How Much of a Risk Taker Are You?
Or, a story about the time I went to Cuba without speaking any Spanish
Way back in 2006 I was knocked down by glandular fever. I was 25 at the time, living on a houseboat on the Thames which had a tendency towards dampness, it was the middle of winter and I’d just broken up for the second time with the person who’d handed me the illness. It was the middle of winter and I was thoroughly hacked off, so I decided that I would book myself a holiday. To Cuba.
Why Cuba? Well, during the several weeks when I’d been too sick to do much else than lie on the sofa and watch cheesy movies, I’d repeatedly watched the “saved by the power of dance” classic, Dirty Dancing 2: Havana Nights. That’s right, Dirty Dancing 2. The Sequel. Not even the original. That’s how sick I was. As you might have guessed from the name, the film is set in Cuba at the end of the 1950s as Castro overthrew the government. (In a bizarre move, they’d tied it into the original film by bringing Patrick Swayze back, trying to blur the fact that he was supposed to be younger than he was in the original film with a shed-load of plastic surgery. Patrick deserved better.) By about the fifth rewatch of this cinematic tour-de-dance, I was convinced that I needed to go to Cuba. The beauty of the cities! The colours of the buildings! The beaches! So I booked a trip. It was only years later that I discovered that while the film had fictionally been set in Cuba, it had been filmed in Costa Rica. You live and learn.
Nonetheless, a few weeks later I was on a plane to Cuba by myself. I’d bought a guidebook (this was 2006 kids, we didn’t have TripAdvisor) and I’d booked a hotel for my first night. Beyond that I didn’t have any plans. I’d been carried away by the romance of the moment - a young woman, heartbroken, travelling the world alone - and I’d ignored the fact that no matter how many times I read it, I couldn’t get a clear answer from The Lonely Planet about exactly which currency I should be taking with me. So I was somewhat shocked when I got to the airport and realised that a) nobody spoke a word of English and I didn’t speak a word of Spanish, and b) the dollars I’d assumed would be fine where in fact (very much) not fine. Not fine at all.
I suspect I was nearly arrested about five times on that trip. Most of the time I was saved by a local hustler, the only people who spoke English, who realised I’d be good for a few dollars (they were happy to exchange them for me) if they just got me out of whatever piece of trouble I’d got myself into at that point. It was an amazing trip. Did I drink Mojitos in five different bars claiming to be THE place Hemingway had frequented? Yes. Did I get taken dancing by a man who drove a 1950 Chevy for tourists and who was clearly hopeful that his hips were his passport to a green card? Yes. And did I learn Spanish along the way? Sadly not.
When I look back on that 25 year old who just threw some clothes into a bag and hoped for the best, I’m unendingly proud of her. Yes she was an idiot who should have done more research and realised that the whole “overthrowing colonialist rule” thing probably also included the English language. Could it have all ended horribly? Probably. But she knew something that I think we forget as we age; most things, good or bad, are random so you might as well take your chances where you can. We can plan for every eventuality and still find ourselves ambushed by bad fortune so sometimes it’s worth taking a risk just for the joy of the experience.
A few months ago I saw a financial planner who had me fill out a risk questionnaire. I came back with a higher than average tolerance for risk. This backs up what I believe about myself but I was pleased to see it in black and white because I was beginning to worry that I’d become a bit too cautious in my old age, that I’d forgotten the joy in just going for something, even if failure is a very real possibility.
Recently I’ve found taking risks harder and it’s taken me a while to work out why, even now I’m not sure I’ve got it 100% but here are some of the reasons why I’ve become more risk adverse, and what I’m doing to mitigate this. Maybe you recognise yourself in some of these.
I’m getting older. All the research suggests that as we age we become less inclined to take risks, we become more aware of our own mortality, more aware of how time is working against us and so wasting any of that time becomes a bigger risk. We don’t want to do something we look back on and think, “shouldn’t have done that” not just because the outcome will be bad but because we will have wasted our precious time too. My mitigating strategy is to remember that the time I’ve spent asking myself “should I / shouldn’t I?” is time wasted too. Deep down I know if I really want to go for something or not, I should just listen to that and accept that the time will pass either way.
I’ve had a few things go wrong. 2021 was my Annus Horribilis and honestly, I know now why the former Queen found it so hard. When you have twelve months which completely knock you off your feet it can be comforting to just stay lying on the ground, at least you’re already there. So you keep your head down and hope for the best, and time passes and you wonder why you’re beginning to feel dead inside. As humans we are designed to take risk, we need it otherwise we begin to rot. There is no way around this other than by doing the risky thing. I think a good strategy is probably to do something which feels risky to you but isn’t betting the house… earlier this year I bet my house. I moved out of the city I’ve lived in for 20 years, rented a new property and tried to make a life in the countryside. As every one of my best friends will attest, it has been a bumpy ride. But I did it! Was it one of my better decisions? The jury is still out. Will I change my mind and move back to London? Maybe. Does that mean it’s failed as a risk? I don’t think so. I’ve learned a lot and I had an experience, and isn’t that what we’re here for?
Which brings me to my final point, sometimes you have to do things “for the plot.” As part of my ongoing midlife crisis, I regularly lose hours of time to watching young people do strange things on TikTok (what did I say about precious time?!). Apparently they are all out there taking risks and doing the unthinkable “for the plot” - because they want to have a great story to tell at the end of their life. I love this attitude! When I think about whether I want to do something or not, I often ask myself, “will this make a great story?” If it will, I’m more likely to say yes. Now is this a strategy for a calm and contented life? Probably not. But does it help you say yes to a risk or two when they present themselves? Absolutely. When in doubt, do it for the plot.
And if all of this doesn’t inspire you to take a little risk somewhere in your lives, here are three times it went well for me:
When I mucked up (in a massive way) a job interview for a job I really wanted so I spent the whole of the next day at my temp job making an A1 poster filled with reasons why the interviewer should hire me. I couriered it over to them (on the account of my then employer, sorry!) and got my first proper job in journalism.
When I replied to a friend of a friend’s Facebook post asking if anyone could look after their dog for six months as they had to move out of their house and the dog would have to go into kennels unless they could find her a home. 48 hours later she was in my care and seven years later, the sweet, angelic looking puppy I saw in the post is now my beloved, diva dog who I wouldn’t be without.
When I took the last £120 in my bank account and entered a charity poker tournament because I thought it would be good networking. Then it turned out skill, and a lot of luck, meant that I ended up winning the entire tournament and walking off with a Birkin Bag worth £15,000. I sold it and used the money as a deposit on my flat. Because sometimes you bet the house, but it’s always better to win it.
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Gosh they birkin bag story! I read this missing a more risky former me 💪🏻
I mean, Dirty Dancing 2 was epic. Second, I loved this essay. I never knew about the charity poker match, that is a very cool story.