Financial enablement is when we help people out with money. Whilst it’s something that most often comes from a position of love and care, it ends up slowly weakening the person we’re helping.

Like all things in life, when it comes to financial enablement, there’s a fine line between helping out and enabling. Like a piece of chocolate vs a slab or a ball of ice-cream vs a tub. As one of my mum’s friend put it, “the difference between your kids having a safety net if stuff happens, and them lying in a hammock”.

One of the places i’ve come to see it is in the supporting of a loved one starting a business venture. It’s about to get going – so more money gets sunk.

I recently woke up to the cold reality I’d been financially enabling myself.

For the last 3 years of Working Women’s Wealth, I’ve dug into my savings to support it. I haven’t had to make the hard calls because the money I’d saved was always there. I also enabled myself to NOT do the work I hate most – selling. My fear of rejection got the better of me.

So I didn’t. Instead of building revenue streams, I covered my expenses with my savings.

Life is a struggle, and requires us to prioritise. For me, face the fear of sales or go back to corporate. For adult kids, learn to sacrifice wants for needs, short term ‘happiness’ for long term character.

Listen here as I share with you my recent encounter with Rock Bottom, and the personal revelation of the dangers of enabling in a family, with your children, or financially enabling yourself

Show notes

  • [0:30] What happened to cause my rock bottom
  • [1:52] The difference between my Good Reasons and Real Reasons
  • [3:22] What financial enablement is, and when it’s most commonly seen
    • [3:38] Financial enablement of university and first jobber kids
  • [4:48] The fine balance between support and enablement
  • [5:38] The parable that explains why financial enablement doesn’t help those you love
  • [8:27] How I financially enabled myself to the detriment of my business
  • [10:05] The hard decisions I should have made, but didn’t in the last few years
  • [10:50] My fear of sales
  • [13:05] Why we need to walk through the discomfort
  • [16:05] The decision I’ve made for Working Women’s Wealth

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The tough times seem to come in multiples! – Lisa Linfield

How did I end up here?  What did I miss? – Lisa Linfield

Working with Good Reasons for something is like treating the symptoms, not the cause. – Lisa Linfield

Financial enablement is when we help people out with money.  – Lisa Linfield

Our job as parents is to get our children to independence in all ways, but especially emotionally and financially – Lisa Linfield

There’s a fine line between helping out and financial enablement – Lisa Linfield

Financial support needs to be gradually weaned from our kids so that they can build the skills and strength to stand on their own – Lisa Linfield

The journey of life is to make us stronger, to make us braver – Lisa Linfield

Life will keep bringing you the lesson you need until you walk through it – Lisa Linfield

The issue of financial enablement is tough, as it enters into the world of ‘showing love’, providing and protecting, safety and security – Lisa Linfield


These last few weeks have been really hard for me business wise. Some would say ‘the perfect storm’, others would call it ‘the black swan events’.  Both imply that it’s really rare.

But, the truth is, these things are in actual fact more common than their terms would like you to believe.

Whenever I look at my own, and other people’s lives, I see so often that stuff seldom happens in ones.  It seems to come in twos, threes, fours.  Put that together, and you have your perfect storm. The tough times seem to come in multiples!

Hindsight is the perfect science.  And looking back, if I’d listened to Wisdom, to the still small voice in my head, the signposts were there.  The things I could have done to avoid this perfect storm were all available to me. I just didn’t see them.  So, as I’ve been in deep prayer and reflection over the last week, I’ve asked God to show me where I went wrong.  How did I end up here?  What did I miss? How can I, a person who teaches about money, end up with a cash flow crisis in my Working Women’s Wealth business?

There are many Good Reasons I could sprout off.  Coronavirus has dried up sales.  Everyone is in financial trouble, so no one’s buying… and the market has crashed.  And on it goes. 

But Good Reasons never help you to move forward.  Working with them is like treating the symptoms, not the cause.  Treating a sore ankle with cream when in fact it’s broken and needs surgery.

So we need to focus on the Real Reasons.  The simple answer is that I didn’t have the guts to do the sales.  But as I speak about in my book, we need to dig deeper – to ask Five Whiskeys and a Heineken.  Keep asking Why, What, Who, Where, How until we uncover the underlying thinking patterns that enabled the behaviour to surface – the Real Reason.

When I look at where I am now, the Real Reason is that I was financially enabled.  That enabled the behaviour to surface.  In this case it happens to be by myself.  But it comes down to being financially enabled.  And ironically, it’s something I’m vehemently against, so it frightens me that I had such a blind spot to it and couldn’t see it.

So let’s start from the beginning.

