16 Surprising Things That Happened When I Got Laid Off And Started Freelancing

Welcome to my "my whole life is a side hustle" era.

As the Great Resignation keeps on going, more and more Americans are getting into freelance work. This kind of work comes with some big ups and downs, and I know from experience.

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In 2016, I got laid off from a company where I'd spent five years. There weren't a lot of similar positions in my area at the time. So after a frustrating job search, I decided to try my hand as a freelance writer. Using boards like Freelance Writing Jobs and freelancing sites like Upwork, I slowly but surely built up a base of clients. 

I also took a part-time job to make ends meet, as well as occasional contract jobs, and I'd recommend a similar arrangement to anyone who's just starting out as a freelancer. It really helps to have something you can depend on as you're building up your business. Then, after about a year and a half, I was able to make the leap and go full freelance.

Here's everything I loved, hated, and learned in my time as a freelancer:

1. I loved how flexible my working hours were.

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As a freelancer, I mostly stuck to traditional work hours so my free time lined up with when my partner and friends were also off. But knowing that I didn't *have to* stick to a schedule really freed me up to take better care of myself. For example, I've always had trouble sleeping and waking up, so being able to sleep in after a rough night made a huge difference to me. Plus, I could go grocery shopping and run errands during off-hours and hit the gym in the middle of the day, and I only had to answer to myself. 

2. I missed the camaraderie of having work friends, but being alone more was actually kinda good for my other relationships.

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I formed some really strong friendships at my last IRL full-time office job, and I still miss our coffee chats, lunch walks, and Cheeto-salad Fridays (FYI, a Cheeto-salad is when you go to 7-Eleven, buy all the different Cheeto flavors they have, and mix them together in a bowl. Enjoy!). 

But at the same time, missing that companionship throughout the day actually got me to spend more time with my outside-work friends. I've realized that as an introvert, I only have so much people-juice to get through the day. Spending less time with people in an office actually improved my ability to be present with others in my life.

3. At first, I really struggled with setting my rates.

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Putting a price on your work can be really tricky. Sometimes I underestimated the time a project would take and ended up wishing I'd charged more. Other times, I accepted rates that I knew were too low because I was newer to freelancing and thought I had to "pay my dues." 

To start out, I looked for data on how much other writers were charging. The Editorial Freelancer's Association has a very handy list of median rates that can give you an idea. At first, I set rates just below the middle of the range, but later on I realized that it was actually better for me to set my rates slightly higher than what I actually needed. That way, when I ran into clients who wanted to negotiate, I had a little room to do so. And if they didn't want to negotiate, even better! It took about a year or two for me to gain confidence in setting my rates and sticking to them. 

4. I loved how many different kinds of jobs I ended up getting to do.

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As a freelance writer, I got to dip my toes in sooooo many different pools. For example, I wrote email newsletters for a cannabis dispensary, guitar scale tutorials for a major music brand, and SEO-driven blog posts for an escape room company. The variety of clients I took on kept my work-life really interesting, and I was always learning something new about completely random stuff.

5. But I also realized that, for me, there's such a thing as too much variety.

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My freelance years were the time when I started writing more about work and money and ultimately decided to make these subjects my focus. I love learning new things, but at a certain point I realized that I needed to narrow my focus. Keeping five different style guides in my head was hard, and I sometimes felt scattered.

I got my start writing about personal finance on a random gig, and when I applied the things I was learning as a writer to my own finances, it genuinely helped me. That's when I knew that I'd found a niche where I could see myself thriving.

6. I fell in love with working from home with my cats at my side.

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As much as I missed my office pals, I did NOT miss the office itself. Fluorescent light headaches, finger-numbingly cold AC, and other peoples' lunch smells were a thing of the past. And in their place, I had control of my environment, a pants-optional dress code, my cats, and my kitchen. 

With remote work becoming more and more common, this has become sort of a moot point in the freelancer vs. employee debate. But back in 2016, wow, this was a huge life upgrade for me.

7. Getting my own health insurance was... Let's just call it a learning curve.

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Going without health insurance is not a great option for me, so I signed up through my state's healthcare exchange. But I soon ran into a very annoying problem. Because I didn't really know what to expect, I underestimated how much I would make in my first year of freelancing. This gave me a pretty nice subsidy on my health plan up front. But when I filed my taxes, I ended up owing a good chunk of it back. It suuuuuucked.

It went much more smoothly in the next couple of years because I used my prior year's income to make a more educated guess. But if I had to do it all again, I would definitely make a higher income estimate for the first year.

8. Speaking of taxes, doing taxes as a freelancer was another challenge I wasn't 100% ready for.

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When you get a paycheck from an employer, it lands in your account with taxes already taken out. But as a freelancer, you're responsible for doing it all. Instead of only dealing with taxes once a year, I had to figure out how to make estimated quarterly tax payments and keep track of all my expenses. To be able to make those four tax payments throughout the year, I stashed away about 30% of every invoice that got paid out to me. 

After a year of struggling on my own with spreadsheets and equations, I signed up for Quickbooks Self-Employed, which made tracking all this stuff a whole lot easier. But taxes were still not one of my favorite parts of the freelance life.

