And the Envelope Says©

Recently, my Mastermind group embarked on our annual magical mystery tour trip. If you’re not familiar with a mastermind group, it’s a concept written about by author Napoleon Hill (Think and Grow Rich) involving a group of people that help each other grow both personally and professionally. Our group has been together for many years and consists of seven business owners and leaders. Now back to the magical mystery tour.

On a recent Wednesday morning, the seven of us gathered early at Hopkins Airport with our carry-on bag packed for a three day getaway. We were all excited and looking forward to our trip and time together, but there was one difference between us and everyone else (I’m guessing) at the airport – we didn’t know where we were going. That’s right – we did not know where we were going for our three day trip. This is the magical mystery tour and thus the reference to “and the envelope says.”

Standing together at Hopkins Airport we opened a large envelope that contained seven boarding passes to – drum roll – Boston. This is what makes it a mystery trip because we don’t know where we’re going. We came up with this idea several years ago and this was our second magical mystery trip (our first trip was to Nashville) as a way to spend some time together away from work and home, but also to have a unique experience and that is what makes these trips magical. It’s all about the experience.

Some quick details: We have a third party book our flights (Thank you Nan Morgan) with our credit card information and birth dates based upon parameters we provided. We wanted direct flights to avoid spending our time flying and making connections and the ticket price would be under $400, which offers a wide range of options (there are approximately 40 direct flights out of Hopkins). Our only other parameter is that we agree (for the experience) to only take a carry-on bag, which is not a big deal for a three day trip, but it’s a challenge given that we don’t know where we’re going (or the weather). That’s the end of the details because there are no other arrangements or plans made. Let me say that again – there are no other arrangements or plans made, so the following is a partial list of what we don’t know or have:

  • We don’t know where we’re going
  • We don’t know what the weather will be like (so we don’t know how to pack)
  • We don’t know where we’re staying and we have no hotel reservations
  • We don’t have transportation arranged
  • We don’t have any schedule or plans

In short, we have a boarding pass to a city that any of the seven of us may or may not have ever been to. And this (the unknowing and non-planning) is the part that makes the trip an experience generally and why (we believe) the entire time away is more an experience of the city, rather than a trip to the city.

With your indulgence and hopefully your interest, I’m going to share with you a quick overview of our experience and then highlight a couple of most memorable moments on the trip. We arrive at Boston’s Logan Airport and, first things first; we had to figure out transportation. Because we knew that Boston is a good walking town we decided to not rent a car and we headed out on a search for transportation to Boston’s fine train system.

As soon as we hit the Boston airport, we had started searching the Internet (yes, we do have our smart phones) to find a place to stay. As you may know, hotels in Boston are not inexpensive so we had an immediate challenge to find accommodations without paying (hopefully) $350 – $450 a night for a hotel. Several of us starting researching online for hotels, but our search quickly narrowed to three sources: 1. (for hotels and the mystery is you don’t know which hotel you’ll get – you do know how many stars – and you can find great hotel values on last minute reservations); 2. (where you can rent people’s homes or rooms); and 3. (similar to Airbnb). We immediately found what we thought was a great option on VRBO – a houseboat on Boston Harbor – but it turned out that it was not available. Disappointed, be continued our search and finally found and booked a hotel in the Back Bay area of Boston (via Hotwire) for a reasonable rate where we would share rooms for our two nights (Loews Hotel).

After standing in line for one bus (which we realized was the wrong bus – oops), we got the correct bus to the train station. Great start! We then go on the train and, after the first stop realized that we were going in the wrong direction (away from downtown Boston). Yes, you heard me right – seven supposedly intelligent business leaders ALL got on a train going in the wrong direction. It was easy to correct at the next stop, but a humorous start to our adventure.

Upon arriving at the station in downtown Boston (with bags in tow), the whirlwind experience started simply when one person said: “I’m hungry.” So it was time to find somewhere to eat, and here’s The Boston List:

  • Lunch at Bell and Hand Tavern (America’s oldest tavern – 1795)
  • While waiting for our lunch orders, small groups of us meandered across the street to experience the New England Holocaust Memorial
  • Discovering that our hotel was only5 miles from the Bell and Tavern, we decided to walk to the hotel
  • When it started pouring rain, we ducked into King’s Chapel (what we didn’t know is that King’s Chapel is on the Freedom Trail) and we spent an hour exploring and experiencing this historic Chapel. Interestingly, when we did the Freedom Trail the next day, King’s Chapel was closed so we only had that experience because we happened to duck in there due to the rain. What a coincidence … or was it?

