Should You Be Cocky or Confident in Your Freelance Job Search?

I read somewhere recently that freelancers need to be cocky when looking for work. I’ve been thinking about that statement, and I don’t think that is the case.

When I think if a person who is cocky, it brings to mind someone who is conceited and arrogant, to be sure. This is a person who apparently has no issues with low self-esteem. Instead, they have a greatly exaggerated sense of their own importance.

Did you notice that everything in that description has to do with the person him or herself? This is someone who is definitely embracing the WIIFM (“What’s In It For Me”) mindset.

Now think about what it means to be confident. This second person is self-assured and knows him or herself well enough to understand exactly what traits they bring to the table.

The person in the second example is interested in making a contribution and adding value to the projects he or she takes on. They are ready to roll up their sleeves and get their hands dirty to get the job done.

How does this relate to looking for freelance writing work? When you are talking to a potential client, you need to walk the fine line between being confident in your abilities and sharing information about what the client can expect if they decide to work with you, and coming off as being cocky.

How do you know you’ve stepped over the line? If your focus stops being about the client’s needs and becomes mostly about you, it may be time to reign things in a bit. You can be proud of your work and what you have accomplished without getting it into your head that you are doing your clients a favor by deciding to work with them.

Does being cocky ever pay off when looking for freelance writing jobs?


4 responses
  1. Trish Lambert Avatar

    Very good distinction. Like you, I take issue with advice to be cocky as a freelancer. It is important to be confident and assertive, but not arrogant and demanding. I’ve seen freelancers be very demanding with new clients, as if it’s an honor for the client to be working with them. On the other hand, I’ve seen freelancers turn themselves into doormats for thankless and abusive clients.

    The WIIFM mindset IS important to embrace…but from the CLIENT’S perspective, not our own. Understand that the client is looking from a value perspective, asking what they will get out of working with you, and then color in the picture for them.

    Set boundaries for yourself, and go a long way toward avoiding abusive clients, by having policies in place that you can communicate objectively and up front to new clients–preferably in written form (I use an “engagement memo” to get away from the potentially negative perspective of a “contract”). A client who is worth working for will respect your professional needs as a freelancer and business owner (e.g., minimize business risk by getting a deposit up front, have set “open for business” hours, stipulate that any phone meetings must be made in advance, etc.).

    I love freelancers…and I love seeing freelancers be really successful. Being confident and assertive about the value you bring to the client’s table will get you A LOT farther than being cocky and demanding!

  2. John Avatar

    I think you can do both, but I definitely feel that I err on the side of cockiness. One of my standard subject lines is “Your best [industry] writing candidate today, guaranteed.”

    It opens up a conversation, even from people who told me I was second or third-best. I still got the gigs based on other factors that I brought to the table.

    Perhaps I’m brash, with evidence to back it up. But being cocky has gotten me every gig I’ve had, however.

  3. Jodee Avatar

    @ Trish: Some clients expect writers to be difficult and perhaps that’s why they come off as being abrasive at the beginning. You can’t control how someone else behaves, only your own behavior and keeping it friendly and cooperative will go along way toward smoothing out any rough patches in your working relationship.

    @ John: If the cockiness thing is working for you, then go for it. You are right that the big swagger isn’t enough – you also need to have the writing chops to back up what you are saying.

  4. Debra Stang Avatar

    I think the idea of being “cocky” is part of my problem with marketing myself effectively. I don’t want to sound arrogant. Thanks for the reminder that the emphasis should always be about what’s in it for the client and not the magic tricks the writer can do!

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