Five Tips For Freelancing

Starting a freelance business for yourself can be daunting and intimidating—like starting up one of those old timey lawn mowers with the rusty pulley string thing. When it’s all new to you, it’s all frustrating. Even more frustrating is managing multiple clients across multiple countries and time zones all while trying to grow your business. Did you know it’s tomorrow in New Zealand right now?! If you’re company sells calendar software to Kiwis, that could be super important. 

As someone who has spent many years working for a company made up of me, I’ve developed a number of helpful tips to ensure your freelance business operates and grows and to keep yourself sane while doing it.  

1. Make a Routine

When you’re your own boss, it can be tempting to throw the rules out of the window. When there’s no one telling you when to be at your desk, you might start work later and later until you go full vampire. Want to microwave fish in the company kitchen? Once a faux pas, now you can do that crazy thing every day. 

The point is it’s important to develop a daily routine to keep yourself in check. You should designate time every day for work, time for connecting with existing clients, time for looking for new ones, and, most importantly, a time each day when you’re officially off the clock. Starting and maintaining your own business requires a huge amount of time, but it’s important to structure in some time for yourself. It’s better for you, your clients, and your business. And your loved ones might want to see you too, or whatever.

An optional routine tip I have found useful if you work from home is that it’s important to dress like you’re going to work in an office. There’s something about real pants that make me feel more productive than sweatpants. Something about a clean shirt that makes me feel more confident on client calls than my ancient Batman tee full of holes that I have slept in since seventh grade. But again, if you’re most comfortable working in a burlap sack with a rope for a belt, that’s up to you.

2. Become a Black Belt at Collecting

A great baseball player once said, “ninety percent of freelancing is half mental.” Now while that doesn’t make any sense, and maybe is only partly true, what is true is that a large part of many freelance careers is collecting from clients on work done. And you will have to become a pro at it.

Freelance businesses don’t receive a check every two weeks. It’s important to keep very careful bookkeeping records and time-sheets to ensure you know what’s coming in this month and which clients are dragging their feet on payment.

Many larger vendors have policy built into their contract that they don’t have to process invoices for thirty, sixty, or even ninety days (depending on state laws). This can mean that work done today won’t complete payment until the next quarter. It’s important to realize this ahead of time so that your projected income is accurate and you don’t count income that you technically don’t have.

Speaking of income you don’t have, there will come a time in every freelance career where you have to deal with “crud clients.” Now, as the name might suggest, crud clients are not the world’s best clients. They delay payment on work completed. Sometimes they don’t pay at all.  

If a client isn’t paying, it’s important to stick with it. Schedule a time each week to gently remind them that your payment is overdue. While this isn’t glamorous, but it’s part of the job. And whatever you do, don’t call a crud client a “crud client.” That’s not a consumer-facing term.

In the event your crud client is a double-crud client and skips out on the bill entirely, you may need to reach out to an attorney or file a claim in small claims court. Be warned that if that double-crud client is located out of the country, you will have few resources, if any, to remedy this wrong. So tread lightly when accepting work outside the country.

Small business insurance may also be able to help you offset these kind of collection liabilities. Small business insurance like the kind offered by CoverWallet. (That’s right, I saved the hard-sell for once you were already hooked into the article). Moving on…

3. Make Tax-Time, Fun-Time

“Wait,” you say, “taxes can never be fun.” And you’d be right, but it was a catchy title. The point is freelancing has very different considerations when it comes to managing your income than your last job as a telemarketer did. And if you think about taxes ahead of time, your freelance business will operate more smoothly and give your fewer nightmares than that telemarketing job did. Some nights I still wake myself up in a cold sweat trying to sell caller ID to elderly couples.

So that you’re square with Uncle Sam and don’t get hit with a huge payment every April, it’s important to make quarterly income tax estimated payments. That’s why the bookkeeping mentioned earlier is so crucial. Four small payments per year is always better than a giant one right before Easter when you’re going to want to have liquid income around for Easter eggs and chocolate rabbit omelets. (I’m Jewish, so I assume that’s what people do on Easter).

Depending on what kind of freelance business you have, you may want to form a Limited Liability Company. As a sole proprietor of a business, an LLC can potentially offer you better tax breaks, depending on your income and industry. I’m too busy writing about freelancing to evaluate your business, so please go Google “Should I start an LLC,” or go Bing “Why in the world would I use Bing? Is Bing even still a thing?”

My last suggestion for tax-time is best explained with the business mnemonic “A.B.C.”— Always Be Considering retirement. Lame, I know, but aren’t all business mnemonics? Working for yourself requires you to set aside money for when you no longer want to work. Consider an IRA that you contribute to each year. As a business owner, you even have access to this thing called a SEP IRA, bonus amirite? Again, I don’t have time to research this for you, so go Ask Jeeves or the Lycos dog.

4. Networking for Work

The last two tips are pretty straight-forward. When you work for yourself, no one is going to find you more work except you. At least at first. Once you begin getting a stable set of clients and grow a good reputation, you may be able to get your clients to find new clients for you. But you can’t count on that, so that’s why it’s important to find industry events, clubs, conventions and unions to get to know other freelancers in your field.

5. Networking for sanity

Finally, it’s important to network in your industry not just to find work, but to keep yourself sane. Freelancing has many upsides, but one downside of a one-person company is that it can get lonely inside your own head. Make sure to make an effort to meet others in your industry not only to find work but to swap stories and share a beer with someone who knows exactly what you’re going through. You may even meet what psychological and anthropological scientists are calling a “friend.”

Bio: Farley Katz is a freelance writer and cartoonist based in New York. His clients include Esquire, GQ, The New York Times, MAD, Sports Illustrated, and the New Yorker where he’s been a staff cartoonist since 2008.

IG @FarleyKatz



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