9. I actually really missed getting in-depth feedback on my writing.

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As a freelancer, you either get the gig or you don't, and you never really know why. But even after getting the gig, I often didn't get much communication back about what clients liked or didn't like. Without this feedback, it was hard for me to figure out how I could improve and progress as a writer. After a few years, I actually genuinely missed having a manager or mentor to give me guidance and help me get to the next level. 

10. And I felt like without having regular learning opportunities and trainings, I was missing out on chances to grow my skillset.

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I'm a nerd and I love to learn, so it's not like I was stagnating. But like my dad always says, you can't know what you don't know. When I work a job that offers trainings and webinars, I like to take advantage — even when it's a subject that seems kinda random or that I think I already know. I always learn something, and I think it makes me more well rounded.

As a freelancer, I had to look harder to find these kinds of learning opportunities. And I sometimes had a nagging feeling that I should be brushing up on more skills, but I wasn't really sure which ones. I missed working for a company where educational invites landed in my inbox with regularity.

11. It was great being in control of my workload.

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If you want more money from your full-time job, you're pretty much at the mercy of your boss. But when you're freelancing, it's up to you. I always had the option to seek out more clients if I needed more cash or to say no to new gigs if I was feeling overwhelmed. 

And since my freelance and contract work tended to be more project-based, work became more about getting things done than putting in hours at a desk. If I finished all my projects for the day by 2 p.m., I could simply stop working. The pressure to appear productive by spending time in my desk chair was 100% gone. 

12. But it was also kinda scary sometimes, because jobs that I counted on as steady could disappear in an instant.

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The first December, one of my biggest clients suddenly let me know that they wouldn't need me at all that month. A few days later, another one did the same. Over half of the money I'd been counting on for the month basically evaporated, and I was totally freaking out. 

It's pretty common for freelancers to hit a holiday lull when companies are winding things down for the year, but in my first couple of years I wasn't prepared for it. I ended up doing odd jobs like driving for GrubHub just to get through it. And if I had to do it over, I would save more in the months leading up to the holidays to make sure I'll be OK if my work suddenly dries up.

13. I learned how to start saving for retirement without a 401(k), and I wish I'd found out so much sooner.

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I didn't have much saved in my old 401(k), but as I learned more and more about personal finance, I knew that I needed to figure out how to start saving more for the future without an employer-sponsored plan. Enter the Roth IRA. 

A Roth IRA is an individual retirement account that anyone over 18 with earned income can open. You don't need an employer-sponsored plan to make contributions. I chose this type of retirement account because it offers more flexibility than other options. For example, after you've had it open for five years, you can withdraw money you've contributed before retirement without paying penalties. I love this flexibility because I really want to invest for my future, but I'm also nervous about locking up my funds in case I need it before I'm in my 60s.

One potential downside of the Roth IRA vs. a 401(k) is that the yearly contribution limit is much lower. In 2022, you can contribute up to $6,000 to an IRA if you're under 50. The limit for a 401(k) is $20,500. As someone who was nowhere near maxing out my old 401(k), this wasn't an issue for me, but it's definitely worth considering.

I opened my Roth IRA with Acorns, but many other banks and investment apps offer them too. My only regret is that I didn't do it sooner. I didn't get a job that even offered a 401(k) until I was 27, and I could have started investing so much earlier if I'd known that this was a thing.

14. And I absolutely hated how often I'd find myself chasing clients for late payments.

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My favorite thing about being an employee again is the fact that my paychecks come when they are supposed to — I just love it! It is the biggest relief to know that I have money coming in when I'm counting on it to pay rent, buy food, and just, like, live. And it honestly should be criminal how common it is in the freelance world to have to send countless messages just to get what you're owed. Like, how is this normal?? Working my buns off on a project only to work them off again just trying to get paid was hands down the worst part of freelancing. 

One thing that helped me was cc-ing everyone on my emails and following up persistently. Once a payment was overdue, I'd be sure to include my editor, accounting, and any and all other contacts I had at a company to make sure that I got paid. 

15. However, having multiple sources of income was very, very cool.

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Early in 2020, after a lot of thought, I accepted a full-time role as an employee. But I didn't anticipate how anxiety-provoking it would be to go back to just one source of income, even though it wasn't far from what I'd been making. As a freelancer, I had gotten really good at being resourceful. If something fell through, I had other gigs to rely on and ways of finding more. But with one job, I only have one job — and that kinda freaked me out. I'm OK with it now, but it was definitely an adjustment that I wasn't expecting.

16. Even though there were some things I didn't love about freelancing, ultimately I'm so proud of all the things I accomplished.

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My freelance years were a roller coaster, and one that I wouldn't mind riding again some day. I'm really proud of myself for taking on so many new challenges and learning how to manage myself well. Being your own boss isn't the easiest, but I put in the time to figure out the routines and tools I needed to keep myself on track. For me, it's all about using my planner religiously, taking notes even when I think I don't need to, and knowing my limits — all things that have also been tremendously helpful in this remote work era. 

In the end, my ability to make it as a freelancer was up to me. I did it! And that's something to be proud of.

Have you worked as a freelancer? What did you like or not like about it? Share your experiences in the comments!

And for more stories about work and money, check out the rest of our personal finance posts.