My First Full Year in the Hustle: Freelancer Wins and Fails

Illustration by Viet Vu

This marks my first full-year as a freelancer. And while it definitely wasn’t always easy, I managed to get through it. There were times when I suffered massive anxiety and thought about getting a job at See’s Candies (my teen dream job, no joke). But the truth was, I was doing fine. I was landing clients, worked my butt off, which eventually led to netting a pretty solid income.

What’s funny is that a lot of my more seasoned freelancer friends tell me that the first year making a go on on your own is the hardest. And while I politely nod in agreement, I can’t help but wonder, “What could possibly change the second year? And in the third?” To be honest, I am not even sure if I feel that much more confident. Obviously, there will always be unknowns, and that will never change. That being said, looking back I learned a lot about myself, upped my freelancer game, and have set things in place to make it a bit easier for 2017.

If life can be neatly compartmentalized and labeled as such, here are some of my top wins and fails this year:

Win #1: Making more money than at my old day job. While this wasn’t necessarily a goal of mine, I was curious as to how much money I could earn going solo. Despite working less and having a few slow months in the spring, I managed to net more income my first 10 months of the year than what I was making in an entire year at my old day job and working less hours overall. I decided to “take it easy” the last few months, only to discover how much of an fretful workaholic I am.

Of course, I will need to factor in expenses that are a part of being self-employed (i.e., self-employment tax, health insurance, business expenses), but it feels pretty awesome to know that I can pull off making money on my own.

Income goals are great; they make sure you are able to eat, and that you can sock away some money toward all the fun and cool things you want to do. I try not to tie too much of my identity into my income. Knowing that your income can fluctuate wildly has kept me most grateful and humble.

The question I get asked the most is “how can I get started making money as a freelance writer?” and in the new year am excited to share how I make money writing, and tips on beefing up your income.

I’ve also grown a lot as a writer. I’m now spend about 4-5 hours a day writing, and as writing is a muscle and a craft, I feel as if I’ve learned a lot, from SEO keyword best practices to branding guidelines. Plus, I’ve been on editorial teams with some super talented editors and content strategists. I’ve learned a lot from working with different people with different editorial backgrounds. And to boot, my writing portfolio is definitely more robust than it was a year ago.

Win #2: Learning to work in different locales.
While not a huge traveler, I’ve been able to see more of the world than I have in previous years because I didn’t have just 2 weeks of paid vacation. Of course, any time I took off from work was unpaid, but being the Cheapster that I am, I made it work.

Whether it’s been at a McDonald’s in Joshua Tree, a train en route to Chicago, or a coffee shop in Honolulu, I’ve tried out different schedules in different time zones to get my work done. I’ve had to do the 2/6 schedule, meaning I work 2 hours, then take the rest of the day off, to stay afloat.

Win #3: Coming up with a solid budgeting system.
After experimenting with different systems, I’ve figured that the percentage method is what works best for me. This has helped me make sure I have my monthly bases covered, and that my other money goals are slowly chugging along. I am a firm believer—in fact, I know—that creative types can totally conquer handling their moola.
I’ve been able to invest on the regular in stocks with Vanguard and the Acorns app, and sock away money in both a Roth IRA and SEP IRA fund.

I also opened an health-savings account. My friend Kate over at Cashville Skyline has written a great post on how HSAs provide a triple-tax benefit. Plus, it’s nice to have money in case unexpected medical bills creep up.

Top Win:
Realizing how much I really need a community. Whether it’s reaching out to a fellow freelance writer to talk about rates, or meeting up with pals for a work party, I need people. My friends have kept me anchored when I was stressed to the balls and provided help when most needed. I’ve been able to meet some great people through Freelancer Union’s local Spark events, and through Freelance Friday meetups in Los Angeles.

In 2017, I would like to focus on community. How to build a community online, and sharing info and resources with freelancers and artists in person and digitally. I’m super stoked to figure out ways on how we can help each other stay sane, grow, and learn.

Fail #1: Not spending enough time on personal projects. Ah, the eternal struggle persists. Part of the reason I decided to do this whole crazy freelance thing was to make more time for my creative stuffs. You know, live the life of someone who could wake up and really focus on improving their craft.

Well, that was an idealized notion that vanished in two seconds flat.

Besides getting a Cheapsters ‘zine out with the tremendous help of my dear cousin Viet and making some headway on some short stories, I didn’t spend as much time as I would like to on creative projects.