Financial enablement is when we help people out with money.  In my work I see it most when it comes to parents with children, and other family members. In parents, it starts usually at high school or university.  We give money to help out, but in the end we end up hurting those we helped.

Simply put, our job as parents is to get our children from being fully dependent on us (in primary school) to being able to stand on their own two feet in all ways but especially emotionally and financially.  In theory, that’s a gradual slope of letting go for parents, and assuming decision making responsibility as high schoolers, and then slowly starting to take over the responsibility of not only the decisions, but earning the cash – until we stand completely financially independent. 

For most of the world, that happens after school, when student loans are sought to pay for university, and jobs are got to pay for life.  For the lucky few, it at least needs to happen in that first job after university.  In my business, I see parents still paying for kids to live in their 30s and 40s.

Now, like all things in life, the issue is balance. One glass of wine is fine, five bottles an evening by yourself might be a challenge.  And so it comes with financial enablement.

When I was reflecting with a client still supporting adult children a few years out of university, she shared that the reason she did it was to give her girls the best, to prevent her daughters from having it hard, like she did.

When I asked her if, in hindsight, she may have over-compensated, she stopped, reflected and then totally agreed.

It comes from a place of love, of care – but it ends up hurting the enabled more, and here’s a parable to explain why.

It was a warm day, not a breath of wind in the air as little Mary was playing in the garden. As she looked at the beautiful flowers, her eyes rested upon the cocoon of a butterfly. It was moving, causing the flower it was attached to to bounce around.

As she watched more intently, she saw that there was a hole in the top of the cocoon, and the butterfly’s head was starting to peep out the top. It was fascinating, and she got totally engrossed in watching the little creature, with great effort, get its ‘shoulders’ out the top.

But, she soon noticed that the butterfly was tired.  And it seemed to need to stop and rest.

Mary’s heart broke, and so she went over to help the butterfly out.  She made the hole wide enough for it to climb out without having to exhaust itself. Sure thing, a little while later, the butterfly emerged.

Mary felt so relieved and proud of herself, and happily looked on – proud she would be the first person to see this amazing creature fly off and flutter, exploring the world.  Sure enough, the little butterfly pushed off with its legs to fly.  But, unable to get its wings up, it dropped and fell onto the floor.

Desperate, Mary shouted for her grandmother to come over to where she was.  Feeling something was gravely wrong with Mary, Dorris ran over to find her little granddaughter in tears.

‘Nana, Nana, the butterfly can’t fly.’

As the story of what Mary had done, and how proud she was of helping this little creature tumbled out, Dorris knew with that sinking feeling in her tummy exactly what had happened.

‘Mary,’ she said. ‘What you did was a kind and generous thing to do.  The problem is, there’s a reason for the butterfly’s struggle.  As the butterfly struggles to get out the cocoon, the process pushes the blood from its body into its wings.  That blood, together with the struggling is what makes it able to get the strength to fly.  Although you did what you think would help, the butterfly will never be able to fly as there’s no way to strengthen its wings.’

And so is the problem with financial enablement.

Whilst it’s something that most often comes from a position of love and care, it ends up weakening our children and whomever needs the money so they’re unable to fly. It’s why it’s so important that financial support is gradually weaned from our kids so that they can build the skills and strength to stand on their own.

Which brings me back to what happened with me.

When I started my business, I’d worked for six months as a consultant in the corporate I left so the money I earned could stock the business with cash.  It was enough to be able to do what I wanted – get the software I needed, the help I needed, and start not only my financial planning business, but also Working Women’s Wealth.  As my wealth management business grew, it helped out to provide that cash that Working Women’s Wealth needed.  For me, Working Women’s Wealth is my passion project – to teach women how to manage their money better, support their businesses and careers better, and live their best life.

As money ran out because the revenue wasn’t there yet, I would ‘put my hand in the cookie jar’ – the money we’d overpaid into our home loan or mortgage, which I could access.  I justified to myself that that was okay.  John and I had earned similarly our whole life, and so half of everything we’d saved was mine.  And that was the story I was sticking to.

But, I’d promised John that at the beginning of this tax year – starting 1 March – I wouldn’t take any more money out the cookie jar.  And as ‘asking for money’ has ALWAYS been a major issue for me, I would rather die than take money out of our savings.

Anyway, a ‘perfect storm’ of issues arose, and over the five months of this year, I found myself with more expenses than there was cash flow.

As I looked back over the last week, I saw that I had been financially enabling myself. 

You see, when you have access to an ‘unlimited’ or ‘easy’ supply of cash, you don’t make the hard decisions.  You don’t hustle.  It’s not to say you waste money on the grand life – none of that.  But you put in place things that maybe you should only have further down the track.  You don’t treat every penny as a prisoner. 

