The Cruel Cycle that Turns Overthinkers into Underachievers

Have you ever met someone that won’t start something till everything is perfect? Someone that over analyzes every little detail? Someone who isn’t reaching their potential because they are stuck in their head? If not, then nice to meet you. I’m that someone. I used to blame many things for my slow progress but the facts are in, and I can say that I’m to blame. My perfectionist habits of overthinking and overanalyzing are at the core of the reasons why I haven’t been able to achieve the success I dreamt of as yet.

When you spend more time in your head, than actually doing things it delays your successes.

I can admit that even though I fall into that category, that I have made strides of progress from how I used to be, and because I have been there, I can identify the disease in people I meet. Now I want to help others escape the trap of overthinking by identifying the cycle and escaping it. I think it’s important to escape the cycle because perfectionism leads to inactivity, and all that is left is the feeling wasted time. When you spend more time in your head, than actually doing things it delays your successes. Compound that with the terrible feeling of watching people who are less qualified than you, execute your ideas. Now I want to help you get out of that cycle as well.

Ironically, I did a lot of introspection into why my habits had caused me to underachieve. Then I noticed a common cycle that I went through continuously that has kept me from progressing as I would like. In this blog I will go through what perfectionists might go through in the pursuit of creating something great. It’s a vicious cycle, but I think that if you can identify it, then you can take action to break out of it.

1. The Spark

If there is one good thing about overthinking, it’s that you will come up with some of the best ideas on the planet. The spark is the birth of the idea of something you want to pursue. For the purposes of this blog, let’s say it’s a business idea that you want to start. You would have probably envisioned exactly what you need to create, why it is needed and who would benefit. From the business model to the type of tiles you will use, you will think of everything. The problem with us is that, we probably have a great idea every other day. So identifying what should be pursued is our first challenge.

2. Research and Planning

So you settle on an idea you want to pursue and of course you have to get it done perfectly. It must match your vision precisely so there must be a research and planning process afterwards to see the viability of the idea and what has to be done. Sadly enough, many ideas don’t even reach this stage because they are either discarded in pursuit of others, or the owner of the idea is stuck in fantasy island, thinking about how great it could be and never actually does anything. This phase is the start of the real problems we have. Overthinkers can fall in love with researching and planning. We will have our saved images, bookmarked websites, sketches of designs and plans for the next 10 years. You can see why it’s easy to drown at this stage because planning is never truly done, and if you keep trying to get everything planned perfectly before you start. You will never start.

3. Do something

If you have reached this stage then I applaud you. You are actually stepping out of your head and making progress towards the thing you want to create. It’s a great place to be and if done right, you can escape the overthinkers trap. However for the sake of completing the cycle, let’s use the worst case scenario. You actually create your first thing; your design, your film, your logo. After spending weeks trying to get it the way you want, you just don’t like it. Is it really that bad? Maybe it is, but the issue is with your desire to have a perfect product to unveil as your first piece. Maybe it’s your own high standards, or your fear of what people will say, but you fail to accept your first offering as something viable to put out there. So it’s back to the drawing board to either improve it, or start from scratch.

4. Depression from the failed reality

Despite the fact that overthinking can cause stagnation at any stage, this one is the real quicksand. Realizing that what you may not be able to reach your own self-imposed standards on your first run is paralyzing. You question yourself, you question your purpose and even what you had for dinner. This is the worst part for the creative overthinker as we try to analyze why we aren’t good enough. Facing perceived hours of wasted time and effort, it’s natural for the overthinker to give up here and pursue one of his many other ideas which might be more in their area of expertise. However my advice for my fellow overthinkers is that we have to realize that we can’t be Steven Spielberg at 28 years old on our first film. It’s ok if it’s bad because it’s a learning process and you will get better on the next attempt. Just put your pride to the side for a while and put it out there.

“Education and motivation can be an addictive drug with little reward if it isn’t implemented immediately.”