A quick note – one thing that’s a key part of our magical mystery trip is that we consistently ask the people that we meet what we should do in their city, which also includes asking for recommendations of things to do that are unique and not the traditional tourist activities. We started this with the waitresses at the Bell and Hand and was a regular part of our entire time in Boston. I’ll try to offer some insights into how we discovered some of the things we experienced in Boston. Now back to the list …

  • When the rain didn’t let up, we decided to Uber our way to the hotel which was, for some of us including me, our first Uber experience (Loved it!)
  • After checking into the hotel, we began a walk in the Back Bay area near our hotel which lead us to discover Trinity Church on the way to our destination – the main Boston Public Library (a suggestion provided to us by the volunteer at King’s Church)
  • Main Boston Public Library (beautiful center court garden, renowned map room and amazing architecture)
  • One Masterminder walked across the street back to Trinity Church and sat in on a service that included the children’s choir singing in Latin (one of his most memorable experiences of the trip)
  • Top of the Hub (Prudential Center) for drinks with one of the finest views of Boston at night from the 52nd Floor
  • We then headed to our scheduled (we found this after arriving in Boston) Escape the Room experience (a fun, interactive game offered in many cities where your group is locked in a room and you have an hour to try to figure out how (using clues) to get out of the room. In case you’re wondering, we did NOT get out of the room.
  • This was followed by a humorous and at times frustrating late night search for food in Boston’s Chinatown area, which ended a frenetic dinner at Gourmet Dumpling House
  • Walked the mile back to our hotel along the Boston Commons
  • Late night cocktails at Back Bay Harry’s for some great conversations about the day and life

Day two consisted of the following:

  • Walk through Boston Commons
  • Picture on the carousel at Frog Pond in Boston Commons
  • Discovering the Freedom Trail starting at Massachusetts State House and the Robert Gould Shaw Monument
  • Exploring the Granary Burying Ground where many famous names are buried (e.g. Paul Revere, Benjamin Franklin’s parents, Samuel Adams, John Hancock)
  • Faneuil Hall, where we discovered a line of several hundred people who were awaiting a ceremony to become citizens of the United State (more on this experience later)
  • Long, long, long walk (our GPS mislead some of us) or cab ride to the No Name Restaurant in the Seaport area of Boston
  • Several hours at the District Hall Innovation Center, a public private partnership facility that hosts entrepreneurs and devoted to innovation. We spent several hours there watching companies create, meeting with the managers of District Hall and talking to one of our group’s business partners in Boston about business and innovation.
  • A couple of us visited Brattle Book Store (one of America’s oldest book stores – 1825)
  • Traveled to Cambridge and spent time exploring the Harvard Campus, including Harvard Commons and the Chapel
  • Dinner at Toscano in Cambridge (which happens to be owned by one of our group’s relatives), and the amazing meal ended up being fully comped to us
  • A shared Scorpion drink (alcohol and juice in a giant bowl) at the Hong Kong Restaurant in Cambridge
  • Drinks next door at the Grafton Street Pub & Grill
  • Late night exploring and drinks at the Liberty Hotel and specifically the Alibi Bar (a former jailhouse) [This was a suggestion from one of the Uber drivers on the first day]

Day three (our short day due to flying home) consisted of the following:

  • Tour and beer tasting at the Samuel Adams brewery in Jamaica Plain
  • A humorous ride on the Samuel Adams trolley with our driver (acting the role of Andrew Dice Clay) to DOYLE’S!!!!!
  • Lunch at Doyle’s Café, one of Boston’s most famous and oldest restaurants (1882)
  • Bus ride to the airport which was quite an experience
  • Train to the airport where our flight back to Cleveland, which was delayed a couple of hours

Whew! That’s it – that’s all we did in our 50 plus hours on the ground in Boston. Notably, people we met and friends or relatives of group members commented (after seeing our travels on Facebook) that we did more in two days than many of them had ever done in the many years that they’d lived in Boston. We also had many comments about how we done experienced things in Boston that many of them had never experienced, and that’s one of the main points of the magical mystery trip (the experience).

