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How to be fearless

by Estela Torres (2020-08-16)


‘What if it goes wrong?

What if it goes right?'

Fashion designer Tabitha Webb has always lived life on the edge, and bounced back from multiple setbacks, failures and even bankruptcy. Here's why she still believes passionately that taking the big risks in life is her secret to happiness  

I've always been a risk taker.
When I was 19 I did one term at university then ditched it to move to Florida, because I'd fallen in love with a surfer boy. I turned up on his doorstep and it was obvious he didn't want me there. I thought, ‘Never mind!', found a hostel and a job in a bar.

My parents sent my two elder sisters to rescue me and bring me home.

They both failed. I lived in Miami for a year. I danced in music videos, did some modelling, dyed my hair bright red. It was one of the best times of my life and I've never regretted it.

Of course, when you're 19, you can take a risk like that.

You've nothing to lose.
It doesn't matter if it all goes wrong. But 26 years later, with my own fashion business, a husband and two daughters, aged eight and two, I've learnt that without risks there are no rewards. If anything I take more risks now that I'm older, because I don't want to look back 26 years from now and wish that I'd done more with my life.

My absolute belief that midlife is not the time to settle is at the heart of my new novel, No Regrets.

Life is far from over; we need to get out there and grab it. You can still go and get your dream career. You can still fall in love. You can still move abroad and start a whole new life. But you have to embrace risk if you want to make it a reality.

Fashion designer Tabitha Webb has always lived life on the edge, and bounced back from multiple setbacks, failures and even bankruptcy

There's no better time than now to play your wild card.

Months of lockdown have given us the chance to look at our lives differently. The world has suffered a massive shock. But once it's all over, do you want your life to be exactly the same? Or do you want some of it to change?

I know that a lot of people find taking risks incredibly uncomfortable.
But trust me, it's worth it. Here's what I've learnt from a lifetime of jumping in at the deep end.

Accept that risks don't always pay off 

When I came back home from Miami, I got a job in advertising.

I answered a newspaper advert and one role led to another and another. By the age of 26 I was a producer at a prestigious advertising agency. I was on my way, climbing the ladder.

But one day I thought, ‘Do I want to stay in an ad agency for ever?
Do I want to do this for the rest of my career?' I decided what I really wanted to do was set up a handbag business. Friends told me I was insane. I had a fantastic job. I was successful. Why would I risk all that? I remember telling them, ‘I don't see this as a risk.

This is about the next part of the journey.' I had no idea how to make a handbag. Not a clue. I went through the Yellow Pages, found a leather merchant, bought some skins, then turned up at a factory begging them to make me some handbags. That's how my first business, Orca, started.

Tabitha and Dannii Minogue launched a clothing range together

If this was a movie, that's where the story would end - but life is more complicated.

The brand got really big, really fast. I went to a trade show and got an enormous order from a huge retailer. I was riding high. But the suppliers ran late and the retailer cancelled the order. I was stuck with all the stock and couldn't pay for it. I had no choice but to put the business into administration.

I took a risk and it didn't work.
But people liked the bags… so obviously something worked. And when my friend, the Aussie singer and TV presenter Dannii Minogue, asked me to launch a fashion line with her, I immediately got on board. If I'd played it safe, I knew I'd regret it. We had an amazing time.

Our label, Project D, was stocked in Selfridges and stars including Miranda Kerr wore our designs on the red carpet.

Financially, it wasn't as successful. After four years that business also ended in administration. It was heartbreaking, gut-wrenching.
I felt as though I was finished. It was actually my investor who said to me, ‘You are never, ever done. You are a serial entrepreneur, which means you're a serial risk taker. Dust yourself off and go again.'

And so I did. I took yet another risk and launched my own clothing label, under my own name.

It's still going strong after two bankruptcies, and each risk I took - however catastrophically it went wrong - was part of that journey. 

Turn around every ‘what if...'

When my book publisher approached me about writing a novel, I had no idea if I could do it.
The ‘what ifs' bubbled up: ‘What if it's sh*t? What if I get terrible reviews? What if no one buys it?' But I've always been able to flip those ‘what ifs' around. ‘What if it's great? What if people love it? What if it's a bestseller? If I don't try, I'll never know!' I'm sure the book is going to shock some mums in the school playground.

