How to Plan Your Very Own Retreat - Streetlamp Creative
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How to Plan Your Very Own Retreat

How to Plan Your Very Own Retreat

Estimated reading time: 6 minutes

Last month, we took our first annual Streetlamp Creative corporate retreat. The two of us holed up in an Airbnb for two full days with an agenda, plenty of snacks, and lots of butcher paper and markers to write down our ideas. On the first day, we reflected on the past year – our accomplishments, lessons learned, revenue and expenses, client “wins” – all of it.

The next day, we delved into our goals for 2020 and beyond. We empowered each other to share our challenges and priorities, and we worked together to distill them into action steps. We came out of the experience feeling a little exhausted but incredibly motivated and inspired for the year ahead. Now, we have fresh mindsets, ambitious but achievable goals, and a clear path forward.

If you’re finding yourself a little drained at work, consider carving out some time for your very own unique corporate retreat. Below, we’re sharing a step-by-step guide for your 2-day “refresh” session. Whether you do this solo, with a business partner, or with your whole team, setting aside the time to think intentionally about your work is a total game-changer. Here’s how to do it.

1. Create an Agenda

A month or two before your retreat, make a list of what you want to accomplish during that time and use that as the basis for your agenda. Include a mix of “business talk,” breaks and meal times, and team-building activities or a field trip. Be as detailed and creative as you’d like – remember, this is YOUR retreat – it can look like whatever you want!

Need some help thinking about your business’s growth? Chat with a business coach or consultant during your retreat! Craving more confidence when it comes to risk-taking? Look up ziplining companies in your area and plan an excursion. Been working hard all year and need a break? End your retreat with a massage or other indulgence. The key is to find what works for YOU. Here’s what our agenda looked like:


  • 9:30 AM – Celebratory breakfast at The General Muir
  • 10:30 AM – Drive to airbnb, check in
  • 11:30 AM – Review 2019 revenue, accomplishments, and lessons learned
  • 1:30 PM – Virtual meeting with business coach
  • 2:30 PM – Lunch & break for client work
  • 3:00 PM – Review results from Clifton Strengths assessment
  • 4:00 PM – Review budgets (actual for 2019, projected for 2020)
  • 5:30 PM – Open discussion


  • 9:00 AM – Meet at airbnb, breakfast & coffee
  • 9:30 AM – Discuss 2020 goals: client goals, admin goals, and professional development goals
  • 11:30 AM – Break
  • 12:00 PM – Discuss 2020 goals: marketing goals, business growth/revenue goals
  • 1:00 PM – Lunch & break for client work and emails
  • 2:00 PM – Brainstorm for Streetlamp Creative anniversary party (stay tuned for more news on this front!)
  • 3:00 PM – Revisit retreat topics that need more discussion
  • 7:00 PM – Celebratory dinner at Chai Pani

2. Find a Location

If your team is small (just you and 1-2 colleagues), we recommend booking an Airbnb or other rental home for your retreat. There are a few reasons we love choosing an airbnb over a rentable office/workspace:

  • You can come and go as you please, offering more flexibility for the timing of your retreat
  • You can find rental properties with privacy, so your team doesn’t have to worry about being loud and disturbing others, which can be a concern in a coworking space or traditional office
  • You can leave all your work supplies, laptops, snacks, etc. out in the open overnight
  • Having an equipped kitchen and a fridge allows everyone to bring the food they like and prepare meals together – which, in and of itself, can become a team-building activity
  • Even when renting the space for 3 nights (for a 2-day retreat), we found our particular airbnb of choice to be cheaper than a lot of rental workspaces!
  • You can seek out the specific things that would make you feel most comfortable. For us, that was lots of natural light, a huge table where we could spread out our work, and lots of houseplants and other fun decor.
  • Fresh, fun surroundings can inspire new ideas and spark your creativity in a way that a more corporate setting might not.

3. Set Your Out of Office and Pack Everything Up!

Make sure that you clearly communicate ahead of time to clients, colleagues, and friends if you’ll be unreachable during your retreat. Setting clear expectations and turning your “out of office” message on can help you focus on the important tasks at hand, rather than wondering if your inbox is filling up while you’re away.

About a week ahead of time, make a list of supplies you’ll need for your retreat. That way, you can purchase and pack everything up ahead of time – eliminating the stress of last-minute errands.

  • Laptops, chargers, and phone chargers
  • Printed copies of any key documents you plan to review (agendas, profit & loss statements, etc.)
  • Sharpies (in every color!)
  • Big rolls of butcher paper
  • Lots and lots of snacks, meal ingredients, coffee, and La Croix
  • Creature comforts: fuzzy blankets, cozy socks, tea

4. Do the damn thing!

Don’t worry if your retreat doesn’t go perfectly to plan, if you discover something you missed along the way, or if you run out of time to check every single item off your list. The whole point of a retreat is to pause from the daily grind and spend time being intentional about where you’re headed. Rather than viewing your retreat as your one and only time to accomplish this work, try thinking about it as a starting point and catalyst. You can even plan a “mini-retreat” on a quarterly or monthly basis if you enjoy the practice of setting aside this time for yourself. At the end of the day, setting aside time for a retreat is an act of self-care that should leave you feeling clear, relaxed, and confident about the road ahead.

Our airbnb hosts had the sweetest dog!
Have you ever planned a retreat for yourself or your team? Where did you go and what did you do? Do you have tips to share? Drop us a line at hello@streetlampcreative.com – we’d love to hear from you!