Why’s that? Well, money is a huge motivator. That being said, the times when I had a lull, I was so anxious about finding work that I didn’t allow myself to just relax and work on other stuff.

So this next year I would like to devote more time on my creative projects. I think 15 minutes 6 days a week is totally doable. Perhaps right before I start my work, or in the afternoons.  I can definitely bump it up as I get deeper into my projects. Here’s what I would like to work on:

+This blog! (woot.)
+ (Not so) super secret book series to help artists with their $$$$. More details to come!
+ Fiction: Short stories in particular
+ Music: Learn basic audio engineering, improve my guitar skills
+ Random art projects

I know. It’s a lot. And I need to seriously sit down and allocate time to specific projects. But it is a wish list! But wise person said if you get a wish out into the cosmos, the universe has a way of conspiring to make it happen. That might just as well be a bunch of mumbo jumbo!

Fail #2: Not having a freelancer contract. We all know how getting a freelancer contract can help you earn and save more money, but it also is there to protect you. I learned the hard way when a client changed the author of a blog post I wrote to his name. Having only signed an NDA before working with this client, it wasn’t clear who owned the rights. As a result we parted ways—and not amicably, either.

In hindsight, having a freelancer contract I could give to clients when I first work with them could have totally prevented this from happening. Womp. So in the new year I plan on having my own contract, to make sure all bases are covered.

Fail #3: Not getting enough sleep. Seriously. I’ve been struggling with insomnia and sleeping problems for a long time, and freelancing has only made it worse. There have been countless times when I’ve sacrificed sleep, waking up at 3 or 4 a.m. so I can hit all my deadlines. No bueno. Am gonna really try to improve this in the new year, and get my Zzzs!

!!!Top Fail!!!
Lack of work/life balance. Well, it’s weird. In some ways I’ve had more free time, but the crazy ebbs and flows of freelancing, really created a lot of unnecessary stress and anxiety. As Carrie Smith of Careful Cents says, you either need to embrace the craziness,  or try to find a way to strike that ideal balance.

Although I am generally an anxious person, I’m stoked to see how the new year shapes up!

What were your major freelancing wins and fails this year?

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7 thoughts on “My First Full Year in the Hustle: Freelancer Wins and Fails

  1. Thanks for the mention, Jackie! I’ve failed at some of the same things you mention — lack of sleep and not enough time on personal projects. We talked about this at FinCon, but I do want to start singing again. Or experimenting with some new forms of art. Modern calligraphy? My brain needs a break from money sometimes 😉 Happy New Year!!

  2. Jackie Lam says:

    Yes! It’s so hard to make time for things that only you are accountable for. You totally should start singing again and experiment with different kinds of art! I totally hear you about taking a break from money; I feel that way at times, too. Or doing something physical, that doesn’t require staring at a computer screen for hours…Happy New Year! 🙂

  3. Centsai says:

    Congratulations on all your success this year! We wish you even more success with this new year and hope you can learn from your fails and use them to succeed even more in 2017!

  4. Jackie Lam says:

    Thanks so much, and thanks for taking the time read this. Same to you! 🙂

  5. Forrest says:

    It is odd that the top fail is work/life balance, since many would think that is more attainable when you’re on your own. Since going solo, that seems to be the hard part for me as well. I’ve given myself a set amount of “PTO” for the year, but I generally feel guilty using it (and I think I should probably save some of that PTO for those inevitable lulls that arise here and there). I think I also feel a little more pressure to live my “ideal lifestyle” since I should be more able to do that, but of course the realities of needing income still apply regardless of where your income is coming from.

  6. Jackie Lam says:

    Hi Forrest,

    I know, right? I found it strange as work/life balance is a top thing people tout is a benefit about freelancing. The thing is that when you have multiple clients instead of one boss, it’s hard to keep track of scope and your workload can balloon out of control. Also I found that you have to make a lot more decisions on the fly, when onboarding with new clients, negotiating rates, and so forth…

  7. Jackie Lam says:

    Hi Forrest,

    How many days of “PTO” do you give yourself a year, and how do you save for it? That’s interesting. I’m trying to make enough the first 11 months so I have enough to take off a month for holidays, vacation, and sick time, but haven’t perfected it by any means. Just curious what your strategies are. 🙂

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