Every decision is a trade on problems. But you probably don’t think about it that way.
Most people act like there’s one right answer. One side is a burning path of destruction. The other is a glowing, high-gloss version of life where everything works.
But the truth is, both sides have shit. You have to decide which problems you’re more willing to deal with.
I once spent nearly a year agonizing over whether to change our 401(k) provider. The system we had was clunky and high-maintenance. I had to manually initiate retirement contributions every payroll cycle. One slip and I’m staring down compliance issues and investment delays.
The alternative? A more automated (and cheaper) provider with stricter rules, tighter deadlines, less funding flexibility and a shorter vesting schedule.
Neither was perfect. Each came with its own set of tradeoffs. I had to choose which ones I could live with.
Eventually, I made the switch. The problems didn’t disappear, but I was happier with the new problems. I got back hours of mental bandwidth every month.
People have told me I’m “good” at making decisions. Maybe. (Thank you?) But I think it’s less about being good and more about having a useful lens.
Once I saw that clearly, I stopped chasing “right” and started working in trades. It made everything faster. And a lot more honest.
A Bigger Trade
Switching a 401(k) provider wasn’t going to make or break my business. What if the stakes are higher? Does the framework still apply? Absolutely.
Repositioning my company was one of the most pivotal decisions I made. Four years in, we moved from being a generalist design practice (designing anything for everyone) to a niche firm focused on branding and wayfinding for the built environment. I believed this change would catapult the business, drive revenue, streamline our process and deepen our expertise. There was a lot of upside. But there was also real risk.
One of the biggest consequences of the decision was that we’d eventually have to let go of our largest client—The World Bank Group.
Some clients are minnows. You can afford to lose them. Then there are whales, the clients that account for 35% or more of your revenue and dominate your team’s hours. When a whale leaves, you feel it.
The World Bank was beyond whale status. So we couldn’t just cut ties the moment we repositioned. We had to phase it out which meant preparing for the incoming storm.
We knew revenue would dip. That was expected. We paused hiring, tightened spending and got lean. But the hardest hit was cash flow. The Bank paid every invoice within five business days, like clockwork. That level of predictability is rare and I didn’t realize how much I relied on it until it was gone.
Letting go of that client meant giving up short-term money for a long-term strategy. We knew this going into it, and we hoped the trade would pay off.
And it did.
Within a year of fully repositioning, our RFP win rate jumped from 0% to 90%. We weren’t just showing up as a capable design studio. We were the studio for our niche. Our proposals were sharper. Our pricing was stronger. Profitability was higher. Our work got better because we built deep, focused expertise.
The problems didn’t disappear. There were months we had some serious cash flow shortfalls. So we made adjustments to our onboarding process. Instituted deposit requirements for new clients and 15-day payment terms. We developed workflows to solve our new problems.
It’s true. Some things got harder. But a lot more became clearer.
Make the Trade
I think this is why a lot of people believe I’m “good” at making decisions.I make them quickly and in reality. I’ve taken off the rose-colored glasses and learned to see the truth:
And when you combine that with the fact that most decisions are reversible (a different framework for a different day), you start to realize that there’s no good reason to stay stuck. These guidelines help you move faster. No more delaying and extending the life of a problem you no longer need.
Eventually, you stop asking, “What if it goes wrong?”And start asking, “Can I live with the problems on the other side?”
The power of this framework is that it forces you to consider the trade, not just the upside.
It makes you name the possible problems.
It prepares your mind for consequences and invites you to move anyway.
Make the trade. Move forward.