In 2013, I moved further away from my home town, quit my job, and gave my car to my nephew. I wanted a fresh start and to dive headfirst into the music industry. I attained varying levels of success, depending on how you look at it, but that’s a story for another post. I bring this up now because it was the first time I realized how important it was to be in the company of good people.
While I was grinding away at my musical masterpiece, my friends and family were at work continuing with their lives. My colleagues who I’ve build strong relationships with over the years went on with their lives as well.
I could no longer rely on accidents of circumstance to maintain the relationships I’ve built over the years. I had to be proactive or else those relationships would wither away.
The people I felt closest to were the friends who I’ve grown to call brothers over the years. With this realization, I decided to get all of my brothers together for a retreat—a weekend of fun, conversations, and collaboration. I called this event the Brothers’ Retreat and it went on to be a success by all accounts.
Since the time of its creation, we’ve maintained our yearly retreat. This tradition of brotherhood and fellowship has been so valuable to me that I want to share the secrets of its success in this “how-to” guide.
Step 1 — Guestlist
Compile a list of your best friends and send them an email with your motivations for going on a weekend retreat. If you want, encourage them to add more people to the email thread whom they think would be interested. Friends of friends are always welcomed at the Brothers’ Retreat. It’s an easy way to make new friends who have already been vetted by the people you trust. Overall this email is to gauge interest and get a confirmed list of attendees
Step 2 — Pick a date
You can use Doodle to find a date when all or most people who are interested are available. Suggest a couple of options that are at least two months in the future to give those with busy schedules and/or families to make arrangements.
Step 3 — Find a rental
Pick an environment that is most appropriate for you and your friends. We usually head to the Pocono Mountains in Pennsylvania because it’s convenient and outdoorsy. Once you know where you want to go, use sites like VRBO, Home Away, or Airbnb, to find a house that can accommodate all of your attendees. After you’ve found your favorite rentals, send the top three options to your group for a vote. Reserve the home with the most votes for your dates.
Step 4 — Collect payment
Booking a rental home for a weekend usually requires a deposit of half the total cost upfront. I split this cost equally amongst all the guests and ask that every one provide a non-refundable deposit at the time of booking. Whenever the second payment is required (the timing is different for each site) I ask for the second half of the money from everyone. You can use the Cash App, Venmo, and the like for fast transfer of money into your account.
Step 5 — Plan/book activities
Look for nearby activities that you and your friends would appreciate. We usually go to the shooting range, fishing, and ATVing. Canvas the area around your rental and find out what local activities are available. You may also be able to get this information from the homeowner or property manager. Pick a few options you think your group would like and ask them to rank them in order. Choose the top three activities book it ahead of time to lock it down for your group.
Step 6 — Food
If you or a few folks in your group don’t mind cooking and/or appreciate the cost savings, consider buying groceries and cooking meals for the weekend. It’s a key feature of the Brothers’ Retreat. We have family-style dinners around a big table every night and have great conversations. I highly recommending it. For meal planning, I ask/assign one or two people to be in charge of making the menu and going grocery shopping. During our trips, extra folks usually help out with cooking and the people who don’t cook are responsible for cleaning.
Step 7 — Collect payment (again)
This second wave of payments is to cover the groceries, the balance of the rental costs, and any group activities that needed a deposit to reserve. During the trip, there might other group expenses. In that case there would be a third wave of the collection after the trip is over. Tools like this one can help to figure out who owes how much to whom in a clear transparent way.
Step 8 — Distribute information
After all the arrangements are made with the house, activities, and food, send an email providing your guests with the details. If you’ve received information on how to access the house (lockbox combination, key codes, etc…) forward it to your guests as well. This is helpful if you all are arriving at different times. You want to make sure that everyone can access the house without you being there.
Step 9 — Enjoy the trip and take pictures
Have fun and enjoy the company of good people.
Things to watch out for
The number of beds – Before you book a rental, get an accurate accounting of the number of beds in the house. Some houses may have room for 10 people but only has four queen-sized beds and two sofa beds. Be sure to confirm with the property manager or owner the number of beds there are in the house so you know ahead of time.
Cleaning dishes – if you decide to cook get a place with a big kitchen and a dishwasher. Ask the people who didn’t help cooking to help clean.
Distance to activities – try to find activities within a 15 min drive. Traveling long distances will eat away at your total time of hanging out.
The number of activities each day – leave free time for spontaneous group conversations, phone calls with loved ones back home, or to recharge.
Buying too much food – It’s easy to overestimate how much food everyone will eat, so be conservative in your grocery shopping. And it’s no big deal to have to make a grocery run throughout the weekend.
That’s it!
These types of trips are not difficult to organize but do require some effort. If you decide to host please let me know how it goes in the comments.