5. Seeks wisdom

So you flopped on your first attempt and you are still coping with the negative reviews. The overthinker that is determined to create his dream will retreat back into his hole to begin researching and planning again. He will seek motivation and guidance for encouragement as he works towards for his bounce-back moment. While I applaud this effort, I would remind him not to get stuck in this zone again. I mean yes, seek knowledge on how to improve and find appropriate mentors, but don’t wait months again for your comeback. Education and motivation can be an addictive drug with little reward if it isn’t implemented immediately. The ovethinker craves enlightenment, but will take very little action. At some point however, the overthinker gains enough knowledge to adapt his idea, till he gets another spark.

Unfortunately, the cycle repeats itself from there. The spark helps us get renewed vision and helps us to get better, but the minimal gains acquired causes very slow progress. The majority of the time spent in the cycle is in stage 2, 4 and 5 where the overthinker isn’t doing as much as he should to make progress. My suggestion is to use this cycle to identify where you are so you can escape the cycle.

How would a more productive cycle look like?

After your spark moment, still spend some time researching and planning, but not as long as you think. Get the necessary information, then start taking action as soon as you can. Even while you are researching and planning you can do something productive. At the next stage you might fail, but don’t get too down about it, keep on creating, learning and adapting to create the much needed momentum for success. I can’t say that I have mastered this technique but I have witnessed it first hand and have implemented it into the progress I am making myself. So I challenge you Mr or Miss Overthinker, what can you do today to help you make some progress?

Don’t forget to subscribe to get my blogs directly in your email, also connect with me on my social media handles below.

Header Photo by Olhar Angolano on Unsplash

Still Got it by Flappel

Photo by Irene Kredenets on Unsplash

On this edition I will develop a campaign using random information I have from 5 different categories that will create a fictional product, client and situation. The concepts are open to the public but if you are interested in using it for your own company please notify or accredit me. Second one, let’s go.

Case Study info

  1. Product – Hand Bags
  2. Brand Archetype – The Innocent
  3. Target Audience – Women 50 and Over
  4. Business Objective – Recognition
  5. Differentiating Factor – Emotional Connection

Still Got It by Flappel

Format: Experiential marketing – Authentic Interviews and use of product


Ten women over 50 will be invited to do candid interviews about their sex appeal from the past (in their 20’s) compared to present day. We will probe them with questions surrounding changes in their confidence between these 2 time periods.

We intend to dispel beliefs that they lose any appeal when they hit 50. Whether they feel like they don’t have a strong appeal anymore or are confident that they are sexier than ever, we want to reinforce the them that they “still have it.” After the first interview, we will give each of them a light make over; make up, heels and the Flappel Handbags as the central focus of the transformation. Then, they will be asked to walk down a runway, equipped with an audience, lights and photographers. We will capture their confidence walking down the runway. Their smiles, laughs and strides of confidence will all be captured along the way. Follow up questions afterwards will include; how they felt throughout the process and what they think was the biggest change over the years. These questions should lead to them discussing less concern for clothing as family life came to the forefront. They discuss their “baggage” as to what has kept them back. The core message is that “we all have baggage, you might as well rock it.” Flappel helps to show women over 50 that they still got it, and dressing the part helps bring it out.

The Big Boy Wallet

Photo by Web Hosting on Unsplash

Welcome to my daily creative exercise. On this edition I will develop a campaign using random information I have on a master list that will create a fictional product, client and situation. The concepts are open to the public but if you are interested in using it for your own company please notify or accredit me. Here we go.

Case Study info

Product – Wallet

Brand Archetype – The HERO, he wants to prove himself

Target Audience – Boys 8 – 13

Business Objective – Engagement

Differentiating Factor – Unique

Campaign Name: I can buy what I want

Approach: A one minute ad that can be used to show how the wallets can empower boys to get everything they want. The Ads can be run on YouTube with a target on videos watched by boys in that age category to stimulate interest. It can also be run during programs/ videos that focus on business or money management, as parents are the ones with the purchasing power, and those who look at these programs/ videos will be more likely to want to see their children improve their financial responsibility.


A Nintendo Switch sits on the showcase behind in a store window with a boy’s reflection looking inward. He tugs on his mother’s dress and points to the device. Annoyed, she glances at it before brushing him off. The boy looks disappointed.

