10 years of freelance

January 17, 2013 |  Category:   life me

2013 will be my 11th year as a freelancer. I’ve actually freelanced off and on longer than that working projects and PT jobs during my years at grad school, but this February marks 10 full years as a freelancer. I sometimes wonder how I’ve managed to make it this far as I didn’t have any expectations beyond the fact that freelancing was the best solution to the conundrum of working without full time childcare, which was unaffordable for us at the time. Indeed, at the end of every year there is always a sigh of grateful relief at the acknowledgment that I made it through another year.


I have on a few occasions wondered if I’ll ever go back to a full time office job (and now that I think about it, I’ve only actually had 4), but those thoughts are usually driven by fear and insecurity and not necessarily by any pressing financial need. The truth is, freelancing has been very good to me. I’ll admit that I haven’t had to hustle that hard for jobs because the majority of my projects come from long-term steady clients and referrals that I’ve built up over the years, many of them from grad school contacts. Though the nature of freelance is up and down (and I know that I have expressed weariness of that instability here), I’ve been fortunate with a steady stream of work. For the most part, benefits aside, I’ve been able to earn a higher salary than any full time job I’ve had. The flexibility has played in integral role in the way we have raised our kids and it’s enabled us to build our business, but the girls are older now and in school. We still have childcare needs, but they are less pressing and working a full time job is more of a realistic possibility than ever.
Last year was a down year, the first since the early days when Mia was a baby. Many projects were put on hold and some went away. For the first time I seriously wondered if it was time to get a full time job. I’d like to believe that I would never compromise the livelihood of my family for this freelance lifestyle that I was used to and quite frankly, preferred, but I have to admit that the thought of a full time job was daunting. I had been working from home for so long that even the thought of looking for a job was intimidating. I didn’t even know where in an agency hierarchy I would fit in. What position would I apply for? How would I adjust to a daily commute or a desk job and what would that mean for my general health? (I can’t sit for more than an hour or 2 at a time without pain because of back and tailbone issues). How would we be able to run our business if I was gone 9-10 hours every day? Although some of these concerns were very real, I wondered if they were just excuses to deflect the fears and insecurities I was feeling about my career as a designer, and one who wasn’t getting any younger. All of this made for some serious soul searching.
In the end, we pushed through the Fall which was admittedly tough and I’m back to juggling multiple deadlines this month. I know we are in a good place and we try to do all the responsible financial things. I may not, however, be any closer to facing some of these tougher internal questions and maybe I won’t have to if the work continues to stream in, but I also know that anything is possible and nothing is forever. If there was ever a point where I would feel like I’d need to find a full time job to put food on the table, I’d “man up” and do it in a heartbeat, but I’m committed as ever to making freelance work for another 10 years as I enter into my 11th. I know that this in part is due to the fact that I know so many other freelancers and small business owners now like us and I’m inspired by anyone who is committed to making this life work. This wasn’t always the case when I was starting out 10 years ago. Perhaps I wasn’t looking in the right places for support or maybe the recession has forced many of us to be more creative with our employment, but there are a lot of us out there. Even though last year was the toughest year we had in awhile, I’m glad to have gone through a rocky period. Upon reflection, it just proved once again that we could adapt and be flexible. It was a good lesson learned and everything ended up being ok. It makes you a little more humble and it makes you question everything. That is always a good thing.

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  • Rachel January 17, 2013 at 11:16 pm

    thanks for sharing your thoughts on the realities of freelance work! interesting…

    life will have ups and downs no matter what situation or job you are in

  • cantaloupe January 18, 2013 at 6:34 am

    Your lifestyle makes me very jealous. I wish I didn’t choose a career path that can’t be turned into freelance. I feel that I could be excellent at a freelance job and a more free schedule, but alas, teaching is not likely to ever become freelance. Although I suppose I could somehow manage to turn tutoring into a full time job. Especially here in the UAE…. If I end up here for years to come, I will totally try for it, haha. But all the same, it’d be nice if it was more plausible.

  • Dee January 18, 2013 at 9:24 am

    What an encouraging post! I do have a full time job, but recent events have made it likely the job will end before I expected. I read your blog most days for the glimpse of such a different life than my own (although we share being moms to wonderful girls), but today your thoughts are most helpful to my own situation. I will try (harder) to view this as an opportunity to practice flexibility!

  • Jenna January 18, 2013 at 9:46 am

    @cantaloupe yes, that is absolutely true that freelance is possible for some careers but not for others. I do recognize that it isn’t possible for every type of job and feel very fortunate about that.

  • Jenna January 18, 2013 at 9:48 am

    @Dee oh, good luck! A job ending is devastating and we’ve been through it before, but sometimes if you look at it as an opportunity to do something that you didn’t think you’d do because the alternative is safe, then it could definitely be a blessing.

  • Renita January 18, 2013 at 2:13 pm


  • paige January 18, 2013 at 11:06 pm

    i swear, you are such a breath of fresh air. thanks for being so real. i cant tell you how refreshing it is.

  • Fruitful Fusion January 19, 2013 at 12:22 pm

    Thanks for sharing this Jenna! I’ve been following your blog for a while and love checking in with what’s going on. This post in particular really spoke out to me as someone who’s been eager to get going as a freelance graphic designer for some time but just not quite there yet! Thanks for the inspiration. I see your kids are as mixed (ethnically) as mine, who are 1/2 Algerian, 1/4 Indian, 1/8 Bangladeshi and 1/8 Ugandan! British by nationality lol! We’re global!

  • Pink Ronnie January 19, 2013 at 7:56 pm

    Thanks for sharing so honestly with us as always, Jenna. Always appreciate your thoughts and being able to understand a bit more what your year was like.Even though I decided to end my design business last year, I’m still eternally thankful for the six years that I had doing freelance design work. It got us through the four years while Rick went to college and it saw us through to starting our family and Rick being able to work full-time. It has been a real blessing…
    Ronnie xo

  • sanae January 22, 2013 at 3:38 am

    What a wonderful post, Jenna! I’ve had both full-time and freelance work, and I have a small child. I find that there really is no perfect job situation, especially when kids and childcare get thrown into the mix. (I’m now a stay-at-home mom for the interim trying my hand at some creative pursuits, but of course, this has its own set of challenges of the financial kind). It’s a testament to your talent that you’ve been so successful as a freelancer for so long and I agree, questioning things is always a good thing. Keeps us on our toes.

  • Bethley January 22, 2013 at 11:45 am

    Great post. My husband runs his own small business and the flexibility has been great for our family. Your words relax me. I can’t really explain it. Thanks Jenna!

  • annak January 24, 2013 at 11:26 pm

    long time reader. its funny how i came upon this post because i’ve been going through some of those same issues about the status of my career. It’s like a blink of an eye, 14th yrs (could be 15th, but who’s counting) of self-employment. last yr, i felt the biggest slump from my longtime clients and it made me think about where my job will be. can i continue this? will i have to find a FT job? what kind of job? do i have the skills? am i too old? at the same time, i love working from home and enjoy the flexibility i have to do other things all these years. i don’t know. I guess i’ll have to wait and see…