How to Stop Working and Be More Productive

And exactly how to use your break if you want to be happier and more productive.

Courtesy of
Courtesy of

The more successful I become, the less my day-to-day activities look like work. Often my friends look at me funny when I tell them how I’m “working” while chatting with “village-minded” investors on horseback in Montana or luxuriating at a fancy hotel in upstate New York for two weeks surrounded by “unreasonable” social change leaders.

While my friends and others might view them as distractions, I firmly believe that work retreats are often the most productive use of my time.

While my friends and other entrepreneurs might view these adventures as frivolous and unnecessary distractions from work, I firmly believe that work retreats are often the most productive use of my time. Since day one, my startup Kuli Kuli has held at least annual, and often quarterly retreats, and, after seeing results, I’ve realized there is no way my company could afford to not host a retreat.

Running a startup can sometimes feel like being an emergency responder — someone is always reaching out to you with an urgent issue that needs immediate attention. I personally find working in a high-stakes environment exhilarating, but even I have to admit that constantly managing the business’s life or death is exhausting. Even worse, it doesn’t lend itself well to insightful discussions and strategy.

Enter team retreats.

Kuli Kuli’s team retreats allow us to take a step back from the day-to-day fires and take the thousand-foot view of our company while giving our team time to connect on deeper level. We structure the retreat to allow equal time for productive group discussions about company goals and objectives while also dedicating time to creativity, personal development, and connection building.

If you’re convinced and ready to make your team retreat happen, here’s a structure that I’ve found works really well for a 2.5 day retreat:

Day One – Focus on Knowing Yourself

Drive or fly somewhere remote enough that you and the rest of your teammates aren’t tempted to firefight. If you have the budget, hire a retreat facilitator so you can participate in the activities instead of leading them (we’ve loved working with StartHuman). Ask your team to take a personality test in advance, like Myers Briggs or StrengthsFinder to help the team get to know each other.

Our team retreats allow us to take a step back from the day-to-day fires and take the thousand-foot view of our company.

Start with a goal or expectation-setting exercise for the retreat and then review everyone’s personality test results, ideally through a fun activity. These tests can be hugely beneficial for surfacing facets of personalities, communication styles, and working preferences that we may not otherwise know about our teammates. I recommend complementing a discussion of the test results with a discussion about communication between personality types. We also often do a Founder “Ask Me Anything” over dinner.

Day Two – Hone in On Values and Trust

We love doing this Marble Jar activity inspired by Brene Brown to discuss instances that make us lose or gain trust in our teammates. We then talk about our values, and learn about the importance of starting with why from Simon Sinek. Hold a grown-up version of a talent show with a five minute “share your passion” activity.

Lastly, you can combine all of these elements of team trust with a fun dinner. We had a Top-Chef style dinner competition where we split into teams and everyone was assigned a recipe, but only one person knew what the final product was and had to direct everyone else on the team.

Day Three – Envision Success and Show Gratitude

Using sticky notepads, have everyone on the team brainstorm their one year, five year and 10 year vision for the company. Then ask everyone to rank those visions until you drill down into the core of what you want to accomplish. Spend the rest of the afternoon focused on your rocks for the quarter and the coming year. If the word “rocks” doesn’t make sense in this context, Gino Wickman’s book, Traction, is a great resource that will change the way you think about goal-setting.

It is so easy to get stuck in our daily tasks and forget to be intentional with the relationships and people we spend much of our life working alongside. In getting too caught up in the success of the business, CEOs can lose their humanity and start thinking of employees as numbers, rather than living, breathing, opinionated humans. Each employee is an investment with the goal of adding value to the company, which is exactly why you need to take the time to get to know them.

Each employee is an investment with the goal of adding value to the company, which is exactly why you need to take the time to get to know them.

Although I do what I can to acknowledge everybody’s contribution during the work week, an inevitable hierarchy of sorts ensues in the business environment. By taking a step back out of the office and into a neutral playing field, magic happens. One of my favorite parts of Kuli Kuli’s recent retreat was the “share your passion” activity. I’ve spent years working with some people on my team and never knew that they were artists, musicians, surfers, and comic book collectors.

After our retreat, our entire team was energized, connected, and ready to tackle Kuli Kuli’s grand challenge — how to increase economic opportunities for women in need while also addressing malnutrition which, according to World Hunger Statistics, is a reality faced by 13 percent of today’s global population. This beautiful mission of ours often gets lost amongst emails and meetings. Only when my team and I get to leave the confines our Oakland office, can we evaluate our work and mission on a larger scale.

Tackling the world’s toughest challenges is easier in a group. We are social creatures and other people are always more motivating than our own inner voices. When one human thinks “I want to end malnutrition”, it can only go so far. At a work retreat, when you can organize a whole team and collectively press pause on everything else, you are able to target the same problem with animation and passion.

Originally published on

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