seeing the signs – when everything points to here

November 7, 2014 |  Category:   life me


So this new job of mine officially became A JOB this month, and by all caps, I mean I went on payroll in November. Big stuff around here considering I haven’t been on payroll anywhere in 11 years. And the thing that clinched it? Health insurance.


Obamacare hasn’t worked out well for families like ours – middle class, freelancers, a family of four in NYC. When ACA rolled out this time last year, I largely ignored it because I quickly realized that the health insurance that I had through Freelancers Union, a plan that I had switched over to 4 years ago to save on skyrocketing premiums, was still a better deal than the plans that were on available on the health exchange. Our insurance was far from the best (high deductibles and a frightening out-of-pocket max), but it worked for our healthy family and our premiums were relatively low (“relative” being the key word here since most would still balk at the number). What I didn’t know, however, was that Freelancers Union negotiated a year extension to keep their plans while most of the other trade plans that existed were eliminated because they didn’t comply with ACA. I was blissfully unaware.
During the summer, however, I somehow caught on to the fact that our insurance would end this year and that we’d have to purchase a new plan through the marketplace. So I went and searched around and quickly became despondent at what I was facing; the plans weren’t affordable at all. A letter from our insurance company in October confirmed my fears: an end to our plan and a significant increase in premiums for worse coverage.
I always made a deal with myself that if freelance no longer worked for our family I would go get a job, but a freelance career did end up being the best option for us while the kids were little because we were able to save on nanny/daycare costs while juggling flexible schedules and tag teaming on childcare. If you’ve been reading here for the past 6 years, you know all this. It wasn’t always easy and I feel like we paved our own way in somewhat uncharted waters back then, but it was the best of both worlds in a lot of ways.
But getting back to the deal I made with myself…well, I never really had to make that decision because freelancing went great for so many years – 11 years, in fact. Sure, there were dry spells like every freelancer experiences and it was in these moments of sheer panic that I’d promise to look for a full time job if I couldn’t support the family anymore, but work always managed to come down the pipeline.
The truth is, I was also afraid of looking for a full time job. It was a terrifying thought in a lot of ways. How would I adjust to commuting and working in an office everyday? I LOVED working from home and was lucky as a freelancer to never have to work onsite. The flexibility and freedom meant everything and I fought so hard to build and protect it. Whenever I turned a job offer down in the past – even jobs that I would have considered “dream jobs” – freedom over my time would always win out. I couldn’t justify the huge change in lifestyle, not even for a steady paycheck and benefits.
But sometimes you have to see the writing on the wall and I recognized for the past few years that the industry that I was working in was changing. Technology, media, design – it all moves so fast. We’d be foolish to think that the jobs that we could rely on will always be there. While I did have one of the best years as a consultant this past year, the work that I was doing was shifting – less web and more print. The big web projects that used to be my bread and butter projects were less frequent and harder to come by. Parallel to all this is my complicated relationship with design. I think one of the hardest and truest things you can do in life is to recognize and acknowledge when something has run its course. Maybe that’s leaving on your own terms when you’re still on top. Maybe it’s about letting go when it’s time. Whatever it is, it’s not easy acknowledging when something is over.
So it’s true that The Job sort of just happened. I didn’t decide to look for a full time job, there wasn’t a formal interview and this all came down during one of the most difficult times in my life. But sometimes things just fall into place, you know? And then it all started happening really fast, and I found myself helping to set up health insurance for the company and deciding on a job title for myself. And this is why it feels right. I’m helping to build a company and a product from the ground up and it’s going to be wild ride. I’ll admit that I had a moment of panic when I signed papers the other week. It sort of felt like I was signing my freedom away (though part of the deal is I get to keep some flexibility and only go into the office 3 days a week so I can still run our business and work on some freelance on the side. Look, if you want something you have to ask). When I made a little announcement on Instagram about this new venture, it all felt too real. But I’m ready to step into this new role and I realized that the promise that I always made to myself about finding a job if I couldn’t support my family any longer as a freelancer was only half true. I’m not only doing this for them or the health insurance or a steady paycheck; I’m doing this for me.

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  • Siobhan November 7, 2014 at 4:35 am

    Congratulations, Jenna! Sounds like you’ve found just the right thing for you. Best of luck!

    • Jenna November 7, 2014 at 9:28 am

      Thanks Siobhan!

  • Gretchen November 7, 2014 at 7:40 am

    I’m a long time reader of your blog but have never commented! 😉

    I just wanted to say that it sounds like you made a good decision here. Things aligning just right work wise and having your input valued, getting healthcare and going for it for your family and YOU just make the decision right in so many ways. Good for you! Good luck!

    • Jenna November 7, 2014 at 9:28 am

      Yes, sometimes things really do align. Thanks for the comment Gretchen -so nice to hear from you.

  • Christine Jimenez November 7, 2014 at 8:05 am


  • Mary November 7, 2014 at 8:31 am

    Congratulations. I am sure it will be a transition, but it sounds like a wonderful opportunity. Good luck!

  • Britta November 7, 2014 at 10:48 am

    This sounds like an amazing experience. Enjoy the wild ride!