Christmas morning the boy sits with his family and sees a rectangular box with his name on it and excitedly opens the gift. His excitement turns to disappointment when he notices that it’s a wallet and not a Nintendo Switch. His father comments that if he knows how to use it, then he can get anything he wants. The boys eyes brighten.

Montage Scene of him collecting money through various activities

He cleans up the yard and receives payment that he places in the wallet.

He saves the change from his snacks in the wallet and even stashes his birthday money in the wallet.

The boy drags mother into the toy store, he grabs the Nintendo Switch and rests it on the counter. The annoyed mother awaits for him to count all the money he has to pay. The cashier smiles as he drops the final dollar. She bags it and gives it to him. He hugs the box and kisses the wallet. His mother rolls her eyes. 


What did you think of the campaign concept? Would I be able to meet all the objectives identified? Your productive critique is welcomed 🙂

The Extra Mile

I’m tired

of running late

of running from place to place but still in the same place

of running racket on myself, I’m I’m robbing my health

of running down cents to trade for my skill sets…

to chase another man’s dream? I guess

my dream was less important and decided to take a rest, I am tired

I bep

and remember what it was like before I had to pay a rent…

I could go for hours and never miss a step, never felt stepped on and never felt inept

Then a wise one said, “You running out of time

and if you don’t chase your dreams, you’ll be running all the time”

But I don’t think I could take another step,

I’m running out of air, I’m running out of breath

He smiled,

and said “You could finish this rat race in last place and die, or

you could go the extra mile”

RIP Jason Marcano: A tribute to those we lost in 2019

Can you imagine logging into Facebook, just to browse through your feed only to see that you had passed away? With friends sending “R.I.P’s”, you see first hand reactions of how your friends and family would take the news. It’s chilling… but that was my reality on May 31st. My name sake, footballer “Jason Marcano,” tragically lost his life in a car accident. The incident was the third in a 2 month period where I lost 2 other colleagues. All 3 of them were in their 30’s like me, so I was already reeling from the “what if that was me?” syndrome. Actually seeing your name associated with death hits you a different way. Death has a way of making us reflect on our own life, as we remember the ones we’ve lost and their stories. While we honour them, we seek a deeper meaning in the tragedies and see how we can lay rest to our past negative habits as we learn from the lessons they had taught us in their presence.

Lesson #1 – Do What You Love

I never met Jason, but it felt like if I lost a relative. We weren’t directly related, but I had known him for maybe 10-15 years due to his celebrity status. People always asked me if I was him. Having gained his reputation as a talented footballer and even playing for the Trinidad and Tobago national team, he was well known in the football circuits. To me, his existence represented an alternate reality for what my life would be like if I pursued a career in football (and if I were any good). I had actually wanted to be a footballer when I was younger, but never liked the idea of training, so it’s no surprise that dream only reached as far as being good at playing FIFA.

Ironically, we only connected for the first time a couple months before his demise, on Facebook. We discussed him moving away from football to start building his business, and by perusing his page I was happy to realize that he seemed like a down-to-earth, progressive, family-oriented man, much like myself. At only 38 years old, despite achieving so much, it feels like he would have continued to reach his goals because of his drive. I know he can rest easier knowing that he had pursued a career he loved and was successful at it. My philosophy is that as long as you are doing what you love and earning a living, you’ve won.

A lot of times our “coulda woulda shouldas” haunt us with the regret of things we never pursued. I’m glad that Jason was successful in doing something he loved, and to me that is how life is meant to be spent. We can’t control how much time we have here, but we can control what we do with our time here. Thanks Jason.

Lesson #2 – Inspire Positive Change and Lead by example

The first person who passed away within that period, was someone who worked within my organization. Again, I only met him for the first time about a month before he died, but his reputation preceded him. Lyndon Jackson was a Librarian attached to the Arima Public Library. I met him at a meeting where he sat on the executive for the Library Association of Trinidad and Tobago. Quite an ambitious role for someone so young, I thought to myself. I assume he was the youngest person there, and was impressed by his dedication to his craft, even slightly envious. Just like with Jason, I feel like people who find a job they are passionate about and can make a career out of it are the lucky ones.

