A TaskRabbit, a Dumpster, and an Unexpected Leadership Lesson

This week, I got a small but meaningful reminder about communication, clarity, and leadership — all from a TaskRabbit named Tony.I’d hired Tony to help clean up after a recent move. It was a solid few hours of hauling, breaking down boxes, and wrestling with the cardboard aftermath of city living.

He was focused, friendly, and efficient — the kind of person who clearly wanted to do a good job.As we wrapped up, I pointed to a stack of oversized boxes and casually asked, “Would you mind taking those bigger ones out to the dumpster too?”He smiled and said, “Sure!” And I went back to my day, assuming it was handled.

But just a few minutes later, Tony called out, “Hey Laura — actually, I have to be at another job in five minutes. Is it okay if I come back tomorrow to finish the dumpster run?”And I was genuinely impressed.He could’ve rushed through it and left the job half-done.

He could’ve tried to squeeze it in and ended up late to his next gig. Or worse — he could’ve said nothing, driven off, and left the boxes behind. But he didn’t. He paused. He spoke up. And he handled it clearly and respectfully.That moment stuck with me — not because it was dramatic, but because it was honest.

And in work and leadership, that kind of honesty is surprisingly rare.Most people say yes because they want to be helpful. Because they don’t want to disappoint.

But sometimes that automatic yes leads to unmet expectations, missed deadlines, or avoidable stress. ‍

Tony reminded me that it’s okay to reassess — even after you’ve said yes.