What I want to share to wrap up is two of our most memorable Boston experiences. Outside of Faneuil Hall we stumbled upon a large group of several hundred people who were waiting in line for a swearing in ceremony to become citizens of the United States. This led to us having a conversation about how humbling it was to see so many people who want to become citizens of this great country. Who have studied and take a test to become a citizen, thereby knowing more about the United States than most of us who were born in this country. These are people for whom being a citizen is a privilege, rather than a birth right. It also reminded us about how easy it is to take for granted the honor of being citizens of this great country. After taking in this experience and discussion, we began to walk away to continue our journey. At this point, Robert Schepens (one of our mastermind group) graciously shouted out to the group “Congratulations,” which was a very kind gesture. What happened next was our goose bumps moment of the trip as approximately 100 of the soon to be citizens shouted back “Thank You” in all different languages and accents. This brought it all home to us – hearing the reality of this melting pot of people longing to become citizens of this great land left an emotional mark with all of us and reminded us to never take for granted the amazing honor and privilege of being citizens of the United States of America.

Our lunch that afternoon proved to be THE experience of the trip for all of us. One quick back note – when we took a mystery trip to Nashville a couple of years ago, our highlight was meeting a man named Mancil, who turned out to be our gift and special person on that trip. On the way to Boston, we pondered who we would meet on our Boston trip that would be our most memorable person. Well, we found him – Nicholas – at the No Name Restaurant in the Seaport area of Boston. Nicholas was ostensibly our server, but he was our gift and teacher on this Thursday afternoon. Nicholas is a short, thick and smiling man, approximately 70 years old, with a heavy European accent. We learned that Nicholas was born in the United States, but he was raised in Europe by his Italian mother and Greek father. He is a retired school teacher who taught special needs children for his entire teaching career.

To say that Nicholas gave us great service is to damn with faint praise. To even say that Nicholas delivered a great experience would be to say too little. What Nicholas did over the course of our lunch (in dozens of different ways) was to love us up. From the ways that he helped us place our orders (suggesting certain meals because they were the freshest seafood, even if they were less expensive), to humorously delivering drinks to bantering with us throughout the entire experience, Nicholas made us feel more like friends than customers. He also brought us several complimentary food items “on him” just to enhance the experience. He personally oversaw the cooking of one of the meal for one of our group who has extreme gluten allergies to make sure that it was properly and safely prepared. At every step of the way, Nicholas made us feel like we were the most important people not only in the restaurant, but in the world. Most important, you could see only one thing in the way that Nicholas lives and serves – joy. This was the magic of Nicholas.

When we walked out of the No Name, one of our group talked about what a great server Nicholas was, but we quickly corrected that description to say that what we had just experienced was a true servant leader. Someone who humbly and without title or position had modeled what it means to care about others and to serve them from a place of love (for us and for his job). We all learned so many lessons from Nicholas that we will carry forward with us forever, and this blog is dedicated to Nicholas.

That’s it (for now) on the magical mystery trip. As I said at the beginning, we stumbled upon this idea as a way to bond personally while having an experience. We experienced Boston different than most people and certainly visitors. We also paid attention to different things – not just the sites, but the people and what was going on around us. We purposefully interacted with people, rather than just walking by them on the street or at a place we visited. Everywhere we went we told people about our mystery trip and everyone was fascinated with the story and wanted to know more. It’s easy for life to be all about doing and going places, but it’s the experience where we learn the most and truly fill ourselves up.

These trips and experiences make me a better person, teach me more, expand my thinking and understanding, and help me going forward as a person, leader and contributor. I encourage all of you to create similar experiences for yourself, your friends and your team members. In fact, stay tuned for upcoming news about the opportunity to experience a mystery trip of your own that I will be helping you to create and facilitate. As you go forward with your day and week, keep in mind that life and relationships are meant to be experienced, not just lived or had.

Nicholas No Name Boston


  1. Joe Smucny says:

    This is a beautiful story about leadership, friendship, service, and being American.
    Well done, and looking forward to more stories about Magical Mystery Tours.

  2. Bob Arnold says:

    Jeff – That is a fantastic trip you all took!

    I have been contemplating a similar thing for my mastermind group and it is great to see how it ‘really’ works out for others who are doing it. Tell Ron F. that I see him in the picture and am very glad to know he participated also.

    You all are a great bunch of entrepreneurs and Americans. Thanks for making others feel welcome to our great country and for sharing your experience with us in this way.

    ONward, Bob Arnold
    Networking Success Mastermind

  3. Kimmie Durham says:

    Jeff, thanks for sharing this wonderful story! It’s amazing what happens when one slows down, takes in their surrounding and truly interacts with others using all of their senses…..and the rain on your first day was divine intervention!! Until the next installment of the Magical Mystery Tour…..

  4. robert schepens says:

    Our trips touch our hearts. Which is difficult to accurately explain, in words. Jeff, you did a great job!

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