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Why You Should NEVER Ask Yourself, “Should I?”

Eleanor Beaton

Hi Fierce One,

Of all the questions a person can ask herself, the ones most likely to go nowhere fast begin with these two words:

Should I.

Should I have spoken up, or should I have been more patient?

Should I target big, publicly traded companies, or should I target mid-size firms?

Should I confront him about this, or should I keep it bottled up?

The problem with “should I” is that it’s a dead-end, binary question — to answer it, you MUST choose one of two responses:

Yes, I should.


No, I shouldn’t.

If you knew the answer, you wouldn’t need to ask the question in the first place.

To put a finer point on it, when I am in a minion headspace, I ask myself, “should I.” When I am in my queen headspace, I ask myself, “how might I?”

How might I is a non-binary question: it opens the door to exploration, possibility, intuition and deeper wisdom.

How might I confront this person in a way that enhances our relationship?

How might I market my business more effectively?

How might I make the time to write my book?

Stepping into your next level of leadership is not about having faster, more definitive answers. It’s about having deeper, more provocative questions. “How might I,” is a great place to start.

Stay fierce,


PS. We have just released a brand new white paper, 7 Unconventional Strategies to Build Your Personal Brand. You can get your copy here.


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