Lyndon wasn’t there for the glory, his humble persona hid his enthusiasm for his job. He seemed truly passionate about helping people, using libraries as a vessel to do his life’s work. He had gone above and beyond the call of duty multiple times to serve in whatever way he could. He was mentioned in conversations about bringing positive changes to the library service, he was the silver lining in a dark cloud. Despite only learning most of this at his funeral, I could tell that the impact he made was monumental. Colleagues knew we had lost someone special. I can’t say if Librarianship was truly his passion because I never asked him, but Lyndon gave everything to his job, helped people along the way and inspired people to emulate him.

At the end of the day, our short time here should be meaningful and we should do our best to help people and change anything we can for the better. Lyndon’s inspirational journey inspired me and many others to do better. Thanks Lyndon.

Lesson #3 – Brighten Someone’s Day

The third person who passed away in the time period was Karlene Flemming-Fortune. At 34, she was someone I knew better than the others I mentioned. I had known her for a few years well from working within the same building. She was just one of those persons who could turn the mood around. We traded stories, and she offered an encouraging word when necessary. Even with colleagues who were troubled, I saw Karlene take the time to speak with them and make them smile.

I never saw her sad or upset until the weeks leading up to her demise. While I reached out to her to assist, I was really helpless to do anything because of her medical condition. Mere days before she passed away she posted an eerie status, it was the first time I saw her speak this way and it was a sign of what had ultimately happened. If Karlene was ever going through any major issues prior to that I would have never known, as she always wore a smile and was positive. While I do feel like Karlene was doing work she enjoyed, my main lesson from Karlene was from our personal interactions.

You have the power to make someone’s day better, so you should. It’s not always about trying to be the next big thing, your impact can come from every interaction you have with someone, making their day a little better than it was before they met you. Thanks Karlene.

If there was an overarching theme to this all it is that death causes us to reevaluate how we spend our time, because we remember our own mortality and the finite nature of our presence. Are we truly bringing enough value to this world? Apart from footballer Jason Marcano, I would like to put another one to rest. The old Jason Marcano, my old habits, my old approach to life, because despite trying to do a lot, I know I can do better, and utilize the lessons learnt from my 3 colleagues to be rebirthed with their values.

I will:

  1. Do What I Love – What sense does it make to live this life without fully pursuing your passions, you will never know how far it can take you.
  2. Inspire Positive Change – You can impact help make so many persons lives better while being here, why not try to do that.
  3. Brighten Someone’s Day – Be a beacon of light to the people you meet. A warm smile might be enough to lift someone’s mood.

I pray that these three amazing souls rest in peace and their impact helps them to live on forever.

September: the start of something new



September is a month of new beginnings. The new school year begins, the Premier League really starts (minus the distractions of the transfer season) and the government sets their budget for the upcoming year.

My life has obeyed the laws of September and together with August as it’s sidekick, they have always been life changing months for me. I’ve started jobs, started relationships, and achieved milestones. Just in August of this year (2016), I achieved a milestone of some sorts… I made it to 10 years of working at my day job.  Most people might praise this achievement but many years ago I insisted that I would  be handing in my resignation letter at this juncture. Unfortunately I couldn’t… I was unprepared to do so, unless I wanted to live a life of poverty. I hadn’t taken the necessary actions to ensure that I had the means of acquiring income that could sustain my expenses.

This moment cemented the fact that saying I would leave and actually leaving are two entirely different things. For me to reach this stage of financial independence, these actions needed to be more aggressive and intentional than the ones that I took in the past.

I’ve always loved the concept of entrepreneurship; the autonomy, the potential for financial independence and the ability to make a living through doing your passion. It’s all very idealistic to me. However appealing this vision is, the actual process of becoming an entrepreneur is much more difficult than it seems, especially having worked for the government for 10 years (I’ll do a piece on the dangers of this on another day). The process involves self-awareness, having a clear vision and being prepared to do the necessary work to achieve that goal. Through this blog, I will document my jump from employee to full-time entrepreneur, with the aim of reaching that goal in September 2017. I hope to help those in a similar position to find clarity on your journey, so you can find your own new beginnings. Stay tuned every Saturday for a new blog post.