There's a lot of sex in it. And if it does get slated, of course, it will be mortifying. But, if that happens, I will just have to own it.

It's the same with the podcast I recently launched with my sister Merryn. She's a financial journalist and we talk about money: she's the expert and I'm the dunce that makes it funny.
Merryn kept worrying, ‘What if no one listens? What if it doesn't work? What if it's all a waste of time?' And of course I said, ‘What if people really like it? What if it's a huge success? We won't know if we don't do it!'

Every time you think, ‘What if it goes wrong?' I think it's a good rule to ask yourself: ‘What if it goes right?

What if it's actually the best thing I ever do?' You have to assume every risk you take is going to work, otherwise you won't give it the energy it needs to succeed.

The biggest obstacles are in your head

My husband Gavin is very risk averse; we're at completely opposite ends of the spectrum.
I've been trying to persuade him to move abroad; just pick somewhere on the globe and go. He can only think of the obstacles. ‘What about our jobs? How do we earn money? What about the kids' school?'

It's always the same argument: I get frustrated that he only sees the negatives and the boundaries; he thinks I'm crazy.

My attitude is that there's always a way around those obstacles: you figure it out. When you focus only on the problems, rather than the potential, you put roadblocks everywhere and cut yourself off from opportunities.

Left: with Daughters Primrose and Betsy Right: Tabitha with her husband Gavin

Gavin often says to me, ‘This nice life we have could all go away.' And I can see that if you have quite a comfortable life, you might be wary of losing it.

Why do something - start a business, change jobs, 중년 질건조증 솔루션 get a divorce, move home - that might threaten that comfort?

But my mantra is that there could always be something more brilliant out there. And unless you open those doors, you don't discover what that something could be.

I remind my husband that we had a baby when I was in my 40s. That was a risk - we were perfectly happy with having our one daughter, Betsy, and if something had gone wrong we could have turned our lives upside down unnecessarily.
But, of course, now we never regret having our youngest, Primrose.

So we've come to a compromise. We'll spend a few months of the year - when our daughters aren't in school - living in the US. As we spend more time there, we'll see how we can change our life and make it work.

Of course, if it was up to me, we'd just pack and go and run a paddleboard school by the beach. But at least now we will deal with the obstacles as they come up, rather than letting the thought of them stop us.

Allow yourself to want more

I have a friend who fell in love, age 39, with an Australian man. She chucked it all in here and emigrated to be with him.

She told me, ‘All I think, every day, is why didn't I do this sooner? Why was I always stopping myself - thinking, "This is as good as it gets" - when I wasn't actually happy?' If you're not happy with your life and you're trying to change it - that's not even a risk.
That's just correcting something that's not right.

Just because we're in midlife, or have a family, doesn't mean we have to sit still and accept our lot.

I think that, a lot of the time, we don't take risks because we don't think we deserve to have more - we've had our time, it's too late for anything else.

I will always look for newness and change.

When people ask me if our house in Hampshire is our ‘forever home', I can't think of anything worse. I will undoubtedly be bored out of my mind in a couple of years and will be moving on to try something else.

When will enough be enough?
When will I have achieved what I want to achieve? Honestly, I don't ever see that happening. I will just keep on going. I won't ever stop taking risks if I think they can bring me happiness. I look at my mum, who is 74 and considering moving to Africa. I think that's fantastic.

She's not concerned about contemplating such a bold move at her age - she's asking the question we should all be asking ourselves: ‘OK, what's next?'


Allergic to risk? 

Tabitha's advice for breaking out of your rut 

Write down what you're really afraid of

Instead of automatically saying no, pick apart what's going on in your head.

What are you scared of? Failure? Embarrassment? Now ask yourself what you stand to gain if everything were to go right. Adventure? Excitement? Happiness?

Don't seek everyone's advice

It's tempting to ask other people ‘What do you think?' when you're about to make a big life change.
But there will always be naysayers - usually people threatened by or jealous of you doing things differently. Only you know what you need.

What's the alternative?

If you don't take this risk, are you really happy with this being your forever?

If the risk you're considering seems too extreme, is there a way to say yes to parts of it?


No Regrets by Tabitha Webb will be published on 23 July by HQ, price £7.99.
To pre-order a copy for £5.49 until 26 July go to and enter code YOUREGRETS at checkout.

Book number 9780008228262. For terms and conditions, see