Forgive me if this already common knowledge or the basis of a book I haven’t read yet.
But this idea for a newsletter came to me on a drive recently and completely took over my brain. It’s all I can think about. So here goes…
The 5 W’s and H (who, what, where, when, why, how) are the six basic questions for gathering information. In the case of you, the creative person reading this newsletter, we use these questions to decide which work we want to take on.
3 of these questions are already answered for us:
Where?
Exactly where you are. The internet is a thing. We can work from anywhere.
When?
Right now. We’re never not looking to take on creative work.
Why?
There’s something in us that yearns to be creative. An itch we’re always trying to scratch.
That leaves three more questions — who, what, and how. And when it comes to creative work, you’ll likely always need to make a choice… which answer do you care about most?
Who?
Who is the client you are working for?
Who are the actual connections (contacts, managers, etc.) to this client you are working with?
Who is the end user/consumer/audience of this work?
What?
What type of work are you doing?
What are the deliverables?
What are you being paid?
How?
How does the work get done?
How smooth or frustrating is the process?
How does your taste affect your ability to enjoy the project?
What each question really means
The “who” questions are, of course, about people.
First, there’s real value in working for big name clients. A photography gig for Nike means a lot more for your portfolio than one for a local mom-and-pop shoe store. This is obvious.
What’s less obvious (and potentially more important) is who are your connections at this client? If you’re doing videos for Snoop Dogg, you aren’t actually working with Snoop Dogg — there’s managers and coordinators and a whole bunch of stakeholders you’re working with in the middle of you and Mr. Dee-Oh-Double-G. Are these people nice? Easy to communicate with? Understanding? Respectful? If it’s a longer-term partnership, do you see yourself being friends with them inside the work and out?
“What” means scope. You can be a “video guy” but is that social video, YouTube, film, commercial, paid ads? Is it one video you’re signing up for, or 100? Are you being paid a number that makes sense?
The scope helps you decide if this is work actually worth doing.
The “how” questions center around the specific emotions that come up within the work. How does the client communicate? Do you align with the style they want? Would you be proud to do this work? Are they asking you to make something you particularly don’t like making (or consuming)?
Simply put, how does this project make you feel?
Who, what, and how carry different levels of importance for different creatives.
Maybe you’ll never make a video for less than $500, or you’ll only edit documentary-style YouTube videos — in these cases, “what” means the most to you.
Maybe you’ll cut a client off the second their work starts to become too annoying, or maybe it’s because their process is super messy and you’re always having to track down the next task — in these cases, the “how” is what drives you.
Or maybe you only take on work with clients who will help your portfolio, or ones who work in a certain industry — if this is you, the “who” is how you make decisions.
My take
I have been all three of these people at different points, but I have my answer now:
Who > what > how.
I find myself to be right where that yellow dot is. Where are you?
To me, the people I work with and for are by far the most important thing in my career.
Not just having big-name clients (though I do love to flex those), but the people I’m actually in the trenches with day-to-day on projects.
(Sorry for the use of ”in the trenches” — mark B5 on your Corporate Bingo sheet and slap me the next time you see me.)
I’m realizing now that I’m willing to give up a lot of the other stuff… as long as I’m working with the right people.
You need this video tonight?
You don’t have the budget right now?
You aren’t sure if you’ll even use this?
No problem! I’m on it.
I’m willing to work on video projects on uncomfortable timelines and budgets because I have extreme belief in the people I’m working with — and because they’re my dawgs.
Part of me wishes I wasn’t wired this way. I’d probably make considerably more money if I only optimized for high-budget clients and tried to squeeze every dollar out of them. I’d also work less and have a bit more peace of mind.
But I find the most joy in doing a good job for the good people I’ve met on this journey — friendly, talented, interesting people who have taken a genuine interest in me… even when they don’t have to.
If I’m being honest, every single career and client decision I’ve made has centered around this. When it’s immediately clear I want to align myself with the person on the other side of the screen, the deal is already done. When it’s not, it gets so much tougher to say yes.
Ben Johnson, the offensive coordinator of OUR Detroit Lions and the hottest name in the upcoming NFL coaching carousel, laid this feeling out perfectly when talking about head coach Dan Campbell in a 2021 Ringer feature:
“He makes it to where you come into work every day and there’s no fear; it’s all love. And as a coach working for him, man, I don’t want to disappoint him. That would crush me. If I knew that I disappointed him … he wouldn’t have to yell. He wouldn’t have to say anything. Just knowing that I let him down would do it.”
Some advice on standards to hold for the “who” part of work:
Could you go bowling together and enjoy it? Self-explanatory.
Do you feel good after talking to them? There are some people who can say and do all of the right things, but still give you an icky feeling. This is okay, but not for too long.
Do you believe them? When you’re planning out your future working with them, can you see it going well? Is their trust there?
Do you speak the same language? Not just English, dummy — are you both embedded in similar aspects of culture & behavior? For example I can talk creators, video, social content, internet culture, marketing, business, sports, music, kindness, anxiety, self-awareness… and it’s a flashing red flag for me when the person on the other side doesn’t get any of these (or isn’t willing to with me).
Would you help them out, even if you didn’t work together? This isn’t a test of your character or “doing the right thing.” It’s important to work with people who have clear talent and bankable skills you can recommend in the future. There’s not many forms of social currency greater than being able to say “I’ve got the perfect person for you.” Red flag if you’re unable to tell what they’re good at by talking to them.
Are you comfortable saying exactly how you feel around them, in all moments? Another self-explanatory one, but potentially the most important. You won't survive in situations where you can’t be your full self.
Last thing… I think the easiest way to find these who give you the warm and fuzzy feeling is to become that person for others. Be present, reliable, consistent and 100% yourself. Take a genuine interest in others, not just what they can do for you. Meet them where they’re at. Help without expectation. Talk about stuff other than the work.
If you look around one day at who you work with and there’s no good people left… you’ve put yourself in a dangerous spot.
But if the people you’re working with light you up, you are richer than you could possibly imagine.
