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3 Questions To Ask Yourself Before Becoming A Freelance Writer

When I first dreamt of becoming a freelance writer, I obsessed over what my day-to-day would look like. Every day I would envision a future version of myself grabbing a giant mug of coffee, heading to my own home office, and filling up my days with hand-picked creative projects. Over time, I pictured this so often that I completely convinced myself that I could do it, and eventually, I did.

Now I make more money than I ever did at my former job (I was a full-time editor at a women’s website, if you’re new here) and I’m happier than ever. I also am fully aware that I didn’t ask myself any of the right questions before transitioning into full-time freelance life. Zero. Not one. Instead of thinking of logistics, I meditated on the fantasy of freelancing — the dream of it, rather than the reality. And don’t get me wrong, full-time freelancing is a dream. I make my own hours, choose my own projects, and have time and energy to focus on the creative endeavors that inspire me. I feel more successful than ever, and in a way that doesn’t tie my personal worth to my title or how many hours I’m working. I feel challenged and balanced. I recommend going freelance to anyone who will listen to me (I made a whole digital course about it, actually).

But freelance life is far from easy. It’s full of hiccups and frustrations just like any other job. The difference is that at the end of the day, freelancing means that you and you alone are in control of your career — not your boss’ boss’ boss or the powers that be or anything else. However, freelancing is easier if you ask yourself a few key questions before you make the plunge. I know that now. So here are the questions that I wish I would have asked myself all those times I was fantasizing about drinking coffee in my home office. Hopefully, they help you on your freelance journey, too.

Are you ready to be rejected? Are you excited to be rejected?

I have a vivid memory of sitting down my second or third month of full-time freelancing and typing and re-typing a pitch email to an editor I’d never spoken to before. I edited the email, re-edited it. I did this again and again. I had spent years yielding pitches as an editor and longer than that writing stories myself. And I was still terrified. I knew that freelancing would involve pitching, and I was ready for that part of things, but I hadn’t prepared myself to be rejected. What’s more, I didn’t know how good rejection could be. OK, let me explain.

When you pitch stories every week, no matter what — when you force yourself to — a few things happen. First, your brain starts to work faster. You become better at brainstorming new ideas for stories (more tips on that here), and doing it at a faster pace. You also become completely unfazed by rejection. Not only that, you become energized by it. Sure, it still stings when an editor doesn’t like my idea or flat-out ignores me, but I always look at that rejection as a two-fold win. Not only did I think of a new idea and put it into words (woo!), but I let myself be vulnerable enough to put it out into the universe. I gave myself the opportunity to get feedback on the idea and if it is ignored/rejected, to pitch it elsewhere in the future. I look at it as doing myself a favor, every time.

Do I still get nervous to send pitches? Sometimes, yes. More often, though, I am excited every time I open myself up to the possibility of being rejected. Once you start to look at things this way, sending pitches becomes more fun. You make more money. You get more creative. You feel better. It all sounds a bit woo-woo but it works, I promise.

Are you ready to earn money on a delay? What’s that delay going to look like?

Before I went full-time freelance, I had had a few freelance pieces published at the same time as I was working full-time — but not enough, which I almost instantly regretted. Because I hadn’t freelanced regularly, I hadn’t yet realized just how delayed my income was going to be when I started freelance writing. Let me break it down for you with an example I use to talk about money + freelancing in Zero To Freelance, my freelancing course.

Let’s say you start full-time freelancing on January 1. You’re excited and ready to go so, on that same day, you start pitching stories. Let’s say you get lucky and have one of your first pitches accepted within the week. By the time you and the editor work out the details of rate and due date, it’s January 7. Your agreed-upon deadline is January 21. By the time you’ve submitted the story and gone through edits, it’s January 25. Maybe you get distracted and don’t send an invoice until January 28. A few days pass after you send it to accounting, and then a new email pops up in your inbox — turns out, you have to do a whole bunch of onboarding with this new publication to get paid. Oh, and the payment time is net-45. When all is said and done, the payment for that story that you first thought of on January 1 won’t hit your bank account until mid-March, maybe — and that’s if there aren’t any delays.

Now imagine this for every single payment. Every single publication. This is why I tell freelancers to overlap freelance content with their current job as much as possible. This way you are getting paid on a rolling basis on that first day you step into full-time freelancing. Now, of course, not every publication pays net-45 (in my experience, 14 or 30 days is more normal), but it’s worth understanding the above scenario before you start your freelancing journey.

How can you use freelancing to supplement other goals, projects, or dreams?

This is a question that isn’t necessary to earning money as a freelance writer, but it’s incredibly helpful for scaling your career and remaining focused while freelancing. When I first started thinking about going freelancing, I had already started thinking about how I could use the experience and insight I had as an editor to create a course for those who want to go full-time freelance and have no idea what it looks like. During every step of my freelance journey, from the very beginning, I had this digital course in mind. This made every roadblock and frustration in my freelancing life seem somehow productive. I asked myself how I could use this experience to build my course, and to help other people avoid similar pitfalls.

Later, when I was more settled in my freelancing career, I started to think how I could use the freedom and flexibility freelancing gave me to explore other passions. So, just because I had always dreamt of it, I started writing a novel. When you design your own workdays, it becomes increasingly easy to re-design them to work for you. To get creative.

The truth is that freelance writing is a lot like other careers in some ways. It can be easy to feel stunted or to feel lost as to how to grow your career if you don’t have a vision. I always tell people to think of how freelance writing can help them pursue other passions or grow their career in other ways. Maybe you’ve always wanted to offer one-on-one consulting to people who are looking to improve their writing skills. Perhaps you want to get into personal blogging. Maybe there’s a digital product you can create that teaches people how to copy write for beauty brands. Perhaps you can use your flexible schedule to create the company you always dreamt of, or write the book you’ve always dreamt of writing.

You don’t have to have answers right this second for any of the above questions (and especially the last one). You don’t have to have your entire career mapped out and know all the ways it will grow and shift in order to be a successful freelancer. You don’t have to anticipate every single roadblock to come, because you can’t. I can’t predict it all, either. What I can tell you, though, is that at its core, a successful freelance career provides you with something that is completely invaluable: Freedom, possibility, and confidence.

Interested in more freelance writing tips, tricks, and inspiration? I’ve got you covered. Click below for more teaching tools and one-on-one consulting options.

Interested in dipping your toe into the world of freelance writing and finally getting paid to write? No idea where to start? My pitching guide, How To Pitch (Your Ass Off), covers all that and more. Learn more here.

Sick of dreaming of a full-time freelance writing career and ready to make it a reality? Ready for a start-to-finish guide on how to create the career you want? My top-to-bottom freelance writing course, Zero To Freelance, shares all that and more. Learn more here.

Looking to schedule a phone call with me and get some advice and direction on all things freelance writing, digital branding, and more? Schedule a one-on-one consulting session here.

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