The start of 2015 would mark over ten years, in which I hadn’t traveled out of the country; the last time was when I was around 14 visiting family in the West Indies. I’ve had some travel opportunities come up but felt complacent in staying domestic, travel soon became a fear.I spent much of my younger years building my inner world (mentally), able to keep myself entertained and I would eventually develop a very strong level of self-awareness, discipline/self-control, and independence through this inward focus. Another thing I’ve noticed that came from living in my head for many years was a strengthened level of intuition and ability to visualize complex and abstract concepts/system in my mind and think far out into the future. But enough of justifying my loner tendencies.

As I got older I began to understand how important travel is for personal growth and understanding other people’s culture and perspective.

Something I’ve started to do to get me out of my comfort zone and expose me to more opportunities for personal growth has been employing the “barbell strategy”, which I was inspired by from reading Nassim Nicholas Taleb’s book Antifragile.

Taleb describes the “barbell strategy” as “a dual attitude of playing it safe in some areas and taking a lot of small risks in others, hence achieving antifragility.” Playing it safe reduces the potential downside of volatility and taking small risks exposes you to the potentially massive gains from the same chaos. – The Art of Manliness

The way I’ve been applying the barbell strategy is mapping out things I do a lot or I’m comfortable with on the left side (safe) and finding opportunities for growth in my fear on the right side (risk), that I become aware of and work to overcome through a series of Fear Setting exercises. With the Barbell approach, you seek to move away from the center or average, and you manage your extremes through equilibrium, by spreading the weight at the opposite ends of each other. I have been applying this approach to my personality as a means of personal growth, getting out of my comfort zone by doing things I am not accustomed to doing as long as they are not harmful to me or someone else.

Traveling was a fear and I needed to take action on and I began to fish for opportunities to test my ability to overcome this fear.

One Friday night, I posted on Facebook that I needed to get out of my comfort zone and travel a bit more.

Facebook Status Inquiring About future travel destinations

My friend Sam, who I went to Fordham with commented on Saturday that he was going to Iceland on Tuesday. In my mind, I thought, “O Well, I guess I missed that boat.” I had been so conditioned for preplanning out everything that I became afraid of being spontaneous. I was about to disqualify this cool opportunity to travel even if the date hadn’t passed yet.


I had posted that statement as me thinking far out into the future; I was just gathering ideas so that a future me (distant) would have ideas. The upcoming week would be the last week of work at a consultancy company, and we had an important client with a project in its final stages. My co-worker, who was the senior engineer on the team had gone on vacation to Vegas leaving me as the only developer on the project; he had no fill-in. As it was my final week of work, the client was still throwing requirements and suggestions for the application my way, and I needed to keep the client happy, so I accepted his last minute requests.

The trip to Iceland was still on my mind, it was Sunday, and I had around 24 hours to decide if I would go. I asked Sam if I still had time left, he replied yes, but told me the disclaimer. He was going with a select group of people, and it wasn’t all fun and games(I actually prefer this). It would be a retreat format where the attendees would set the agenda for the trip on arrival (Un-Conference) as well as share professional experiences and life lessons. I learned I would have to write a short essay, and the organizer would decide if I could get into the group that was traveling to Iceland.

When I heard essay, I thought, well I tried, really wanted to go on this trip, but had flashbacks of college entrance exams and my nerves were telling me I give up and save my travel plans for another time. I was still curious, and went to the organizer’s site to apply and saw that the writing requirements weren’t too difficult and it was mostly some simple questions and forms to fill out. I completed the form and waited.. and waited.

It’s Sunday night now, and I hadn’t heard back from the organizer. I reached out to my friend Sam to try to get a hold of the organizer, but he was busy, which makes sense as the trip he had been planning for three months or so was about to happen in less that 24 hours.

This travel opportunity to go to Iceland would be an extreme for my personality because of how spontaneous of a decision it would be, but there were many other obstacles I would have to overcome to give this a chance.

It’s now Monday morning, and somehow the thought that I was the only developer working on the project somehow slipped my mind, while I was frantically planning to find a way to make it to Iceland. I could have just gone on my own sometime in the future, but that would have fallen right into my comfort zone of planning things out with as much lead time as possible. I felt uncomfortable, with the hours dwindling away and so much out of my control, I still wanted to solve this dilemma.

I gave myself a couple of hours to focus on work. It was like I was possessed by some Rockstar Computer Programmer. Almost like the one’s you see in those action movies where the clocks ticking and the team or government brings is some shady computer programmer to hack into the system or defend it and he’s typing so fast the sound of the keyboard is like an orchestra of tapping shoes just clickity-clacking away.

Blitzing through some code

I was able to get through half a weeks work of coding in a couple of hours. I had experienced a state of epic flow and focus. I coded like a madman and presented the results to the client, who was very impressed.

