Hell No or Yeah
As you may or may not be aware, Derek wrote a book called Hell Yeah or No which I think is summarized by: "If you’re not feeling “hell yeah!” then say no".
I do think is is good advice, but not for everyone. Derek admit's this in the podcast:
So I said yes to everything, which is gonna come up later with the “hell yeah or no” thing, but I think it’s a really smart to switch strategies. When you’re earlier in your career I think the best strategy is you just say yes to everything, every piddly little gig, you just never know what are the lottery tickets.
The way Derek tells the story, he was definitely "Hell yeah" on being paid to do music. But he also said yes to everything.
Debbie Millman, in her interview, has a story about saying yes (the following is slightly abridged).
I harbored this hope that maybe I could write for Print magazine one day. A couple of months later, [Joyce] writes me and asks me if I want to participate in something she’s putting together for the upcoming HOW conference the next year in San Diego.
At the time, reality TV had just sort of burgeoned into culture, and there was a very popular TV show called Iron Chef about cooking in real time, and the audience voting. She wanted to do a riff on that called Ironic Chef, where three designers would create work on stage in real time and the audience would vote. This to me sounded like the definition of hell
And I’m afraid to say no. I feel like if I say no, I’m never going to be offered an opportunity to do anything with Joyce again. So, I say yes, and I’m further humiliated when I get to San Diego when I realize that I have to wear a chef’s outfit on stage. There are pictures of this by the way; I’m not lying or exaggerating. So, I go through with this. I’m on stage with the emcee, Steve Heller, who I had never met
He is the judge. I am terribly intimidated because he is Steve Heller, one of the greatest people who has ever lived. And there are three of us. I come in second, which is not terrible. I don’t win but I don’t lose. And in another abhorrent moment of courage, I ask Steve, because he was nice to me that day, if he would like to have lunch in New York City when we were back. He lived in New York City as well. He agrees. We go to lunch.
I had some book ideas. Steve told me they were both bad. I went away a little bit discouraged but still happy that I had met him, and he told me I’d get a book; just be patient. Four months later, a publisher calls at the recommendation of Steven Heller with a book that he had turned down. They had wanted him to write with the horrific title, How to Think Like a Great Graphic Designer. Once again, I think if I don’t say yes to this, I’m never going to be asked for anything again and I take on this book. But I ask them if I can do it in a different way because I didn’t believe there was just one way for a great graphic designer to think.
There are a myriad of ways, and could I interview great graphic designers and reveal how they think? They agreed, and that became my first book. In the meantime, Joyce Redder Kay, the editor of Print magazine, reaches out and asks me if I would like to write a review about Wally Owens’ then upcoming book on branding. I agree. I write my first piece for Print magazine that year, and I’ve written for every single issue since.
If you have opportunity after opportunity coming in, it makes sense to adopt "Hell Yeah or No". But if you are just starting out, saying yes now, even to something that "sounds like the definition of hell" can open up opportunities to fulfill your dreams later.
By saying yes to Ironic Chef, Debbie Millman opened the door to meeting Stven Heller, which opened the door to writing a book, which opened the door to writing for Print magazine, not just once, but for every single issue. Likewise, Derek said yes to doing this "piddling" little show, which opened up all sots of opportunities for him.
I do think there is wisdom in "Hell Yeah or No", but I wonder if the lesson is make your yeses 'Hell Yeah's, rather than "say no to almost everything".