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The Wrong Side of Maybe

We’ve all been there, that murky space where the answer is neither yes nor no. Without a definite answer, you are stuck in a limbo, which is exhausting. I think of it as the wrong side of maybe.

I first noticed this in business. On a sales call, the best answer I can get is “yes.” The second best? “No.” Either one gives me clarity, which allows me to determine the next steps.  But “maybe”? That pulls you into overthinking, second-guessing, planning for both eventualities, and waiting for an answer that may never come.   It doesn’t just happen at work. “Maybe” shows up in all kinds of places: career decisions, relationships, friendships, and even the way we talk to ourselves. It’s that moment when something matters, but we’re not in control of the outcome. And the not-knowing is a burden.

Years ago, I was chasing a big opportunity. All signs pointed to yes, until they didn’t. The client kept pushing things back: a week here, a month there. They wanted revised proposals, said they were “still very interested,” but nothing moved. We continued to invest time and energy, checking our phones for updates that never came. Eventually, they chose another firm.  When I look back at this, I realize we weren’t just on the wrong side of maybe, we set up camp there, hoping the wind would change.

What I’ve learned since is that the longer you stay in “maybe”, the more it drains you. Not just your time or resources, but your focus, your confidence, your momentum. It’s like emotional quicksand; the more you wrestle with it without direction, the deeper you sink.  But here’s the surprising part: “maybe” isn’t always a dead end. Sometimes it’s feedback in disguise, perhaps your pitch isn’t landing, the message is unclear, or your timing is off. Maybe it’s as simple as the situation has changed for the person answering, and they don’t know how to tell you.  If you listen carefully, you may learn exactly where to improve to get the clarity you are looking for.

And sometimes, “maybe” is a test of how resourceful and persistent you’ll be, if you will try a new approach instead of simply repeating the old one in a louder voice. I’ve seen a lukewarm maybe turn into a yes simply because we stayed curious, not desperate. Of course, not all “maybes” are worth chasing. The key is learning to tell the difference between the ones that ask for more and the ones that are quietly telling you it’s time to let go.

So, if you find yourself on the wrong side of maybe, don’t treat it like a wall. Treat it like a mirror. Ask what it’s showing and asking of you, and decide: do you lean in, shift course, or move on? “Maybe” isn’t the end of the story; it’s just a moment during the story.  What you do next with it defines you.

“Indecision is the greatest thief of opportunity.” – Jim Rohn

Ever found yourself stuck in a “maybe”? What did it teach you, or push you to do? Share your story or pass this along to someone who might need a nudge forward.

Have a good weekend.

-Vijay

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