True Story: I Went From Self-Employed to 9-5. And I Love It!

This is one of many True Story interviews in which we talk to people who have experienced interesting/amazing/challenging things. This is the story of Freya, who left the corporate world, worked for herself and then joyfully returned to an office job.
Tell us a bit about yourself!
I’m a 27 year old whirlwind of Southern belle jet setter with a few dashes of circus and beatnik thrown in. I’ve been an avid reader and writer my entire life, and have always loved playing with words. By day I write, edit and work with words, and by night I’m a fire eater, burlesque dancer and teacher, and a yoga instructor. It keeps things very busy!

When did you originally become self-employed? And what lead to that decision?

In 2009, I was unsatisfied with my corporate job (long hours cooped up in a cubicle inside a warehouse), and itching for something new. Layoffs were happening left and right, and while my department hadn’t yet seen the cuts, I decided to try for something new. I’d been freelancing for several publications and was blogging regularly, so I did already have a base of clips and clients to start with.Can you tell us about a day-in-the-life when you were self-employed?
I’m more of an evening person, so I started my days around 9am, made a little breakfast and checked in on emails and any holdover work from the day before in my pajamas. Then, depending on the client needs, I went out to interview sources, had phone conferences about brochure copy, or, more likely, went to the local coffee shop (my freelance office) to hunt for new clients. I usually took a break around 4 p.m. to make dinner for me and my husband, Keith, spent a couple hours chatting, and then went back to work from about 7 p.m. until 10 p.m. or so. I teach classes five days out of the week as well, so somewhere in there, I’d be changing and leading a yoga workshop or shimmy class.

What did you like the best about working for yourself? What were the biggest challenges?
Having my own schedule was both of those! I could take an afternoon off to go to the park, or a museum, or just a long lunch, but being always available for clients and classes definitely takes a toll when you teach until 8:30pm, finish a brochure by 10pm, and then have a 6am class to teach.

Why did you decide to go back to the 9-5?
Economically, it was becoming more and more difficult to find clients. They would come for a new brochure/website/etc and that’s pretty much what they needed written for the entire year. So much of my work was hunting down new clients, and hunting down payment. I also grew very tired of running multiple businesses, as I had my copywriting business, yoga, and burlesque all to balance financially and time-wise.

So when one of my former students mentioned an opening for a full time writer at her company, I was wary, but interested. Did I really want to go back to working for someone else, on their time frame and their project schedule? I actually went on a couple of interviews with different companies and one was so bad I literally ran away from the building! But this company felt good, like a place I could grow into while keeping only one of my businesses, instead of running three.

Can you tell us about the job that you’re doing now?

I’m an internal writer for a mental health non profit. I re-purpose press releases and newswires, interview staff and clients for stories, write articles on the mental health industry, and basically keep staff up to date on all company and state happenings. With many of the therapists based remotely and spread through two states, I’m the hub to keep everyone in the loop.

When you started interviewing, how did employers react to your self-employment?
Online applications are the devil for the self employed! The “previous employer” section was always troubling, but often I’d just list my most often worked with clients. Having a good portfolio is key when interviewing, and having a standout cover letter with links to your work is better. In interviews, it was a little different to talk about “how do you take direction” or “work with supervisors,” but so much of freelancing is project management, and challenging clients can be great interview stories of your deft abilities.

Have you ever reconsidered your decision? Do you think you’ll continue to work 9-5 for the long term?
I very carefully considered this, and right now, I couldn’t be happier with the position and place I’m at. I’m in a gorgeous spot in the city, overlooking a park I go to almost every day for lunch, and my employer offers a generous time off plan, which is really important to me. I love to travel, so having the flexibility to do so was a big consideration.

As of right now, I plan on being here for a few years. I’m still working in the same field, so if I ever decided to go back to freelance, I still have clips and project managing years to add to it, and the community of an office is really welcome after only having my cats as coworkers the past few years!

I do miss the variety of blogging for a small printing company one day and writing scripts for a hospital television network the next, but I don’t miss the gaps in work, or the “it rains it pours” of too much client work at once.

What advice would you give to others who are interested in returning to the workplace?

Write down what you want. The job market is tough right now, so don’t get discouraged by the silence but also don’t settle. The self employed life is wonderful, so find out what’s worth it to you to give up your time and freedom of space. That might be, like me, a lot of paid time off, or frequent travel with your job. Or you might just want health insurance (a big plus!) and the camaraderie of working in a team. Good luck out there!

Have any of you made the switch from self-employed to office job?  Would you want to?

Welcome to Yes & Yes!

