My Quarterly Retreats

I had heard of the idea of taking personal retreats from many sources, but Sherry and Rob Walling’s podcast was what got me to actually try it. They do have a short PDF for sale about the topic if you’re interested. At this point (it’s September 2020), I’ve gone on retreats for about three years and have found them so useful that I moved from semi-annual to quarterly. The retreats have been so helpful that my wife reminds me to go (and has even acted as travel agent a couple of times!). Yes. She wants me to go even though that means she’s home alone with our toddler. That’s how valuable this has become for us as a family. And, yes, she gets to have a weekend away as well!


The retreat is not a vacation, but it’s also not “work.” I’m not sending email or writing or doing my usual daily tasks. Instead, I’m zooming way out. I’m thinking and planning. In one way, it’s much harder work than a typical day, because it’s all reflection and planning and decision making. This is high-level thinking. But it’s also fulfilling and refreshing. By the end of the retreat, I’m always excited to get back to work. Work and life are always entangled – especially if you run your own business. The retreat can be about both. For me, the real purpose of my business is to give my family a better life – not just in terms of financial security, but a better day-to-day existence. I want to prioritize our joy, not our wealth. The retreat should support that goal.


A change of location is necessary. Go somewhere that’s not at all a part of your typical workday. I live in Oregon, so I’ve often rented AirBnBs in forest-y locations. You might pick a desert or a beach. During the pandemic, I’ve stayed at a hotel around the corner. You probably don’t want to go to Las Vegas or stay in Manhattan. The location should support reflection and thoughtfulness. I think that a retreat needs at least one full day, which means staying two nights. This gives me an afternoon, an entire day, and then a morning before I head home. I’ve done a three-night retreat, but there are definitely diminishing returns and I’m often eager to get back home and resume my routine after two nights.


Every retreat has been different since it’s so intertwined with where I am personally and professionally. Don’t schedule your hours out – let the retreat guide you! It’s important to unwind. Don’t listen to podcasts or talk on the phone on your way to the retreat. Think of it as entering a new space. Be intentional about changing your mindset.  Here is the general pattern I’ve settled into after a bunch of these retreats.

1. The First Afternoon and Evening: Personal Reflection

After arriving, getting unpacked, etc. I look at two questions which I learned from Sherry Walling:
  1. What has given me life?
  2. What has taken life from me?
These two questions are so sharp. It takes no thinking at all to answer them. I know immediately what is feeding me versus killing me. So I always start here. Over three years, these two questions have helped me whittle away the parts of my business and life that don’t fit me well. As I jot down my feelings, it starts to give the retreat shape. Ah yes. Task X is killing me. How can I get rid of that task before my next retreat? I also take this time to look back at notes from previous retreats. This is fun and quickly reveals patterns. Do I keep complaining about the same thing – have I fixed it yet? Why not? Do I keep saying I want to do something new, but haven’t started it? The retreat takes shape! If it’s your first retreat, you won’t have these notes, so something I did was review the results of a few “personality” tests I had taken (StrengthFinder, Meyers-Briggs, etc.). While I’ve done these before, they, along with the “what’s feeding me/killing me” questions, make it really obvious what I should be doing in order to be happy and what I should avoid. They always remind me that I like learning, working by myself, and tackling larger tasks. Reviewing these findings helps me start to shape the next quarter. So that first afternoon and evening are really about me as a person. I orient the retreat around how to improve my business in the next three months, so it fits me better. I also try to have a fun dinner, do some reading, and get a good night’s sleep.

2. The Full Day

The full-day is all about planning the individual tasks for my next quarter to fit the larger goal. Again, each retreat is very different. For me, the last couple of retreats have centered on the 80/20 principle. I end up wondering:
What hugely important things am I undervaluing?
Instead of thinking about what I should add to my life, I look at what I already have that needs pruning, fixing, deleting, adding to, etc. Last time, I opened my website analytics and exported the 100 most-visited pages over the past year or so. This was eye-opening. Five webpages generate probably 80% of my traffic, yet I hadn’t touched those pages in years! Much like the personality tests, these findings were obvious (I probably could have guessed those give pages), yet I would never have gotten to this obvious point without removing myself from my day-to-day life. The quarter begins to take shape!  At other retreats, I’ve realized that my email list was underused, or that I should stop trying to reach certain customers who don’t fit me well, or that I’m missing a huge topic that’s relevant to my audience (hello search analytics!). I try to find one major theme or topic to address. Then I start breaking that down.  I also resist the urge to start working on anything! ⚠️ The biggest cause of less-successful retreats is when I allow myself to start working on tasks. Resist the urge to work! You’re here to think. You have the rest of the quarter/year to implement these ideas. For this reason, it’s helpful to hamstring yourself a bit. Don’t take your laptop, take a tablet or phone, or just a pad of paper. Opt for (yes) a place with slower internet if you can! You don’t want to waste your time doing something you can do back at home or in the office. I’ve started to track four categories of tasks:
    • What I’m starting
    • What I’m stopping
    • What I’m continuing to do
    • What I’m continuing to not do
I’m very careful about the first category. I’ve learned that starting something also means maintaining something, which is almost always unpleasant. The fourth category is the most interesting. I have a list of things that seem like interesting ideas, but I’ve intentionally held off on. It’s fun to revisit those ideas and note that, yep, I’m going to continue not doing this. I’ve had “start a podcast” and “write a Byrdseed book” in that category for years now. Neither is a bad idea, but their time just hasn’t come yet. By the end of the full day, I’m pretty wiped. I’ll eat another fun dinner and get a good night’s sleep.

3. The Final Morning

Then I have the last morning before I check out and head home. I want to wrap up the retreat. I don’t want anything left hanging or half-resolved. So I switch from rough notes, sketches, and todos, and start writing up my quarterly plan as an essay. At the last few retreats, I’ve called this the “Shareholder’s Report”, written for my wife, who is Byrdseed, LLC’s primary shareholder. This is a summary of the last quarter, both financially but also in terms of what I’ve accomplished. I also explain the next quarter’s plan. Then I present this to her when I return home. We get a kick out of it, but it also creates some accountability. She knows how the last quarter has turned out and what I’m planning for the next one. Again, something that seems obvious (talk about how our family will continue to pay rent!), but it so easily slips by. I also plop all of the quarter’s tasks into a new project in Todoist so I can check them off as the months go by. Usually, by the end of the quarter, I’m getting to the dregs here and am ready to plan another retreat. In fact, I’m about two weeks away from the end of a quarter and can definitely feel the urge to zoom out and plan the final quarter of this year.