I got the best software for my business, when I could have done with a lower version.  When things didn’t work, I kept them going for way longer than I should, hoping it would ‘get better’ rather than cutting them and trying something new.  I got the Porsche of business services, when the entry range vehicle would do.

I’ve worked myself silly over the last three years.  It’s not a case that I didn’t work hard enough.

But, what I more recently uncovered, is that I enabled myself to stay away from sales, human sales.  My biggest fear.

These last 2.5 years of Working Women’s Wealth, I have tried to build my business through Facebook advertising and social media posting.  And whilst that’s a fine strategy, in my case, it was my way of avoiding approaching influencers and people to be affiliates (or help sell my course for commission) for my courses.  Or approaching people who own speaking companies and events organisers to get them to promote me.  

You see, if the Facebook Advertising or the online speaker’s bureau’s could take off, then I’d never have to approach anyone.  And if I didn’t approach anyone, I wouldn’t get rejected.

And that’s where the real reason sits.

I didn’t want to approach affiliates and influencers to do partnerships with them to sell my courses or my speaking because I was terrified they’d say no.  Because my fear of rejection, fear of failure, fear of sales was so great, it paralysed me.  So I spent a huge amount of money on Facebook advertising to avoid having to do it.

And I could do that because I assumed that by the time my deadline came, it would all be up and running, a well-oiled advertising machine, and I would never need to approach anyone.  And never be rejected.

But that’s not how life works.

The journey of life is to make us stronger, to make us braver, to make us able to use every single weapon at out disposal.  And by avoiding doing human sales, I enabled myself to stay safely in my comfort zone.  Don’t get me wrong, the Facebook campaigns that didn’t work killed me and I grew and learnt until some did.  But fundamentally I was staying away from overcoming my big fear.

And God loves us too much to let us hide from the journey we need to be on.

As Joseph Campbell the writer behind Star Wars says – “The cave you fear to enter, holds the treasure you seek”.

Life will keep bringing you the lesson you need until you walk through it.  Until you pick up your LightSaber and enter that cave and defeat it.  And I know in my soul that for me personally, my businesses will not work until I take on this challenge and become good at sales. 

Remember my definition about Good, Great and Hum.  Anyone can be good at anything, with enough work, practice, sweat, hours and a good enough teacher.  To be great at something, you need to have a passion or natural talent on top of that.  And to HUM, you need to be called to it, to serve others through it. A purpose.

So I have no aspirations of becoming great at sales.  It’s not my destination.  It’s a means to my end of building enough revenue that I can keep Working Women’s Wealth running.  That it doesn’t drain our savings, but pays for itself.

And sales, or revenue, is the life-blood of any business.  And if my choice is to not be employed by someone else, I need to become good enough at it that I can earn enough money to eventually get others to do it for me.

But more importantly, I need to enter the cave and conquer the fear. For me, for my personal growth journey, and to unlock the door to grow my business.

By enabling it with money, I enabled myself to avoid it, to avoid the fears and pain.  It works in the short-term, but enablement never works in the long term.  And I just prolonged what I should have done in the beginning – pick up my LightSaber, enter the cave, build the muscle, skill and strength to fight and fly.

The issue of financial enablement is tough, as it enters into the world of ‘showing love’, providing and protecting, safety and security.  Money is always entwined with the bottom of Maslow’s deepest needs for human beings.  It’s difficult to know what exactly the right amount is – where that line between supporting and enabling is.  And for each child and each human, that line is at a different place.

One of my mum’s good friends says, “You need to give children a safety net, not a hammock”.  They need to know that if they fall from the tight rope of life, there’s a net to help them bounce back, and they don’t just park there, enjoying the hammock and never leaving.

And sometimes, tough love is needed.

For me, I should always have known that if any disaster had ever happened, that money was in my homeloan that I could have used.  But wasn’t for me to sit in the hammock and avoid the hard lessons I needed to grow.

So, whilst I could definitely put my hand in my cookie jar and take the money I need to get myself back on track, I’ve chosen not to.  I’ve chosen to embrace the struggle.  As hard as it is, I’m going to fight my way out of my cocoon, cutting every expense possible.  And then, I’m going to pick up my LightSaber and enter the cave, and build the relationships and deals I need to get the revenue so that I can teach a million women about money.  I know it will be hard, but if I don’t do it now, it will keep coming back until I learn this lesson.

If you loved this episode, please do share it with one person who you think needs to hear this.  In that way, we will build the strength and encourage those around us.