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

You might also like…

3 Pieces Of Mentor Wisdom + Their Unlikely Sources

3 Pieces Of Mentor Wisdom + Their Unlikely Sources

This post is brought to you by career-improving wisdom, accidental mentors the world over, the letter F, and the Forté Foundation. What do you picture when you picture a mentor? For a long time, I pictured someone a couple of decades into their career, beckoning me to...

read more
True Story: I Did Teach For America

True Story: I Did Teach For America

What's it like to do Teach For America? Would you ever want to become a classroom teacher in a low-income area ... after five weeks of training? That's exactly what Samantha did! This is her story. Tell us a bit about yourself!  My name is Samantha. I'm from Michigan,...

read more
True Story: I Reinvented Myself at 50

True Story: I Reinvented Myself at 50

What does it mean to reinvent yourself and your life at 50? I know sooooo many people who feel trapped in their lives or career and they're not even 35! I LOVED this interview Judy and I think you will, too. Tell us a bit about yourself! Hi! I'm originally a New...

read more


  1. Melissa Wellham

    You read so many posts from the perspective of someone leaving the 9-5 for self-employment, so it's really interesting to see it from another perspective! Thanks, Sarah and Freya!

    Melissa @ Melicious

  2. Corrine/Frock And Roll

    Melissa took the words right out of my mouth. This was an EXCELLENT read! Thanks for sharing, lovely ladies?

  3. Sarah Rooftops

    I used to freelance, but my heart wasn't really in it and I missed the security of a guaranteed pay cheque – I went back to employment and didn't regret it. Now, I'm thinking about going back the other way…

    It's nice to read something from this perspective, though; both options have their good points but I usually only see one being sold on blogs.

  4. Kim

    Very interesting article!

    As someone who's been self employed for just over a year, I always wonder what I'd do if the perfect job landed in my lap.

    Financially I don't think that any type of employment is safe right now, what with the economy still the way it is, but there are still interesting challenges & opportunities in full time employment!

  5. Sian

    Thank you for this! Like others have said, there are so many articles out there about the benefits of leaving your job and going self-employed so it's nice to see things from a different perspective.

    I'm not self-employed but I do work from home and it definitely has both advantages and disadvantages.

  6. Freya

    Thanks ladies! So glad you enjoyed the article. I wanted to share the other side of the coin 🙂

  7. Bernie

    This was an encouraging read.
    After being self-employed in the education field for 13 years, I'm not only going back to regular employment, but switching careers to boot! I'm starting work next month as a mechanic, but will alternate between that and working as an information designer for the company brochures. This works perfect for me, as I still get to use computers, which I love doing, and working outside, without having to talk to anyone! (Which I also love doing!).

    Giving up the freedom to travel home to the UK whenever I want (I live in Japan), is going to be hard, but being able to pay my bills on time, and provide for my family, will be worth it.

    Like the writer of this article, I just got disheartened with the whole working-for-myself thing as clients no longer bring a great deal of requests to the table any more. Plus the market is getting highly competitive and being undercut is growing into a regular phenomenon. It's just not worth it.

    As someone else said – if your heart's not in it, there's just no point. I had it all – my own great office, a great set of clients and my own hours. (I'm definitely not a morning person, which will have to change). But, my heart just wasn't in it. Clients can have a serious attitude problem if they don't get what they want in terms of money, service, goods, etc…and I just grew sick of dealing with that.
    And I'll still have my side business of making websites and flipping them, in my spare time.
    Looking forward to my new JOB! 🙂

  8. Anonymous

    I just recently went back to a corporate salon from booth rental/self employed salon. At first i felt like a huge failure, but the idea of benefits, steady paychecks and the ability to budget my time and money was so worth it. I'm only a week back into my scheduled salon and it took me just until yesterday to adjust. I'm still competitive, but not in a way that says "I need to see 20 new clients this week or not pay rent."

    Thanks for writing this.

  9. Jen

    I only just saw this, but yay – it's almost always in the reverse, I'm so glad to see this! The steady paycheck and paid sick/vacation days are a dream. My job is a DAY job, but I have the resources to both take care of myself and I can make what I like to without worrying about volume or price points or marketability or anything. There's no pressure to conform, or to make lots of something because it sells well or that's what the client wants. It's the freedom to say no!

  10. Anonymous

    I am starting back in full-time employment next week after being self-employed for the past year and this is a really refreshing read! Like others above, my heart wasn't really in the self-employed work and while I'm a bit aprehensive about slotting back into the 9-5 I am looking forward to it. Great to hear that it has worked out for others too!

Pin It on Pinterest