3 Reasons Why I Decided to Work with my First Life Coach

Ever since I was a child, there was something about travel and life abroad that drew me in. I honestly can’t tell you why I wanted to be able to travel so badly. There was no bucket list of dream destinations, neither did I fantasise about it daily – it was just a decision that I made and stuck to until it became my reality.

The thing that 10-year-old me could not foresee was that when you find yourself in a completely unfamiliar place it is the perfect opportunity for life to teach you all the lessons you would have glossed over had you stayed in the environment that raised you.

You know what they say,

You cannot heal in the same environment that made you sick.


Okay, that quote might be a bit alarming, because I wasn’t “sick” per se, but I certainly had a lot of emotional baggage that I remember refusing to deal with growing up. Around my teenage years I began feeling a lot of things I couldn’t quite process, and instead of dealing with it (I didn’t know how to at that age, let’s be honest) I just packed it away for later.

When you work 20-hour weeks teaching English abroad, you get to experience a new type of freedom that not many people are fortunate to have – time. Suddenly, I had all this free time which began to force me to spend more conscious time with myself than I was used to. Needless to say, moving to Spain was that sacred “later” I had kept telling myself about.

Where I Was… Mentally

I moved to Madrid, Spain after two years living in Colombia. This wasn’t my first time at the rodeo, but I could intuitively tell that this new experience was going to be very different from any other experience I had had before.

It’s interesting to reflect on past iterations of ourselves and do a then vs. now comparison – without judgement of course. Here’s what I remember about the person that I was at that time:

Aneakaleigh in 2017 was an anxious overthinker, who pretended not to care what other people thought just so she would not have to deal with the weight of their expectations. Even though an onlooker would imagine that living abroad and the frequent travels that entailed meant that she liked adventure and taking risks, the opposite was actually true. She was always playing it safe and trying to stay as small as possible. Why? Because by flying under the radar, she didn’t have to open up and share anything about her that would make her look weak.

In those days, I spent a lot of time worrying about making new friends, and feeling like I belonged. Not that those things are inherently bad on their own, but reflecting on how I felt in that period of my life vs. now always reminds me of how much I struggled to keep up with others by neglecting my wants and needs, and basically pretending to be someone I was not just so I could fit in and be liked.

Where I Was… Emotionally

Emotions? You mean that classic song by the BeeGees that Destiny’s Child remade into an R&B banger? No? You mean, actual feeling type emotions?

I would have done anything at that time to be an emotionless void, because the truth is my emotions were very much present and they were eating me alive. I don’t know how I managed to go so long with numbing myself from experiencing “negative” emotions, like I used to call them. Anger, guilt, shame, embarrassment etc. gave way to self-judgement, self-pity, resentment.

Where I Was… Professionally

When I graduated with my Spanish degree from the UWI, St Augustine campus in 2016 I was excited to start a life teaching English abroad … indefinitely. Until I realised that although I could keep doing this forever, there were parts of me that were struggling to accept the idea that I had found the thing I was going to spend the *rest of my life* doing.

I am not sure how many people reading this can relate to feeling unsure about making a career decision at 25 years old. Sure, it works for now and the life I am living right now, but in a few years time is this what I will still want to be doing? If I have these doubts now, what can I do to explore them instead of pushing them away to resurface later and bite me in the ass?

So How Did I End Up Working with a Life Coach?

I don’t know if by reading that brief description of what it was like being me in 2017 gave you any insight, but after a while merely existing became intolerable.

Also, when you’re coasting through life and merely existing in a city like Madrid it feels like some kind of hell on earth. There I was surrounded by all of these amazing, talented, opinionated, stunningly sickening people every day and I felt like I was not enough.

On top of that, life kept throwing these curveballs at me bringing into question everything I had thought was true about who I am and what I wanted out of my life. I was quickly realising that I had no idea what any of that was. An inexplicable pressure to become something or someone I was not materialised, and I hated every second of it. The incessant negative internal chatter that came along with that became overbearing, and eventually started affecting my day to day life.

I remember at the peak of it all I was experiencing severe anxiety on a daily basis. I’m talking shallow breathing, racing and sometimes skipping heartbeats, inability to concentrate on anything for more than five minutes at a time – just overall a complete mess of a person on the inside. I think on the outside I became a caricature of who I was expected to be by those around me, and it wasn’t because they demanded that of me – it was just because I didn’t want to seem weak or appear to be helpless.

