Can Turning Down A Free Year On The Beach Ruin Your Life?

Dump the regrets you carry from every fork in the road.

Jul 01, 2024

Life is going to thrust big decisions on you without serving notice.

Not the kind you can defer or delay. In your face, pick now, gun to your head style. You know the choice is a big deal and will have immediate impacts. Here’s the kicker - you will never know if you got it right because you didn’t do the other thing. Scary, right?

Here’s how to approach these decisions and minimize pointless regrets afterward.

Life’s a beach, and then you get a job

The one where I turned down a free year on the beach.

I wasn’t a great student at university. I threw myself into a broad social life centered around a bar, where I became the manager. Two of my closest friends were my assistants, and we had a great time running it together.

We were completing our final year when one of the guys, through his dad, shared an opportunity to spend a year running a bar on the beach in Barbados.

A dream come true, surely? We could live out the movie Cocktail (hopefully minus the death). We would hang out in the mornings, chat, and serve drinks to partying holidaymakers for the rest of the day. Somewhere to stay for free with a disposable incomine in paradise is an appealing proposition.

Yet these were the days of the corporate “milk rounds” when graduates had their choice of big companies fighting over them. I had significant student loan debt and a burning desire to repay it.

It was classic heart vs. head. Ultimately, my head won, and I joined a corporate graduate scheme at the end of the summer. I couldn’t spin my conscience through another year of debt and was keen to join the ‘real world’ I’d been training for. The decision seemed straightforward at the time.

Looking back, I was driven by subconscious guilt at goofing off into bar work rather than studying and failing to fulfill my academic potential. I didn’t want to continue that narrative.

I still think it was the right choice, so what’s the lesson here? It’s the power of regret.

Of all the choices I’ve made in life, I still ponder this one the most. I took the safe, easy, and least risky path. It worked out well. So, I should be happy with it. But:

Who would I have met in Barbados?
How would it have shaped me?
Would I have set up a home and still been there?

Most regrets in life burn far harder when you have chosen a safe path that involves turning away from an exciting one. Run towards the unique and scary things that set your heart fluttering - usually, the safe path will still be there if it goes wrong.

Any dream will do

The one where an unplanned audition for a reality TV show landed me on stage with the love of my life.

2007. I have a day of meetings planned for an insurance company client. The night before, I traveled to London to have dinner and stay with the bar friends from the story above.

Just as we’re wrapping up the evening and heading to bed, I get a text from the client. An internal issue has arisen, and they cancel our meetings. Doh. Always seeking the bright side, I look for plans on a free day in town before my train home tomorrow.

Even in the olden days, Google knew my penchant for karaoke well enough to suggest open auditions for a Reality TV show. Sir Andrew Lloyd Webber was seeking to cast a lead for a new production of Joseph and the Amazing Technicolor Dreamcoat. Thanks to my mum, I had been heavily exposed to this musical. So - even though this show was open to professionals - I closed my eyes, drew back the curtain, and made plans to attend in the morning.

I filled in my forms; an interviewer dug (in vain) for a dramatic backstory. We lined up in groups of five. One guy in a time at a time to sing for the panel, then back to hear our yes/no results as a group.

After my group had sung, they broke protocol and called me back alone.

“We wanted to let you know that although we’re not putting you through, you sang really well and we’re sure you’re a credit to your local theatre group.”

I shared that I was not a member and had never been near one. After the theatrical gasps from ALW’s peeps, I was encouraged to seek one immediately upon my return to Nottingham.

As luck would have it, one group was having auditions for a show that weekend—the same auditions where, 17 years ago, I met my beloved wife.

Think of all of the tiny decisions that had to line up:

My uni friends' availability and draw convinced me to travel in advance.
An insurance company leader denied entry to consultants in a crisis.
I summoned the enthusiasm to go and sing in a contest I was never good enough to win.
A judge decided to interrupt the conveyor for an act of kindness.
I acted on their generous encouragement to try out for a local group.

And that, kids, is how I met your mother.

It’s easier to analyze and run the pros and cons when you know you have a significant decision on your hands. Yet, what about your many small and often unconscious daily choices? The ones that never hit the radar of importance.

Many small choices drastically altered your path in ways you will never realize. So, don’t sweat the choices too much, however big they seem. Fate gives you many opportunities to mess it up.

Threading the space needle

The one where I said the right thing in the right place at the right time.

A casual comment on top of the Space Needle in Seattle in 2014 led me to decide with my family whether or not to uproot and move to the United States.

My partner and I wanted to share more of the world with our children, allowing them to be global citizens. Unbeknown to me, I shared this dream with the right person to make it come true.

Within a week of that conversation, a surprise resignation arrived Stateside. Several phone calls later, we stared down the barrel of a monumental choice.

Even though I’d learned not to worry too much about each choice, Barbados weighed heavily on my mind as I advocated for the move. I couldn’t stomach another dose of the same regret in the face of such an exciting opportunity.

The UK would always be there if I needed to return, despite their best attempts to float away from Europe with Brexit and become a different country in my absence.

This decision was a shared one with impacts beyond ourselves, creating more layers of complexity. In the end, I don’t remember us hesitating that much. My partner and I had grown accustomed to taking risks and dealing with tricky situations when, five years prior, we had returned from a 4-month trip around the world, spending all our savings and returning ‘with child.’ Other things feel a little easier once you’ve battled through that (during a global housing crisis).

Even when presented with the ‘administrative hurdle’ of getting married to secure a visa, we largely shrugged it off. Our conviction led us to pursue this opportunity, which checked many boxes.

Our underestimation of the cultural differences between the UK and the US is a story for another time (or available in book form on Amazon). Still, we launched into the journey with excitement. Nine years later, it’s been one of the best family choices ever made.

The story's moral is never to be afraid to share your dreams—you never know when the person hearing them might be the one to make them come true.

When an opportunity to seize your dreams presents itself - it may not be fully in the shape you’d imagined or feel like the perfect time. Nevertheless, you should grab it with both hands anyway.

Fork in the road

It’s timely for me to recount these stories as I stand on the precipice of new choices from a career perspective. I have become tired of the corporate Game of Thrones and, as such, decided to step out of it for a while to reconsider how I want to earn my living.

Others have admired my courage to step into the unknown. Beyond courage, the combined experiences above have equipped me with the will and belief to pursue a work-life more aligned with my values and strengths. Even though I don’t know what form that takes yet, I am unwavering in my confidence that I’m doing the right thing for the right reasons. As such, I look forward to the journey excitedly and not bewildered with fear and doubt.

For those of you out there standing at forks of your own, remember:

Run towards the unique and scary things that set your heart fluttering - usually, the safe path will still be there if it goes wrong
Many small choices drastically altered your path in ways you will never realize. So, don’t sweat the choices too much, however big they seem.
When an opportunity to seize your dreams presents itself - it may not be fully in the shape you’d imagined or feel like the perfect time - grab it with both hands anyway.

Trust yourself to choose well, push forward to the next fork, and don’t waste time on what might have been.

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Shifting Perspectives