How I’ve Learnt to Take More Risks in Life

How to Take More Risks in Life

As an Aries I’m supposed to be daring, spontaneous and courageous. Yet throughout my life I have always preferred to err on the side of caution (following my rising sign, analytical and anxious Virgo). However, I’m currently thinking about taking a very big risk and moving across the pond to New York. There are a million silly reasons not to do it, but I don’t want fear to hold me back. So lately I’ve been trying to train myself to feel more confident about taking risks. And here are the positive thought patterns I’ve been adopting…


I’m currently reading The 4-Hour Work Week by Timothy Ferris, which is all about redefining the way we live and work, and one particular passage completely transformed my way of thinking. A few years ago Ferris was working 15+ hour days at the company he founded, and felt completely miserable. He decided to take a year-long sabbatical and travel the world, but immediately came up with a long list of things that could go wrong if he took such a risk. Until one day he adjusted his way of thinking…

“I realised that on a scale of 1-10, 1 being nothing and 10 being permanently life-changing, my so-called worst-case scenario might have a temporary impact of 3 or 4,” he writes. “I believe this is true of most people and most would-be “holy sh*t, my life is over” disasters.”

So now, whenever I start to freak out about moving outside my comfort zone, I sit down and clearly define the worst-case scenario. And once I’ve put it out there I usually realise it’s:

A) Not really that terrible.
B) Fairly easy to correct.
C) Unlikely to happen anyway.

Find the Courage to Take More Risks
Karen Millen White Boho Dress


When Stella & Dot founder and CEO, Jessica Herrin, was in London last month she told a great story about how she learnt to take risks. And I’ve since started applying her decision-making framework to my own life.

After graduating from Stanford, Herrin was torn between two jobs. One offered a high salary that would pay off her student debts, and the other was a startup with endless possibilities. Herrin eventually took a risk and went with the second option after she received some brilliant advice from a cab driver in Texas…

“He told me to think about the best and the worst-case scenarios. Then he asked, ‘Would it be worth the possibility of the best upside to go through the worst-case scenario? In other words, if the worst-case scenario of failure isn’t that bad, then go for the bigger opportunity without fear.’ The worst-case scenario would have been that I would lose my job. I figured if that happened, I would still have my education and could always go back to get the safe job. So I went for it.” [source]

“Everything you want is just outside your comfort zone.” – Robert Allen

Stella & Dot Bespoke Necklace


No-one ever created an exciting life without taking risks. And everyone fails at one point or another. So the worst-case scenario may indeed happen. But that doesn’t mean it’s game over. A recent episode of The Lively Show podcast looked at what happens when we give up or lose something important to us – be it love, a job or a home. And Jess Lively introduced the positive mindset we can approach such set-backs from by recalling the time she had her wallet stolen.

“They took my wallet. They could steal my wallet. But they could not steal my ability to earn money,” Jess said. “So although you can steal what I have collected at this moment in time, you cannot steal what I have the ability to earn in the future.  And I think this is so empowering for us to realise… That when things we have cultivated in our lives are taken away from us – either willingly because we give it up, or unwillingly because someone takes it from us – we are no less powerful than we were before.”

So if you quit your job to go travelling for six months it won’t take away your ability to get a similar job in the future. And if you end a relationship it doesn’t mean you’ll lose the ability to fall in love again. Because, as Lively says, “You’re not all or nothing.”

STYLE NOTES: Karen Millen dress (sold out online) and Stella & Dot Bespoke necklace

Are you a confident risk taker? Or do you need to step outside your comfort zone and start to take more risks? Leave a comment below to share your thoughts…

P.S. The life lessons I learnt in my early twenties and inside my struggle with perfectionism

  • Yes! You should definitely move to NYC! Three years ago my husband and I moved from NYC to London and it was one of the best risks we’ve ever taken. We move back this Oct/ Nov for his new position and for me to start my own company. No great success ever came without risk! Hope to follow you on your NYC adventures too. Just prepare for freezing winters and buy yourself a good coat at Saks or Bloomies 🙂

    • cocos_tea_party

      Yeah the winters are one of the main issues I’m still a bit on the fence about it…

  • Go for it, living in New York will suit you perfectly!

    • cocos_tea_party

      Here’s hoping! xx

  • cocos_tea_party

    Hi Michelle. So good to hear your big risk paid off!

  • I’m a 100% virgo but how can you be thinking about this?!

    I make decisions based on whether I’d regret something: which would you potentially regret more, going or not going?

    Becky ⋮ a c c o o o h t r e m e n t s . w o r d p r e s s . c o m

  • Limelight Team Fashion

    Looking adorable 🙂

  • Nital Shah

    Great read – you should so move to New York City – it’s fantastic. It’s so funny I had a dream last night that I moved to NYC – I would love to move there! Go for it!

  • WOW! that’s huge! I am not a risk taker at all and live a little too cautiously X

  • monicawelburn

    Absolutely adore this article Ella, and these photos are simply stunning!

    Monica x

  • Cait

    Fantastic article. Definitely giving me something to ponder.