A post-it note-to-self that’s been on my laptop since 2018

Preparing myself to be wrong

james helms
4 min readMay 6, 2021


If you know me, if you’ve seen me speak, if you’ve read some of the other stuff I’ve written — I have a three-word philosophy. How I try to operate, and how I coach others: Humility, Curiosity, Bravery. I believe these behaviors are a path to successful work that matters and grows your career in the process. Recently, I’ve been reflecting on the barriers to these behaviors — because it’s easy to dispense advice and in practice, much trickier to take it. For lots of reasons.

A quick definition check:

Humility, for me, is about embracing the fact that I don’t know it all, that I can be wrong. Identifying my assumptions is a key part of framing what I need to go learn to really understand.

Curiosity, as I like to say, is something you DO. It’s not wondering at your desk. It’s actively learning by doing. By going there. By asking questions — sometimes the dumbest questions. It’s getting beyond your assumptions with experiments.

Bravery is tied to the other two. It’s being unafraid to be wrong. It’s being unafraid to experiment and fail. It’s being unafraid to look a little stupid in pursuit of getting smarter. It’s aiming impossibly high.

What I have learned is that humility, curiosity, and bravery can be privileged luxuries. For example, humility requires self-confidence and self-awareness. Curiosity requires psychological safety. Bravery requires trust and empowerment. It’s very hard to stretch your muscles of inquiry, experimentation, and risk-taking if you’ve experienced patterns of being judged, treated differently, patronized, dismissed, or outright attacked. We develop armor, defense mechanisms, and visceral responses to protect us from a world that can be unforgiving. And it’s easy to say “take a risk” when you have a pretty tightly knit societal safety net. Privilege in the form of time, money, a network, the generosity and benevolence of others, a second chance etc. It’s much harder to take risks when, historically, people have let you fall flat on your face and blamed you for being unreasonable, emotional, stupid, naive, over your head, or reckless. For not working hard enough. For taking yourself too seriously.

I have a privileged viewpoint. I am wildly appreciative of my patient friends and colleagues who stood quietly beside me as I fell flat on my face and resisted the temptation to give it me as it’s been given to them. They are better humans for it and I am grateful. And as I’ve learned — privilege can be a platform. Awareness of the psychological safety it provides me is a chance to take more risks on behalf of others.

Be ready to be wrong. I can afford it — the financial cost and the potential cost to my credibility and organizational capital. In fact, if there’s anything my organizational capital is good for — it’s creating space for my team to take risks: bold experiments, a “less-than qualified” hire (a myth grounded, many times, in bias and fear). Not every risk pays off. Sometimes we have to walk them back. The same could be said for “more qualified” candidates. As leaders, we need to learn to take risks on behalf of those who can't afford to. Air cover comes in many forms: psychological safety, coaching, grace, and kindness.

Being wrong is learning. As long as your risks are framed with hypotheses and measurable targets. And as long as you are intent on measuring these experiments — you can afford to be wrong. In fact, you can’t afford to be wrong and not know it. Learning you are wrong is a huge moment that makes you better and improves outcomes.

Learning you are wrong is a busted assumption. Facts. Opinions. Guesses. FOG! Clearing the fog is a full-time job. In your work and in your life. Designing risky experiments to tackle your most pivotal assumptions is valuable to your job AND your life. So by virtue of what you might learn, the risk all can be quite relative. The data you uncover could be life-changing. For you and for someone who needs you to take a chance on them.

Being wrong requires change. Learning you are wrong should be a forcing function of improving. Sometimes that means confronting years of faulty decision-making. Sometimes it means apologies and amends. Sometimes it requires confronting things about yourself that you don’t like and would prefer not to have known. Pleading ignorance, or barreling ahead despite information that tells you to do otherwise is the definition of irresponsible. Take responsibility. It’s the quickest path back to being productive, being part of the solution.

I still believe that Humility, Curiosity, and Bravery are the keys to unleashing value in your work and in your life. I still believe that well-calculated risks with an intent to learn yield the best learning and can foster the most transformational change. Sometimes being wrong is the best kind of right. But I also see that we aren't all playing by the same rules. And as someone with a particular kind of advantage, I have an opportunity to create a more forgiving space for others to take risks, learn and act in ways that have an impact that likely could be much more important than mine.



james helms

Design Leader, Advisor, Speaker, Student, Advocate, Enabler.