Seven friends and I did a Caribbean Cruise focussed on growth & productivity. Team Cruise 2016 included:

  • self-facilitated workshops on hacking psychology, aikido, functional relationships, overcoming chronic pain, unhinging creativity, life principles and “how to read Chinese good enough that you wouldn’t die if you got lost in China”;
  • a hostile takeover of karaoke night;
  • pre-meal base layers, aka we ate a shit tonne of spinach;
  • coconut harvesting in Grand Cayman and Mexico;
  • put put, ping pong and sauna talks;
  • curious artifacts: the Tripod of Stability, Harmonica of Silence, Medal of Awesomeness & Bandanas of Solidarity;
  • soooooo many level red icebreakers.

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Our Crew! Not Shown: Richard :- (

If you have never been on a cruise, I 100% recommend it, and you should 1000% go with a group and plan out activities. The rest of this article lays out some of what we did so you can learn from our wins and mistakes.

Here is a video Nick made about the cruise:

Planning the Cruise: First Steps

Getting 8 people on a trip is legit difficult. The first step was sending a super quick email to about ~20 people with the basic idea: let’s do a group cruise in 2016, focussed on self improvement and productivity. I sent the invite to people who I expected a) could be available to go, and b) would fit in well with the group dynamics I expected. A bunch of positive responses came back, so we did a Google survey to poll on cruise timing, ideas, etc. All the folks live in different cities or countries and are working on vastly different projects, so the three most important questions were:

  1. when are you available?;
  2. how long can you go for?; and
  3. which port?

We found cruise options on Cruise Sheet. After a couple rounds we settled on 5 days in mid-November, leaving from Tampa, Florida. If you are organizing the cruise, you may have to just force a decision on the date that may exclude some people. Everyone booked their tickets individually and paid somewhere between $500 to $700 per person, with various bonuses for on-board credits, etc. We optimized for cruise line, date and route first, and price second. I vetoed fancier cruise lines in favour of Royal Caribbean because RC is really good at gluten free (they have an entire section for it in the buffet and can do made to order too). Most of our crew arrived in Tampa the day before and stayed at the Tampa Marriott Waterside, which was a 15 minute walk to the ship.

Quick, everyone look unimpressed!
Quick, everyone look unimpressed!

Crew Bios

Early on, we made a bio sheet of the possible crew with blurbs about what they do, etc. This is important as “marketing” early on, because prospective crew members want to know who else they could be sailing with, and then as some background information to help facilitate early conversations on board. The crew list oscillated for awhile, and in the end included Nick, Richard, Jesse, Julia, Tasia, Justus, Chris and me. The blurbs included bits like, “runs a company called Museum Hack and is obsessed with…”, or “here’s him in front of the giant ad of him in Times Square.”

Okay, here are the full bios…

Julia Kelly

Julia lives in San Diego where she runs her caricature empire — which spans the US and includes clients like Disney and BMW. She also lifts and is sarcastic in a fun way. We once spent a lovely afternoon together in Central Park. Julia is going to teach us how to make fun of someone’s face — which I hope means we get to draw each other.

Julia’s Caricature Artist Site

Justus Eapen

Justus leads innovation for a Boston software development firm. He is pretty much the ultimate lifehacker, e.g., the pushup rule, where if one person drops and starts doing pushups everyone has to follow, “basketball hangouts” where you go and shoot hoops together instead of just sitting around, and dream butter — which is now my favourite bedtime snack. Justus is also an avid meditator and really into sustainable agriculture. He wants to teach us about digital product development or scaling small teams, but I kind of want to learn how he has mastered every habit ever.

Justus’ personal blog

Chris Schelzi

Chris is a go-to example for what you can be if you eat perfectly and workout even more perfectly. But he’s also ready to try new stuff and push the edge on the whole quantified self thing. In fact he may actually have become a number by now. We met in Boston where Chris was revving up PR for Pavlok, but he recently relocated to Austin. I actually don’t know what he is doing, but part of it seems to include a collaboration with Charlie Hoehn. I want Chris to teach us about our quantified self, or maybe how to get chiseled abs, whatever. Oh, by the way, here is a picture of him at Times Square.

