11 Career-Defining Questions Every Creative Person with a Job Must Answer

Number one — “Why doesn’t this feel right?”


Tealfeed Guest Blog

3 years ago | 5 min read

If the traffic on Broadway had been moving at all, I would have strongly considered jumping in front of it.

Only 30 days into a new side hustle and I was already a complete failure. Really, it was lucky the iHeartRadio project went so poorly. I learned I am terrible at client work.

I remember standing there, craning my neck to see, if Joe Jonas had taken the stage yet. I refreshed my phone, again and again, waiting for the bomb to drop. A message came through like I knew it would:

“Why isn’t the graphic you made showing up?”

In other words: “where is that thing we paid you to make?”

The real answer was “Well, my card bounced, and anyway I didn’t set the Snapchat geotag up correctly, so the thousands of people here won’t be able to see the project you’ve been promoting all week. ”

I didn’t say that. I ran. They never heard from me again. The business was done before it had even started.

When you alienate a client that big, there’s often no point in going on.

That question — “where is that thing we paid you to make?” — was the first in a series of difficult ones I’ve had to answer throughout my career. In addition to the train wreck of the business above, I’ve also held a seven-year tenure in an office job, written four books (launching three of them entirely on my own), and have done odd creative jobs for as long as I can remember.

The questions asked by bosses, clients, and coworkers have made or broken my career. Answer these questions well, you do well. Answer them poorly, you sink.

That first question is a big one. Here are 10 more you’re sure to face.

Why Doesn’t This Feel Right?

Alternatively, this may come as a command. “Make it feel more energetic.” It’s as if every boss expects you to have a button that says “Add Energy.”

Your career will be made or broken on your ability to translate emotional direction to technical choices. Does “more energetic” mean you need to add blur? Remove it? Should it be a different stock photo? Should the colors be neon? Pastel?

There is usually no clear answer to any of these questions. It depends on the brand or client. If you take the time to understand that, you’ll save yourself months of headaches.

“Why isn’t this more exciting?”

Here’s the answer that you will want to give, but won’t:

“Because so and so executive didn’t let me make it better.”

Sadly, that answer will be true a lot of times. The path to making exciting creative work in a job always leads through an executive. Executives don’t like change. They like results. This is not malice at work. They’re just responsible for the results.

There are two schools of thought when it comes to getting exciting work approved.

  1. Make a wild and crazy first draft, then settle for something a bit less interesting.
  2. Make a boring first draft, and then sneak in fun stuff over time.

The best choice depends on your relationship with the executive in question. Is this a person who will listen to your defense of the fun version? Or is it a person who will dismiss you out of hand? If the former, go nuts early. If the latter, play it safe.

“Can you get along with people?”

Yes, Steve Jobs was a turd to his employees, but he was the owner of the company. Also, he had to constantly watch his back and make sure he held all the power cards at all times. If Apple were Treasure Island, he’d have been Long John Silver, trusting nobody while still trying to keep a ship pointed one direction.

That sounds like a lot of work for me. It’s easier to just smile.

“Did you do what you were asked?”

You’ll bristle at this one. Nobody will even have to ask it outright. Even implied, this question flies straight in the face of an artist’s spirit.

You don’t like to do what you’re told. You like to add your own fire, your own special sauce. Special sauce is fine. It’s good. But only if you’re making the company burger correctly, to begin with.

If you aren’t answering this question well, your talent doesn’t matter.

“Did you come in on budget?”

I once wrote a script for work. It was brilliant. Who cared if it was a short, internal film highlighting product features. We needed helicopters. We needed to rent a red sports car. We needed to collect a permit for a highway in Los Angeles. We needed at least 6 actors.

If this was to be a product video, it’d be the mother of all product videos.

As it turned out, we didn’t need an award-winning video. We needed a good video that stayed on budget. You will be asked the budget question no matter if the check is coming from Disney or your mid-level manager.

“Is what you did worth the money?”

This is why you have to answer the previous question in the first place.

You are probably aware of this, but businesses like to make money. That means if they are spending $1, they usually want to get at least $1 back. The logic of this is not evil. Business keeps people employed and communities thriving. No matter the amount of money involved, the answer to this question matters a great deal.

“Who is this thing for?”

This is the only question on the list you will need to ask AND answer.

Rare are the occasions when you will receive a full, thorough brief with the target audience and goals of your assignment. It’s more likely you will receive a message that says “Hey Sue, we need a video.” Since you love what you do, your first instinct will be to jump into action immediately. Avoid that trap.

When you don’t ask this question, you’ll find yourself doing 17 million final versions, cobbling together edit after edit with a tornado of disorganized files. By the time you name a file “Final_Final_RealFinal_V12_AHHHH,” you’ll wish you’d done the work upfront.

“Did you meet the deadline?”

Creative people have a reputation for being flaky. There’s a reason for this. It’s the reason spawned from 80% of the population saying “I could write a book!” and then never actually doing so. When you are the person who misses the deadline, it sends a domino effect down the line. Depending on the scope of your project, hundreds of people could be affected.

Don’t be that creative. Deadlines are often the only difference between a useful creative person and a disposable creative person.

“Have you ever considered management?”

Okay. Let’s think about this.

Managers get paid more. Why do managers get paid more? Because they are either making decisions or because they are creating a good flow of information. What is required to do those things well? More calls. More meetings. More collecting reports. More research. More data.

A creative person who is promoted to management does less creating. Remember that before you get blinded by the paycheck.

This article was originally published by Todd brison on medium.


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