Why I Hope You Fail – And Soon


I failed spectacularly!

It sucked!

I really hope you fail too!

In fact, I really hope you’re going to fail soon.

My great wish for you is that you fail a whole load – over and over and over again.

Perhaps you’re looking for the unsubscribe button and thinking – “Ann, you have finally lost it!”

But before you flip away, please watch the video to find out why failure is my greatest wish for you…

You are going to fail!

Recently I did my yacht skipper’s sailing license.

The first week was all the theory and I got reminded that I love to win!

I love to succeed.

I love to do well.

There’s a super needy nerd inside me that craves approval and the best way it knows how is to do well in tests.

My little (actually rather big) success monster got well fed during the theory part as I blitzed my exams and thrived on plotting courses and working out tidal streams.

But then along came the week of practical sailing!!!

I have sailed extensively, but always as crew or doing navigation, and had very little experience handling the boat in and out of moorings and marina and under its engine. To get my skipper’s licence, this had to be mastered.

I had to do it under sail and under motor. Coming in on the port side, coming in on the starboard side, coming in backwards even!

This I found darn quite scary. Manoeuvring this big yacht around with a lot of other yachts around that cost quite a lot of money that I could bash into.

I flashed back to those days of learning how to drive but this time with a much bigger, and way more expensive – yacht.

I was with other learners too, doing their thing and they all just seemed to get it perfectly right -going back and forth in and out of the docks with ease. That made me more tense.

And then my worst nightmare happened. In one particular manoeuvre I managed to come in and spectacularly “F” it up!

Yip, I was getting all nervous and spun the helm the wrong way, resulting in a spectacularly impressive (and loud) crash into the dock.

Boom – the yacht crashed into the dock!

As the marina reverberated with the impact, heads started popping up like ground hogs, over the railings of the other yachts where all the residents and ‘yachties’ were peacefully having their breakfast.

I felt mortified!

I had made a mistake!

I had failed!

Everyone else had succeeded and I hadn’t.

Now here’s my truth.

I felt awful.

For a good day, I sulked and tormented myself.

I berated myself up with choice phrases guaranteed to enhance my worthlessness.

  • “You’re a total mess up, Ann”,
  • “You can’t do this”,
  • “How stupid were you to think you could do this”,
  • ” You should give this up because you obviously don’t have what it takes”

and those are the ones I can include in a blog…

And then I remembered to use one of my super powers.

This is one of the key techniques I know to significantly enhance my overall wealthy life experience.

This is also helping me learn new things, bring more things abundantly into my world, and…

… this is why, I believe, I live such a juicy life…

… because

…I’ve been learned how to fail well.

Do you know how to fail well?

The way to fail well is to wallow.

Dive in and wholeheartedly feel as crappy as you possibly can.

Instead of the taught response to pull yourself out of it by going something along the lines of…

….“ don’t be stupid, “suck it up, everybody fails, it’s part of learning” (which is just another way of making yourself feel wrong because now you are telling yourself you can’t even do failure well,)…

… is acknowledge that it feels crap, it feels shit!

I’ve learned that, instead of going “Come on, Ann, pull yourself towards yourself, get over it”, I must give myself space to feel what I’m feeling.

To acknowledge… “wow, yeah, it does feel crappy!”

The more I’m able to go towards that feeling of failure and be with the stuff that comes up …

…to sit with it and not make the feeling or me, wrong…

…the quicker I’m able to move through it and learn from it and continue with the journey and adventure I am seeking.

Rather than beating myself up and resisting the feeling I most fear (failure) –  which would more than likely make me get off the yacht – I must stay with me and feel crap.


You cannot learn without failing.

You cannot grow without failing.

Your failure might not be as spectacular as smashing a yacht into a dock.

Your failure may be significantly more spectacular.

You might lose some money.

You might have some uncomfortable situations with people.

You might let someone down.

You might disappoint some people.


…only through your failure are you going to experience the life you really yearn for.

For me the greatest tragedy is…

…as adults, we’ve become terrified of making a mistake.

We’ve become terrified of failure and that is why my great hope for you is that you are going to go ahead and fail spectacularly and enjoy it (after you’ve felt crap of course).

Let’s do this..

…Right now, think of something you can go out and consciously fail at?

In the comments below tell me what you’re going to fail at and come back and let me know how it went.

