Category: Careers

When people ask me about why I freelance, I’ve been known to talk about everything except freelancing itself. “I love setting my own schedule,” I’ll say. Or “I don’t have a commute.”

Those things sound great, of course. But they’re the facets of my life outside of freelancing. This comes into focus each March when John and I do our taxes together. I do my taxes four times a year, but spring is the real test of whether I did a good job the rest of the time. And every year, for five years now, turning my records into a tax return is a day-long effort.

I became a freelancer because I love writing, designing websites, and experimenting to create high traffic blogs. I did not become a freelancer because I’m a good boss or bookkeeper. But because this is the career I picked, I have to learn to be better at those things.

My book Otaku Journalism is about the practice of freelance writing (especially for geeks and niche topic specialists). But there are a bunch of freelance aspects that Otaku Journalism doesn’t really cover, the parts of being a freelance writer nobody thinks about.

Over the next few weeks, I’ll be writing a blog series that I hope to turn into a book. Every week I’ll pick a topic about the other side of freelancing that feels timely to me. That’s how I’ll motivate myself to keep going, but it probably won’t be the final order of the chapters.

This post is going to be the table of contents, but the first chapter is already up.

Table of Contents*

• How to do your taxes as a freelancer
• How to establish your freelance business from Day 1
• How to invoice and keep financial records
• My guide to creating a reliable client experience
• Developing a daily routine with structure
• How to adapt and improve your professional skills
• How to market your skills to potential clients
• Networking 101 when you never leave your house
• My guide to taking vacation or sick leave as a freelancer
• How to outsource and work with contract employees
• Metrics to measure your career success

*Want to know about another topic? Email me to suggest it!

Lead photo by Simon Hattinga Verschure on Unsplash

The hardest paycheck you’ll ever make in your freelance business is the first.

Going from $0 to $100 is a lot harder than going from $1,000 to $10,000 because you’re making something out of nothing. It involves a new mindset. When you’re employed by somebody else, your only job is to do well at the assignments you’re given. When you’re self-employed, you suddenly have two jobs: to do good work, and to find work to do in the first place.

If you’re at $0 in your freelance career, I’ve listed a few places you can start your search.

Get the word out

You might already know your first client. The best way to find out is to write an introductory email to your social circle outlining your product or services. Frame it as an announcement: “Friends, I wanted you to be the first to know about my new web design business,” include your new website with a list of ways to work with you, and show people where they can contact you if they or anyone they know might be interested.

This might seem like surprising advice from me considering how outspoken I am against multi-level marketing stuff like Mary Kay. The reason is that they force you to make constant sales pitches to your friends and family in an unnatural (and unfriendly) way. By treating your friends as nothing but marks, eventually you’re going to be left with no friends.

Your friends don’t want to be your regular income stream, but they do want to see your business succeed. That’s why I think one initial email to people who care about you is perfectly fine, and in fact something you’d be remiss not to do. I always ask prospective clients how they heard about me, and some of them are friends of friends, or know one of my college professors, or a previous client suggested they work with me. There’s a world of difference between pitching your social circle just once and endlessly exploiting it, and you’re smart enough to recognize it.

Embrace social media

I started working at the Daily Dot after then-editor Owen Thomas read an article I wrote and offered me a job on Twitter. (This is also a good example of why guest posting works.)

In 2017, I got several clients simply by checking my inbox on LinkedIn. One of my biggest mistakes early on was ignoring LinkedIn because I thought that just because I didn’t have a traditional job, LinkedIn was no longer going to be useful for me. I completely underestimated how many employers use LinkedIn searches to find freelance contractors like me.

Right now, I get the majority of my writing jobs through a Facebook group for freelance writers. My favorite group is women-only, but it can get even more exclusive than that—I’m in groups for just video game writers, or just finance blogs. Editors post what they’re looking for and invite writers to pitch to them. In my experience, this can lead to regular, recurring work.

Join a freelancer community

I joined Solopreneur Circle DC in order to meet “coworkers” and get out of the house. Twice a month, we gather for knowledge sharing and/or brunch. I’ve met business owners who do all kinds of work, from graphic design to real estate to styling hair to styling Instagram photos. Some of them make a lot more money than me, which is highly educational in its own way. All of us have stories about dealing with clients, dealing with taxes, or which bookkeeping software to use, so being in a community has helped me refine my business a lot.

It’s also grown my business through new income. Since we all have different lines of work, it means that we frequently pass clients to one another. I had a web design client who needed a print pamphlet designed, so I forwarded her to one of the entrepreneurs I know. A logo designer was asked if she did website maintenance, and since she didn’t, she recommended that client to me. I still do regular web upkeep for that client today.

Local communities are great because what we have in common is our location instead of our profession. That means I have a local network of business owners who know to recommend me, and I always have a specialist to recommend to clients who want a service I don’t do.

