When to Quit Your Day Job

Today I’m running a guest post from Juliana Weiss-Roessler, who quit her day job pursue her dream of writing full-time and making her own hours. Take it away, Juliana!

When to Quit Your Day Job

When to Quit Your Day Job

When I embarked on my freelance career, I was bored during my day job. I had a lot of down time on my hands (seriously, a lot of down time), and I thought, why not try to do something productive with it?

But within a few months, I noticed that I was sometimes earning more with the handful of writing jobs I took on than I was in my full-time position. What’s more: I found the work more enjoyable. I loved the fact that I could jump around to different projects, learning about new things and switching it up if I needed a break from a particular topic for a while.

Still, I wasn’t willing to let go of that regular paycheck. Not yet. The idea of letting go of a “real” job at a time when the economy was struggling made me nervous. I had enough regular clients that I would likely have some income, but I would have to rely on getting new clients and one-time projects to make up the difference. Would I be able to find enough of them regularly to make ends meet?

But in the life of any successful freelancer, there comes a point when you have to pull the trigger. A full-time position may provide consistent pay, but it doesn’t give you the opportunity to grow your own business and become truly independent. Eventually the workload from your side jobs becomes so overwhelming that you risk affecting your reputation as a freelancer if you don’t focus on it.

Before you take that big step, though, you have to make sure you’re really ready for it. Just because a lucrative one-time project comes your way doesn’t mean you should quit your day job immediately. In some cases, making use of vacation time (or sick days) might be a better option.

So how do you know when it’s time? I spent a lot of time crunching numbers and planning for a worst-case scenario. If you rely on your current clients as well as a spouse’s employment, what would you do if one or both income streams dried up? How much time would you have to get things back on track?

Don’t think it can happen? Well, it did for me. Just a few weeks after I left my full-time position, my husband unexpectedly lost his job, along with our health insurance. Even worse, I found out I was pregnant just a few weeks before, so that insurance coverage was more important than ever.

Luckily, we had ensured that we had enough money saved up to cover us for at least 6 months – longer if we cut back on optional expenses like our nice cable package and our monthly maid service.

In the end, his job loss ended up being a blessing instead of a curse, allowing both of us to focus whole hog on building our freelance careers, and within a few months, business was booming enough that shelling out for those expensive COBRA payments didn’t seem so painful. We even restarted our maid service (we never got rid of the cable, that was just too painful!), and now we’re both able to be at home with our new baby.

If we hadn’t planned for that worst-case scenario, we likely would have both rushed back into the job market, accepting any position that came our way. We’d do this to the detriment of our freelance work (and our happiness).

If you’re still struggling to balance your full-time position and a freelance career, do the math. If you’re not ready today, prepare by building up your safety net and cutting back on your lifestyle.

But don’t wait forever, because you’ll never be 100 percent certain. You just have to trust in your talents and skills, close your eyes, and take the leap!

Note from Paula: Thanks Juliana, for today’s great guest post! I love stories of people who have made the leap into chasing their passions … and who complemented that leap with a ton of common sense and number-crunching!

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16 Responses to “When to Quit Your Day Job”

  1. Lance @ Money Life and More
    08. Aug, 2012 at 9:41 pm #

    Congrats on making the leap and having the backup to be able to keep at it despite the unexpected job loss and pregnancy! I think I might have panicked myself but kudos to you for stick it out! One day I think it’d be interesting to see if it is my ideal lifestyle but I’m very far away from that date. If my income ever exceeds my day job though I’ll have some soul searching to do.

  2. Money Beagle
    09. Aug, 2012 at 8:08 am #

    I always try to make the best of it if I can, trying to explore new opportunities, new skills, etc. If the company is making an active effort to keep me down (refusing to allow training, etc.) then I will leave, but it’s a pretty big decision. I also keep my eyes open for other opportunities even if I’m not actively looking.

  3. Call Me What You Want Even Cheap
    09. Aug, 2012 at 8:41 am #

    Great story of going after what you want. Many people in your shoes would have just looked for another job. But the two of you stuck with it and found your way. Congrats!

    I wish you both much success!

  4. AverageJoe
    09. Aug, 2012 at 12:52 pm #

    Great post. I think that people who reach for a “safe” employer never find it. I feel much safer working for myself. Good advice on doing the math before you jump.

  5. Ornella @ Moneylicious
    09. Aug, 2012 at 1:28 pm #

    Excellent piece Paula! Definitely need to plan for the worst-case scenario—that’s where the critical thinking comes in to play!

  6. Kathleen @ Frugal Portland
    09. Aug, 2012 at 7:38 pm #

    Build the net, then jump!

  7. femmefrugality
    10. Aug, 2012 at 5:31 pm #

    Oh, my gosh…I’m so glad it worked out for you guys! Congrats and good job on being prepared. Otherwise that could have been so devastating. But now you’re living the dream :)

  8. William @ Drop Dead Money
    11. Aug, 2012 at 1:35 pm #

    Thanks, Julia, for sharing. Striking out on your own (or dreaming of it) is another reason for having and bulking up that old emergency fund…

    A timely termination from a safe job is often the kick out of the nest we need to fly out on our own. Congratulations on making the move, and making it work! :)

  9. Congratulations, Paula! This is very inspiring. It was a good thing that you prepared your finances before you jumped the ship. A lot of people do not realize that we should always plan for any worst-case scenario. Thank you for sharing your story.

    • Afford Anything
      14. Aug, 2012 at 1:49 pm #

      @Manette – Thanks, but just to clarify — this is a guest post written by Juliana, who shared this story. (I am also a freelancer, but my story is different).

  10. Jill
    15. Aug, 2012 at 10:32 pm #

    I am currently writing freelance while working full-time. I’d love to quit my day job but I’m not earning nearly enough at this point to feel comfortable making that leap. I’d love to hear from Juliana what exactly she writes about that makes her so much money and how she built up her client base in such a short time. That’s the advice I really need right now!

    • Afford Anything
      17. Aug, 2012 at 6:40 pm #

      @Jill — I can’t answer for her (this is Paula), but I used to be in the same boat as you: freelance writing while working full-time. When I started, I didn’t have a ‘niche’ … I wrote about anything, for anyone. And as I quickly learned, when you write about everything, you write about nothing. Once I started narrowing my writing to one specific topical focus, I got a lot more jobs.

      My focus happens to be personal finance/real estate, but you could focus on anything … wine, the environment, public health. The key, in my opinion, is just to have a focus, regardless of what it is.

  11. Natalie
    24. Aug, 2012 at 2:48 am #

    Decide what you will do to earn a living if you quit your day job.Determine how long you can go without work with the money you have available. Make a budget from your expenses from the past six months to see exactly where your money is spent, and see whether you can cut back on any expenditures until your cash flow returns.

  12. Amanda L Grossman
    01. Sep, 2012 at 5:37 pm #

    This is a timely piece for me as I am currently strongly considering leaving my work to become a full-time writer (freelance, and frugal confessions).

    Lots to consider! But it’s nice to hear of others taking the leap first:).

    • Afford Anything
      12. Sep, 2012 at 5:11 pm #

      @Amanda — (This is Paula) — I’m a full-time writer, and I’d be happy to answer any questions you have about making the transition, or help in any way that I can. I’ve written plenty of articles on this site about my own experience making the leap. (And just so you know, I make more now than I did when I had a traditional job).

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