A Personal Strategy Retreat
When we plan, it’s quite easy to take what’s already on our plates as the default, making whatever “strategy” we come up with really just a form of: “How can we do today’s stuff a tad bit better?”
I’ve certainly fallen into that trap before. That’s why I’ve learned to organize my year-end planning specifically to avoid it. Instead, it’s designed around reflecting on the fundamentals—what really matters.
Hence, the annual strategy retreat.
As we get into the season of year-end reflection and goal setting, I thought it might be useful to share some of the insights and tools I’ve found to make these activities most effective.
Design and Intention
Having a “retreat” is about creating a physical and mental space that allows the mind to think creatively and outside of our day-to-day concerns.
This is the single biggest difference between regular planning and the kind of reflection that I describe below. It’s about an intention to go deep and about designing a time and space to match that intention.
The goal isn’t just to devise plans or even “resolutions” for the coming year. Instead, the goal is to pay an extended visit with your core values and aspirations.
That’s how you realize what’s not on the to-do list but should be and what is on the to-do list but shouldn’t be.
Example Agenda
The agenda for the retreat might include the following:
Looking Back: What grade would I give myself on the key dimensions of my life? What factors most contributed to my successes over the past year? What factors most contributed to my shortfalls?
Bold Visioning: What would make for the best year of my life? (Key: starting that answer without thinking of constraints or feasibility.) If I had to write a Post-It note to put on my bathroom mirror to motivate me each day, what would go on it?
Goals: To achieve my vision, what milestones would I need to reach?
Implementation Plan: What specific actions do I need to take? What’s likely to get in my way? Who’s required to help me or say “yes” to my actions? What do I need to STOP doing to make room for success?
I have a bunch of structured activities for each part of the retreat, but I’ve found that the specific activities matter less than diligence in asking and specificity in answering those questions.
Key Success Factors
A Framework for Personal Success and Fulfillment
The retreat works best if you have a clear definition of success against which to judge yourself. If you haven’t written one down, that may be a worthwhile activity before you start your planning.
As an example, here’s mine:
The magic isn’t in the high-level dimensions; it’s in defining specifically what each means to you and how you’d define “success” in each dimension.
Start with a Blank Canvas
By starting fresh—a blank sheet of paper or a blank Word file—you give yourself a better chance of identifying bold new approaches rather than being captive to what’s currently on your plate.
Second-Order Thinking
Don’t just identify what is going well and what is not. By identifying what factors drove your successes and shortfalls, you’ll likely get at the heart of what it will take to be more effective.
For example: “Four of my five biggest mistakes came when I was short on sleep.” Or: “My biggest breakthroughs came whenever we got out of the office and actually observed customers using the product in real life.”
Immediate Action
Turn everything into next steps, and start doing them immediately.
A QUOTE I’VE BEEN THINKING ABOUT
“It’s not about getting more stuff done. It’s about getting more of the right things done. It’s not about efficiently doing what’s on the to-do list. It’s realizing that the most important thing isn’t even on the to-do list.”
—Greg McKeown, talking about Essentialism on the Tim Ferriss Show