The 3 Stages of Success as a Freelance Writer

Note from Jennifer: I’m on vacation this week so I’m sharing one of my favorite posts from five years ago. 

People often judge the success of freelance writers by the amount of money you make. Or the prestige of your clients. But I use another marker: your ability to choose your own clients. And I actually divide my career progression into three phases based on my ability to turn clients down.

Stage 1 of Success: The No A-hole Rule

After a few years of freelancing, I was getting enough decent paying work that I decided I was tired of working with jerks. So I made the “No A-hole Rule” meaning that I would not work with anyone who was an a-hole. I started screening my clients more and the minute I got a gut feeling that client was a jerk, I either didn’t take the project or didn’t work with them again. I wasn’t very good at spotting the jerks from the beginning yet, so this mainly involved not working for clients a second time. I had to drop some clients and turn down a few new clients.

While it seems like a no-brainer to stop working for a-holes, it’s actually a pretty big shift in mentality. It means that you no longer take any high paying client that comes along, but instead actively screen your clients to see if they are a match for you. Most of all, it changes the dynamic from a client interviewing you to a two-way interview/screening process to see if you are a fit for each other. You also have to start actively letting clients go that are not a fit for you, which is another shift in how you run your business.

I let go of a client that was a jerk. And turned down two other potential clients because they made comments during our initial phone call that ranked on my jerk radar. When I began turning down people that were hard to work with, my stress level went down, my productivity went up and my income followed. It was around this time that I broke $50K for the first time. While I think that some of the results were from lower stress, I think a lot of it was because I turned from a freelancer to a business owner by actively accepting and turning down well-paying clients that were not a match for me. 

Stage 2 of Success: Only Working with Nice People

I learned pretty quickly that there is a big gap between not being an a-hole and being a client that I genuinely like. Really big. I got a little more success and higher paying clients, so I took my rule a step further—I decided that I would only work with nice people.

I thought it would hurt my income, but the opposite happened. I made more money. And I was happier. Much happier. I honestly think that this is the biggest reason I broke six figures for the first time in 2015. This one decision changed my entire life and my career.

This meant never taking a client without having a “get to know you” phone call. And it meant turning down well-paying work, sometimes really well-paying. But it was worth it. Originally, I thought it would be hard to tell who was very nice in a 30-minute phone call, but I developed a screening process. If the phone call felt like an interview, then it wasn’t a fit. Even more, if the client didn’t have the time or desire to get on the phone with me before the project, then it wasn’t a fit. But if the conversation flowed naturally and was comfortable then the client passed my “nice” test and I would usually take the project.

Stage 3 of Success: Only Working With Very Nice People

Over the next two years, I started being booked up most of the time and having little availability. I had to say no to potential new clients and referred them to other freelancers. But I realized that I could always find room for a client that I really enjoyed working with to create great content – often by letting another client go. At this point, I decided to get even pickier and I changed my rule to “I only work with very nice people.”

When I tell this to other freelancers, they ask how I can tell if someone is a very nice person. My first answer is that, during the call, I ask myself if this is someone who I would want to go to dinner with if they came to Raleigh on business. If the answer is no, then they probably aren’t going to turn into an anchor client and someone I love working with.

The other way I do this is that I simply tell the potential client my rule during the phone call. If the phone call has been stiff and formal then I don’t even bother because I know that they aren’t a fit. But if it is a comfortable conversation then I simply tell them that I am at the point in my career where I can actively choose my clients and that I only work with very nice people. I explain about the no a-hole rule and then how it turned into the nice people rule and now I am successful enough that I only work with very nice people.

If a client is a good fit for me, then at this point they are usually laughing and always chiming in with “Oh my goodness. I totally agree. Life is too short.” Or even better, “I have the same rule and wanted to talk with you to make sure you were very nice before we hired you.” And if a client doesn’t fit my personality and what I’m looking for, then there is a bit of uncomfortable silence and they don’t know what to say. The conversation usually ends shortly thereafter.

Then throughout the relationship, I keep asking myself if I still think the person is very nice and if they are not, then I finish up the current project and let the client go. It’s not a one-time decision, but something I think about continuously.

Creating Your Own Criteria

Your criteria for who is a nice person and very nice person (I find that the definition of an a-hole is more universal) are likely not exactly the same as mine. It’s more than okay that your criteria for your perfect client looks different. That’s actually the point. You likely have different flags for someone being an a-hole and someone qualifying as very nice. The key is knowing these flags and actively screening your potential clients for those requirements.

If you aren’t at the point of being able to be this picky with your clients, that’s okay. It takes time. To get to this point, you typically need to be established to the point that the majority of your work comes to you instead of you hunting for work. I didn’t get to the third phase overnight, either. It took eight years of freelancing. So if you are still struggling to make ends meet, then start by instituting the no a-hole rule and go from there.

But that’s the important part—starting to screen your clients based on criteria that works for you. I personally consider this the biggest marker of a successful freelancer—not income, not household brands, but the ability to choose your clients.

 

Do you have a “No A-hole” rule already? How can you tell whether a potential client might be an a-hole?

