When Will You Bet On You?

We love the idea of backing ourselves. We talk considerably less about what happens when there’s actually something to lose.

There’s a version of midlife reinvention that sounds absolutely fabulous.

Leave the job.

Leave the relationship.

Move somewhere new.

Start the business.

Choose yourself.

Take the leap.

It’s all very empowering until you remember there’s a mortgage, a pension, a bank balance, people you love, consequences, and quite possibly several decades of life still to fund.

I’ve made some pretty significant changes to my life over the last few years. From the outside, some of them probably looked brave. A few may have looked reckless.

There were certainly moments when I wondered whether I had completely lost the plot.

But I’ve realised something.

I’m actually not very good at leaping.

I’m much better at calculating.

And I no longer think that makes the bet any less bold.


I Didn't Throw My Life in the Air and Hope It Landed Nicely.


When I eventually left corporate life, I wasn't standing at my desk one Tuesday afternoon thinking, Sod this, I'm off to find myself.

I had spent a long time thinking about it.

Too long, probably.

I knew the environment I was in was costing me more than I wanted to keep paying. I knew my health had suffered.

I knew I didn't want to keep spending the best of my energy tolerating things that had stopped making sense to me.

But knowing you want to leave something and being able to leave it are two very different things. So I planned.

I looked at my finances. I thought about what I needed. I thought about what I already had. I considered what life might cost without the salary landing every month.

I didn't remove the risk.

I made the risk survivable.

That's a distinction I don't think we talk about enough.

Because we have somehow turned backing yourself into an act of blind faith.

Close your eyes.

Jump.

Trust the universe.

No, thanks.

The universe has never offered to pay my American Express bill!


Backing yourself doesn't mean closing your eyes and jumping. Sometimes it means spending two years building somewhere safe to land.


The salary wasn't the only thing I was betting.

Money gets most of the attention when we talk about leaving a career, but that wasn't the only thing on the table.

I was betting that I could build a life outside the identity I'd spent decades creating.

That mattered.

I'd been successful in corporate life. I knew who I was in that world. I knew what I brought to a room. I knew how to lead, influence, fix, challenge and navigate my way through complicated organisations.

Leaving meant walking away from something I was very good at without knowing what would replace it.

That's a strange thing to do in your fifties. Because you're not starting with nothing.

You're starting with something you've spent years building, and you're deciding whether you're prepared to loosen your grip on it.

That's where the real bet was.

Not whether I could survive without the job but whether I could trust myself without all the things that had previously told me I was successful.


Then I made another bet.


The Life Edits was one of them. I created something from nothing.

I learned technology I had no business understanding. I wrote. I built. I coached. I created products. I launched things. I changed them. I got things wrong. I spent money on things that turned out to be useful and other things that absolutely did not.

And for a while, I thought the success of that bet would eventually be determined by how big The Life Edits became.

That's what we're conditioned to do, isn't it?

If you start something, grow it.

If it works, scale it.

If people want it, sell more of it.

But here I am, a couple of years later, deliberately changing what The Life Edits is. I'm making parts of it smaller.

I'm stepping away from things I once thought I wanted it to become.

I'm keeping the parts I love and questioning the rest. So was backing myself to build it the wrong bet?

Not remotely. Because this is something I've come to understand about betting on yourself.

The thing you choose doesn't have to last forever for the decision to have been right.

The Life Edits got me here. It gave me somewhere to put my thinking. It gave me a completely different set of skills.

It introduced me to women and conversations I would never have encountered in my old world. It gave structure to a period of enormous change in my life.

And now I want something slightly different from it.

I don't consider that a failed bet. I consider it evidence that I can change my mind without turning everything that came before into a mistake.


I've made bets that were far more personal too.


Leaving work wasn't happening in isolation.

My marriage had ended. My life had changed. I moved to the Middle East and began building something that looked very different from the life I'd imagined I'd have.

Then eventually, I made perhaps the most emotionally uncomfortable bet of all. I let somebody in again.

There's no spreadsheet for that one. Believe me, I would have found it.

