How To Win At Failing

This week I've been sitting in a big ol' glass case of emotion feeling sorry for myself and my perceived 'failures' over the past couple of months. 

And for anyone who's familiar with wallowing in their own failure based self-pity, you know that shit basically drags up every single record of your failings from birth til now. It's fucking relentlessly brutal.

People often ask me how I get through it. So here you go. This is what works for me, and there's no hard and fast rule to say that it'll work for you, but it's worth trying, right? This whole life thing we're all doing, it's a game! May as well have fun along the way.



A powerful process of self-enquiry is my go-to whenever I start feeling down and out about something. Have you guys ever stopped to realise how many of the beliefs that we have about ourselves are B.S stories that we've actually made up in our own heads?! Seriously, stop and think about that for a long hard minute.

On the topic of self-enquiry, no-one does it better than Byron Katie. I'm a huge fan of her work, aptly titled 'The Work' and the 4 questions she asks herself whenever she's in an emotional shit-spiral. I'll give you a real life example to work with.

The feeling/thought: "I am a failure because my latest program didn't sell any spots"

The 4 questions to ask yourself:

  1. Is it true? With the fire of a thousand suns, YES! (That's my nasty little bruised ego speaking)

  2. Can I absolutely know that it's true? Well......I guess not

  3. How do I react or behave whenever I believe that thought? I get really down on myself, allow negative self-talk to take over, eat un-nutritious foods, stop leaving the house and withdraw from my friends/partner.

  4. Who would I be without that thought? I'd be able to look for the lessons in my perceived failures, I'd be moving forward despite my setbacks and I'd be really positive and inspired and pouring all of that good juju into my other programs.

Want to try it for yourself?

I've created a positive self-enquiry worksheet using the above 4 questions, that you can download for free here.


What if I fail?

What if I succeed? 

What if I do nothing? 

Bet that last one kicked you right in the guts, didn't it?

One thing I always say to people is - if you're not failing at something, you're not playing a big enough game. It really is that simple. I pity the people who spend their lives living within the safety of their comfort zones; I really do. They are usually the people who had their first car bought for them, their first home deposit laid down, and were awarded an 8th place trophy in their year 7 athletics competition by their parents who were never taught that failure is our biggest vehicle for growth. If/when I have kids I am going to make sure they lose with dignity and grace.


figure out what it is you're actually afraid of

Is it the fear of rejection? The fear of looking like a screw-up? Are you still not over that time that your boss at your weekend job at McDonald's at 16 told you off for not putting the burger patty on right and humiliated you in front of that cute girl Sharon who worked on fries? Many people's stories around failure were embedded from a young age; often the result of someone in a deemed position of authority, i.e a parent, teacher or boss, making us feel like we'd messed up profoundly. Don't underestimate the power that this type of emotional 'trauma' can have on the beliefs we grow up to live by. In order to unpick these beliefs, we have to identify them, bit by bit. Once you feel like you have unearthed yours, do the self-enquiry as above. You may never get to the bottom of what your fears mean and where they came from, but that doesn't mean you should stop being curious.


take the opportunity to check yourself

When something 'fails', it's information. We get to take the opportunity and check whether it was aligned in the first place. Did we put the right energy into it, or were we just throwing shit against a wall and hoping it would stick? It goes back to the old adage of 'you get out what you put in' and when it comes to energy, that speaks volumes. 

I didn't sell a single spot on my last group coaching program because I had a shitty energy around it. I assumed that people would find out about the program organically without me having to market it (a serious block of mine that I'm monumentally aware of), and the results delivered a capital F for failure. Except it wasn't a failure to me, it was information. Maybe it wasn't the right timing to be doing the program? Maybe you need a rest? Maybe your energy is needed elsewhere? Maybe your peeps want different content?

A great question to ponder....Based on results, what has this failure told me about myself and how did I contribute to it? That might sting a little but suck it up.


finally, fall in love with the process

Gary Vaynerchuk, someone I look up to and would happily marry in a heartbeat, is a proponent of falling in love with the process. In fact he calls it 'foreplaying his business' because he never wants to get to the climax. He LOVES losing. He froths on it. Watch this vid here,  and this one here to hear Gary's take on failure.


For me personally, it's been a bit of a slow road but I am definitely beginning to love the challenges and opportunities on this journey of self-employment. They say that relationships are your biggest spiritual teacher, but I'd say entrepreneurship is pretty up there. What it comes down to for me is building up an inner resilience, so that I can face whatever life throws at me, and having the self-worth and the belief in myself that I am deserving of good things coming my way. 

Bottomline, the ONLY reason you're scared to fail is because you care about what other people think of you. You care more about what other people think than what you think about yourself. You're prepared to let the ONE life you have to live be dictated by someone else and their perceived opinions of you. When you think about it like that, that's kinda a waste of time, no? 

So what are you waiting for? What's the worst that could happen? Replace your mantra of but what if I fail with but what if I WIN?

If you'd like 1-1 support in this area, because you are looking to launch a new product, a business or a side-hustle, or, you're in total daydream phase and just want to run your wild idea by someone, I'd love to invite you to consider my Ground Up program, which is a 4 week intensive mentorship with me to support you with mindset, systems and getting shit done. 

Love you,

Anna x