16 Comments

  1. Jessica Brown on May 30, 2018 at 1:43 pm

    Oh gosh, I love the way you think, Jennifer! This is so good. You’re right; life is too short to work with people who stress us out, or even with people who are only moderately nice, haha.



    • Jennifer Goforth Gregory on May 31, 2018 at 7:26 am

      I’m glad you like it! It really has been a game changer for me. I think it’s partly not being stressed but partly because it changed the dynamic of finding clients.



  2. Maria Veres on May 30, 2018 at 2:58 pm

    Great insights, Jennifer. I’m bypassing Stage One (or trying to). I have two side jobs, and I’d rather work more hours at those jobs than take on high-stress freelance clients. I’ve found it’s just not worth the stomachaches. So if my gut tells me it’s not a good fit, I refer the work elsewhere.



    • Jennifer Goforth Gregory on May 31, 2018 at 7:23 am

      Very good point. I totally think bypassing Stage 1 is the perfect plan. I am a huge proponent of trusting your gut. And YEAH!!!! for referring work elsewhere – that is totally awesome.



  3. Lori Ferguson on May 30, 2018 at 3:54 pm

    I, too, operate on the ‘very nice’ rule, Jennifer, though I’m not sure that I’ve ever codified it quite so clearly.

    One thing I look for is a sense of humor. The client doesn’t have to be a stand-up comic, but he/she has to be a *little* loose, because no matter how hard you work or how much you plan, things sometimes go wrong…a source won’t return a call, an interview yields nothing of value, you think a story’s going one way and it goes in the totally opposite direction. Things happen. And you need to be able to laugh about it or at least say candidly, ‘Houston, we have a problem.’ If you can’t have that type of discussion with your client, it’s been my experience that sooner or later you’re gonna hit the wall.

    Plus, this is what I do all day every day. I talk to people and I write. So I want it to be enjoyable as well as productive….



    • Jennifer Goforth Gregory on May 31, 2018 at 7:25 am

      Love that! Me too! I think I’ve written this before, but I look for a well timed cuss word in the opening call by the client. I’ve never once had a client cuss (not vulgar, but funny and appropriate) and not had the client be a perfect fit. I think it shows that they are comfortable with me and they are real. That’s obviously not the magic clue for everyone, but it works for me!



  4. Alma on June 4, 2018 at 2:08 pm

    I actually laughed out loud during the part where you tell potential clients your rule, and the ones who are not a good fit respond with “a bit of uncomfortable silence and they don’t know what to say”. Good for you! I love that you were willing yo turn down clients to get to a place where your productivity actually went up. I hope I get there, too!



  5. Taka on June 18, 2018 at 9:12 am

    I like how you broke it down, Jennifer. Like you say, it takes time to get to that last phase but that’s where you want to be. Let them come to you instead of you begging them to come to you.



  6. Vanessa S. Lewis on May 4, 2023 at 11:43 am

    In every industry I’ve ever worked, nicest people are also the best paying… or is it the other way around? In my experience, once someone says yes to hiring you and signs the contract, if they are paying a high amount, they trust the expert and leave it to them. Has that been your experience?
    Thanks, Vanessa



    • Jennifer Gregory on May 5, 2023 at 12:40 am

      That has been my experience is well. I”m not exactly sure why. But it has been true most of the time.



  7. Mia Taylor on May 4, 2023 at 12:39 pm

    Love this post. Thank you for your honesty, it is so helpful! Would love to hear more details about “how you let a client go” – I have not had the courage to do that yet. Do you email them? do you have a phone call? Do you tell them why you are letting them go? or just say you’re too busy to keep them? Thanks for this great post!



    • Jennifer Gregory on May 5, 2023 at 12:41 am

      This is an upcoming post! How I handle it really depends on the client. I usually tell them why unless they are jerks then it’s just we aren’t a match. I’ll post this one in May!



  8. Lucy Banwell on May 4, 2023 at 12:51 pm

    This is such brilliant advice, Jennifer! I loved reading this. Thanks for pointing me towards it in your email. Such a great reminder. I’m not in a position to pick and choose my clients just yet but I’ll definitely be taking your filters on board. And I have just swapped out one client for a higher paying one so I am putting your advice into practice! The wisdom you share is invaluable and I keep finding myself copying and pasting links to your blogs when I come across a writer looking for advice re landing great clients. Thank you.



    • Jennifer Gregory on May 5, 2023 at 12:43 am

      Thank you so much for the kind words and sharing my advice! That’s great you already dropped a low paying client! That’s the key to success!



  9. Sarah Zimmerman on May 9, 2023 at 7:53 am

    I love this post, Jennifer. Simple and unconventional but very wise advice. I think the jump in self-esteem from saying no to not-nice clients is what helps usher in the better ones. Not to sound too woo-woo, but it’s like the universe can tell that you’ve set really good boundaries, and rewards you for it.



  10. Sophia Auld on May 10, 2023 at 7:18 am

    Great advice as always Jennifer. I remember the first time I let a client go: she was very moody – nice one day and cranky the next. Also not receptive to raising my rates (which were pretty low at the time). It was such a massive relief, and made room for better paying and nicer clients. This is a good reminder to always be reviewing and changing your business as it evolves. Thank you!