Chris’ personal site

Nick Gray

Nick is the founder and CEO of Museum Hack, the company I’m working with in NYC. Nick has been featured in the media for some cool stuff, including being a “connector” that hosts awesome parties, being one of the top 41 bachelors in NYC, and being a master at working with virtual assistants. Nick is also big on quantified self, eating well, etc. FYI, this whole cruise plan is inspired by a cruise that Nick did last year with a few friends. He is going to teach us icebreakers, and how to quickly connect with people and a team.

Nick’s personal site

Museum Hack’s site about museum tours, company team building activities, consulting, etc.

Richard Garand

Richard is a fellow Canadian hailing from the middle of the country, where he keeps homes in both Regina and Calgary. When I met Richard he was a WordPress Developer but a couple years ago switched to marketing, with clients like Toptal. Richard travels a lot, including some favorite spots in Italy. Two days ago, Richard was skiing on real snow.

Richard’s site

Jesse Anderson

I interviewed Jesse for Ramit years ago. Now Jesse runs a training business where he helps programmers/coders learn big data. I’ve interviewed a few of HIS students and the consensus is he is a master at taking complicated topics and making it fun and interesting to learn. Random cool fact: Jesse was featured in a *ton* of major media for a data project he did on Data Monkeys Randomly Generating Shakespeare — it was the first time Shakespeare was ever successfully created by random generation.

Jesse’s personal site

Jesse’s big data training company

Tasia Duske

Tasia lives in NYC and is the funnest / smartest / coolest HR person I know. She has brought joy and competitiveness to the lives of many through the best game ever: Champion of the World. She is very into yoga, her favorite book is the Alchemist and her bag was lost on the way to the cruise :- (

Tasia on LinkedIn

Michael Alexis

Blah blah blah China. Blah blah marketing. Blah blah blah Chipotle.

Cruise: Day 1

Try to get on the boat ASAP, which could mean going early in the morning. For our group, we got on board around noon. You should definitely do the online check-in in advance because it expedites the process. On board, some of us met up and explored the boat, grabbed a quick lunch, etc. We coordinated via a Facebook Messenger group because everyone could still use their phone while we were near land. Once on board, I printed out itineraries for the cruise, but I recommend you do that in advance.

Our first committed meetup was dinner. Nick taught us his framework for icebreakers, which is basically:

  1. Start with “green” or “yellow” icebreakers and work your way up to “red”;
  2. Whoever proposes an icebreaker goes first, and gives the next person a heads up by asking for permission to send it their way.

A green icebreaker is fact based, e.g., “What is your name?”, “Where do you live?”, “What did you eat for breakfast today?”

A yellow icebreaker is fairly basic too, but takes a little more thought, e.g., “What do you usually eat for breakfast?” or “What book would you recommend to this specific group?”

A red icebreaker is the most personal, “Who did you vote for and why?”, “What is something you have been thinking about lately that no-one has asked you about?”

After the icebreakers, people naturally gravitated to “what’s the plan for the week?” So I pulled out the itinerary to share, point by point. The first item was rules, of which we had 3:

  1. Pushups. If you are late for a workshop the penalty is 1 pushup for every minute you are late.
  2. Disagreements, are welcome and encouraged. If a decision needs to be made, it will be resolved by Hunter, Ninja, Bear.
  3. Brothers and sisters. Everyone here is cool, how “open” we are w/ new folks is kind of a spectrum, and this is a great opportunity to be open and make new friends. Like brothers & sisters some disfunction is okay and normal, as long as we approach it all with respect.
  4. Others?

These rules are important for keeping order on the boat. The pushup rule keeps people accountable for arriving on time. We did a lot of pushups.

