For the past five years, I’ve hosted annual planning offsites for myself.

The goal is simple: Get anchored in my personal and professional goals and set a clear intention for the year ahead.

If you run your own business or are thinking about doing so anytime soon, I strongly recommend doing this. It’s so important to find a way to get yourself out of your day-to-day and see what kinds of things you think about and care about and write about when it’s just you.

While I’ve been doing this for some time, I realized I’ve never shared out publicly about this process so I decided to make my “warmup exercise” for this year’s offsite a blog post about how I run these that you can copy if you like.

1. Rent an Airbnb or hotel room for one somewhere out of town.
   You need a minimum of three days to get any real work done. Pick a place where you trust yourself to get work done. If that means quiet for you, pick somewhere quiet. If you need the buzz of a city, pick a city. For me, since I spend most of my work days in highly over-stimulating environments, I intentionally go to the same place in the same small town every single year. I like it because it’s boring to me. It doesn’t matter where you go, just make sure you can keep yourself focused.
   

2. Set a general intent for that offsite ahead of time.
   It’s important to identify the reason for your offsite and a light intention or theme. You can come back to this if you get lost on day two or three. If you’ve never done this before, you might start off with broader, more introspective intentions like, “Identify what I like at work” or “Clarify my personal mission statement.” As you mature in your business and operations, I’ve found that my intentions have also followed suit. In recent years that have included things like, “Find a way to productize my work” or “Formalize a go-to-market plan.”
   

3. Identify a few structured exercises to help you plan.
   Spend a few minutes identify some prompts to get you anchored in goal-setting, reflection, and planning. Since it’s just you, you don’t need to overplan this. I tend to spend the first hour or my offsite (which starts for me on my train ride upstate) writing my loose agenda for the next three days. (I’ve included a sample agenda for you to draw from, if it’s helpful.)
   

4. Play or experiment a little.
   If you’re in the business of building or creating things, come up with a micro-experiment or two that can serve as a “proof of concept” for your year ahead. Last year, when I first started developing mini-apps and software, I used most of the time in my offsite to see if I could actually build a new feature to my app on my own. That proof of concept weekend build is part of what motivated me to keep building more all year long.
   

What I’d suggest doing this year is to just voice dictate to ChatGPT what you’d like to get out of an offsite and maybe include this template as an example structure, tell the AI how many days you’ll have alone and then ask it to come up with a rough agenda for you.

• Set a Single Intention or Goal
  What’s one short phrase that captures the intent or theme for this session?
  

• North Star Vision Alignment
  Is there something you’re aiming for this year that you want to keep in mind to anchor your planning? This could be work-related, personal-related, or both.
  

• Choose Big Focus Areas
  Pick 3-5 buckets that matter the most right now and identify what needs to happen next to move these forward. The buckets have shifted for me over the years but in general they tend to rotate between:

  1. Product / Services

  2. Brand / Identity

  3. Work / Revenue

  4. Operations / Systems

  5. People / Support

• Current Tactical Work or Operational Loose Ends
  Is there anything that’s already in motion that you need to move forward during these three days? If so, what is it? (I’ve found that sometimes just writing down current obligations into buckets to help to create systems around them.)
  

• Identify Short-Term Experiments
  Are there any small tests you’ll run in the next 1-3 months to learn something important? Is there anything you can practice or “dry run” while you have a little free space?
  

• Journaling Prompts
  I like to keep a few tailored journaling or reflecting prompts on hand to guide me as daily warm-up exercises for each day. You can pick any prompts you want (or as AI to help you), but the big anchor ideas are:

  1. Reflecting: What happened this past year? What changed? How do you feel about it?

  2. Looking Ahead: What’s one change you want to see happen next year? How can you imagine yourself getting a little closer to that thing?

  3. Clearing the Cache: What’s on your mind right now that you need to get off your chest before you can get real work done? Why is this blocking you?

Don’t set your expectations too high or judge yourself too hard based on what comes out of these offsites. Some years, I’ve noticed that I need to spend more time creating. Other years, I’m too burned out and just need to spend time consuming. Be gracious and invite your present self to guide the work. You might be surprised by what comes out.

One year, I went into my retreat with a full intent to write a business plan for my fractional work year. Instead my starting journal prompt of, “What’s getting in your way right now?” led me to write 10,000 words about my past experiences in various educational institutions. This ended up taking up the bulk of my entire time away. I wrote all weekend long. While that choice surprised me at the time, I was glad I leaned into it because it eventually led to me writing a pretty formative essay that has continued to drive a lot of the thinking behind my current business.

That’s why I’ve grown to appreciate that any time away is beneficial in its own right. Like a lot of things in life and business, it’s about the relative direction, not the final destination.