One day I had had enough of the endless loop of feeling stuck, worthless, and anxious all the time and said a prayer to the Universe. Surprisingly, it wasn’t one of those snotty nosed, teary eyes desperate calls for help that most people write about in their self-help books. Nope, I was standing in the bathroom of my friend’s apartment getting ready for a 6am flight to Malta for a weekend day trip when my iPod fell and the screen cracked. Exasperated, I told myself and the Universe out loud, “yep, that’s a sign. I am ready and willing to do anything to stop feeling like this. Send help – whatever it is, I’ll do it.”

Then I got on that early morning flight and had a really fun time reconnecting with friends, taking amazing photos, and soaking up the beautiful island’s history. On the flight back I had homework to complete from a workshop I had attended a week before titled “Navigating the Quarter Life Crisis”. One of the activities I had not completed was a visualisation exercise about where I saw myself in five years. You already know how I felt about those kinds of questions. Needless to say I bullshitted my way through that question, landed in Madrid, and made my way to the café to meet up with Kerry-Ann – the life coach who had hosted that workshop.

Life-changing Conversations

Our conversation that faithful Sunday afternoon at the Rodilla near metro Bilbao would change the trajectory of my life and my relationship with myself. To cut a long story short, she told me she didn’t believe a word of what I had written on that plane and that I was scared to become the person I knew I could be.


Actually, I am paraphrasing here because what she really said was much worse than that and part of me was horrified, embarrassed, and upset that somebody who did not know me from Adam or Eve (an expression we say in Trinidad) had the audacity to read me for filth – IN PUBLIC!

The other part of me who asked for help a little over 24 hours before that, though, felt seen, validated, and like this was a lifeline. I didn’t realise it then, but looking back I now know that our meeting that day was the Universe’s answer to that prayer. Everything you want is closer than you think.

When Kerry-Ann offered me a 3 month coaching package I didn’t need to think about it. I had asked for help, I wanted help, and she could read through my bullshit so I would take her up on that offer.

For three months between March and May 2019 we met at that very same Rodilla in Chamberí. On Sundays I met up with a friend for brunch, and then I’d go to “therapy” (at that time I didn’t know coaching and therapy were not the same thing!). The similarity between the two for me, however, was being able to be open and honest with someone who a) did not know me personally and b) I was paying to help sift through all that internal chatter and make sense of it – not just to correlate it to my past, but mostly to help me move forward and become the best version of myself.

At our weekly meet-ups, Kerry-Ann would ask me questions about how I was feeling and what had been going on in my mind and I would talk and talk and talk. I don’t think people understand how important it is to get things off your chest!

I used to be the kind of person who would hold everything in and tell myself it would eventually go away if I locked it up and threw away the key! Working with a life coach really give me a much needed outlet to not just get it off my chest but to make tiny changes week by week to get myself out of the loop of self-judgement, fear, and shame and into a more empowering story about who I am and where I am going.

Towards the end of the session we would come up with an action plan of what I could do to work through whatever I was struggling with. Sometimes it looked like reaching out to friends and having a quick chat. Other times it looked like scheduling time to cry at least once for the week. She also recommended books to read, podcasts to listen to, and how I could just let myself be me a little more each week.

How Coaching Helped Me

I remember at the beginning of our coaching relationship, I used to worry about how I would be able to keep up with everything – all the new tools and ways of thinking I was learning and all the changes I was making – when our time together was up. By the time we wrapped up our three months together I was a completely different person.

It’s not that I had changed, so much as I was more aware of the patterns in my life that kept me stuck and feeling horrible. In my experience working with a life coach, I became more self-aware, and less codependent on others for help. I learned to be my own best friend first and set healthy boundaries with others that prioritised my wants, needs, and values. Most importantly, I learned not to worry about what other people thought about me and focus on what I think about me. That was one of my biggest takeaways – that I can like myself … wait, no LOVE myself and be proud of my life every day and that I didn’t have to wait for some distant future to enjoy life and be happy.

Can Coaching Help You?

Joy, happiness, and fulfilment exist in our every day life if we slow down enough to reconnect with ourselves and pause to find them.

Coaching is for you if you feel stuck, overwhelmed, or unfulfilled in your life and you feel like there’s more waiting for you but you don’t know how to find it. That’s exactly where I was, and that’s why I decided to become a Life Coach after my transformative experience working with my first coach.

Wanna Chat?

Hey there! Thanks for stopping by and reading my blog!

I am a Self-Reinvention Guide & Mindset Coach, and the Founder of The Caribbean Millennial community.

I help multi-passionate Caribbean Millennials across the diaspora overcome overwhelm and create fulfilment in their every day lives.

Interested in working with a Life Coach? I’m offering free 30 minute clarity calls – schedule one below!