What I Wish I’d Known About Being a Writer

This post was previously published on my blog, Caroline in the City but has been updated.

The saying goes that hindsight is 20/20. But as I approach my ninth tenth year as a freelancer, and third as a full-time writer, there are a few things I wish I’d known before starting down this path. I hope these lessons keep you from making the same mistakes I did!

How to Invoice and Manage Expenses

Why is it that every journalism major has to take media law but there aren’t any classes about managing your finances as a freelancer? This has been the hardest part to learn, but thankfully I had some idea of what to do since my dad works for himself.

The short answer is to keep track of everything you spend that is considered a “business expense” and keep a separate bank account (mine is a PayPal business account). There are a number of apps that scan your receipts, but I keep them and add to a spreadsheet at the end of the year. This includes the monthly fee for my co-working space, professional courses, and equipment like my new computer. It makes it easier come tax season.

In addition to a separate bank account, I recommend also setting up some sort of retirement account since you won’t have one from an employer. I’ve also only recently set up an IRA. We are pretty screwed when it comes to health insurance in the United States, but hopefully that will improve at some point. Expect to pay more for less coverage for the next few years and have a cushion just in case something happens.

Feedback is Essential

Criticism is definitely hard to hear, but is an important part of being a freelance writer. It’s not for everyone. What is even more frustrating, however, is no feedback at all. How are you supposed to improve or know what to do better for next time if an editor makes changes without telling you?

So I wish I had taken charge in seeking it. These days, I ask editors what they want specifically when it comes to pitches and stories.

Everything is Open to Negotiation

I’ve only recently started negotiating better pay for my work after a few times getting burned with extra tasks like sourcing photos. Sometimes the editor really is providing you with their best and final offer, but it never hurts to ask if they have an additional budget for short turnaround work or extra edits. I generally calculate if it is worth my time based on how long it would take to write it. I might charge more for a shorter piece that requires a lot more front-end research than a longer blog post I can write in an hour.

Time Loses All Meaning

Most “normal” jobs are paying you for the time you’re at work whether you’re actually working or not. When you’re a freelancer, the majority of your day is spent doing things that don’t directly contribute to your bank account. That might include sending out pitches, following up to emails, and researching outlets to pitch. The $500 I got paid for a story doesn’t cover the time it took to track down the photos or harass the editor into sending my check on time. That’s why so many of us have to take on side hustles and still end up working over 40 hours a week.

You Are In Charge of Your Rewards

In traditional jobs, there’s someone there, a boss or manager, to tell you when you’re doing a good job and reward you with bonuses and praise. The self employed rarely, if ever, hear such things. It’s up to you to provide your own praise and celebrations. It goes hand in hand with self care.

When you’ve finished up a big project, treat yourself with a day at the spa or a nice dinner out. At the end of my book writing process, I had a splurge-worthy treatment at a spa in Atlanta. It’s also important to get outside every now and then as well, so take the chance to go for a walk during the day.

Tools I’ve Found to Be Helpful

• Trello– I have boards for each of my blogs as well as freelance clients and can set due dates and reminders. They also have a calendar function to give you a glance at upcoming deadlines.
• Google Drive– I keep all of my files on here to easily share with clients, keep in folders with photos, and it doesn’t bog down my laptop. I also have a spreadsheet of every pitch I send, when I invoiced, and the link when the story is live.
• Hubspot– I downloaded the software so that I can at least know my email has been read by an editor (or finance department when I’m trying to get paid).
• Hunter– This website allows you to look up editorial contacts that can be found online. For example, you can search for the New York Times and if you know the editor’s name, cross reference it to find the right format.
• NeuYear Calendar and At-A-Glance Planning Notebook– These are two items I purchase year after year because they make my business run smoothly. The NeuYear calendar allows me to see my travels and deadlines for the entire year. After a few other brands, I’ve settled on At-A-Glance for its full pages for the day and calendar pages at the back.
• Unroll.Me– If you aren’t using this, you should be! It allows you to combine all of your pre-selected email subscriptions, like shopping-related emails, into one digest, saving you valuable time scanning through your inbox. You can also quickly unsubscribe from mailing lists you don’t want to be on.