I don’t doubt that you’ve had to ask for tricky things in your life. The sort of requests that you fret over in bed the night before making, the ones with risk attached. Laced with hope.

The ones that will advance your life in the long run but immediately may not show results. The ones that may lead the other person to sense caution.

A loan; a raise; a donation, anything that requires someone to help you out — except for the fact that they haven’t offered to.

But you MUST ask for those things, even if the answer could be no. Where you previously felt fear, you must now feel power. And power alone. You did not come onto this planet to play small.

If it’s scary, good. All the best things in life are scary at first. They’re scary to want; even scarier to pursue.

Here are five reasons why you must always ask for the tricky things.

Always Ask for the Tricky Things

5 Reasons to Always Ask for the Tricky Things

There is freedom waiting for you,
On the breezes of the sky,
And you ask ‘What if I fall?’
Oh, but my darling
What if you fly?

– Erin Hanson

1. If you don’t, you will implode with regret

If you don’t ask, be sure that someone else will – and it will hurt. It will hurt watching another person live out your dream so much more than one meagre rejection might have. Imagine a person on the edge of their seat shaking, begging to ask a question; the only weight holding their arm down being fear. Never be that person. Because there will always be someone more confident in the room ready to ask if you do not. Just ask the question, then move forward with your life regardless.

2. It will give your life motion

Norah Casey, quoting Elbert Hubbard in a TEDx talk, said “The cure for grief is motion.”

My argument is that the cure for anything is motion. The cure for stagnation is motion, the cure for not achieving our goals is motion, the cure for sitting on the couch all day feeling sorry for ourselves is motion. The cure is waking up, getting out of bed, and doing something about it. And, in this circumstance, the cure for wanting to ask for something that scares you — you guessed it — is motion! The motion is asking for that loan anyway; asking for that pay rise anyway; asking if there are any job vacancies at your local restaurant anyway! The formula for motion, inspired by the same-titled book by Susan Jeffers, is to Feel the Fear and Do it Anyway.

3. The answer might be yes

We spend so much time quivering with terror over the worst imaginable outcomes when in fact the response to that tricky request could be YES! Think back to just how long you spent as a child fretting over whether to ask your parents/guardians for pocket money when their answer could only ever be yes or no.

If they said no, the world didn’t end – and if they said yes, you got to have a ball at the bowling alley or cinema with your best friends! Either way, you most likely weren’t disowned there and then just because you asked for money.

The tricky things we have to ask for as adults come with just as simple yes or no responses – we just need to get mindful enough to realize it.

As Seneca phrased it, “We suffer more in imagination than in reality.”

4. You can promise reward – it’s not about never paying it back

You are likely wanting to ask for something tricky – perhaps a donation or loan – because you want to advance your life, and not because you want to blow it all at the casino or on clothes with no intention of ever paying it back. So here is your opportunity to start thinking positively.


Visualize yourself paying back whatever you have borrowed or been donated in abundance, either directly to the person or to an equally worthy cause. Imagine yourself – whether next month or in ten years’ time – giving back. Consider the tricky thing you are asking for not as a one-off payment to get you out of a rut, but instead as rocket fuel to send you up, up and away to the most prosperous future for yourself. This will free you up to feel less guilt about making a tricky request, because you’ll have faith in yourself to someday pay back whatever you owe with generosity.

5. You will live a braver life

Bravery comes from being willing to put yourself in more uncomfortable (but rewarding) situations than the average person daily. It comes from having faced the truly, most likely, worst possible outcome – rejection – and still being able to move forward; to maintain motion.

Nobody else has to think of you as brave. It is an inner-knowing. A knowing that you do not let fear prevent you from advancing in your life; that you will always ask for the tricky things despite the risk of rejection, and that you will always do the scary thing first despite the risk of failure.

Because, in the words of Neil Donald Walsch, “Life begins at the end of your comfort zone.”


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