Adventures in Freelancing: A Professional Gap Year

Ah - the college gap year. Thrust into the spotlight by Malia Obama's announcement that she plans to cultivate outside interests before heading to college, a gap year can help post-grads begin a journey of self-discovery. But what about the rest of us, those who aren't fresh out of high school or college?
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Ah - the college gap year. Thrust into the spotlight by Malia Obama's announcement that she plans to cultivate outside interests before heading to college, a gap year can help post-grads begin a journey of self-discovery.

But what about the rest of us, those who aren't fresh out of high school or college? Once you have a few years under your belt, it can be challenging to stay in touch with career aspirations, passions and professional goals. As a result, professionals of all ages are frequently faced with the desperate need for change--a career refresh, or "professional gap year" so to speak, to re-center and chart a career pathway with purpose.

Our economy, and definition of the traditional workforce, is rapidly shifting. According to new research, there has been a sharp rise in alternative work arrangements (i.e., on call workers, freelancers, independent contractors, etc.), up from 10.1 percent in 2005 to 15.8 percent in 2015, suggesting the number of workers engaged in these arrangements has increased by approximately 66 percent.
As someone who works with freelancers every day and has experience in a variety of work environments - from corporate to start-up, and as both a full-time and part-time freelancer - I know that going off on your own can be daunting. To help decide if taking a professional gap year is the right move for you, here are four lessons learned...the good, the bad and everything in between.

1. The perks of freelancing are everything you expect them to be. When I speak with professionals in the freelance community about the perks of the job, I hear words and phrases like "freedom," "ability to be my own boss," "flexibility" and "work-life balance."

These descriptors couldn't be more true. One of the perks of taking a professional gap year is the ability to craft a work experience unique to your needs - in my case, taking on graphic design gigs designing logos and packaging, outside of my day job in website design.

Maybe you have a newborn and can't work traditional hours or feel creatively stifled working in a corporate office environment. Freelancing allows you the opportunity to dictate the terms of your employment, honing in on the priorities that are most important to you. An added bonus? Working on your own allows you to discover strengths you never knew you had and can propel you into rapid professional development (and if all goes well, significant financial gain!).

2. Unexpected challenges abound. Before taking a dive into freelancing, there were two unexpected challenges I wish I'd been prepared for: the need to market yourself and the emotional aspects of the job. If you're thinking about becoming a freelancer, remember that no matter your area of expertise, it's essential to put on your marketing hat. In order to make a living wage, you'll need to always be networking and selling yourself and your services. Tapping into other freelancers and their networks can be a great way to start.

The emotional challenges of freelancing were also unexpected. Working on your own can be lonely and stressful, as you are 100 percent responsible - and will be held accountable - for your work. At times, this can require a thick skin, especially when dealing with negative feedback and tough clients.

3. New skills are required. As a graphic designer who specializes in product and user experience, I never thought I'd try my hand in accounting or human resources. But as a freelancer, you're going to deal with time-consuming and complicated tasks that fall outside of your traditional skillset: setting rates, creating estimates, invoicing, planning for retirement and considering insurance needs. Being organized, through research and diligent documentation, will help you stay on top of the administrative burden, as will recognizing when it makes sense to outsource help. Staying on top of these tasks will help you establish a positive reputation in your industry and, as a freelancer, reputation matters.

4. But You Can Have It All: Embarking on a freelancing journey - whether for a stint or the long haul - is a personal decision. For those looking to make the switch, connect with peers that have taken the plunge. And sometimes, the answer isn't as clear-cut as a traditional job or full-time freelancing. I wanted the best of both worlds and was lucky enough to find it in my current gig: working at a company dedicated to helping freelancers thrive in our changing economy. An added bonus? I still freelance on the side, pursuing the projects and passions that spark my interest outside of my 9:00-5:00.

Michelle Israel is the Co-Founder, Head of Product at Eagerto, a professional liability insurance platform and community for freelancers. Eagerto helps protect freelancers' reputation and financial security by covering costs if something goes wrong. Michelle's background is in UX, Product, and Graphic Design with experience in luxury, CPG, and insurance markets. Her work has been featured in Times Square, Vanity Fair, Target, Walmart, Sephora, and of course, the World Wide Web.

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