Waikiki in the Spring | 10% Work and 90% Play | Digital Nomad Travel in Hawaii

JSE’s View:

Waikiki is often known for its views of the Diamond Head Crater (technically a caldera, see below) and a continuous flow of gently rolling waves which are perfect for sun burned tourists; with a possibility of riding a big wave, surfing for the first time.

For us, it was a time for a week-long getaway, a bit of traveltrepping, and an exploration of historical sites. On this trip something incredible happened, I (JSE) did not even inquire about wifi. An anomaly indeed. Perhaps it was the colorful cocktails with a slice of pineapple. Maybe it was the obvious decompression I felt when my feet his the sugary sand. Not sure. Don’t care. It was just great.

being a digital nomad in hawaii

Our mobile office view of Waikiki Beach

Until our third day on the island, I just used my iphone to check emails, text and do a couple google searches to settle a couple debates fueled by passion and colorful drinks on the beach. NOTE: I (JSE) was felt compelled to make a geological point. (insert snicker here…) Diamond Head is called a crater, and I called it a caldera. I exclaimed a crater can be caused by man, a meteor or other space objects in addition to Earth-bound events. A caldera is a hole (a crater) specifically created by the cone collapse of a previously active volcano. I digress. We’ll talk about our hike to the top of Diamond Head in a bit.

I’m generally not much of a typical, touristy kinda person. I like doing more of the Anthony Bourdain type of adventures. The less well-worn path. However, I was excited to see the USS Missouri and the USS Arizona memorial. It was on the deck of the USS Missouri where The Unconditional Surrender of Japan took place, which effectively ended WW2. The ship was the last destroyer built for our U.S. fleet. Apparently unmanned drones, long range missiles, and well-trained soldiers do just fine now. 

Going to the USS Arizona memorial is something every person should see. It’s not especially pretty or grand. The memorial is simple. It’s more a matter of symbolism. We all need to know and remind ourselves of two things: We need a strong military and war stinks.

things to do in waikiki

When you come to Waikiki, be sure to indulge in one of the sunset cruise options.

On our fourth day, I logged in to check email. I found two complains from customers that they could not access one of my services. I emailed tech support (located in Florida, France and South Africa). Within minutes I learned that our server – and a hundred others around the world – were attached from hackers located in China. Awesome! I know my tech team is really smart and will solve the problem. I just get bummed when people are let down. Within 4 hours, the attack was stopped and the server had resumed 100% function.

As you know by know, I’m a martial arts junkie (training in 4 styles each week). However, there comes a point where your body needs a break from getting punched, kicked, slammed or choked. So, I decided for the week I was in Hawaii, I would turn myself into Laird Hamilton. Laird is a waterman (i.e. a surfer, stand-up paddle boarder, ocean swimmer, and all-around freak of nature when it comes to the ocean and activities reliant on it. The result was inevitable. I haven’t surfed since I was in high school and I was okay at best. Stand-up paddle boarding is tougher than it looks. It is a great workout (lots of core). We went on two catamaran rides, which were a lot of fun. We also surfed waves on an outrigger. I went for a couple easy ocean swims as well. Nothing too serious. I did a couple workouts in the gym, but wasn’t really into it this week. We went on many walks throughout Waikiki. I found a park on the east end of the strip and it had some cool outdoor fitness equipment. I did a fun outdoor workout (pull-ups & dips kinda stuff).

Hike to the top of Diamond Head

At the top of Diamond Head looking back at Honolulu

This leads us to our hike to the peak of Diamond Head. From our hotel (Waikiki Outrigger On The Beach) it was about 6 miles round trip with a total elevation gain over 1,600 feet. The last 1/4 mile is really steep. However, with any moderate level of fitness, you can do it. There were three guys in flip-flops who got to the top. Not the smartest fitness trend I’ve seen, but they get 10 points for effort.

