If you’re an entrepreneur, at the end of the year you’re probably excited about the prospect of time off, but also daunted by the new year’s potential and all the deadlines you should be setting.
Traditional planning methods like to-do lists and calendars are no longer enough for the complexity of modern careers and lives. This year, I leaned into AI to approach planning differently.
When used thoughtfully, AI becomes a partner in strategy, and a system that helps you transform aspirations into structured, executable plans.
Here’s how I recommend using AI to clarify where you’re headed and offer more clarity on how to get there.
Redefine the role of AI
Most people use AI like a junior assistant, asking it to summarize things or spit out a process or recommendation based on relevant input shared. But what I realized is that AI can be extremely helpful as a thought partner, forcing clarity where you’re vague and exposing blind spots you’d otherwise ignore.
One of the first prompts I ran this year was “If I repeat the same behaviors I had this year, where will I realistically end up in 12 months?”
That question alone reframes everything. AI is excellent at pattern recognition, including your own.
Before planning forward, I let AI show me the trajectory I’m already on to help me decide what needs to change.
Plan like a portfolio manager
We have a tendency to approach planning as if every goal deserves equal attention, but let’s face it, that’s rarely the case.
This year, I asked AI to treat my time like a portfolio. I said, given my goals, which 20% are likely to produce 80% of meaningful outcomes?
The result was uncomfortable to see but important to make me realize that several projects I thought were “important” turned out to be just draining my energy.
For example, the AI flagged two goals as the most important: clarifying and focusing on one user problem to make sure the team was pushing in one direction, as well as building a regular feedback loop, so that we can iterate the product based on feedback as most important. Everything else on the backlog had to come second.
Use AI to run premortems on your year
One of the most powerful ways I use AI is by asking it to assume failure.
Before finalizing major goals, I run a premortem, by providing context as if it’s already December next year and the plan failed, helping me see what went wrong.
This helps me surface predictable risks, such as being overly optimistic on timelines, or trying to do too many things at once.
For example, last year I ran a premortem on what looked like a “perfectly reasonable” plan of scaling my company while simultaneously launching two new agent products, expanding partnerships, and tightening our internal tooling, all within 12 months.
The AI flagged that I’d assumed linear progress in a year that would almost certainly include regulatory friction, hiring delays, and long integration cycles with partners. It pointed out that running multiple launches in parallel would fragment leadership attention.
This single exercise has saved me months of wasted effort by planning ahead for what can keep me stuck.
Turn goals into systems
Traditional planning tends to be driven by milestones like “scale by Q4.”
But what if, instead of asking what do I want to achieve, you ask: What system do I need to follow to ensure I reach this milestone? This could look like a weekly publishing system with feedback, as opposed to just saying you want to write more.
AI helps design these systems, and refine them over time.
Let your plan evolve in real time
The biggest flaw we tend to make in our annual planning is pretending the future is static.
What’s changed for me this year is using AI agents to continuously adapt my plan based on new information, such as meetings added to the calendar or opportunities emerging that I didn’t anticipate. You can just sync your preferred chatbot with your calendar to help you do this.
This turns planning into a living conversation, not a once-a-year ritual.
AI won’t magically give you discipline, but it will expose contradictions between what you say you want and how you actually allocate time.
Used well, AI becomes a mirror that reflects your priorities back at you in uncomfortably precise ways.
The people who will get the most out of AI next year will be doing fewer things, more coherently, with systems that adapt as fast as life does.
Using AI to help you in this process is what will make a difference between a plan that looks good on January 1 and one that works all year long.