Maybe it’s baking cupcakes that you know are going to flop.

Try something new.

I’ve decided to try teach myself how to crochet. I know I’m going to fail spectacularly.

Maybe for you it’s learning about and getting involved with cryptocurrency. If you haven’t yet watched the free Cryptocurrency Masterclass I’ve created for you, you can get access to it now by clicking on this sentence. 

The point is we learn by taking action.

I’ve now learnt how to be a great yacht skipper by crashing into a dock.

Thanks to my failure I went back out and I practiced over and over and over again and now I can pretty much whip anyone’s ass at docking a yacht. LOL.

I forgave myself, I sat with myself, I held myself, I gave myself the compassion and the love to feel what I was feeling and then I got back up and got out there.

This is my dearest wish for you, that through failure you’re going to realise …

Let yourself fail in your relationships, try something new in your sex life and let yourself be clunky and hideous with it.

WOW – I’ve mentioned sex, money and sailing all in one blog. This could prove to be spectacular or just another awesome failure.

The point is, get out there, experiment, try new things because this is what we’re meant to be doing in this thing called life.

Expand, grow, reach more people and with your failure have massive compassion, which will allow you to journey through it and come out the other side with the extraordinary exhilaration that comes from experiencing and learning something new.

So, until next time, just keep it juicy and keep learning how to get your money and all your resources supporting you to live the richest, juiciest version of your life.

Big love






P.S. That week of sailing also reminded me, once again, just how precious this life is, and how vital it is that we choose to make each moment count.

On a particularly blustery day, sailing in the cold, wild and windy Atlantic ocean off the west coast of South Africa, with gale force winds howling over the icy ocean we spotted a strange orange thing bobbing in the swell and through binoculars realised there was someone sitting on it.

We quickly changed course and ended up rescuing a young guy who had been blow out to sea on a small Halcat which had capsized. He had been in the freezing water for over two hours trying to right his boat and was dangerously close to hypothermia and completely exhausted.

If we hadn’t happened to pass by and hadn’t happened to spot him and hadn’t happened to go over and be prepared to be flexible and change our course… he would now be dead.

This is a photo of him taken three hours later, with him still being warmed up by the emergency heat blanket as we neared a port to drop him and his boat off, which we also managed to save. (you can see the over turned orange hull in the photo being towed.)

Having an empowered and healthy relationship with my money and having it working effectively to meet my various needs goes a massively long way, to enabling me, to be more present and conscious with life, which enables me to really appreciate each precious moment, never knowing when it could be my last.

This is why I am so passionate about you getting to this place too.

This is why I want you experiencing the liberation of money fully supporting you.

This is why I hope you will join me in this commitment to live fully and do whatever it takes to create the environment and financial base to enable you to fail spectacularly and live fully.



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  • Johanna says:

    Before discovering The Wealth Chef, I miserably failed with my finances.I was overwhelmed,but the tide has changed.I am blitzing my debts

  • Beula C Rosin says:

    i recently failed at NOT using my shop account to continue JFDI as I have been going without some needs and a few wants. i have not bought new clothes for many a year, just do with what you have! I was invited to a special friend’s wedding and found myself with out anything to wear for the occasion. JA I used the shopping card to purchase a new dress for the occasion! I it is the most expensive dress I have ever purchased
    but I fell in love with it the minute I saw it. OOps I let some sand fall back into the debt hole I have been so diligently getting out of step by step.
    I did feel bad and even guilty about the dress price. I know this will cost me double with compounding but I learnt it is not the end of the world. It also made me appreciate how free it feels when you can buy an item cash only. What a great free feeling it is to be able to pay cash only. with no anxiety as opposed spending money you don’t have.

  • Rawdené says:

    Dear Ann,

    So true!! I have failed in several areas lately.

  • Nosipho says:

    Helli Ann
    My name is Nosi

    Have joined the conversation

    Yhank you

  • Terry says:

    I’ve failed plenty. Yes I have. I’m still guilty of the not trying things because I don’t want to make a mistake. But, I’ve also tried, and failed, and succeeded. One big failure was losing a business building I bought. It was the building that my retail store was located in, plus it had other spaces. Turned out that it had more issues than anticipated. I couldn’t manage the financial burden of all the repairs plus the payment, taxes, insurance, utilities, etc. That was hard.


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