

Learn how to start outsourcing in your business without feeling overwhelmed. Discover small, practical tasks you can delegate, from email and social media to bookkeeping and scheduling, to save time, reduce stress, and build consistency.

job-hopping

3 Ways I’m Finding New Clients in May 2026

Looking for new freelance clients? Discover 3 simple ways I’m finding more clients this May using AI SEO, Google Business updates, and LinkedIn.

Want to know more about how I can help?

See everything I offer and sign up to my newsletter for more advice and recommendations on running your freelance business!

Show me more!