Can you afford to support your family as a freelancer?

Can you afford to support your family as a freelancer?


“Yes, but a couple of steps I took turned out to be key to making it work. First, I didn’t just immediately quit my day job before entering the uncertain life of an entrepreneur. Instead, after working from ‘9 to 5,’ I would gradually build my freelance income from ‘5 to 9’ and during the weekends. This allowed me to build a financial foundation and client base to the point where I was ready to quit the full-time gig. And because of that early development work, I’m able to comfortably support my family as a self-employed person today.

“Second, I focused on quality over quantity with my clients. I’ve found that it’s far better to have four clients on a monthly retainer that each pay you, say, $1,250 (so $5,000/month total) than 10 clients who each pay you $500, for the same monthly total. This way you can deliver excellent work to four clients rather than mediocre work to 10. And that’s the advice I give to the freelancers I work with today.”

—Antonio Neves, millennial workplace speaker and executive coach, dad of two, Santa Monica, Calif.

Gen Xer

“I was laid off in mid-2015, and while it took me several months to develop an understanding of my new position as an independent contractor, I’ve come to realize that in today’s ‘gig economy’ world, it’s completely possible to support a family as a freelancer. The caveat is that while in some cases your work product will stand on its own, you still need to get comfortable with branding yourself, because you are your business. Whether it be placing ads in local publications, attending networking events, or posting on social media, letting people know that you’re out there ultimately puts food on the table.”

—Trae Bodge, smart shopping expert, mom of one, Montclair, N.J.

Baby Boomer

Can you support a family as a freelancer? My answer is yes. I never had a real job. A job with a boss, an office, performance reviews, sick days, pension, health insurance and all that. I started at the bottom in the film/TV business out of college and worked my way up to producer/director. I’m a documentary filmmaker and I’ve had some success in that area, but the reason I own a nice home, have significant retirement savings, and was able to send two kids to private colleges is that I do marketing, corporate image, and training videos for large corporate customers. Supporting a family when you’re self-employed is all about making choices. And a lot of those choices are made for you once decide to start a family. It’s amazing how focused you can be about finding work when baby needs a new pair of shoes. For me that’s meant taking freelance gigs I wasn’t excited about. But I don’t regret my decisions at all. My work has taken me all over the world, I meet new and interesting people all the time, and not having to go to the same office every day is something that most people can only dream of.

“One big issue, however, is soaring health care costs. There are no good options for the self-employed. My wife and I pay huge premiums for so-so coverage with gigantic deductibles. We’ve managed to muddle through so far—we have always had health insurance—but I feel bad for folks who want to work freelance who are just starting out and have to face that burden.

“What it really takes to support a family as a freelancer is the same skill set you need to be successful in any job: have a good work ethic, and deliver a quality job on time. You need to be thinking about where your next job is going to come from while you’re working on your current job. And it helps to have a great life partner (in my case, a wife) who can roll with the punches with you, and who works hard and contributes to supporting the family. Is the life of a freelancer stressful? Sure. Is it more stressful than a real job, with a boss, an office, etc.? I doubt it.

—Carl Leander, film and video producer, dad of two, Bend, Ore.

(Quotes have been edited for style and length.)

baby boomers boomers entrepreneur Family freelancer freelancing gen x generation gap gig economy gigging millennials money conversation money conversations self-employed self-employment side hustle

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