The Stories We Love
I listen to How I Built This a lot. If you haven’t heard it, it’s a podcast where Guy Raz interviews founders about how they built their companies. And there’s a pattern that shows up in almost every episode that I think about constantly.
The founder hits a wall. They make a call that looks wrong to everyone around them, and sometimes even to themselves. They ignore the advice of people who probably know better. They do the thing that doesn’t make sense on paper. And that decision, the one that went against best practices and conventional wisdom, ends up being the turning point that defines the whole company.
Sara Blakely cutting the feet off her pantyhose. Howard Schultz insisting Starbucks should be a “third place” when the business model said just sell beans. James Dyson building over 5,000 failed prototypes when every reasonable person would have moved on. These aren’t stories of people who followed the playbook. They’re stories of people who touched the stove and learned something that couldn’t have been learned any other way.
We glorify these founders. We celebrate their stubbornness, their perseverance, their willingness to ignore the experts and trust their gut. We tell these stories at conferences and in business schools as examples of what it takes to build something great.
There’s a saying in startup culture that a bad decision is better than no decision. I used to think that was reckless. But the more I listen to these stories, the more I realize what it actually means. Momentum teaches you things that planning never will. The founders who build something real aren’t the ones who waited until they had the perfect plan. They’re the ones who moved, got burned, and used that burn to figure out what actually works.
But What if Your Client is a Real Idiot, and You’re the One Standing in the Way?
Here’s where it gets uncomfortable for people like us.
As creative leaders, we’re often the expert in the room. We’re the ones with the taste, the judgment, the pattern recognition. We can see when something isn’t going to work. We’re trained from day one to justify every design decision. Nothing is random, every choice has a rationale. And that’s valuable. That’s what people pay us for.
But what happens when a founder comes to you with one of those decisions? The kind that looks wrong. The kind where your experience and training are screaming that this is a mistake. Do you block it? Do you fight until they come around to your way of thinking? Or do you step back and let them make the call, knowing it might fail?
Because here’s the thing nobody talks about: for every Sara Blakely or Howard Schultz, you were probably the person on the other side of the table. The expert advising against the thing that ended up working. Or advising against the thing that didn’t work, but taught the founder something that no deck, no data, and no amount of expertise could have taught them.
I had this exact situation a few years ago. A client wanted to completely overhaul their visual identity three weeks before a major product launch. New colors, new typography, new direction, the whole thing. I pushed back hard. The timing was terrible, their audience had just started recognizing them, and launching under a brand nobody knew yet was going to create confusion. I laid it all out clearly. My team backed me up.
They heard us, thanked us for the input, and did it anyway.
The launch underperformed. They spent two months rebuilding momentum they’d already had. But that experience did more for our relationship, and for their understanding of how branding actually works, than any of the wins we’d delivered before it. They felt the consequences in a way that no presentation could have communicated. And the next time we worked on a brand transition together, they were a completely different client.
I couldn’t have taught them that. The stove did.
This Is Their Journey
This is the mindset shift that took me years to internalize. When a founder or client makes a decision you disagree with, your instinct is to protect them from themselves. But that instinct, as well-meaning as it is, can cross a line from guiding into gatekeeping without you even noticing.
Founders are supposed to make bold, sometimes crazy decisions. That’s literally what makes them founders. The same stubbornness that drives you nuts as their creative partner is the same quality that got them to build a company in the first place. If you strip that away, if you insist they always follow the safe, expert-approved path, you’re not helping them. You’re flattening the thing that makes them who they are.
“Best practices” feel like the right path. They feel responsible. But best practices are just a consensus of what’s already been done. They’re the average of past successes. And the most interesting things in business, design, and branding almost never come from following the average.
That doesn’t mean every bad decision is secretly genius. Most of the time when something looks like a mistake, it is a mistake. But your job isn’t to prevent every mistake. Your job is to give your best advice, make sure they understand the risks, and then respect that it’s their company and their call.
The Framework: Protect, Warn, or Release
So how do you decide when to fight, when to advise, and when to step back? Here’s how I think about it.
