«Return to Blog List Being a Successful Freelancer: 25 Things I Learned the Hard Way

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“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!

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

  1. Excellent points, Casey. For #7, I imagine that you limit the impact by obtaining downpayments from your clients. It’s also helpful to retain copyright until you are paid in full.

  2. Casey Hibbard says:

    Hi Susan,

    Yes, good reminder! For brand-new clients, I may get part of the project upfront, but no longer do that with existing clients with a good history of paying on time. And interesting idea to retain copyright and one I had not thought of before. Do you have that in your contracts?

    Thanks for your comment!

  3. Tess Wittler says:

    Thank you for writing this, Casey, at the time you did. It was like you are talking to me! It is so refreshing to hear you say that freelancing really is up and down (#11) and that everyone calls around planned time off (#21). It made me chuckle to know that I am not alone!

    You’ve made so many great reminders in this post that I printed it out and it is hanging front-and-center on my bulletin board. Thanks!

  4. Casey Hibbard says:

    Tess, great to hear it was reassuring. I’m honored that you hung it up! I don’t know what’s going on with #21 but it never fails. And oddly, those are the times when a brand-new client wants to get started after I’ve talked to them for a year or more.

  5. Hi Casey! What caught my eye (in addition to the valuable 25 items) was your statement, “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.”

    Strangely I have experience in both, but from a different angle, on the net. You, or anyone without the initial marketing expertise, may actually have the advantage. No preconceived notions. Sorry, but I’ll say it… “There is no spoon.”

    For me it’s getting past the spoon I know into the realm of “companies versus individuals” (largely) to make a real go of branching out.

    (This may not make a bit of sense to anyone but me.)

    TY for the 25 freelance tips!

  6. Casey Hibbard says:

    Hey Theresa,

    Great insights! I love “There is no spoon.” I imagine past sales experience in another realm could help and hurt in different ways. You get accustomed to doing things a certain way. But maybe you have a little sales confidence going in.

    The only part I don’t understand is the, “companies vs. individuals” you mention. Can you explain?

  7. Abdullah says:

    Hi Casey!
    I found these points very helpful. At first when I start freelancing, there were so many problems I faced. But now I have a very clear idea and management. One thing I want to add that “Continuous Struggle” is the compulsory part for new freelancer.
    Well, this was a very nice post. Points16, 20, 23 and 25 was very helpful for me.

  8. Sandra says:

    Hi Casey,

    I love this so much I printed it and have it hung above my laptop. I think #17 is so simple, yet explains why so many freelancers fail. The lack of planning and then monitoring what’s working and what isn’t to reach one’s goals is probably a big reason why people quit.

    Thanks for sharing this, it certainly puts things into perspective.

  9. Casey Hibbard says:

    Thanks Sandra! I’m honored that you printed it out! I need to do the same because I get off track at times.

    Yeah, it can be so hard to hold yourself accountable as a freelancer. I’m guilty of it too, still. If you have a friend you can share goals with, do so, and keep each other accountable.

    All the best,

  10. Ariel says:

    This is some great info! I also found some more good information and advice at http://www.creativeagencyfreelancing.com/finding-work/what-it-takes-to-be-a-successful-freelancer-part-1