Once at the top, the view is incredible. Kelli took some pictures and then got an email and text at the same time. A drank some water and she closed to deals before we walked back down. Now that’s Traveltreppin. NOTE: We suggest starting this hike early because it gets hot. The ocean breeze rolling up the face of Diamond Head does refresh you and rewards you for your effort.

There is one thing I found interesting, which made me smile, as I did my “work” on my balcony. The vast majority of work I handled had much to do with future travels and outsourcing work so I can travel more. One email was from my agent’s office arranging my

UFC Gym in Hawaii

BJ Penn has always been a big influence on my passion for martial arts. So, I had to visit his gym, make some business contacts and get a T-shirt only available on the island.

flight to shoot my new TV show in Orlando, FL. I then received a message on Facebook to work out the details of my upcoming trip to London to speak at a fitness industry event. I then got an email requesting payment for 10 articles I ordered from my friend Cameron who is a Traveltrep himself. He and his fiancé (both teachers) live in Thailand where he trains and fights in the national sport of Thailand called Muay Thai. 
To make a living, they both teach English, freelance as writers and also teach online. The Traveltrep circle continues. Sidebar: Cameron asked if I needed anything else this month, because they will be traveling through Asia and Europe for 6-8 weeks. We acknowledged we’d like to live each others’ lives for a couple weeks.

On the last full day of our trip, Kelli stayed with the girIs and I took a cab to the UFC Gym owned by UFC champion and mixed martial arts icon BJ Penn. Of course, once I got there I wanted to train, spar and learn from their great coaching staff and great members. Everyone was cool. The gym is awesome. The equipment is epic. The energy was palpable. I made some business contacts, took some pictures, and got a cool t-shirt only available for purchase on the island.

Kelli’s TrepViewpoint

Just like every trip, I carefully pack my ipad, laptop and iphone in their respective decorative, matching covers (I am a designer after all) knowing full well, I have work to do and waves to ride – I am a professional Trepper and ready for the task!

With our teen daughters and parents in tow, we have a lot of family time and fantastic photographic memories ahead. Like many of you, traveling with kids an family, you know it’s a delicate balance. Time with Mom, time with Dad, time with my girls, time with my husband, time to myself and of course, time to answer my emails and my business partner. All whilst catamaraning, hiking, paddle boarding, touring, and sunbathing.

catamaran options in waikiki

Heading out on the catamaran for a sunset cruise

While exploring Waikiki the first day, John and I were struck by the unusual Banyan tree – as wide as it is tall, brilliant in its design, the Banyon drops delicate roots from it’s longest limbs, that over time become strong and bark covered acting as auxiliary supporting trunks. What a symbolic and simple lesson to all – when support is needed, create it.

So to when Trepping, enjoying your family or the sites, when work must be accomplished reach for your support! With my smart phone, atop volcanic crater or lounging beachside, I could perform 70% of my work with ease. Because I manage a website for my Design Camp business, it’s imperative I have my laptop. When the work emails flood in and you know it’s time to create some more “Banyan tree” support, I highly recommend finding the best wifi connection, grabbing a fancy fruity drink and allow yourself the time to satisfactorily complete your tasks.

Banyon trees in Hawaii

The Banyan trees are beautiful and symbolic. When they sense a need for more support, they grow additional roots from any point on the tree where stress is felt. Incredible.

Unless you work on the beach with your favorite libation everyday, it is definitely still a vacation. The beauty of Traveltrepping is finding the balance between work and play and not feeling guilty about either. I’ll drink to that!


Final Traveltep notes:

Kelli’s technology for this trip: iPad, iPhone, Macbook Air
John’s technology for this trip: iPhone, Macbook Air, iPod

Work/play percentage:
John 5% work, 95% play
Kelli 15% work, 85% play

Biggest take-away:
Wifi in the room was not great (slightly better than Satellite on a cruise ship)
The business center near the lobby had a strong connection.

SPECIAL NOTE: All of our meals on this trip were paid for my money earned with our Nutrition Business Blueprint.

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