Pros and Cons of Freelance Life (P.S. It’s Worth It)

I want to quit my 9-to-5 job and do what you do. What advice can you give?

Above anything else, this is the question I see most in my inbox. I don’t know what it is people think I “do,” but I do work… I just work random hours and random days, and can just as easily sit in my home office, getting it done on the iMac, as I can lounge on a couch, tapping on an iPad. Sometimes I work when I’m supposed to be “on vacation” and sometimes I don’t work on Mondays.

My situation is unique in that I’ve been a freelancer ever since high school; I don’t even know what it’s like to be employed by someone else. I’ve made it work by cobbling together several part-time gigs and turning them into full-time income. I pay my own health insurance and put away for my own retirement. I take out my own taxes and pay much more for an accountant than any of my 9-to-5 friends do.

This lifestyle is not for everyone, and if you’re used to having vacation and sick days, employer-paid insurance or company 401K match (not to mention a steady paycheck), do think long and hard about whether it’s the right leap for you.

Most freelancers will tell you they work longer hours than any 9-to-5er (or even 8-to-6er) out there. While it’s true we can make our own schedule, we sometimes sacrifice our weekends when work calls or put in 12-hour days for weeks at a time. (That said, no one should ever have to slave over work. Deadlines come and go, but no amount of money is worth your mental and physical well-being.)

With an “outside” job, your work is done when you come home. But in our world, disconnecting from work is difficult because we’re usually working from home.

Despite all that, I feel the pros of freelance life far outweigh the cons, especially for someone who strives to live simply. As long as I have wifi, I have immeasurable freedom in where and how I work. (In fact, I’m writing this from a sunny deck outside my husband’s childhood home on Mount Tamalpais, where we’ve been spending the past week. Having two freelancers in the family means plenty of impromptu road trips.)

I love what I do, and would do the same thing even if I weren’t paid (of course, being paid is a perk and a necessity). I never fear being laid off or having my salary cut, and I’m used to (and prepared for) the ups and downs of my industry. I have the best job security there is because I’m good at what I do and I can always make it work. Being self-employed means you rely on no one but yourself, which I feel is very empowering — truly taking control of your own destiny.

I’ve always believed that one should work to live, not live to work. That means you work to support the lifestyle you want to have. You don’t work to buy the things you think you should have but never have time to enjoy. When it comes down to it, time is our most precious asset, our most important investment — not a new car, not a bigger (and more expensive) house.

I don’t need to sock away a million dollars for my future imaginary retirement; I’d rather take a semi-retirement now, while I’m young and healthy and able to explore all that life has to offer. I want to be the Mexican fisherman who strums guitar in his village… relishing every year that I have, not just the last 20 years.

I feel sad for retirees in their 60s and beyond who spent their entire lives working and saving like dogs, reluctant to take their much deserved vacation days, only to find themselves stressed with health issues and unable to enjoy their golden years. (Hell, I even know people in their 30s who are like this now.) But that’s another story.

It’s important to mention that all this can be done independently. If you have a partner who’s willing to support you financially while you pursue your dreams, you’re luckier than most and have leeway when it comes to making certain business decisions.

But on the flip side, it’s totally possible to go about it on your own. I’ve never relied on a significant other for my share of the expenses and continue to be financially independent, even now that I’m married. I like it that way, I’ve always been that way, and I need to be stimulated by my own ambitions.

Freelancing can take many forms. Some freelancers, like myself, are creative night owls who thrive at odd hours and love to have their hands in many projects at once… all while working in their PJs. Others need structure and may even commute to a co-working space; they work at designated hours, focus on a few select projects, and once they’re home, they’re home and the phone is off.

The common thread among all freelancers is that they are their own boss. You can be a lenient boss or a stringent boss, so long as you can motivate yourself to get the work done.

It can be disconcerting to move from a predictable corporate structure to a more unpredictable free agent world. But if you’re often grumbling at work and feel like you’re simply toiling away for someone else, exploring that world, at the very least, is worth it. Work takes up such a large part of our lives, and our lives should be as inspiring and fulfilling as possible. We need to make the most of it, whatever we believe “it” to be.

If you’re an adventurous self-starter who doesn’t mind simplifying, you should stop thinking and start doing. That “some day” is this day.

If you’re the traditional type and have a lot of debt or a lot of dependents, I’d suggest pursuing your self-employment dreams as an earnest hobby or side business first and see where that takes you. Plan your “escape” while saving as much as you can from your current job. But… if fear of going broke has you saving and saving with no end in sight, you might never get off the corporate treadmill.

“You must have chaos within you to give birth to a dancing star.” (Nietzsche) It’s a quote that has often inspired my paths in life. Greatness is born from drive and passion.

It takes a curious, open mind to even think about this “other world” beyond the 9-to-5, so I commend you for that and wish you the best!