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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!

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  • I love reading articles like this, I am currently working full time 9-5 as a designer but I feel the itch to venture into the freelance world… my only hold up is when? When is the right timing for me to take a leap of faith. Thanks for the article,

    • As with many things in life, there’s often not a “right” time to make a leap. You just have to try and trust it will work out. Good luck!

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  • Hi Linda,

    We are on the same boat, I just gave up 9-5 office and resigned from job and relocate in Turkey and do farming. I have walnut and olive trees, chickend and lots of veggies to look after.
    I enjoy the life but as you said I do not have a luxury to have a starbucks coffee like my friends working 9 to 5, I have an amazing lifestyle, extremely happy but do not have so much money to spend which I do not care about.

    • Sometimes, money only complicates things. 🙂 Congratulations on your newfound happiness and lifestyle!

  • Awesome post – been freelancing on the side for a couple years now, and can’t wait to pursue it full time! I’m lucky to have a wonderful job that allows me to balance both right now!

    • I think balance is definitely key, whether you’re freelancing or working a traditional job. You’re lucky to love both sides of your work!

      • Totally! Balance is key! I am definitely excited to one day (soon!) make Sugar and Type my full time gig!

  • Marissa

    Great read! I’ve been freelancing for over 4 years now after working 10+ years as a permanent employee. I considered it for a long time before I took the plunge and talked to many other freelancers first to get a sense of what to expect. The best piece of advice I received was not to do it if you are going to constantly worry about where your next paycheck was coming from; otherwise that stress is just as bad as the stress from the permanent job.

    Working in the agency world, I sacrificed many nights, weekends and vacations as a permanent employee as well as while being a freelancer. For me, the major difference is the excitement you get when you see your hard work end is success is often marred by office politics, the next looming project, etc., when you’re permanent. As a freelancer, you get to relish in the satisfaction of helping out a team in need and there is (usually) an end date in sight which is a great motivator to help you power through. Occasionally after those tough gigs, I’ve chosen to take a month or so off to decompress—a luxury you definitely don’t get as a full-time employee.

    As others have mentioned, saving as much money as you can ahead of time to cover cost of living helps ease that initial fear. And yes, when I have had my moments of panic, the right opportunities have luckily shown up. Overall, I think it’s the best move I’ve made professionally. I’ve gotten to work on some of the greatest projects of my career, that I don’t think I would have had to opportunity to do otherwise, and met so many brilliant people along the way.

    • I’m the same — I’ll sometimes have a month of nonstop work, burning the midnight oil on both ends (just last month, actually!). After the job is done, I feel incredibly fulfilled, excited and proud, and I’ll take a month off to unwind, reward myself, and really enjoy what I’ve accomplished.

      And I totally agree about all the brilliant people you meet along the way; in a freelance environment, great minds are truly unfettered when they come together.

    • Hey Marissa, are you still doing freelance today? Just curious!

  • danielle

    Great article. I have freelanced full time for the past five years. I might also mention to your readers that having some money socked away in a savings account (even 5000 can go a long way) to buffer the lean times during the ebbs and flows of freelance work (when you need a new client, when an old client neglects to pay you on time etc.) is of utmost importance. I have always been more of a hand to mouth person. Until I started following this rule for myself, (and putting 15-20 percent of all I earned into a savings account) my financial life was utterly tumultuous. Fair warning for anyone looking to make the leap. The freedom is worth it. However, use it wisely.

    • Good advice. And don’t forget the 20% (or more) you should set aside for taxes! Freelancers need to be good with money, or have good bookkeepers.

    • Hey Danielle are you still freelancing today?

  • Great post! I’ve been at it full-time for a year now, and it’s definitely challenging. But after 10 years in corporate I could never go back. I finally quit after I spent two months physically sick from all the stress of the job – not to mention the poor mental state I was in!

    I do think sometimes it’s a process of trial and error to figure out what works best for you as a freelancer. I’m changing my business model right now, as I’ve found that my sweet spot is three or four (max) projects rather than lots of stuff flying around from a laundry list of clients!

    I do advise that people save up some money before starting out. It’s definitely challenging to get a livable income going the first few months, even if (like me) you have 10 years of experience under your belt. And I’m still not in a place where I can save much, or save for retirement, so it definitely takes some time. But the freedom is worth the occasional uncertainty!

    • I think one of the reasons freelancers sometimes have a hard time saving money is because we’re constantly reinvesting our money into our businesses. But like you said, the freedom is worth it!

  • Ashley Dufault

    Very insightful! I like that you described pros and cons. I’m thinking of freelancing now that I’m out of college. Everyone I know keeps trying to drag me away from it because of the nature of paychecks, insurance, etc. Personally, I like a challenge, so it sounds exciting.

    • Best of luck! From the sound of it, you’re already in a freelancer mindset. 🙂

  • This is really summing up how I am feeling right now. I’m sick of the 10 hour shifts, 7 days a week and an looking forward to my long-awaited self employment starting at the beginning of April. I think particularly your comment about the working hours is very interesting – self employed people often work MORE hours than in a job where some one else is the boss, but the difference is it doesn’t feel like “work” because its something you’ve chosen to pursue, in which case working in the middle of the night because you are inspired/in the mood for it really works.

    Another thing I wholeheartedly agree with, and one of the main reasons I have made the decision to become self employed, is the idea that I don’t feel like I am truly living my life, and why am I wasting my healthy youth and early years of marriage miserable with no time to actually see my husband or do the things I love? Customers come into my work all the time, telling me they are finally going on that trip they’ve been planning all their lives, and now they are retired they can afford it. It then becomes a sad moment when they go on to say that because its taken them a lifetime to wait until retirement to go, their husband or wife, siblings or friends they always intended to go with have often passed away. It’s good to dream, but its tragic to spend your life focusing on the money to achieve that dream and never actually do it until its effectively too late to enjoy it. I’d rather be poorer and happier than wake up at 70 and realise I missed out on the best years of my life because I chose to focus on money.

    Can’t wait to get started on my lingerie brand/writing/art/jewellery/more time for gardening/family/friends/blogging!!

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  • Vera Greutink

    Inspiring read, thank you! I am a freelancer as well, combining garden journalism and photography with teaching Norwegian and interpreting. We live quite frugaly and grow lots of our food and so far, it has always worked out. But because the magazine industry (currently my main source of income) is really not doing well at the moment, I might have to rethink what I do. Often new oppportunities arrive just when I need them, but it can be tough at times.

    • I love your last line – I’ve experienced that over the years as well. Just when you think you might have to consider other options, the right opportunities come serendipitously at the right time. Have faith!

  • Kaitlin Jenkins

    I loved this post- thank you for your insight! I’ve just fully leaped into the world of freelance in 2014 after experimenting last year. Such a timely article for me.

  • A reader

    Thank you for your inspiration.

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