The Challenges Of Asking For Help (And What Can Be Done): Demons, Debt, Listening, Action, Importance and Qualifiers.

Asking for help can feel brutally hard. The higher the stakes, the harder it feels.

Why then, when it seems so simple, is it so hard?

When I deconstruct my own experience in asking for help, I’ve noticed a few patterns.


Everyone has demons. Here are some of my “friends” that show up when I need to ask for help:

“They’ll find out I’m a fraud.”

“They’ll think I’m desperate.”

“It’s a waste of their time.”

“I’m not good enough.”

“I should have figured this out for myself by now.”

Regardless of the ask, I find the more important the situation feels to me, the more intensely I experience these.


Debt is another insidious aspect of asking for help – the idea that, even before I ask, I might “owe” this person.

There’s a fascinating book called Debt: The first 5000 years. In it, David Graeber writes about the social and psychological impacts of credit – owing money, favours, work, items to other people.

He writes about the discomfort of obligation that can positively form community relationships or turn sour to toxic behaviour and power dynamics or even the dehumanisation of the debtor.


I remember sitting in a mentor’s meeting room high in Brisbane’s skyline to ask for help with a new business right when COVID had hit. I felt exposed putting the truth of the challenges on the table. My “friends” were out in force.

To sit with these and then actually listen to the advice was hard.

It’s hard to hear uncomfortable feedback, pointing out obvious things I’d overlooked. It’s a struggle to stay quiet and truly listen rather than make myself feel better and smarter by going through all the things I’ve already tried.

I had my notebook and pen ready to go.

I know having an agenda, script and key questions is best practice. But on this occasion I didn’t. I was struggling to even find the right question to ask.

So I needed to be present and stay present to have a chance of hearing what I was looking for.


I’ve been blown away by some of the counsel I’ve received from incredible people by simply asking for their help.

This is where debt plays out. Because if I’m going to ask for help, then I better be ready to do something with it.

This is the hardest part. Because it means I’m going to have to change. I’ll need to do something differently and I know in advance that’ll take effort and energy.

To that end, I try my best to do two things once I’ve asked for help:

  1. Send a thank you email/text/note/gift to the helper. Different scenarios and relationships require different gestures.
  2. Keep the helper in the loop of any progress made on the back of their advice even if it’s a dead end.

I’ve found that if I’m truly willing to do the work, then this is the best way for me to repay the debt and clear the sense of obligation.

It’s also helped me build some amazing relationships.


I’ve been fortunate. I unknowingly stumbled across asking for help a long time ago.

I’m a nerd at heart. In year 12 maths, I asked my teacher if they’d be willing to help me for 20 mins before school. They were. Every week. I put in the work and had my best results.

I had some great water polo coaches throughout my career to the Olympics. Each had strengths and weaknesses. My realization though, was that if I had a specific challenge, then I needed a specific answer.

When I wanted to put on muscle, I didn’t speak to my water polo coach. I spoke to my strength coach, Chris Gaviglio a discus and shot put guy who had put on more weight, faster than anyone else I knew.

When I was excruciatingly nervous before my first world championships in Fukuoka Japan in 2001, I asked my captain, Nathan Thomas how he dealt with it. He’d played Olympics, world championships and professional club competitions internationally. I learned from his pre-game routines.

When I wanted to improve my swimming speed and endurance, I went to train with Shannon Rollason, the coach of Jodie Henry and Alice Mills – some of Australia’s fastest swimmers at the time.

My observation here is that, in each of these examples, there was clear importance for me. Reconnecting to importance is a powerful way to work with the obstacles that stop me asking for help. (You might find this 3 min Momentum exercise useful.)


Asking for help is one of my favourite life/time/productivity hacks.

And sometimes any help is good help.

But not all help is equal. So who should I ask?

Here are my qualifying criteria:

  1. I trust and admire their work.
  2. I trust and admire them as people.
  3. They have already done specifically what I am trying to do.

It’s not about saving an hour here or there. It’s about saving me potentially years to get to the outcome I’m looking for.

It all seems pretty obvious, but being specific about the challenge I face and then finding the specific person best in a position to help me, has accelerated my learning enormously. It would be nearly impossible to quantify how many hours this saved me as a student, athlete, entrepreneur, father, husband – in any role really.

And it’s not always necessary for it to be in person. In fact it can be as simple as finding the book, podcast, video from someone who fits those same criteria then doing the work.

Because now, even knowing the discomfort in advance, I’ve come to realise that for me to make progress, it’s just too important not to ask for help.

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