Two years of freelancing: Still not broke!

Boba Fett was a freelancer

It was exactly two years ago today that I said good-bye to my old job working for The Man and said hello to my new job working for The Woman, namely me. It’s been two whole years of designing webs and writing words and I’m still not broke! If I have a freelancing motto, that is my freelancing motto: Still not broke! I should put it on a T-shirt, but that frivolous expense would put me one step closer to being broke, so I’ll skip that. I have adopted that motto because when I first made the jump I wasn’t sure if I’d be living in a cardboard box under an underpass a year later. Nope, instead I’m living in a two-bedroom apartment that was once terrorized by wasps.

Yes, there have been challenges. Trying to find health insurance has been like trying to find Waldo. Right after I moved and bought a couch and a bed, I looked at my bank account and thought I’d be destitute by Christmas. There have been times I’ve overbooked myself and unintentionally left clients hanging longer than I would have liked. I’ve worked through that though, and learning to overcome those challenges has forced me to grow as a person.

I’m much better at asking for what I’m worth, particularly after I underbid a few jobs and realized I’d slaved through a few projects for ridiculously low pay. I have less anxiety talking on the phone because I’ve come to realize some conversations really do need to occur via sound and not text so everyone can be sure we’re talking about the same things. I’ve learned that every client has a different communication style and I need to adapt to that to best serve them. And I’ve learned more about taxes, bookkeeping and invoicing than a non-business major ever thought she would.

When I graduated from college I had a job interview with a web design company. They asked me what I’d like to be doing in 10 years and I said running my own business. This was a lie. I said that because I thought that’s what they’d like to hear, inferring that I was a hard-working go-getter. (Though I’m not sure what I was supposed be go getting for them…coffee?) I was quite sure I would never start my own business because it seemed frightening and completely outside of my capabilities. I didn’t know anyone who’d started a business. It seemed scary and complicated. It was something other people did, not people like me. It was much safer to work for someone else and collect a regular paycheck.

But here I am, eight years later, and I do run my own business. It’s only because of the Internet which allows me to take on clients from all over the world, most of whom I met through my blog or who know people who met me through my blog. The Internet also allowed me to meet several people who work for themselves. They are all smart and capable, and I figured if they could do it so could I. Just knowing someone else has done it, someone just like you, makes it seem more achievable. I guess it’s like weight loss that way.

So, yippee! Two years down. How many more years to go? I don’t know. I just hope they’re good ones.

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  1. says

    One and a half years for me – but I went from at home with kids to slowly growing my freelance editing business, and I already had my husband supporting me so I didn’t have to make that scary jump from salary to self-employed. You were very brave! Yay for still not being broke.

  2. fd says

    I salute all entrepreneurial types and their bravery and creativity and hard work.

    well done! congrats! 2 years of learning and growing and being as independent as they come is no small feat.

  3. Mom says


    It was scary for me too when you went freelance. You had a plan and worked it beautifully. Wishing you continued success and happiness. Loveya!

  4. Barbara Raab says

    Jen(nette)! Huge congratulations. The other thing that I am quite sure needs to be mentioned — so I’ll mention it — is that your success is a direct result of your high quality work. You’re really good! I envy you, having a skill that lends itself to one’s own business — some of us keep working for The Man because He has the stuff we need to do the thing we know how to do. And then we wake up one day and we’re … older. :) Anyway, glad all is going well. I hope one day to have a project for which I can hire you. It would be an honor.

  5. Cheryl says

    This is inspiring. I am hoping to make the same leap in the next year or so and I’ve never been so scared or excited in my life!

  6. says

    Woo Hoo! It was a gutsy move but it has worked well for you. I’m glad you decided to do it, partly for selfish reasons, lol! And can I just say I am constantly amazed at all you’ve accomplished at such a young age.

  7. Dee says

    That is definitely worth celebrating! What lovely irony to have faked the goal, and then it ended up happening!

  8. says

    Yay! We have almost the same freelance anniversary. Just a couple months of difference, mine is May 31st of 2009.

    I always say the same thing — I’m not bankrupt yet. So that’s good, but hopefully soon I’ll be able to say, “And look at me now, I’m a millionaire!” instead.

  9. Dee says

    Wow! Two years already! I can’t believe how fast time goes by. I am so glad that you are staying afloat and hope the warmer climate is agreeing with you.

  10. Elaine says

    Congrats on your 2 year Not-Broke-Yet anniversary. I don’t know what impresses me more: that, or how you changed your Kindle screen saver-lol.

  11. says

    To me, ‘not broke yet’ makes me think of certain cats who have a smash total on your blog.

    Two years of freelancing is definitely something to celebrate. I will raise my glass of virtual (& thus low cal) champagne in a toast.
    Good Job Jennette!

  12. says

    You should be congratulated! I have had my own business (2 employees, soon 3) for 4 years but haven’t quite gotten the guts to quit my day job. I am a little too risk adverse I guess – 3 kids will make you that way!

  13. says

    Congrats, Jen! May you have many more prosperous years working for The Woman! I hope to join you working for This Woman in 2 years. (just starting to freelance as a side job)

    Also, you have one cool, Mom. Not only is she supportive of your decisions. She writes on your blog! Go Jen’s Mom! You Rock!

  14. Ramona says

    I’m exactly in your spot, or almost. Have worked for 10 years as a radio DJ. It was AWESOME, until the station closed. Not being able to get a decent job in the industry anymore (the recession hit us hard), I started focusing on my web design business. It’s been 2 years. I now earn 4 times more than I did, have some great clients and FREEDOM. I’d never look back.

    Best of luck and congratulations for all you’ve done.

  15. says

    Congrats! How you can find clients who will actually PAY for web design in this day and age is a revelation to me. I started designing websites in 1995 when one had to explain what a website WAS but then I had a few very profitable years as I worked for radio stations in town doing their sites. A couple years ago I got tired of begging for work and trying to compete with $69 templates and gave up the web biz. It’s good to know it’s not dead and as a fan of your writing I am happy for you!

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