One More Reason People-Pleasing Fails

People-pleasing is a poor life strategy for many reasons – ones covered elsewhere by many people wiser than me. But let’s just do a quick rehearsal:

It projects weakness and invites domineering. It projects unoriginality/uncreativity and invites management. And it puts a locus of control and standards of quality and success wholly in the hands of other people, reducing you to the role of a butler instead of a trader.

But there is another simple, practical reason people-pleasing will betray the hard work of people-pleasers.

Assuming most people have a tendency to people-please (or at least to conform) – and they do – you can assume about most people what is true about yourself. Namely, most people will never have the confidence to tell you what they really want.

Remember the last time you asked for honest feedback and someone told you that you need more work-life balance, or that you should collaborate more with people, or that you should appreciate yourself more? Sort of feels like bullshit, right?

Most people find it hard to take opportunities (even ones handed to them) to truly voice the things they most want or think. I know I do.

Different people are differently comfortable with openly asking for things. Most of them hold back and repress a bit (or a lot) of what they really want, whether from some sense of fair play or from their own desire to please you.

Of course, (as with most people who repress emotions) they become resentful anyways when you fail to meet those unvoiced wants. The unvoiced wants just boil over later. You find out that your roommate expected you to iron his shirts (odd) or that your coworker wanted you to do his TPS reports (whatever the hell those are). Then you the people-pleaser will be shocked and confused. “Didn’t I do everything they wanted?”

So if you’ll never entirely win with doing what people ask for, what is the solution?

Once again, the old Steve Jobs dictum is true: that “customers don’t know what they want until we’ve shown them.”

Your job is still to please people, of course, but it’s not to please people in the incomplete ways they tell you about.

The only way past the resentments and repressions and strange machinations of the human mind is surprise. If you deliver value that people aren’t looking for and didn’t know they wanted, you bypass all of the junk that would be owning you if you were just doing as you were told.

Instead of being ruled by the people you please, throw them a little off-kilter by taking the initiative yourself. You’ll be happier, they’ll be happier, and no one will have to live with the resentment of half-voiced wants and unchosen obligations.

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James Walpole is a writer, startup marketer, intellectual explorer, and perpetual apprentice. He opted out of college to join the Praxis startup apprenticeship program and currently manages marketing and communications at bitcoin payment technology company BitPay. He writes daily at

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