The Rebel's Guide to Business

This week on the podcast I sat down with Dan Mall, designer, educator, and founder of the design collaborative SuperFriendly, to talk about firing clients, walking away from six figures, and the exercise that tells you when you finally have enough. This post pulls the threads from that conversation I haven't stopped thinking about. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾

Every business owner eventually does a different kind of math on a client. The invoice says one number, and your body says another, and somewhere in the gap between those two numbers lives most of what nobody teaches you about running your own thing. We talk constantly about how to get clients. We almost never talk about the ones we should have let go, or what it actually costs to let them go, or what it costs to keep them. That's the conversation Dan and I ended up having, and it went places I didn't expect.

The $50,000 Dan Left on the Table

Years into running his agency, Dan had a team produce what he called some of the best work he'd ever seen come out of his shop. His art director worked one way, and one way only: a single concept, fully committed. The client loved it. They said it did everything they wanted it to do. Then they asked to see another option anyway, just to know what they might be missing. Dan walked them through the logic: either the second option is worse and you've paid for a downgrade, or it's better and everyone was wrong about the thing you already love. His team stood behind the work, and Dan stood behind his team, and the client asked him directly whether he was really willing to lose the gig over it. He was. They terminated the project at the halfway mark, which meant walking away from roughly $50,000.

The part that stays with me is what happened next. The client called him back, off the record, and told him he wished more people like Dan worked at his company. He'd never seen anybody walk away from a project like that, and it made him want to buy Dan a beer someday and talk about why that kind of backbone is so rare inside his own walls. Dan lost the money and kept something the money couldn't buy back later: a reputation with that exact person for being someone whose yes means yes.

I have my own version of that story. A couple of years ago we had a client whose executive team I genuinely loved. The organization was hungry and curious about the work. But the team we actually had to move through was exhausting, and by the second round of proposal negotiations I told my business partner the truth: the emotional weight of this one client would be equivalent to four clients, and I wasn't trying to have that kind of year. This was a $200,000-plus engagement.

I called their top executive and told them we weren't moving forward, because that client would've been a thief of my joy, and to me there's nothing more offensive than letting someone break your spirit. The executive's response was almost identical to what Dan heard: total respect, more respect than before, and a promise that we'd find a way to work together again. We're still in touch. It was never a burned bridge. It was a boundary, and the right people can tell the difference.

The Cost Is the Point

Dan shared a quote on the episode that I'd put on a billboard if I could.

"It's called values because it costs you something." — Dan

Sometimes the cost is money, like his $50,000. Sometimes the cost is a client relationship. And sometimes the cost of not upholding your values is your self-respect, which is the more expensive invoice even though it never shows up in your books. Dan told a second story that makes the stakes plain: a huge prospective project where every contract revision got worse for his side, and his gut kept saying the sales process was a preview of the next two years. He pulled out. The prospect called him from his kid's baseball game and screamed obscenities at him for a solid thirty seconds before Dan thanked him for everything and hung up. That phone call was the confirmation. That's the person he almost signed a two-year contract with.

We had a signed client once who'd hired us to help them build a more trauma-informed workplace culture, and the people managing the engagement were rude and passive-aggressive in nearly every email. My business partner Alba had me sleep on it, which is her standing prescription for my big feelings. I woke up from some of the best sleep of my life still certain, because I left corporate America precisely so I would never again have to absorb that kind of treatment as a condition of getting paid.

We fired them, offered a full refund, and told them explicitly why, in hopes they'd treat the next consultant better. They never even claimed the refund. I also know we were in a position to say no that not everyone is in, and I don't take that lightly. But the longer I've been out of corporate and the more healing I've done, the less tolerance I have for the things other people have decided are acceptable, and I've stopped apologizing for that.

Courage When You Can't See the Outcome

The firing-clients stories are the dramatic ones, but the quieter thread of this episode was about what courage looks like when there's no clean decision in front of you at all. Dan ran his agency for ten years and shut it down in 2022, partly because he did the math on his own career and figured he had maybe two or three ten-year chunks left, and he didn't want to spend one of them repeating a thing he'd already done, even a good thing.

