Grow some freelance balls: how I learned to ask questions, push back, and be bold

Image via NEOSiAM 2021

I recently asked a potential client a question which cost me the job.

And you know what? I don’t regret it.

You see, the client in question wasn’t ready to start work with a copywriter just yet. The branding wasn’t in place, and more research was needed.

If I hadn’t pushed back and asked questions, neither the client nor myself would have realised the sheer volume of work still outstanding.

Luckily, my honesty won through, and the client asked if I’d wait for him to get what he needed. He still wanted me because I basically made myself look like the baddest bitch alive.

But things haven’t always been this way. It’s taken me almost four years to grow some balls when it comes to clients.

Having the courage to put my hand up and ask difficult (or stupid) questions has always been a problem for me, and I think I’ve discovered why. Not only that — I’ve found a way to prod myself into putting my hand up when it’s needed.

And today, I’m gonna lay it all bare!

The fear of being ballsy

Until I went freelance, I was bullied by almost every boss I ever had.

Asking questions was an invitation to be humiliated in front of my team, or worse, the whole office. Questioning authority wasn’t a smart move; I had to take what I was given and interpret from there, desperately hoping my creative output was correct.

Early freelance life taught me that asking clients for information they didn’t have could cost me the job; they’d rather ghost than spend time writing a brief.

I also fell victim to smooth talkers and bullshit artists — folk who are remarkably good at avoiding the question or giving a direct answer. To push the point is to be pushy, and no one likes a pushy woman. If you get pushy, you lose the work.

Not ideal, I think we can agree!

This year, I committed to being more forthright, asking questions, and being firm with my boundaries.

And whaddaya know!

Great things happened. I felt more confident in my work, I felt like an equal, and I felt like my expertise was being fairly compensated and respected.

Here’s the secret to my success…

Things that prompt me to be bold

• My business bank account
  I cheat myself out of time and revenue when I don’t have all the facts about the task at hand. It prevents me from allocating proper time to the work or giving a fair quote. If I want to run a profitable business, I need enough info for a decent quote.
  

• Work satisfaction
  I can’t do my job if I don’t have a proper brief. If asking questions or pushing back costs me the work, then the client wasn’t ever going to be a good fit for me. I’ve done myself a favour.
  

• Remembering the nightmare times
  Whenever I’m tempted not to push back on something, I recall the nightmare times of freelance jobs past. Times when I was stuck writing on a job that I hated, with absolutely no idea what I was doing. Times when writing felt like a shot in the dark, which caused me to second guess myself over and over again, adding time and stress to the project.
  

• Reminding myself that someone is paying for this
  Every time I take a freelance job, someone is putting their trust and their money in my hands. If I know I don’t have the information I need or a comfortable grasp on goals and expectations; I need to put my hand up. Without that shit, I can’t do the best job possible, and that’s what a paying client deserves.
  

• Expectation is worse than reality
  I remind myself that the reaction to my question might not be as bad as I anticipate. I recently queried a sketchy deliverable on a brief, thoroughly expecting some kick back. But nope! The client agreed that the deliverable was vague and admitted that it probably fell too far outside my jurisdiction. Flippin’ score!

What gives you the courage to ask questions? Find me on Twitter and give me your tips!