Where would your life be if you had been that tiny bit braver and less worried about failing? If you had had the conversations you needed to have? And taken the steps you needed to take? What has the fear of failure stopped you from even starting?

An amazing week of personal success and Covid-19 recovery (my 98-year old grandma is a legend!) has had me thinking a lot about success and the fear of failure. In light of this, today’s episode takes you through the ‘And Then What Process’. It’s a technique I talk about in my new book Deep Grooves: Overcoming patterns that keep you stuck. It’s unbelievably simple, but it’s made me see that the size of our fears is more often than not WAY bigger than the size of the fall out.

Life is about choices, and the act of NOT choosing out of fear of failure is also a choice.

Show Notes

  • [00.25] Stories from a wonderful week.
  • [01.38] 66 days to creating a habit and the companion book I’m currently writing.
  • [02.21] Fear of failure
  • [02.53] Choices and consequences (and ALSO looking at the possibility of success)
  • [03.36] Consciously choosing the path of your life vs. Deep Grooves of behaviour that have evolved over time.
  • [04.59] ‘And Then What Process’ (a role play)
  • [06.51] The real consequences of failure.

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“Our worst fears are always rooted in our fear of the immediate reaction.” – Lisa Linfield

“The upside of success is worth more to our self-esteem than not trying because we’re too scared that people will say NO.” – Lisa Linfield


Hello everybody and welcome to today’s episode of Working Women’s Wealth.

It’s been the most wonderful week as I’ve celebrated two amazing things.  Firstly, my 98-year-old grandma just beat Covid 19.  She not only survived the disease, but she survived two weeks in a Covid Ward sharing a room with 3 other oldies with Covid.  So we’re thinking God she’s home in her own room with her own stuff, in peace and quiet.

The other celebration is that I’ve personally distributed 80 books in less than two weeks for my book Deep Grooves:  Overcoming patterns that keep you stuck.  And the feedback has been incredible.  It’s amazing how many people have struggled to express why and what they’re rethinking in their life as a result of lockdown.  It seems this book is timely in helping people work out how to pivot towards their best life.  So if you want to grab a copy of it, go to my website LisaLinfield.com or check out Amazon.

This week has had me think a lot about success and the fear of failure.

My book has a companion book I’m currently writing called The 66 Day Challenge – because it takes 66 Days to create a new habit, and so it takes 3-5 page pieces of the book and deep dives them with journal questions.  It’s the so what? Of the book – taking the book and making it personal for you.

As I delve deeper into the content, I’ve been struck by new insights – which sounds totally weird given I wrote the stuff myself.  And one of the questions that’s stuck deeply in my soul is “how many great achievements has the world missed out on because people have been too afraid of failure to try?”

Where did we go wrong that we believed the World Out There’s lies that failing is so bad that it’s worth even trying?  That it leads to rejection, which leads to you being kicked out the tribe and scorned.

My dad has a great saying, “Life is all about choices”.  And, every choice we make actively or passively by our inaction results in consequences.

The problem I’ve been thinking about is that so many of the consequences we think of are so one-sided.  We think about all the things that can go wrong – yet we spend almost no time on thinking about what happens if it works?  What happens if even if it does fail, it never results in rejection?  Where would our life be if we had of been that tiny weenie bit braver and worried less about failure?

One of the things I’ve always wanted was to choose consciously the path of my life.  To never wake up one day and wonder, “How did I get here?”. 

But it’s an extremely hard goal to have.  Sure, the big decisions I’ve made consciously… but I’m coming to realise as I work with people as they journey through the book and my courses on the book, that so much of the relationships we have, the road we find ourselves on, the way we live our everyday life is dictated by Deep Grooves of behaviour that’s evolved over time.

Allowing that boss to phone you after hours.  Not speaking to your friends in weeks.  Allowing your family to assume you’ll be fine with going with the flow when you’ve been wanting to speak out for years!

Success at work and in life means we need to be much more conscious about the things we say yes to, and the things we say no to.  But it also means that need to be more conscious when we stop ourselves from doing things because we’re scared.  And we need to journal through what’s really driving us to feel that if we do fail, it will be SO bad.

A technique I talk about in the book is the ‘And Then What Process’.  It’s unbelievably simple, but it’s made me see that the size of our fears is more often than not WAY bigger than the size of the fall out.

Let’s take asking your boss for a salary increase or an existing client to pay more for your services.  You know that compared to the market, you’re significantly underpaid.  Most people never get to go through the steps in Episode 28, Asking for What You’re Worth because they stop at their first thought – he’ll never say yes.  Their fear of failure, and their assumptions, stop them from even doing the preparation to ask.

So,  let’s role play the And Then What.

I couldn’t possibly ask for more money because I KNOW that they’re going to say no.

                And then what happens?

Well, that moment of awkwardness happens, when I back peddle and try and make light of the fact that I asked, and am filled with so much shame that he doesn’t think I’m worth it.

                And then what happens?

I’m going to walk away feeling awful, and awkward every time I see him.  It’s obvious he just thinks I’m useless and not worth it no matter how many times he says I’m his star performer.

                And then what happens?

I’ll probably start looking for a new job.  I know I’m worth so much more, maybe I can get it somewhere else.

                At which stage, the And then what happens splits into two paths:


It may take some time, and a few failed interviews, but eventually I’ll get a new job that pays more…


Who am I to kid… no one will ever pay me more.  I must just smile, shut up, and stay in this job.  Over time he’ll forget about it, and we’ll all go back to the way it was.  I’ll just keep my head down.

So let’s step back and look at the real consequences of failure.

Where our thinking goes wrong is that we all stop our thinking at the first step – how filled with shame we’re going to be when they definitely say NO.

But even if we take the worst case here, you keep your head down for a while, and things go back to normal.  How bad is that really? – and, in light of the upside, is a day or so of feeling yuck not worth the potential of a bigger salary?

But what if it did lead you to be so unhappy and uncomfortable that you went out and found a new job with better opportunities and better pay.  Are those few months of discomfort not worth the reward of success, of keeping your career path in the right direction?

If this example was about asking an existing client to pay more – and it forced you to go out and find new clients that paid you more… again, wouldn’t the opportunities that money gives you to live your best life be worth it?  More importantly, wouldn’t feeling like you were being paid what you’re worth be way better for your self-esteem than knowing that you’re being underpaid because you fear the rejection of them saying no?

Goodness, I’m talking to myself here.  The great part of working with people as they go through the book and course, is that I do the work myself.  I’m becoming so much more clearer about the fact that our worst fears are always rooted in our fear of the immediate reaction.

But, when we go through and play that scenario out, our stories never end that way.  There are always more chapters that happen after the initial defeat.  And it’s those that need to give us the hope and courage that the upside of success is worth more to our self-esteem than not even trying because we’re too scared that people will say NO.

The question we need to think about this week is “Where could I have been if I had had the conversations I need to have had, not been so scared to fail, and taken the steps I needed to take?” Not in judgement, but in hopeful wonder… knowing that the fear of the safe life pales into insignificance compared to the joy of knowing we’d at least given it a try.  We never gave in to the voices of The World Out There.  Never played small when God made us to step out into our purpose.

So, I encourage you all to download the first two chapters of my book for FREE!!!! If you go to my website, LisaLinfield.com, you can get the first two chapters free by just going to the book page.

Be brave this week friends, because the fear of failure robs us of our best life.

I’m Lisa Linfield, and this is working women’s wealth.