Don’t “Should” Yourself to Death - The Secret to Successful Retreats in 2017 #NewYearsResolution

How many times have you caught yourself saying “I should have…”?

Probably waaaay more times that you would like to admit.

A great new year’s resolution for 2017 is to stop ‘shoulding” yourself to death.

Shoulds in the present moment are about staying in lock step with the status quo, rather than listening to your gut and following your heart.

Shoulds in retrospect are about regrets, regrets about not having followed your heart and regrets about not thinking or planning ahead.

At Rebel + Connect we are committed to empowering you as you create custom company retreats that leave you regret free and full of pride.

A successful company retreat requires a lot more planning than you might think.

The best way to avoid the dread of the “should” is to dig deep, clarify your vision, gather feedback from your team on the front end, and do your due diligence to ensure all your retreat “t’s” are crossed and “i’s” are dotted well in advance!

When it comes time to experience your retreat, you don’t want to get stuck reflecting on the shoulds when you could be beaming with pride and bonding with your team.

In order to plan a successful retreat, there are a few core things you will want to focus on.


You made sure to plan an amazing meal for opening night of your retreat. You have eggplant parmigiana, kung pao chicken, and cobb salad... everything looks great and you can’t wait for the other team members to arrive!

Once everybody gets there, only half of the team fills their plates while others hang back. What could possibly be wrong?

What you didn’t think about was that you have two vegans, three vegetarians, three people with dairy allergies, and two people with gluten allergies on your team.

You should have thought about these diverse food preferences on the front end.


You are on retreat with your team and everything seems to be going well, people are really engaged and seem to be having fun.

The next activity is a small-group scavenger hunt and each team will win a useful prize - you’re so excited to watch!

Then you notice two team members don’t seem very excited about the activity. You walk over to them and inquire - what could be the matter?

You find out that the two team members who aren’t excited are introverts by nature and though they like the idea of the scavenger hunt and want to increase their bonds with their  colleagues,they needed some time alone in their own space to recharge before the next activity.

Unfortunately, you can’t add time into the schedule now, the caterers were already scheduled for dinner at 6.30pm and they have an event right after yours.

You’re thinking...I should have thought to schedule more down time!


Your team really loved that day two kicked off with a group surfing lesson, but you didn’t think about how physically strenuous the activity actually is.

Half of the team is very active, so though it was a special activity, their bodies were prepared for the workout. The other half of the team doesn’t engage in rigorous physical activity on a regular basis and they are really tired and sore.

You should have brought in a couple of massage therapists to help them recover. In fact, looking back, sore or not a massage therapist would have been a great add on for everyone! .

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After having an amazing retreat, the time comes to get photos ready for the company newsletter.

That’s when you realize that nobody captured the bonding between the marketing team and the sales team, nobody got photos of the introvert wearing a huge smile, nobody got photos of the beautiful landscape decorated with joyful team members.

You took a few photos, but mostly of the IT team and of your VP, you didn’t even get a good photo of yourself! Your memories are lost forever.

You should have booked a photographer.

You should have created a #hashtag for your event.

You should have brought a GoPro for the team’s surfing lessons!

You should have done so many things differently so that you could remember all of the great times you had as a team… but you didn’t.

While there were so many things that ran smoothly, in general people had a blast, and you have much to be proud of, you are left with a nagging sense of regret.

“What kind of leader am I that I knew so little about my team? I really let them down. If I had just spent that little bit of extra time or money planning, we could have blown this out of the water!”

Well now you know!

Next time you won’t make the same mistakes. You will hire a team of professionals to assist you in designing, planning, and managing your retreat.

After all, you wouldn’t hire a Sales Rep to run HR or a Customer Success Specialist to head up Accounting.

To really cover all your bases and plan a company retreat that will blow everyone away you need to consider the who, what, where, when, why, and how. This requires you to be confident in decisions regarding program development, travel management, and event planning.

The Rebel + Connect team is uniquely qualified to help you do just that.

Retreats are most effective when customized for your team’s specific needs and preferences and all of these snafus could have been prevented had you simply invested in a retreat planning program like our Retreat Discovery Package. 

We work with our discovery clients, remote team leaders like you, to clarify the strategic vision for the retreat and gather feedback from your team on the front end!

We will help you think outside of the corporate company retreat model box, by emphasizing elements such as:

  • Cutting edge science in health and wellness, team building, and leadership
  • Embodiment of individual company values

  • Community service & philanthropy

  • Proximity to nature

  • Immersive travel adventures

And that my friends is just the beginning.

Whether you are looking for coaching, consulting, or full-on project management, Rebel + Connect has your back!

No shoulding, just doing and crushing it!


Rebel + Connect creates custom retreats for remote teams. A Colorado based company owned and operated by Charlie BirchRachel McGehee, and Summer Weirich, we operate remotely and service clients from all over the globe. Join us as we create cultures of meaning and celebrate human connections in a digital world!

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