In the meantime: Passive income

Later, when your freelance business has taken off, you’re going to reflect fondly on those days you had so much free time. I think this is the perfect time to work on something that requires a lot of initial unpaid work, but then generates income for years to come. I’m talking products like my Niche Journalism Workbook, or books like Build Your Anime Blog.

The workbook took me a week to build; the book took me two months—and it’s not like that was the only thing I worked on during that time. I didn’t get paid while I wrote either of them, but I still sell copies of both years later. And since both of them include a call to action in the back about other products I sell and other ways to work with me, they sometimes lead to repeat customers who, after reading, decide to work with me as a web designer or copywriter.

Sometimes your passive income product can also serve as a portfolio. If you’re a writer, your ebook can prove your impeccable grammar. If you’re a web designer, a downloadable theme (like my free Asuna) can prove you can actually code. It may feel like you’re doing it for nothing at the time since you’re not getting paid, but it’ll be something you can sell forever.

I started freelancing full time in January 2013. It took until April 2013 for me to be able to pay my bills with it (instead of just drawing from my savings). I know you can turn that $0 into a sustainable source of income. You just need to know where to look.

If you recall last January, I wrote a four-post series on how to choose a topic, write content, and launch a niche blog. This year, I’m resolving to launch six new niche affiliate properties using the step-by-step I wrote myself. It’s simple enough, but last year I didn’t launch even one.

The problem? New business ventures are always a risk. They consist of a lot of work for no immediate reward—and if the idea is a flop, there might never be a reward! It was hard to chase hypotheticals when I had plenty of guaranteed work to focus on. And once I was done with my regular work, I didn’t have the energy or enthusiasm for an additional project.

This year though, I’ve already launched a new property! While working on it, I’ve realized that there are techniques I can use to avoid letting my day job take everything out of me. If you have a goal to launch a side business this year, here are my tips for you:

Build momentum

This month I sat down for a couple of sessions with Google Keyword Planner to launch my latest affiliate site—a new blog that covers a mental health topic. I’d been sitting on this dot com for 10 months with no energy to do anything with it. So what changed? I decided to just get it all out in one or two sittings: a larger than usual amount of work in a short amount of time.

For a while, I’d had “work on the affiliate site” as a permanent item on my daily to-do list, but I never prioritized it. And the longer I let it sit, the easier it was to continue to ignore.

That changed when I was sitting down to make my 2018 goals—and looking at my 2017 goals to see if there was anything to try again this year. I found this site sitting on the list of goals I didn’t reach and realized I was disappointed about that. But instead of moving on, I decided to start working on it right then—while I had my determination to propel me along. That was enough to keep me going for a couple of days until I finished. I do think it is much easier to build momentum for a short while than it is for a year-long goal, which brings me to point two:

Batch your work

The thing I find tough about New Year’s Resolutions that require a daily commitment is that I have to dedicate a bit of my mental energy to thinking about them every single day. I find it’s hard to build momentum over such a long stretch of time (and studies show it’s not just my impression; it takes 1-3 months of intentional behavior change to form a new habit).

So how do you take that short-term emotional momentum and harness it into helping you achieve long-term goals? I suggest batching your work. The same way that it makes more sense to bake an entire batch of cookies on one tray, it’s easier to do a bunch of related tasks on one project all at once, even if it takes more time and effort in the moment.

Dedicating five minutes a day after work to focus on a passion project doesn’t work for me because chipping away at a big task so briefly doesn’t build momentum. Instead, I’m more likely to block off an entire day to get a project out of the way. I really have launched projects like this—Gunpla 101 was the result of one long weekend with zero commitments.

If you’re procrastinating, ask why

Before I put this affiliate property idea back on my to-do list after almost a year, the first thing I asked myself was, “Do I really want to do this? If so, why haven’t I done it yet?”

Sometimes the reason you are procrastinating on a project can tell you a lot about yourself and your values. Some fears can be dismissed, like “I haven’t done this because I am scared,” since anything worth doing is scary. Others are more legitimate like, “I haven’t done this because it’ll just become another crappy job for me to do.”

That was my main concern—I spend so much time on my existing affiliate properties, I was worried about just hiring myself for work I didn’t want to spend my time on. But I rationalized this by realizing that if one of my new properties is a success, I can hire people to write for me like I do with Gunpla 101. For now, I can create a minimum viable product, the bare amount I need to launch, throw it out there and forget about it for a couple of months. Thinking about my passion project as a one-time commitment and not an endless menial job convinced me to finish it.

As a freelancer who gets paid by the task and not the hour, I have more time to work on passion projects than the average person (and therefore far fewer excuses not to work on them). That means my perspective on the topic may be very different from yours. If that’s the case, what helps you stay focused and motivated to work on passion projects? Let me know in the comments.