I still hadn’t heard back from the Iceland Trip Organizer. I decided to track his info down, and I found his Twitter handle and sent a tweet. A couple of hours later I got a reply, and he later told me that he rarely used Twitter but was pleasantly surprised by the mention notification, so it caught his attention. He had read my application and thought it was legit.


Great! I thought to myself. Now I got over that hurdle; now I have to figure out the work issue. Being my last week of work and being on a major project worth half a million dollars, I did not want to mess this up as my parting gift from the company. It was important for me to maintain the client relationship and be professional.

The Iceland trip was Tuesday, it was now around 5 pm in New York on Monday, and I had just got the ‘OK’ that I could join the group. I called the client and gave him a status update on the project and about all the new features that were technically out of scope within the Statement of Work, but I had gotten in for him as a favor. The application would still need support as the other engineer was in Las Vegas living it up, and I was the only one available.

I pondered on the situation… and then I brazenly asked the client during our call(paraphrased):

Me: Hey, can I work remotely this week?
Client: Sure, you’ve been doing an excellent job and have stepped up to help to get this application ready for launch.
Me: Thanks! And also, there may be a minor time difference.
Client: How much of a time difference? Last time I checked the Upper West Side doesn’t reside in another time zone.
Me: Oh I’ll just be in transit.
Client: Soo How much of a time difference?
Me: Around four hours.
Client: Where are you going?
Me: Iceland.
Client: (long pause)…………. That’s awesome man. Have fun, make sure you get your work in and I can contact you through email or chat.
Me: O_O (my facial expression) Thank You. It won’t be an issue; I’ll work during night time in Iceland, and it will be the middle of the day in New York.

I’m not sure how I pulled that off, but I’m glad I tried. It was now around 6 pm, and I had less that 12 hours to make the final call.

I had not yet bought my tickets, so I called Sam for logistics and found out we would fly out of Boston to get to Iceland. I rushed to buy my tickets, and the price had gone up over 200% since what Sam and the other group members paid, as they had two months of lead time, whereas I had less than 12 hours.

The next fear, I had to overcome was that of purchasing on markup, as I am a very frugal person, raised by a mother who could stretch a dollar like a hand me down shirt.

TWO TICKETS LEFT, I shouted to myself. I needed to make a decision quick, and I knew that opportunities like this don’t come often, but I was going against a fear and the courage required to overcome a fear so engrained would take a lot of willpower….. Which I happened to have from training my discipline over the years 🙂

I snagged one and then went out to purchase my Bolt bus tickets to Boston. By this time, it was around 10 pm, and there were only about 9 hours left till the bus departed from Boston around 8 a.m.

Now, would be a good time to pack I thought to myself. I did research on the weather, and eventually ended up over packing I would soon realize as I made by way to the bus station and noticed Sam with a duffle bag while I looked like I was going on month long expedition. It would only be a week long trip.


We made our way to Boston, where we would meet up with Benji, who would also be accompanying us to Iceland. As we made our way through the maze of Boston’s streets I would get a call from my client asking me to fix some issues. We needed to make a stop anyways, so we stopped by a Starbucks and I spent 40mins – 1-hour fixing bugs before we would make our way to the airport.

2015-04-06-14.26.44During my time in Iceland, I would fulfill my promised to the client, working last night part-time,  going on adventures with the group during the day.

Over the course of the weeklong trip we would go and see some of Iceland’s best landmarks:

The Golden Circle

#nationalpark #Iceland #waterfall #nature

A photo posted by Juvoni Beckford (@juvoni) on


A video posted by Juvoni Beckford (@juvoni) on

The Northern Lights

Adventures in #Iceland #northernlights

A photo posted by Juvoni Beckford (@juvoni) on

The Geyser

#geysir #Iceland #waterexplosion

A video posted by Juvoni Beckford (@juvoni) on

The Blue Lagoon

A photo posted by Juvoni Beckford (@juvoni) on

Our organizer, Michael, managed to bring together 16 amazing people, many of whom, I would go on to build very friendships with. These friendships would eventually lead to some personal changes for me that would help me become more open. My primary life’s mission before this trip was to become the strongest version of myself in Mind, Body, and Spirit. After the trip, I’ve added a 4th area Tribe. The people you surround yourself with WILL have a profound change on your life and who you become as a person. It was some random events that enabled me to be a part of this trip, but I still had to get over a core fear that I had of going out into the unknown.


The passion, creativity and hustle-stories shared were truly inspiring. Michael describes everyone’s gathering as a series of serendipitous(random) collisions of awesomeness, we should aim to fill our life with more of these. 

Iceland was such a beautiful place and I’m glad I took a chance and went. It’s possible to drive around the whole island. And the people are very friendly! I would love to write more about my experience, but some stories have intermissions. Until the next adventure!

How could I not end the trip by sliding down an Ice Mountain.


“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”
H. Jackson Brown Jr.