At one point, she said, “I’m not sure if I should mark ‘meets’ or ‘exceeds expectations.’”

Curious, I asked her to tell me more.

She explained that her boss had clearly laid out what it would take to exceed expectations — and she had done all of it. But she hesitated to claim it because, in her words, “I know I could have done more.”

Our brains are so sneaky, aren’t they?

As we dug deeper, we discovered what was really happening. The salary she was planning to ask for matched what the last person in her role made — someone with more experience who was ultimately let go. The reasoning behind her ask was solid. She had done the work to exceed expectations. She had received specific feedback from the President of her organization that she was “doing far better already than the person who was in the role” and her colleagues backed that up with specifics of how she was doing better yet somewhere inside, she had started second-guessing whether she deserved that same compensation.

That’s when I was reminded of something Rowan Mangan said on the Bewildered podcast she co-hosts with Martha Beck:

“We often protect ourselves from a hypothetical future.”

For most of us, that means preparing for the worst-case scenario.

My client was protecting herself from a hypothetical future in which she didn’t get the raise — shielding herself from potential disappointment.

But here’s the thing:

The word hypothetical means it’s not real. It’s one possible future among many.

What if we spent less time preparing for the worst and a more preparing for the best?

Imagine creating multiple hypothetical futures:

• The one where you put that deposit down on your dream vacation paying for it from the significant raise you deserved and received.
• The one where your boss celebrates your confidence and leadership publicly and you receive it all with grace.
• The one where you realize that acknowledging your own excellence doesn’t mean your bragging. It makes you honest.
• You put “exceeds expectations” and everyone agrees if there had been a rung even higher than exceeds, they would have had you mark that one.

So yes, do whatever you need to do to feel safe about the “worst-case” scenario. But then, come up with at least three more hypothetical futures that are just as possible and a lot more satisfying and exciting.

Because your career doesn’t just exist in the hypothetical land of fear and doubt. It also lives in the hypothetical future of courageous asks, making $ bank, having fun, and shining in your career!