11 Things No One Tells You About Freelancing

freelancing advice
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Here is what I knew about working as a full-time freelance writer before I actually did it: Yoga pants and working from my bed.

I have a feeling this is the idea that most people have about freelancing — that it’s all slippers, lazy mornings over giant mugs of coffee, and dreamily, blissfully rejecting cubicle life.

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But the thing about working for yourself, whether it be as a writer like me, or as a photographer, crafter, consultant, or whatever else your field might be, is that most of us do it alone, which means there isn’t that much talk about what the life — and the work — is really about.

What the struggles are and, yes, what the non-9-to-5 rewards are. How the finances work, and how the taxes work. How to stay sane when you potentially don’t speak to anyone for eight hours straight.

Here are just a few of the things I learned during the years I was freelancing:

1. It’s a Slow Burn.

When you first quit your full-time job to do your own thing, you’ll probably have one or two clients that help you make it by. Sara Horowitz, founder of the Freelancers Union, calls these your “blue chip” clients — the ones you base your financial portfolio on. You need these clients. However, expanding beyond those clients can be tough and take time.

Know that when you see really successful peers with long lists of previous clients, that making those connections has probably taken months or years. Expect the first few months of freelancing to be, well, pretty lean.

2. You Will Need Seed Money.

Once you do start assembling a client list, freelancing is a death by a thousand paper-cuts/tiny checks. In a recent piece on PTSOTL, Luke O’Neil documented his many clients, and how much each of them pays — which, to people who work on a freelance basis, wasn’t that surprising, but may be a little startling if you’re just starting out.

Working for yourself often feels like a game of gathering, wherein you’re constantly trying to cobble together the money for rent and resources out of small amounts of money…or, often, no money. There will be slow months, and there will be months where you face surprise expenses. For that, you’re going to need to draw on your savings and credit cards.


This is a fact of self-employed life, and you need to be prepared. That’s why I highly recommend getting your start with freelancing while you’re still working your full-time job, so that you can build your side income up as much as possible before leaving your day job.

3. Calendars and Lists Are Crucial.

Seriously, have a calendar. Have three. Have them organized within an inch of their lives. Hold yourselves to them. Because missing one client deadline is possibly excusable, but if you get a reputation for delivering late/incorrect/otherwise unacceptable work, it’ll be hard to shake.

Your calendar serves as a proxy for your brain, where you can dump not only deadlines, but also important information, like who to email and what kind of file they prefer. Apps like Google Calendar, Wunderlist, and Sunrise are your friend.

4. Boldness is a Valuable Commodity.

Self-marketing is hard work, and can include anything from tweeting out your most recent work, to actively approaching the people you want to work with, and directly asking if they have anything for you. Start with this list of all the best freelance jobs that are currently available, and frequently build your list of new potential clients as you go.

Timidity is the difference between successfully self-employed people, and people who sit at home in their jammies “working.”

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5. There are Resources to Help You.

No freelancer is an island, even if they feel like they are. Connect with successful freelancers who are where you envision yourself soon being, and seek to learn from their past successes (and failures).

Resources like the aforementioned Freelancers Union and your local Chamber of Commerce are there to offer you support and community. When you’ve got questions, they’ve got answers.

6. Coworking is an Option.

Coworking spaces like WeWork, where you can rent a small amount of space, or work in a large communal area, with access to the internet, phones, printers, and other business necessities — are cropping up across the country.

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Many creatives find them helpful to both stay focused, and to bounce ideas off others. They can serve as a stand-in for traditional office perks, like having a community and getting some social interaction throughout your day.

On the flip side, co-working spaces can be cost-prohibitive; if the idea of paying a second rent is just too much for your current budget, consider reaching out to other friends or colleagues who you know work for home, and offer to have a co-working “date” at a coffee shop. Not only does this break up the bed-to-desk routine of working from home, but working with friends can also provide valuable creative input.

7. Freelance Taxes Suck!

And finances, generally. But mostly taxes. Oh, freelance taxes. Because we dislike them so much, we put together an in-depth guide for how to do your freelance taxes and recently wrote about all of the best deductions for freelancers.

Most freelancers are contractors, which means they don’t pay taxes as they go, out of their paychecks, but rather quarterly or yearly. Saving money is extremely crucial — which is hard, when you feel like you’re not making enough. Tax prep companies like TurboTax can help offer explicit information on this subject, which you should check out if you’re considering making the switch, though even that can be confusing.

Balancing the books is a really challenging thing for those of us who aren’t financial experts by profession. One of the things I wished I’d had when I was freelancing was someone to explain the financial and technical elements of my small business. Chiefly, I wished I’d known about the Money & Life classes that CreativeLive offers. Courses in QuickBooks, funding, and other resources can be really, really useful.

8. Don’t Neglect Your Physical Health.

When you’re not walking to work (or, really, walking beyond your own apartment), it can be easy to get stuck on a routine that neglects your physical health. Which is unfortunate, because most freelancers and self-employed people have way more flexible schedules that traditional workers — meaning they can hit the gym at unusual times. Take advantage of that 11am Power Yoga class at your gym, or take a jog around the neighborhood while the sidewalks are mostly empty. Even just a long walk can help keep you healthy, while also boosting your creativity.

It’s also a good idea to stock your house with healthy snacks and meals. The temptation to graze while working from home is strong, so set yourself up successful munching. Oh, and figure out your best healthcare option, whether it’s under the ACA or on your significant other’s plan. Just going un-covered is not a good idea.

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9. People Will Want to “Pick Your Brain” a Lot.

Almost everyone has fantasies about working for themselves, which means, once word gets out that you’re doing it, contacts will come out of the woodwork to ask you about it.

And while giving some advice is fine, if you start to get the inkling that the person you’re talking with is trying to get valuable business strategies (or, often, leads and ideas) for free, let them know that your services are available… at a price.

10. Pets Are Both Great and Awful for Productivity.

I have a dog. For a while, during my freelance life, I had two dogs. The regularity of their needs (walking, mostly) was great, because it ensured that I got dressed and left my house and walked around the block three times a day.

However, there were also times when they were exceptionally distracting. You never realize how much your pets demand your attention until you’re home all day and they suddenly think it’s always cuddle-time. Just something to consider.


Seriously, get dressed. Even if you’re not going anywhere. It’s so tempting to live your life in softpants as a freelancer, but getting dressed helps to solidify that your work matters, that you matter. It’s as much a mental exercise as a physical one. Your cat may not care if you’re fully prepared to leave the house, but you will. Get dressed.

What’s your best piece of freelancing advice? Share it in the comments, and let’s help each other.

If you’re ready to start a freelance business, or get serious about growing your existing client base, download our free eBook, The Freelancer’s Roadmap.

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Hanna Brooks Olsen is a writer and editor for CreativeLive, longtime reporter, and the co-founder of Seattlish. Follow her on Twitter at @mshannabrooks or go to her website for more stuff.