The 99 Day Challenge

I logged off email, Facebook and Twitter for 99 days to focus on things that weren’t all about money and entrepreneurship. Here is what I learned.

On October 1st 2014, after exactly 10 years of work, I logged off. After years of striving to build up an internet company and make as much money as possible I was burned out.

My goal was simple. Unplug.

I logged off email, Facebook and Twitter and headed out of town in hopes that I could get my mind off all the business+tech+entrepreneurship+money conversations that I was constantly engaging in. Basically, I wanted to do a much longer version of I had also seen an inspirational Ted talk where the guy Stefan took a entire year off after working for 7 years.

Bernard was late.

We had arranged to meet at 10 AM sharp at the, but he was 40 minutes behind. I should have expected it though, for in Belize it didn’t seem like everything always ran according to plan.

Our exuberant, and a little crazy new Irish friend had convinced myself and my three friends to go on a custom fishing trip. However, I should have known something was up when I saw Bernard’s shoes. He was wearing the very rare Nike Jordan 11's that often sell for around $200. Two hundred dollars is a kings ransom in Belize as most of the people I saw were wear shoes worth about $10.

It turned out a Bernard was actually a local drug dealer. He was the same smooth talking dealer that Jack had recently been purchasing marijuana and cocaine from.

As we arrived at the boat we noticed that the captain had been drinking and his eyes were bloodshot. We packed our stuff, turned over the engine and began to the leave the dock. We had already pulled into the bay when one of my friends shouted that we had forgotten the anchor and the ladder. As it turns out the captain had been doing this for 30 years but was still forgetting stuff.

The seas were choppy. Really choppy. So choppy that the boat bounce to and fro on top of the water. My friend Matt began to look grim. A few minutes later I turned around and found him projectile vomiting over the edge.

Then Bernard, who had tried unsuccessfully to convinced us that he was actually a fisherman, began to throw up.

We ended up catching few fish and then finally heading back to shore. Overall it was one heck of a ghetto fishing trip.

Sailing with drug dealers was just one of many interesting experiences over the course of the 99 Day Challenge.

My trip began in Denver and I headed to San Francisco, Washington DC, New York, Houston and then I flew into Mexico City. From there I took busses all over Mexico to over 10 different cities . I then headed to Guatemala for a few weeks and also got a chance to spend a few days in Belize before heading back to fly out of Cancun.

Hierba Del Agua — This natural infinity pool was really impressive. You could take some really good photographs here.

The trip was an amazing experience as I got a chance to leave the first world comforts of United States and spend a good amount of time in the more easy going and-lets be honest-a bit more dysfunctional countries of Central America.

I was blessed to hike through caves, rent motorcycles, swim in beautiful river pools, and go to countless beaches. I went on every tour I could, ate some really awesome, and usually really inexpensive, food and experienced so many of the incredible things that these countries have to offer.

This is Tulum, Mexico. It has some truly incredible beaches. But it definitely is in need of some mid range hotels and hostels. Some of the worst run hostels I stayed at in Mexico were here.

But quite possibly the most interesting part of the trip was simply getting an opportunity to get out of the states and not be tethered to the internet. To experience a place where most people didn’t have a car, and many rode to work on an old $750 motorcycle. I went to places where the culture is heavily based on community and over the course of my time in Central America I don’t believe I saw a single homeless person.

I got a chance to experience some interesting things.

  • All through Guatemala I saw hard working men and women carrying incredible heavy loads of wood they had just chopped down. I was floored as they quietly went about their work. Not complaining, just working hard to continue to feed the fires in their homes that they used for warmth and cooking for their families.
I was completely blown away by the Guatemala men and women who would walk miles carrying heavy packages of sticks without complaining. They use the brace on their heads to support even more weight.
  • I talked to men who were working as bus drivers and who had 12 hour shifts. When I asked them how many days in a row they had worked they said 25 straight days without a break. I couldn’t believe how hard they were required to work.
  • I met a Australian traveler who had recently purchased 10 packets of Cocaine. He had accidentally forgotten one that was stashed in his neck pillow and imported it over the border into Honduras. If he was caught at the border importing cocaine he probably would have ended up in one of the jails in Tegucigalpa-one of the most dangerous cities on earth.

Upon returning my friends would often ask if Mexico and Central America safe?

Yes and no. It depends on how you look at it. Yes, there are horrible things that happen in Mexico. I believe the border between US and Mexico is one of the most dangerous places in the world. However, I was surprised how smooth everything went on the trip. I had no safety problems. I flew into Mexico City and avoided the northern areas. Also I was blessed to somehow avoid getting sick. The worst thing I saw on my trip was quite minor, it was a girl who had her taxi driver drive off after she got out and he took her backpack that was in the back of the car.

Overall I believe that Mexico is actually similar to the US when it comes to safety. Here is an interesting visual about it.

A couple things I learned:

  • Dinner of five tacos in Mexico costs only $3.40
  • A movie at a brand-new movie theater costs $2.40
  • You can rent a three bedroom two bath house in Mexico for $1000 a month
  • Mexican buses are actually really comfortable. There is this great bus company called ADO that blankets the country.
  • Most people drive a scooter or an inexpensive car around town. You don’t see any large RV’s like you do on the highways in America. Most people have simple clothes. There lives seem less complicated.
  • Every person I meet has something interesting about them. No matter what they look like, where they are from, or how much money they make.
  • It’s so nice to use the “llavanderias” and have someone wash, dry and fold all your clothes for you for less than four dollars
  • My physical environment was vital. When I found myself at a dirty hotel or hostel it very much brought down my entire impression of an entire town.
  • When you move from place to place every couple days it’s hard to establish strong friendships. Friendships really do take time and require much more than just a week
  • Google maps is incredible. And when I am in a foreign country it is one of the parts of technology I miss the most.
  • 95% on the world has never been on a plane before. This is incredible to realize. I am so blessed to be part of the 5% .
Cozumel diving was amazing. One of the best experiences of my life.


There’s a lot of value in kindness. While in Central America I was struck by how local people people often would look me in the eye and wish me a good day. In fact one of my favorite stories on the trip was a story about a number of gringo hikers who were hiking through Guatamala many years ago during their war. A squad of soldiers were running down the trail in preparation to attack a village below. As each and every one of the 30 soldiers ran past the hikers they looked the hikers in the eye and were sure to say “Buenos tardes” as they ran by on their way to the fight.

Overall the trip was excellent. I was incredibly blessed to unplug and get an opportunity to see things from a completely different point of view. I didn’t become perfectly calm like I really wanted to. I didn’t get a chance to work out as often as I’d also like to. But I did have amazing experience. I developed an incredible respect for the countries in Central America, especially Mexico. It was great to get away and see things from another point of view

The author on an old dirbike in Guatemala. He rented the bike for the day from a local guy he met on the street.

Photo Credits:


Guatemala man:


Hierba Del Agua: