“We must all suffer from one of two pains: the pain of discipline or the pain of regret. The difference is discipline weighs ounces while regret weighs tons.”

Jim Rohn

Embarking on the quest for clarity in both our work and personal lives often feels like showing up to a costume party on the wrong day—you’re standing there in your elaborate pirate getup, complete with a parrot on your shoulder, only to find everyone else in business casual. Yes, it’s that initial flush of embarrassment when you decide to ask the question that’s been burning in your brain, the one that might as well be, “Excuse me, but can someone tell me why we’re not all dressed like swashbuckling seafarers?”

In the workplace, this moment of bravery—or madness, depending on how you see it—comes when you interrupt a meeting, your voice cutting through the air like a rubber sword at a Renaissance fair. “Sorry to derail, but could we circle back to that acronym you used earlier? My brain keeps interpreting ‘KPI’ as ‘Kangaroo’s Personal Investigator,’ and I’m fairly certain that’s not contributing to my understanding of our quarterly goals.”

The pain of discipline here is akin to the brief discomfort of walking the plank, except instead of a shark-infested ocean below, it’s just a sea of mildly surprised faces of your colleagues. Yet, this fleeting moment of vulnerability is the plank you willingly walk to ensure you’re not just nodding along to the rhythm of corporate speak, only to find yourself lost at sea when it’s time to deliver.

Conversely, the pain of regret in this context is like realizing you’ve been sailing with a map upside down long after you’ve ventured into uncharted waters. It’s the heavy, sinking feeling that comes from pretending to understand, only to botch the job and have to walk back to your team, parrot hanging its head in shame, to admit you were off course.

In our personal lives, the discipline to ask for clarity might make us feel like we’re interrupting a performance to which everyone else knows the script. “Hold the show, please! When you said ‘I’m fine,’ was that with the usual subtext of ‘everything’s peachy,’ or more in the vein of ‘the ship is sinking, but I’m just going to smile and play the violin’?”

Choosing to seek understanding, even at the risk of looking like you’re the only one who didn’t get the memo, is like choosing to don your life jacket even when no one else seems to think the ship is sinking. It’s a little awkward, sure, but it beats the alternative of realizing too late that you’re the only one who didn’t notice the water at your feet.

So, let’s all be a little braver, a little more willing to don our metaphorical pirate hats and ask those crucial questions. After all, it’s better to endure a moment of embarrassment in pursuit of clarity than to suffer the enduring weight of regret for our unasked questions and misunderstandings.

And who knows, your willingness to speak up might just encourage others to hoist their own flags of curiosity, turning what could have been a voyage of confusion into an armada of enlightenment.

Stephen Boudreau serves as VP of Product + Content Marketing at Virtuous Software. For over two decades, he has helped nonprofits leverage the digital space to grow their impact. To that end, Stephen co-founded RaiseDonors, a platform that provides nonprofits with technology and experiences that remove barriers to successful online fundraising. He is an avid (but aging) soccer player, audiobook enthusiast, and the heavily-disputed UNO champion of his household.

Copyright ©2024 Stephen Boudreau.