Freelancing Makes You…Cocky?

Those of us who have found success working in freelance writing or freelance anything are bound to have at least a little bit of arrogance. After all, we’re the ones who’ve figured out how to make the system work for us. We’re not cogs in a giant machine anymore – or if we are, it’s by choice. We’re successful business owners. Ah, independence.

Declaring Arrogance

I’ve known it for years, but I’m going to just get it out there in the open. You might consider me stuck up. I’m not conceited about my great beauty. Two kids, thirty-two years and that’s pretty much a write-off. I’m not arrogant about my superior writing ability. I think we can all agree that there are fabulous writers out there who far surpass just about all of us in ability. But I am cocky about my ability to make my career work out the way I want it to, and I think we can all celebrate some variation of that same theme.

Does that make me annoying to others? You might be annoyed reading this, but we’ll get through it together. To the person on the street, I’m just another schlumpy mom with two kids and too little sleep. To the clients online, however, I’ve been around long enough to be a true asset. I can sell myself and I don’t have to lie to do it.

It’s heady stuff demanding hundreds of dollars for my time. The fact that they come back means I’m not the only one who thinks my time is worth that much. As well all know, I’m not the only one able to claim these bragging rights – you are, too. And so is that guy and the one working from home a few houses down the road. It’s a right of well-paid freelancers and small business owners to be just a wee bit arrogant, and surprisingly that bit of cockiness is respected by clients.

Being Loud and Being Proud

There are a few things working against us in the arrogance department, however.

  • The word arrogance has a negative connotation. Haughty, conceited, stuck-up, cocky, etc. All of those are insults.
  • Some people claim women aren’t proud enough of their achievements. If they were, they’d be more competitive in various careers and there wouldn’t be a significant pay gap for the same job between women and men.
  • Humility is a virtue. Okay. It’s hard to get around that one. The exact opposite of arrogance is a good thing, meaning excessive pride is obviously bad. Hmm. But without pride how can you utilize your talents? An argument for another day perhaps.

So what do we do? If you’re uncomfortable being arrogant in your successes, why not use a word with a positive connotation? You can be proud. You can be confident. I dare you to find a distinction between being confident and being arrogant when it comes to self-made success. It’s just splitting hairs.

Demonstrate Confidence

Hairs, definitions and denotations aside, the take away here is simple. Often it’s not your abilities selling your writing services. It’s your confidence. It’s not your amazing grasp of the subjunctive that is going to make clients pay you lots of money to write a blog post. It’s the seemingly arrogant way you carry on discussions of your abilities. You know what to do, and you can explain it to others.

You understand how to be successful. And believe it or not, many client’s greatest desire is a professional who is exactly that – confident, assertive (there’s another good pride word) and independent. A lot of my clients are relieved they don’t have to virtually hold my hand – it’s actually a huge selling point.

Maybe you’re not there yet. Maybe you never have any desire to be so sure of yourself you’re able to argue a rate with a client or let him know when he’s looking at a business idea that needs serious rethought.

You may be disgusted with me for saying arrogance in business is a positive attribute, and I truly think it is so long as you’re not blinded by confidence to your own shortcomings. But I have to wonder if every successful freelancer isn’t proud and confident to the point of arrogance – even if he or she isn’t actually comfortable with it yet.

Profile image for Rebecca Garland
Rebecca is a full-time everything. She teaches English and reading to her much loved, if challenging, high school students during the day and is a freelance education writer in the evenings. With almost ten years in the classroom and advanced degrees in business and information science, Rebecca specializes in materials that inform, educate and entertain. Rebecca indulges herself by pretending to have spare time and writing about the ups and downs of being a freelancing mama whenever she gets a chance.

9 thoughts on “Freelancing Makes You…Cocky?”

  1. Great post ! I needed to read this. Too often I question if I’m doing the right thing in my freelance business. It’s wise to have confidence and let it shine through in your work. 🙂

  2. I agree with you here. Even though I’m still uncomfortable with being proud of my achievements as a freelance writer, I play this card when I’m in negotiations with a potential client. I also do so when a friend is asking me how freelancing is doing for me so far.

  3. I bet you’re a stunner, Rebecca. 🙂

    I think arrogance is almost necessary in this business. If you don’t have confidence (and the backbone to back it up), you’ll be walked on by clients wanting something for nothing. Humility is a virtue, but it’s not a BUSINESS virtue. Humility in a business setting nets you a lot of footprints on your back.

  4. I don’t think arrogance in business is bad at all. And honestly if you can make a career freelancing, you should be cocky – it’s HARD. But what I think is awesome is that I think freelancing really does boost your confidence & I think the opposite is true a lot of times in the corporate world. It’s good that there is an alternative.

  5. Wow! I’d never visited your site before, but this post happened to come up when I was doing a random Google search. I’m so happy I clicked. I’ve struggled with these questions myself. We have a bit in common. I have two kids too, daughters and I’m a paid writer. I don’t know if you’ve had the same struggles, but when I started out, people didn’t trust me and would act incredulous when I told them I worked from home, as a writer. It was almost as if they thought I was doing something illegal or just being lazy. It took about eight months before I started to surprise and impress those around me. It was quite annoying, especially when I felt so accomplished. I hope you don’t mine, but I included a link to this post on my blog and a response. The link to my website is above. I quote you, but no copying, of course. 🙂

  6. I appreciate you, Rebecca! I too struggle with my demeanor when it comes to doing business. I was even told in a recent meeting that because I did not come off as “confident”, my ability to do the job was questionable. But once I got in there and did the work, this same person is now singing my praises.

    I must admit that I do not feel comfortable telling folks how great I am. It’s not me and I don’t think it ever will be. I prefer to let my work speak for itself and to have my praises sang by those I’ve served. However, there is nothing wrong with being confident about what you do. I love my job and I hope that this passion is what translates into more work in the years to come…

  7. Cathy – Hopefully I’m not indited for anything in my cocky nature. LOL

    Alisia – I checked out your blog and it looks good to me!

    It’s comforting to hear that others feel business cockiness is as common as I suspect it is. Perhaps it’s just a byproduct of what we do. 🙂

  8. Good post, Rebecca!

    I think if you are not a little cocky, clients will eat you alive! I have learned that clients who demand too much for too little should be ex-clients. It is OUR business, and one of the great things about freelancing is we can choose to say NO:)

    There are great clients out there who appreciate what we do and will pay us accordingly– and I’ve even had some of the difficult ones come back after disappointing experiences with other “cheaper” writers. They expect to pay well for good quality.

    I’ve done some project management work and been on the client side, and I can tell you there is a huge difference between a writer who knows their value and prices it well, and those “cheap” writers…

    I say call it what you will– cockiness, arrogance, or just plain old confidence– but stick to your guns and do not work for less than you deserve! Ultimately, you will be happier– you will have less work, and get paid more. What could be better than that?


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