1LINKEDINCOMMENTMORE
Q: When I left my job to start my own small business, I thought I had left the world of bad bosses behind. I do a lot of freelance work now, but what I have found is that now instead one just one, I have four! Working for yourself isn’t always all it’s cracked up to be, Mr. Strauss.  —  Anita
A:  Though there is very little good that can be said about the Not-So-Great Recession (2007-2009), one upside was that not a few laid-off people decided to go their own way, start their own gigs and came to realize that they might be better off without that lousy job and crazy boss.
Indeed, there is a lot to be said about the benefits of going solo: freedom, job security (after all, you can’t fire yourself), flexibility, variety, opportunity.
That said, it’s not all ice cream and candy canes.  No, for some people, the “gig economy” isn’t all it’s cracked up to be. (For those who don’t know, the gig economy refers to a new breed of entrepreneurs, freelancers and the self-employed, who work for themselves either full-time or part-time and who support themselves with gigs and contracts.)
Gigs can be almost anything: It’s the guy who drives for Uber and Lyft or the woman who freelances as a graphic designer. It’s the person who contracts work with an old employer or someone who is a personal assistant, musician, webmaster or pet sitter.
Yes, there really is much that is great about being a gig worker, especially the ability to concentrate on doing something you love. But therein lies the rub: You don’t always get to do what you love. Even when you do create something along those lines, unfortunately, that old self-help book isn’t always right: Even though you do what you love, the money doesn’t always follow.

That is the first downside to the gig economy. Finding work isn’t always easy  —  actually, it’s never easy — and the very nature of a gig is that gigs end. Being a contract worker means you are on a never-ending hunt for contracts. Not only that, but for many gig workers, there is a feast-or-famine quality to the process. Either you don’t have enough work or you have too much. Finding the Goldilocks’ porridge amount of work often proves to be elusive.
This dovetails with another issue many freelancers have: the problem of scheduling. One of the best aspects of doing contract work is that you are the boss. Being a 1099 contract employee means — theoretically — that you work when, where and how you want. Contractors can give you deadlines but they are not supposed to be able to oversee how you work as they would with an employee.
I can hear your chorus: “Yeah, right.” Companies do make demands and often have unrealistic expectations. Bosses can act like you are an employee. Scheduling all of the demands of the work you need to do can be difficult.
What about the lack of benefits? This is a huge issue for any contract worker. When you had a job and a boss, you had a steady paycheck, benefits and hopefully health insurance. Say what you will about Obamacare, but before it came along, there was a phenomenon known as “job lock,” whereby people would stay in jobs, even jobs they hated, to at least have health care.
The last downside of contract work is that it takes a certain sort of person to be able to handle it, emotionally speaking. The very nature of the gig, what with its flexibility and freedom and all, requires no small amount of self-discipline. Similarly, you need to be able to handle the uncertainty that comes with the territory.
Given this somewhat sobering prognosis, is it worth it? You bet. The most recent stat I saw is that over the past 20 years, freelancing has increased by 27% more than payroll employment, according to CNBC. Why? Despite the challenges, the freedom, flexibility, fun, options and opportunity are tough to beat.
With apologies to Jon Landau and Bruce Springsteen, I must say, I have seen the future of work and its name is the gig economy.
Steve Strauss, @Steve Strauss on Twitter, is a lawyer specializing in small business and entrepreneurship and has been writing for USATODAY.com for 20 years. E-mail: sstrauss@mrallbiz.com. You can learn more about Steve at MrAllBiz.