Thinking of getting off of the train of full-time employment in the corporate world to join the gig economy? You are not alone. More and more American workers are opting to branch out on their own, working full-time or nearly that, though not in one place. Many “gigsters” work a combination of short-term projects and/or part-time roles, and more and more organizations are opting to rely on the gig economy as a staffing strategy, both to save money and to diversify the talent to meet their specific business needs. According to Small Business Trends, 1 in 4 Americans are members of the gig economy, and among millennials, that number jumps to 1 in 3.

Organization are becoming more savvy to the gig economy. “As the traditional job and career ladder concepts fade, organizations need to adapt to the new reality and think differently about how they engage what are currently referred to as contingent and/or non traditional workers” says Tracy Burns, CEO of the Northeast HR Association and Co-Founder of Hytched, a platform that connects businesses with experienced HR professionals in search of gigs.

Is it for you? I spoke to consultants, or “gigsters”, in my network about their experiences and “a ha” moments. Here are the top 10 things they advise before you enter the gig economy:

  1. Gigging can be something you do for the short-term, or something you embark on as a larger phase in your career. If shorter-term, gigs are a great opportunity to test out new organizations for culture, values, and fit. It is a also a great way to work in a new industry. Prior to entering the gig economy, I had zero experience working at a startup, manufacturing (aside from an internship in college more moons ago than I would care to admit), or a school. I now do HR work in all of those, and the exposure to new industries has been amazing.
  2. Allison Picott, Founder and Principal of Advancement Advisers, suggests being willing to invite others to partner with you, where appropriate. It is a great way to build your skill sets, professional network, and to learn best practices. While not all of these partnerships will work out, you will learn from each experience, and may find some who become a confidant or soundboard, as well as potentially invite you to partner with them again in the future. You will learn a lot about yourself while building your confidence as a professional.
  3. Independence. You set the days and hours that you are available. No more tracking vacation time, no more asking if you can leave early to go to your child’s recital. For the most part, you are in control of your calendar. Sure, you may you work on the weekend to meet a deadline. Some days you may work 14 hours, and some you may work 4. Having the ability to manage that around your personal life or a client with an urgent need gives great balance.
  4. Meghan Steinberg, founder of Steinberg Consulting, which focuses on human capital management, shared that others in the gig economy will be thrilled to help you. Everyone commented that even the people who work in the same space are willing to help, and we all found that veteran gigsters genuinely want to see others succeed. Before making the leap, talk to some in your area of expertise and geographic area to get a clear understanding of what to charge both hourly or by the project, and may even know of some gigs to help get you started.
  5. Learning, learning, learning. Each project is an opportunity to learn something new, and regardless of the expertise that sets you apart as a gigster, as your own boss you are suddenly responsible for everything. Be ready to handle sales, client service, marketing, accounting, and whole host of other key areas. You will quickly figure out what you excel at and what you need to find other experts to help out with.
  6. It can be confusing to juggle multiple gigs. Not only does each client has little things that you need to keep track of, like their invoicing process or how they want to receive information, but the logistics of multiple gigs can get confusing. One of my gigster friends said that early on she would put a post-it on the mirror in the bathroom at night to remind herself which client she was working with that day, and whether it was at a client office or a day in her home office.
  7. Entering the gig economy takes guts and some tolerance for uncertainty and risk. Gone are the day of the steady pay check or company-paid insurance. If you are not covered by someone else’s insurance, educate yourself and talk to a benefits broker so that you know you are making good choices on that expense, and get a good accountant, as your taxes will be different when you are self-employed.
  8. Do not underestimate the importance of a strong network. If you are seriously considering giving up your 9 to 5 job, start strengthening your connections now.
  9. Get comfortable with saying no. When you start out, it’s easy to fall into the trap of saying yes to everything. Be cautious. If there is a project that will take over your life, will it prevent you from servicing existing clients? One gigster shared an anecdote of the potential client she met with to discuss a large project. During the meeting, she had this nagging gut feeling that the client was going to be a nightmare to work with, but she had only been on her own for a month and was understandably concerned that she did not have enough business. While it would have been lucrative, she decided to trust her instinct. It paid off. She met the person who accepted the gig at a conference a few months later, who shared that the gig was the worst they had ever signed on for. It’s okay to walk away from a gig opportunity if something feels off.
  10. Always be on the lookout for your next gig. It is easy to let it slide when you are busy, but when one gig ends, you want to at least have feelers already out there. Block a few hours every week to focus solely on networking and finding new gigs.

As with any decision of this magnitude, be sure to carefully weigh the benefits and risks of entering the gig economy. Wishing you luck and professional success!

Hire the best! With personalized service and proven results, Pillar Search & HR Consulting provides retained executive search services and human resources consulting for exceptional non-profits and socially responsible for-profit firms. A woman-owned business, Pillar is based in Boston, MA, and works on the national level. To learn more about how Pillar can assist with your hiring and human resources needs, please contact Cindy Joyce at [email protected].


  • Cindy Joyce

    Nonprofit Executive Search and Human Resources Consultant

    Pillar Search & HR Consulting

    My name is Cindy Joyce, and I am the Founder of Pillar Search and HR Consulting, a woman-owned executive search and HR consulting firm that works with nonprofit and mission-driven organizations. In addition, I teach at Harvard Extension School and eCornell, the online education platform for Cornell University. I live in Boston with my rescue lab Neddick, and am a huge fan of yoga, cooking, gardening and extra dirty martinis. I hope you enjoy my articles!