Unhelpful Advice: A Founder’s Dialogue

Vance MacEwen, Kenneth Wayman

A monkey staring at its reflection in a compact mirror it's holding
Photo by Kolar.io on Unsplash

January 20, 2020

Have you ever received well-meaning advice that was utterly unhelpful?

Kenneth: My favorite? “Be yourself”. I have no idea what that means. Sometimes I get really angry and want to punch someone in the face. Is that the self I should be? Probably not.

Kyle: Well, everybody else is taken, after all. I think “be yourself” is an oversimplification of the fact that you have to be true to your values, your reality, and your circumstances. You have to play the hand you’re dealt as best as you can. The privilege we’re born with, we have to acknowledge. And the disadvantages or rough circumstances we’re saddled with, we’re still responsible for what we do with those circumstances. If we’re all being true to ourselves — we know that we’re flawed, and we still give ourselves the love we deserve — we might be less cruel to each other. But those two words don’t convey all of that without wrapping a big advice sandwich around them.

Kenneth: A lot of advice that people give is profound if you’ve done the work to understand it yourself. But when someone who’s done the work tries to convey that to you, it’s often useless. Your understanding of “be yourself” comes from your having done the work already, not from the advice itself. The process of understanding it is what’s important. Hearing the words doesn’t do it.

Kyle: That’s true. Platitudes can seem almost spitefully useless. It’s almost like you need regular support from people who care about your growth…

Kenneth: What about “do something you’re passionate about”? That’s a useless piece of advice. If I knew what I was passionate about, I’d probably be doing it. I’d probably be happy and wouldn’t need your advice. What if the thing I’m passionate about is like, collecting metal? What am I supposed to do for my day job?

Kyle: …Sell the metal? But then you couldn’t collect it. You know, artists run into that problem all the time. Artists are inherently entrepreneurs. Yet the hardest thing for an artist can be putting a price tag on your work. You run the risk of getting soulless commissions that make you feel like a factory robot. Maybe that’s the code you have to crack: how to monetize your passion without corrupting it.

Kenneth: The question I’d be interested in answering though, is how to figure out what I’m passionate about. That’s what I need. You spend your entire adolescence into adulthood being trained to do what other people tell you to do. Then you exit that system and are told, “Now, do the thing you’ve always wanted to do”. Well, what is that? You had always been told what to do til then. So, you probably just keep doing what you were told, even if you have a hard time getting out of bed in the morning to do it.

Kyle: Okay, so what questions do you ask to figure out what you’re passionate about?

Kenneth: What things makes you not feel pressure? What things do you spontaneously want to do? Do you randomly break into song or write poetry on a whim? If you think you want to be a writer, but you never write anything without being forced to, then it’s probably not your passion. What do you do without being forced?

Kyle: I always liked thinking of the intersection of the things that were easy for me to do, difficult for others to do, and valuable.

Kenneth: That doesn’t work for me at all. It’s too abstract. If I’m going to care about something, I’ve got to care about it in my gut. I can’t just intellectualize a passion out of thin air.

Kyle: Fair. What if you take those things you do feel in your gut and write them all down? Start with those because they’re totally authentic. Then think about how they could be monetized, essentially. And I guarantee all the things you’re passionate about doing are not easy to everybody, and somebody finds them valuable.

Kenneth: It’s a start.

Kyle Vaughan and Kenneth Wayman are the founders of Greatest Possible Good, a design thinking consultancy.

A forked dirt trail in a rich green forest
Photo by Philippe Toupet on Unsplash


Kenneth: I still wonder where you start if you have a hard time even writing that list. What if you’ve never had the chance to do your passion? Actually, I don’t even know if that would be a problem. All you have to do is start.

Kyle: Well, that is a good point. I think a lot of us would get hung up in the idealized version of what a passion should look like. If you do write poetry in your free time, it could be a passion of yours. But your image of a poet- a person who does that passion for a career- might be very different from how you see yourself. You might judge yourself for something you haven’t even taken on yet!

Kenneth: We’re going to stray a little bit if we get into self-judgment. Next time, folks.

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