1. Protect: when the damage is irreversible or ethical.
Some decisions you genuinely cannot let slide. If they want to launch something that’s legally problematic, offensive, or going to cause real harm, that’s when you dig in. This isn’t about your creative opinion. This is about preventing genuine damage. Escalate, document, and if they still proceed, consider whether this is a client you should continue working with.
2. Warn: when you have strong evidence it won’t work.
This is the most common scenario. You can see the problem. Your experience tells you how it’s going to play out. But the consequences aren’t catastrophic, they’re costly and frustrating. Give your clearest, most specific recommendation. Not vague pushback like “I don’t think this is the right direction.” Be concrete: “Based on what I’ve seen, this approach is likely to result in X, and here’s why.” Put it in writing. And then, if they still want to proceed, help them execute it as well as possible. A well-executed failure teaches more than a sloppy one.
3. Release: when it’s a matter of taste, or when the failure might be the lesson.
This is the one most creative leaders underuse. Not every disagreement is a hill worth dying on, and some decisions need to be experienced to be understood. If the stakes are manageable and your client has genuine conviction, even if you disagree, let them go for it. You might be wrong. Or you might be right, and they’ll learn something they needed to learn. Either way, you’ve preserved trust for when it really counts.
The hard part is being honest about which category you’re actually in. Most of what we think is “Protect” is really “Warn.” And a lot of what we treat as “Warn” is really “Release.” We just have strong opinions and it’s hard to let go.
Protect Yourself: Document Everything
Regardless of which category you land in, get disciplined about putting your recommendations in writing. A quick email or Slack message before any major decision point. Factual, specific, two minutes of effort.
This does two things. It protects you professionally if the project goes sideways. And it makes the post-failure conversation productive instead of adversarial. You can go back to the documentation together. Not “I told you so,” but “let’s look at what we discussed, what we decided, and what actually happened, so we can figure out what we learned.”
The Conversation After the Stove
This is where the real skill lives. The decision didn’t pan out and now you’re looking at the results together. How you handle this moment defines the relationship.
The goal is not to be right. The goal is to be useful. There’s a version of this conversation where you subtly remind them you warned them, and it feels satisfying for about five seconds before it damages trust permanently. Don’t be that person.
Instead, focus on what you both learned. “The timing issue we flagged played a role. The audience wasn’t ready for the change during the launch window. Now that the launch is behind us, we have a better foundation to revisit the rebrand if you still want to go there.”
What you’re doing is showing them you’re a partner, not a critic. You gave honest advice, respected their decision, and showed up without an agenda when things went wrong.
Think about those HIBT founders again. The ones who made it weren’t the ones who avoided all mistakes. They were the ones who had people around them who helped them learn from the mistakes quickly instead of repeating them. That’s the role you can play. Not the person who prevents every failure, but the person who helps turn each failure into the insight that makes the next decision better.
What to Do This Week
Think about where you’re holding on too tight right now. Is there a client disagreement where you’re fighting for your opinion when the stakes don’t actually justify it? Is there a situation where the “wrong” decision might actually teach something that your “right” recommendation never could?
Pick one of these and try a different approach:
- If you’ve been fighting a small battle, release it. Let them make the call and see what happens.
- If you’ve been giving vague pushback on something bigger, write up a clear, specific recommendation and send it. Put it on the record. Then let go.
- If a past decision already went sideways, reach out and have the learning conversation. No blame, just “what did we learn and how do we use it going forward?”
We spend a lot of time in this profession trying to be right. And being right matters, that’s literally what people hire us for. But the creative leaders who grow the most aren’t the ones who are always right. They’re the ones who understand that sometimes the stove is the teacher, and the best thing you can do is make sure someone’s there to help with the burn.
What’s a time a client ignored your advice and the outcome surprised you, for better or worse? Hit reply, I’d genuinely love to hear the story.
-K
P.S. Share this with any creative leads who take every client disagreement personally. We’ve all been there.
