When someone says they want to challenge me, I hear “we want to limit you”

I’m trying to figure out why this is. I think it’s because my life has
been fairly challenging. Whenever I overcome one challenge I usually
come up with another one to conquer in pretty short order. Overall I
think I’ve done alright.

Being challenged is just kind of where I live. So when I hear someone
say they want to give me new challenges what I hear is “I want to
divert you from your challenges to work on ours for a while”.

I suppose this could just be my comfort zone talking. The trouble with
challenges, though, is that they aren’t always worth tackling. My
first full-time job presented me with the “challenge” of getting a
meaningless piece of paper and learning enough buzzwords to advance
into middle management. This was certainly challenging, in that it was
a deeply unappealing task. There was no real payoff to beating it,
though; it wouldn’t have helped me grow in any meaningful way.

Maybe it’s just the implied power differential in the statement. “We’d
like to give you new challenges” has the implication that the speaker
is giving me the opportunity to advance one step closer to his or her
own elevated position. As someone whose greatest successes have almost
always come from routing around established power structures, this
kind of thing tends to ring warning bells for me. Anywhere someone is
erecting a gate in the road there is usually a perfectly unobstructed
footpath a few hundred yards to the left.

…or maybe it’s that “challenge” implies a test; implies
pass-or-fail. And the longer I’m alive the more I realize the best
results are achieved by saying “you’re going to kick ass at this, and
I can’t wait to see it” then by saying “I want to see if you can hack
this or not”.

Or maybe none of that is it. All I know is that I don’t like the phrase.

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