Why we took the #paid team on an all-inclusive vacation

Our resort, Secrets Playa Mujeres in Cancun, Mexico

This April, we invited 22 team members on an all-inclusive vacation.

18 of us said yes.

Some people might think it’s excessive to take 18 team members on vacation.
I think it’s one of the best investments you can make.

Vacations allow for team bonding, mental resets, and strategic reflection. This leads to cohesive communication between team members, an increase in performance and motivation, and new strategies that can have a significant impact on your business. Besides, it’s also fun!

Richard Wong snorkling outside Isla Mujeres

Team bonding adds efficiencies to the workplace

First, team bonding builds trust. As team members get to know each other more, trust naturally builds. We played games, shared amazing food, partied around the pool, and even took care of each other under the sun (read: SPF80). We also rented a Catamaran and went to Isla Mujeres, exploring a foreign island together. These experiences brought us closer together.

Sunscreen train (left to right: David, Alice, Danielle)

Trust can be leveraged back in the office to improve teamwork, such as delegating with increased confidence. Team members are also given an opportunity to bond with those who they don’t interact with frequently.
An environment of open communication and team bonding fosters success through a broader perspective and sense of shared beliefs, integral to maintaining a steady cultural foundation.

Photo Cred: Richard Wong

Mental resets improve effectiveness

Taking time to relax is an important contrast to the typical work environment. People work hard, stay late, and even work weekends to hit important deadlines. This lifestyle is exhausting and unsustainable. One of our team members, David, had been with us for 2 years and hadn’t taken a vacation! Vacations should be encouraged because it allows your team to destress, refocus, and have fun — so they can bring their best selves back into the office afterwards. Some might feel pressure not to take any time off. That’s when encouraging vacation is the most impactful. Individuals who convince themselves they don’t have time to take a break are usually the ones who need a vacation the most.

Out of office reflection can spark innovations that fundamentally change your business

Lastly, there’s an intangible, unbounded reflection and exploration between all team members. “Remember when” recollections lead to “what if” possibilities that can transform your company through raw, organic energy and conversations. The shift from a heads-down office environment to an open, broader, free-flowing atmosphere allow a new, broader perspective and gut-check of the overall direction of the company. One of the ideas we had out-of-office was to create a new department to help increase our close rate. That department to date has increased our close rate by a meaningful 12%.

Jared hanging out by the pool

Bringing it all together

The team bonding, mental reset, and strategic reflection made the investment valuable. The experience helped us work cohesively together and guide us in the right direction — allowing us to maximize our potential.

Taking a vacation with the team is also a form of celebration. Celebrating your wins as a team is important because the lows you experience on your start-up journey will be deep, so it’s important to even things out. I touch on this point in another article I wrote called 7 key learnings from my first two years as a start-up founder.

The success of this trip led to our next retreat: an all-inclusive camping trip at Fireside Conference, where we brought 24 team members to celebrate, learn, and have fun.

The #paid team does Fireside Conference. Look closely in the middle for the infamous “stick.”

Credit: I was inspired to write this post by Latif from Roadmunk. I admire Latif and while I only found out about his team trip after we came back from Cancun, his blog post about his experience was the inspiration for this post. Thanks Latif!

Thank you for reading! If you decide to take your team on a vacation or trip, please do tweet at me. I’d love to see a picture!


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