What makes that genuinely courageous rather than just bold is that he had nothing lined up. Nearly two years later he still describes himself as unsure what the next thing is. For a man who built a career on designing outcomes, he's now waking up every day and doing the work he's committed to without knowing where it leads, trusting that work he finds creative and engaging compounds into something. He said the reward you can access is commensurate with the risk you're willing to carry, and this season of his life is him living that math instead of teaching it.

I know that ambiguity in my bones. Years ago I left a workplace so toxic that it's not on my LinkedIn or my resume, and the exit came with a 60% pay cut. I told a friend I felt like I was moving backwards after working so hard to get somewhere, and she gave me a reframe I've carried ever since: sometimes life pulls you backwards the way a slingshot does, and the pulling is what launches you somewhere new.

That somewhere new turned out to be UX. And in February of 2023, the worst month of my life, another friend sat with me while I cried that I was losing everything, and she told me some seasons are liquidation sales, where everything must go to make room for what's coming. The following year our revenue grew 1,100%. I'm not offering that as toxic positivity, because I have no interest in gaslighting anyone, myself included, into pretending hard things aren't hard. This is something older and sturdier than positivity. It's the decision that even in the middle of suffering, still I will go forward. Still I will do the next thing.

The Permission You're Waiting For

My favorite small moment in the whole conversation was about Dan's therapist. His new assistant was trying to put recurring sessions on the calendar, and his therapist stopped him and said, essentially, you don't work like that. No standing appointment every two weeks. Finish the emotional project she'd assigned him, then come back. He said it broke his brain a little, because isn't therapy supposed to happen on a schedule? Her answer gave him a lens he now applies everywhere: the usual way is just the usual way, and every time he meets one, he asks whether he actually wants to do it that way or whether he has his own way of doing this thing.

So many of us are waiting on permission we only need from ourselves. Dan sees it in the people he mentors, where the blocker is something like needing to form an LLC before making a single sale, and his job becomes externalizing the permission their own inner voice keeps offering and they keep silencing. Go make the sale first. Figure out the LLC after. Your way of building this won't look like everyone else's, and that's not a defect to correct before you're allowed to begin.

What's Your Number?

We closed on the question I ask almost every entrepreneur I work with, and it turned out Dan had written the same word down in his prep notes: enough. Most people who came up through the corporate machine have no idea what enough is for them. You get the promotion and the number moves. You hit a million and now it has to be two. Dan's version of the exercise was to write down the most luxurious life he'd actually want, without the frivolous stuff he doesn't even desire, so no private jets, but yes to rare sneakers quarterly and a few Michelin-star dinners a year.

Then he priced it.

The number came out to $578,000 a year, which is a lot of money and also is not millions, and the moment it became a real number it became something he could design a plan toward. 

Knowing your number changes your pricing too. Dan now has exactly two rates, full price or free, because he's really good at what he does and should be paid really well for it, and being paid well is precisely what gives him the room to gift his work outright when he wants to. Profitable and charitable were never in conflict. And knowing your number changes your definition of success, which for me these days sounds like this: deepening my sense of peace and clarity, food in the fridge, money in the account, going to bed not hating my life. The awards and the bylines are carrots I was handed to chase, and I promise you I won't be clutching them on my deathbed.

Dan has two Rubbermaid containers of awards in his basement from a season when they mattered to him, and he doesn't regret that season, and he also doesn't live there anymore. Sustainable growth starts with knowing the point at which you're already good.

You Don't Have to Endure

If I could hand every listener one thing from this conversation, it's that enduring is not the price of admission. You have options, even when the options cost you something, and especially then. Dan closed by telling me he does organizational trauma consulting for design and product teams, and he's also building an astrology app for pets, because he wants to, and why not. I hope you ask yourself that question more often than you currently do. Why not this? Why not you?

There's a whole follow-up conversation waiting to happen about pricing from your number instead of your fear, and I'm bookmarking it for a future episode.

If you're already in motion, with clients and invoices and the occasional inquiry your gut says no to, our free guide First 10 Discovery Calls will help you fill your pipeline with the ones who deserve a yes.

Originally aired as Episode 5 on the Choose Courage Inc. podcast.