  • Vandegee November 7, 2014 at 11:31 am

    Oh I was so disheartened when we got that letter from freelancers. Really depressing the coverage that is being offered. Now it seems that in addition to the $20k we already spend each year for the premiums for our family,we will also be hit with the high deductible AND co insurance on basically every service, I wanted to cry. Full time jobs are t on the table for us – were both in film. I’ll have to reinvent myself. But can’t bear to think of that at the moment either.

    Congratulations on the job. It is the right thing for you right now in many many ways.

    • Jenna November 8, 2014 at 5:47 pm

      Isn’t it depressing?! How are those plans supposed to be better for us? I was happy to see the out of pocket max go down considerably, but the co-insurance is what killed me. Hope you guys find a solution. I know that the prospect of a full time job is daunting – believe me, I know! And I hate that GOOD health insurance is still tied to jobs, so in the end the decision sort of made itself, in my case.

  • Lakshmi November 7, 2014 at 12:39 pm

    Onward we go… 🙂

    Here’s to an exciting new job + health insurance + good colleagues, and more cardigans!

    • Jenna November 8, 2014 at 5:47 pm

      More cardigans, yes! I might have to request a space heater!

  • Mieke Zamora-Mackay November 7, 2014 at 2:45 pm

    Congratulations, Jenna. Sometimes things really do align themselves if we let it. Wishing you many successful years at the JOB!

  • Kara November 8, 2014 at 8:39 pm

    Hi Jenna,

    Thanks for the post! As a design student who will be graduating in the spring, I found your post quite enlightening. I’m trying to figure out what I want to do when I graduate (ie work with a design firm, freelance and maybe own my own company in the future). It’s quite terrifying to think about! Your post has encouraged me to keep my options open and not be stuck in a certain mindset. The best of luck at your new job!

  • Dee November 9, 2014 at 12:26 am

    Congrats, Jenna and best of luck! I’m recently back to work after a nearly 5 year stint at home with the kiddos. I’m working for the same small company I did before leaving the workforce but it has grown and has better benefits now (I feel so lucky). Still, I like to daydream and plot my escape from the traditional 9ish-5ish to something a bit more flexible.

  • Janine November 9, 2014 at 5:23 am

    Congratulations Jenna, it sounds like the perfect job situation for you – security and flexibility and creativity.
    I live in the UK so all the health insurance stuff baffles me – I remember reading about your health insurance worries a few years ago and I didn’t understand a word. The NHS isn’t always perfect (currently can’t get an MRI scan to properly diagnose my prolapsed disc for example) but usually it’s great.
    I was thinking about US healthcare last week. We were on holiday in Portugal and my husband banged his head and needed 3 stitches. We went to a private place rather than a hospital as it was closer (hospital treatment would have been free). The total charge for cleaning it up, local anaethsetic and 3 stitches was 55 Euros- don’t know in dollars but much less than $100. I wondered how much it would have been in the states?
    Best wishes for your new career. Oh and fab photo of the waterfall the other week!

  • Em November 9, 2014 at 5:45 pm

    Go you, Jenna! I’m at a point where I am freelancing, but I truly want to have a 9 to 5 job. It’s the benefits, but also the camaraderie. I don’t like feeling like a lone wolf and can’t wait to get back into an office working on something that I and my co-workers are crazy about. Good luck, you’ll kill it!!

  • Clara November 10, 2014 at 12:49 pm

    I wish you the best and stay true to yourself because your such a honest person!

  • victoria November 10, 2014 at 6:04 pm

    Well I’m super excited for you, although sorry about the way in which it’s come about. Health cover, my oh my, it’s a subject which continues to surprise and astound me. I’m in Australia, but a friend from France (where everything is fully subsidised) was astounded at our situation and I at hers. I don’t know there is anything that’s perfect, although I think our Medicare here is really very good and everyone is offered it regardless of your situation, it’s truly health cover for all.

    I’m so pleased for your work situation though and you sound excited and enthused about it overall. I think it can take a long time to reconcile ourselves with the balance between what we want from work and what we want for our family. You’ve managed your lives together so well so far and I’m super confident that you will do the same in this new situation.

  • Christina November 12, 2014 at 2:28 pm

    I love that you always blog about real life issues. It helps everyone realize we are not alone. Congrats on the job! Cannot wait to see where it takes you.

  • Rachel November 15, 2014 at 4:04 pm

    I’m freelancing as well, and while my health insurance plan wasn’t through a freelancer’s union, it is still ending at the end of this year as well…I’ve been putting off trying to find another plan, partially because I’m scared of how much more it might cost, but now we’re midway through November, so I guess I’ll just have to suck it up. One good thing is that I don’t have any kids, so it’s really just me I need to think about, which makes it easier to pick and choose and decide what my priorities are. Congrats on the new job!

  • Jane November 16, 2014 at 3:21 pm

    Hi Jenna,

    Huge congratulations and best of luck with The Job. 🙂

    I’m always so interested in how Americans manage their health insurance. As a freelancer for about the same amount of time as you I quite understand why you’re making a bid for security!

    It’s an exciting time, and being part of a new company is indeed a wild ride. Enjoy!