The disagreements rule gave us an easy framework to push through basic decisions. Also, everyone must go along with the result. If Justus says Fight Club is the best movie ever and Tasia says it’s actually O Brother, Where Art Thou?, then they can Hunter, Ninja, Bear for it. If Justus wins, then Tasia’s new favourite movie is Fight Club.

The brothers and sisters rule was a last minute addition, but proved to be essential. If you put 8 people together for a week there will absolutely be mild conflict, and a reminder about the sibling rule is a great way to diffuse it.

We also distributed the curious artifacts, all of which I bought on Amazon:

  • The Medal of Awesomeness was a gold medal awarded on merit, it passed hands a few times during the cruise based on things like acts of kindness, photo competitions, etc.;
  • The Harmonica of Silence was a tool for quieting everyone down;
  • The Tripod of Stability is actually just a mini tripod for mobile phones, dope name though; and
  • The Bandanas of Solidarity was a 12 pack of orange bandanas that helped us identify each other.

Throughout the week we got a lot of questions from other cruisers, e.g., “what Olympic sport did you win?” and “what are the bandanas for?” We told them we were in a gang, which was funny to us but less so to them.

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Crew Huddle – notice Julia’s Medal of Awesomeness

Sea Days

Our cruise had two full sea days and two full land days.

For sea days, we packed in self-directed workshops. Each person picked their own topic and the only requirement was it be 45 minutes-ish. We did three on the first day, and five on the second day. Here is a list of the workshops in the order they happened:

  • Me: How to Read Chinese;
  • Richard: Aikido;
  • Jesse: Unleash Your Creativity;
  • Julia: Healing Chronic Pain;
  • Justus & Tasia: Hacking Your Psychology & Habits;
  • Chris: Living by Principles;
  • Nick: Relationships.

Workshops don’t take up all the time, so we also did stuff like wall climbing, karaoke (every night…), naps, swimming, sauna, etc.

Sweeeeet Caroline, bah bah bah!
Sweeeeet Caroline, bah bah bah!

Land Days

Land days were less structured. Some people may want to do excursions, which is fine if they break off, but most of us went to the beach. Grand Cayman was mostly us all hanging out in the sun, playing frisbee, swimming, etc. Cozume, Mexico was a trip to a mini resort that was a little disappointing, so we hiked down the beach and found a cool place to sit and talk. Land days are good for group photos, and are basically whatever you want to make of them. We were always back to the boat in time for dinner, which is nice because gluten free options on Mexico islands are sparse.

My view at dinner.
My view at dinner.

Cruise Tips

Here are some things that went well and not so well on Team Cruise 2016:

  • Have rituals. For us the pushups, games, etc. were a great way to bring everyone together;
  • Have an identifier. Bandanas, hats, t-shirts, etc. all could work;
  • Eat healthy. A lot of people eat terrible food on cruise ships and waste a lot. If you live off salads and protein and some carbs you will probably feel good throughout;
  • Chant. We chanted a lot at Karaoke and it was fun. You can chant for your group members AND everyone else on the boat. Leo’s turn to sing My Girl? Leo! Leo! Leo! Also, guaranteed that you can get the entire lounge to chant USA!;
  • Timelines. We generally had times set to meet at, and some folks would be late. You could keep strict start times;
  • No internet. Or at least not much of it, we had some access on land days but generally didn’t use internet on sea days;
  • Room type. We all had different rooms, mine was an outside cabin with a window you couldn’t open. Next time I would get a balcony room. It’s $100+ more, but it would have been worth it to have fresh air at night;
  • Sauna chats. Saunas are a great place to bond;
  • The Harmonica of Silence wasn’t really used, but I’d definitely try it again;
  • Gratitude Letters. One morning we all wrote thank you notes to people back home. Cultivating gratitude = great;
  • Bandanas are great. We used our extras to recruit new members for our gang.
Post cruise wind down at a coffee shop.
Post cruise wind down at a coffee shop.

About three days in, people started asking, “where are we going for Team Cruise 2017?” I don’t know yet, but I’m really happy I got to bring these folks together for new friendships, and even happier to have an opportunity to do so again.

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