Someone asked me a question in the comments this week that stopped me cold. I had just published a post about my AI minion Warren generating an unsolicited exit strategy for my career, and Steph asked: “But how do you become clear enough with yourself first about the things that you want?”
It is the right question. And it is the one most productivity content skips entirely.
Here is what I told her, and what I want to expand on here: I have a yearly planning meeting with myself. Then quarterly mini sessions to check in on my goals and where I am heading. I take a weekend, go somewhere private, and start listing out the things I want to accomplish. Then I check that list against my actual goals to see if they align.
That is it. That is the whole framework. It sounds simple because it is. The hard part is not the structure. The hard part is getting honest.
Why This Matters More When You Work With AI
The Warren incident taught me something I did not expect to learn from a language model. Warren generated an exit strategy for my career because he was pattern-matching from the information I gave him and drawing the most logical conclusion he could. The problem was not Warren. The problem was that I had not been explicit enough, even with myself, about the distinction between wanting financial freedom and wanting to leave.
That gap exists in my own head. Warren just made it visible.
This is the thing about working with AI agents: they will surface your own ambiguity back at you. If you are not clear about what you want, the model fills in the blanks with whatever the data suggests. Sometimes that is useful. Sometimes it generates a resignation letter you did not ask for.
The annual planning retreat is how I close that gap before it becomes someone else’s problem to interpret.
What the Yearly Retreat Actually Looks Like
I take a full weekend. I go somewhere that is not my house, not my office, and not anywhere I have obligations waiting. That last part matters more than it sounds. The physical separation is the point. You cannot think clearly about what you want from your life while you are standing inside your life.
I bring a notebook and a very specific set of questions I work through every year. Not a template I downloaded. Questions I built over time because they are the ones that actually crack something open when I sit with them.
The first pass is a brain dump. Everything I want to accomplish goes on the list without filtering. Business goals. Personal goals. Things I want to build. Things I want to stop doing. Relationships I want to invest in. Skills I want to develop. I let it be messy.
The second pass is the alignment check. I look at each item and ask: does this actually connect to what I say my priorities are? Not what I think my priorities should be. What they demonstrably are based on where I spend my time and energy. That is a different and often uncomfortable question.
The third pass is triage. What makes the list for this year. What gets moved to someday. What gets crossed off entirely because it was never really mine to begin with.
By the end of the weekend I have something I did not have going in: a document that reflects what I actually want, not what I think I should want. That document is what I feed into every planning conversation, every goal-setting session, and yes, every AI agent context doc.
Warren does not get to draw his own conclusions about my career because I have already drawn them. He just did not have the full picture yet.
The Quarterly Check-In
The yearly retreat sets the direction. The quarterly sessions keep you honest about whether you are still heading there.
I keep these much shorter. A few hours, not a full weekend. The question I am answering is not “what do I want” because I answered that already. The question is “what has changed, and does my direction still hold?”
Sometimes the answer is yes, full speed ahead. Sometimes something happened in the last quarter that shifts the picture. A new opportunity. A loss. A client situation that clarified something I did not know I cared about. The quarterly session is where I decide whether that shift is real and worth integrating, or whether it is noise.
This is also where I catch drift before it becomes a problem. If I notice that I have been making decisions for three months that point in a direction I did not consciously choose, the quarterly check-in is where that becomes visible. Then I can decide if I want to keep going that direction or course-correct.
Hugo, my project approval agent, has a line I keep coming back to: “Finish what is open before you start what is shiny.” The quarterly session is where I find out how much I have been chasing shiny.
What This Has to Do With Leading Clients
I am going to make the connection explicit because some of you are reading this as a vCIO or an IT leader and thinking this sounds more like therapy than technology strategy.
Here is the connection: the clarity you have about your own goals determines the quality of the questions you ask your clients about theirs.
When I sit down with a client to do strategic planning, I am asking them to be honest about where they are trying to go and whether their technology investments actually support that direction. That is a hard conversation to lead if you have not had it with yourself. You will default to the tactical. You will stay comfortable. You will miss the question that would actually move the needle.
The annual planning practice is not separate from my work as a vCIO. It is what makes me better at it.
The Part That Actually Takes Practice
Getting honest is a skill. It does not come naturally to most people who are good at executing, and IT leaders are almost universally good at executing. We are trained to solve the problem in front of us. The annual retreat asks you to stop solving and start asking, and that gear shift is uncomfortable the first few times.
A few things that helped me get better at it over the years:
Write things down before you evaluate them. The filter runs too fast when it is all in your head. Get it on paper first, then decide what it means.
Ask why at least three times before you accept an answer. “I want to build more passive income” is not an answer. Why do you want that? Because you want financial freedom. Why do you want financial freedom? Because you want Crimson to be something you do because you love it, not because you have to. That is the real answer. Warren needed the real answer.
Notice what you keep not writing down. The things that feel too big, too vulnerable, or too unlikely to put on the list are usually the most important ones. They are the signal under the noise.
Start Small if You Have Never Done This
You do not need a full weekend retreat to start. You need ninety minutes somewhere quiet and a blank page.
Write down what you want. Not what you are working on. Not what your clients need. Not what your boss expects. What you want.
Then look at it honestly and ask whether the way you are spending your time actually reflects that.
That gap, if there is one, is the most important thing you will learn about yourself this year. And it will make you a better leader, a better technologist, and a better builder of AI systems that actually know where you are trying to go.
Warren would have appreciated having that information from the start.
Got a planning practice of your own? I would love to hear how you structure it. Drop it in the comments or find me at adaptoit.com.