Falling in love again required a completely different kind of trust because there was no financial model that could tell me whether it was going to work.

I could look at values.

Behaviour.

Compatibility.

How I felt.

How we dealt with difficult things.

What we wanted from life.

I could pay attention.

I could ask questions.

I could use every bit of experience I'd accumulated.

But eventually, there was still something I couldn't know.

The outcome.

That's true of every meaningful decision I've made.

You can research until your browser begs for mercy.

You can prepare.

You can protect yourself.

You can ask better questions than you did at 25.

But eventually you reach the edge of what can be known.

And then you decide.


That's the bit I think we've got wrong about confidence.


I used to think backing yourself meant believing you would succeed.

I'm not sure I believe that anymore. Because I don't know whether every decision I make will work.

Neither do you.

Sometimes we get things spectacularly wrong.

We misjudge situations. We trust people we shouldn't. We spend money badly. We build things nobody wants.

We stay too long. We leave too soon. Experience doesn't make us psychic.

And I think pretending otherwise puts enormous pressure on every decision.

If backing yourself means I know this will work, no wonder we hesitate.

That's an impossible standard.

My definition is different now.

The real bet isn't believing everything will work out. It's believing you'll know what to do if it doesn't.

That I can get behind. Because I have evidence for that.

I've had things go wrong. I've had plans change. I've had endings I didn't expect.

I've had moments when the version of life I thought I was building disappeared completely.

And I'm still here.

Different.

Hopefully wiser.

Occasionally still making questionable decisions.

But absolutely capable of figuring out what comes next.

And now I'm standing in front of another bet.

The next one feels different again. Because it isn't just mine.

Christophe and I are starting to think seriously about what our next chapter could look like.

France. A home. Potentially a business. Something we build together.

There are conversations about locations, properties, money, legalities, practicalities and what kind of life we actually want.

There will be research.

There will be spreadsheets.

Obviously there will be spreadsheets.

There will almost certainly be moments when Christophe wishes he'd never mentioned France to a woman who can turn buying a loaf of bread into a project plan!

But underneath all of that is something I recognise.

Possibility.

That feeling of looking at a life that doesn't exist yet and thinking:

Could we?

I love that feeling.

And this time I'm not betting on escaping something that no longer fits. I'm betting on moving towards something that excites us.

That's new.

Calculation and courage can sit at the same table.

I think that's where I've landed with all of this. I don't believe in reckless reinvention.

I don't think women should blow up perfectly decent lives because somebody on Instagram told them they're playing small.

I don't think fear automatically means do it. Sometimes fear is giving you useful information. Sometimes the finances don't work.

Sometimes the timing is wrong.

Sometimes the thing you desperately want simply isn't a good decision.

Backing yourself includes being able to tell yourself no.

Or not yet.

Or not like this.

That's why calculation matters.

Do the work.

Understand what you're risking.

Know what you're protecting.

Create options.

Build your runway where you can.

But also recognise the point when planning has stopped providing new information and has simply become somewhere comfortable to hide.

Because certainty eventually runs out. It always does.

And that's where the bet begins.

Final thought.

When I look back now, I don't think the biggest bets I've made were the moments when I felt fearless.

Quite the opposite.

They were the moments when I understood exactly what I might lose and decided something else mattered enough to move anyway.

Sometimes I built a very substantial safety net first.

Sometimes there wasn't one available. Sometimes the outcome looked exactly as I'd hoped. Sometimes the outcome changed me enough that I ended up wanting something completely different.

That's life.

So I'm no longer interested in telling women to just back themselves.

It's too easy.

Know your numbers. Know your reasons. Know what you're walking away from and what you think you're walking towards.

Prepare properly.

Question yourself. Question the plan.

And when you've done everything you reasonably can, accept that there will still be something you cannot calculate.

You cannot know for certain who you'll become on the other side of the decision.

That's the risk.

It's also rather the point. Because betting on yourself was never really about knowing you'd win.

It's knowing that whatever happens next, you trust the woman who'll be standing there to deal with it.

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