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Being a Successful Freelancer: 25 Things I Learned the Hard Way


“If it was easy, everyone would do it.”


I’m not sure who said that, but file it under quotes that are wise, but still hard to accept. It’s absolutely true for freelancing. It’s not an easy road, but it gets easier over time. Like many things, the beginning is the hardest.


If you’ve ever started an exercise routine, you know it’s rough at the start. You’re out of shape and out of the habit of working out. It can feel like torture. But you get stronger and more disciplined and it feels so much easier – and you start to notice the payoff. Freelancing is no different.


Know this: If I can do it, you can do it. When I started, I didn’t have any special edge. I had writing skills, but I didn’t have a sales bone in my body. At the time, there were a few helpful books on the topic (Bob Bly and Peter Bowerman), but much of what I learned came from experience.


Fifteen years after going solo, I'm in a much better place. Unfortunately I learned nearly everything below the hard way:


1.      Always be marketing. Even when business is good. It can be hard to find the time but keep doing it. Build in some regular marketing in your schedule. Otherwise your pipeline dries up and you’ll hit more “famine” periods.


2.      Prospects rarely need you when you contact them. Just because you reach out to a prospect that seems perfect, that doesn’t mean they need your help now. But they might need you down the road. A “no” often means “not right now.”


3.      People forget about you if you don’t contact them regularly. Regular contact gets business.


4.      Raise rates regularly. Employees get regular raises for cost of living increases, and so should you. When you start a client at a certain rate, don’t keep them there forever. Establish a schedule – such as annually – for increasing rates. And then simply let clients know when you start a new project what the new rate is and that you’re raising your rates to account for normal inflation.


5.      You know more than most clients – about writing projects. You’re a professional writer. Your clients are not. They know their subject matter but rely on you for writing expertise. Be confident in your abilities.


6.      Be willing to take less-than-ideal projects early on. As with anything, you have to put in your time to build your income and experience. You can specialize from the beginning but don’t be TOO narrow at first. Don’t be too choosey early on either.


7.      Clients can take a while to pay. Know that clients can take a while to pay. Set your terms, such as “net 30,” but know clients do what they want. Include a penalty on the bottom of your invoices that says you charge a 1.5% late fee (or other fee) each month that the payment is late. Then send friendly reminder invoices when an invoice is past due.


8.      Don’t panic if a project seems too hard at first. Ask questions, get information, take notes, record interviews, and again, ask questions! They can’t expect you to be a subject matter expert on their products and services but you can learn quickly.


9.      Be detail oriented. Care about everything you deliver to a client.


10.   There’s plenty of work to go around. This is true, though it may not feel like it now. There are lots of writers out there but there are more companies that need help. Capitalize on the type of writing and subject matter you do best and those companies will be drawn to you.


11.   Freelancing is up and down. Everyone calls at once and stops calling at once! You can’t control your workload, unfortunately. Be ready for the feast when it comes, and then use the famine times to market yourself, and get organized and ready for the next feast.


12.   Use downtime to write – for yourself. During slower times, you should always amp up your marketing and sales efforts. Do what you do best, writing. Write articles, guest blog posts, etc. to get your name out there.


13.   Be disciplined. Set a marketing and writing schedule and stick to it.


14.   Paychecks are fixed (i.e. limited) but there's no limit with freelancing. It’s tough to think about it this way when coming off a paycheck, but being on 100% commission actually gives you the potential to earn more. And you give yourself raises with rate increases.


15.   People perceive you as less qualified if you charge too little. If a product like a cell phone or computer is a lot less than another one, don’t you wonder why? We assume that less expensive usually means less quality. Clients have the same reaction.


16.   Confidence sells. State your rates and be confident you’re worth what you charge.


17.   Set goals and check in on them regularly. Along with the discipline tip above, it’s more important than ever to set goals. By when will you finish your buzz piece? How much money do you want to make per month? How many projects do you need to get there?


18.   Referrals are not automatic sales. When a contact or client sends a potential client your way, don’t assume it’s a sale. Follow the same process with the same professionalism you always do. You still need to impress.


19.   You can’t control parts of the case study project. You can’t control how much time clients take to review a story or the time for end customer review and approval. Invoice after the first draft is delivered but stay engaged and committed to the project for as long as it takes to complete, even well after you’ve been paid.


20.   Don’t take lack of response personally. Just because someone doesn’t get back to you after you talk or send a proposal doesn’t mean they aren’t interested. People get busy, go on vacation, or other priorities come up. Follow up every so often.


21.   Everyone calls the day before you leave or while you’re on vacation (including the week of Christmas/New Year’s). You’ll notice the pattern once you’ve been freelancing for a while.


22.   Be a partner, not a sales person. Prospects don’t want to be sold. They want someone who will partner with them to achieve their goals. Always be thinking about how you can be that partner.


23.   Don’t be scared by clients with technical subject matter, especially if the end audience is business decision-makers. You don’t have to understand the bits and bytes behind technology if you’re only writing about the business impact and benefits. Ask your client about the audience before making decisions about projects.


24.   Partner with other writers. Find other writers that don’t write the same things or serve the same audience as you. Get to know each other’s strengths and refer leads back and forth. I do this with all types of writers.


25.   You are your own boss. When you feel like you have the freedom, don’t work with clients that are disrespectful of you or your time. It’s not worth it. There are better clients out there.


Happy Freelancing!


Want to add customer case studies to your menu of freelance writing services?

Get mad skills by spring in this new course for emerging case study writers: The Case Study Writer’s Mad Skills Crash Course. In this 7- week online course, learn from-the-trenches tips from Casey Hibbard. Armed with skills and best practices, you can confidently approach clients and win more projects – helping you break into this lucrative field. Grab early-bird pricing until Feb. 28.

Learn more.


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More Stories By Casey Hibbard

Casey Hibbard is the founder and president of Compelling Cases, Inc. and author of "Stories That Sell: Turn Satisfied Customers into Your Most Powerful Sales & Marketing Asset." She has helped dozens of companies create and manage nearly 500 customer case studies and success stories over the past decade. Casey is featured in numerous books, articles, and teleclasses. She consults with organizations one-on-one and conducts online customer-story classes.

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