cheryl strayed

Talk to me people

cheryl strayed
Cheryl Strayed is one of my writing heroes because she is dangerously honest

My other dream job – apart from my being a travel writer – is to be an Agony Aunt like Dear Sugar aka Cheryl Strayed.

As you all know, I am really open about my feelings. People actually get very freaked out about how honest I am. I get a lot of people looking at me sadly when I talk about my latest romantic failure or how lonely I feel sometimes.

But here’s the thing: I talk about it because it’s important. I talk about it because maybe other people feel the same way. I talk about it because it helps me understand myself and there’s a chance it makes other people feel less alone.

Recently when I was sick with the ‘flu in New York – without travel insurance and moping about the guy who was supposed to come with me – I honestly thought I was going to have to go to hospital. Southern Cross Travel Insurance would have cost me less than $100 for the whole trip but I didn’t get it because I was too broke. I lay in bed for two days freaking about the $10,000 doctor’s bill I was sure to receive because I was going to be admitted with SARS. Turns out I was more likely to be admitted to method acting school  because I was being a hypochondriac.

As I dragged myself around MoMA (not that amazing but maybe I thought that because I was sick?), laboured through the Museum of Natural History looking for surreptitious places to nap and waddled about 30 blocks from the Flatiron Building to mid-town with a seriously upset stomach, I really wished I could have a do-over of the trip. One where I was  Carrie Bradshaw, Lena Dunham or at the very least, Tootsie, instead of the Phantom of the Opera who was haunting room number 3601 at The Warwick Hotel.

My memories of New York are inextricably linked with the Terrible ‘Flu of 2014. Coughing up my lungs in a Brooklyn basement Airbnb, running for the bathroom at Eataly at Madison Square and praying for a swift death outside of the Rockefeller Center. After travelling for 2 hours to get to New York, I felt like I was letting the whole place down by not bringing my A game.

That got me thinking about insurance in general. If you could insure against bad experiences, would you do it? What would be the consequences of never having to experience misfortune?

The reality is that a key ingredient in the wild soup of life is suffering, pain and heartbreak. It’s the bitter and sour. We need it, just as much as we need the sweet, salty and umami (and sometimes – let’s face it – it can be masochistically delicious).

What I am offering you, dear friends, is the chance to talk to me about your problems. Love problems, money problems, family problems; you name it, I’ve probably had some experience of it through stupidity, poor management and bad luck. I am no expert but I did study to be a Lifeline Telephone Crisis Supporter and hell, I love you guys. I am here to listen and maybe I can help you as much as you help me.

You can confidentially email your questions to and I will post a response on this blog within the week. You will remain anonymous unless you specifically ask to be identified.








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