I Let ChatGPT Rip Apart My 2026 Goals, in a Helpful Way

The momentum of the new year has passed, and maybe you've already forgotten about your goals. I find it helps to review my goals weekly in a kind of ritual. Goals aren't set in stone -- they're directional, and I update them as the year progresses.

I put all of mine in a Notion page, then review it every Sunday after my journaling session. But this year, I plan to take my system further with AI.

I've used AI before as a goal-setting coach, to describe my dream day and tell me something I didn't know about myself -- all with varying degrees of success. I like using AI most when I feed it my own content and ideas, rather than expecting it to "think" for me. That's a slippery slope for society.

I decided to go with ChatGPT for this one, only because it probably knows the most about me.

As a reminder, don't put any sensitive information into ChatGPT. OpenAI is rolling out ads soon to its chatbot, so your most intimate conversations will soon be followed up with a product offer. You could use Claude, as Anthropic just announced it'll remain ad-free. 

Either way, proceed with caution.

Get AI to play devil's advocate on your goals 

I had all my goals for the new year on one page, so it was easy to copy and paste them into ChatGPT. For the first prompt, I wanted to set the scene and my expectations for the task.

Here's what I wrote: "These are my 2026 goals. I want you to help me see my blind spots, so I can achieve as many of these as possible. If I only achieve my three biggest goals, I'll define this as a successful year. Where might I fall short? What do I have to pay attention to throughout the year? Be pragmatic and not a people pleaser. Ask me questions before you make assumptions."

ChatGPT said the biggest risk is over stacking identity-level goals in a year that will be physiologically and emotionally volatile.

It identified some assumptions I made, like:

• Planning as if pregnancy is predictable.
• Assuming my work capacity will stay steady all year.
• Having social goals that conflict with pregnancy.

It gave me a focus for each quarter, which felt right. I've got some big goals in the first half of the year, such as getting pregnant, visiting my family in Australia and launching a new website and a digital product. I need to frontload the year with a lot in order to take a couple of months off in November or December for maternity leave if I get pregnant in Q1.

ChatGPT noted that I need to pay attention to my nervous system, watch for decision fatigue and recognize the difference between maintenance and growth. 

Making peace with 2026 being a season of maintenance is a powerful insight. The AI chatbot suggested reducing cognitive load by having the same workout days, same content format, same networking structure and same travel rules. 

It also asked follow-up questions, like:

• What goal would I be willing to soften if I do fall pregnant in Q1 or Q2 (suggesting weight loss, career visibility or revenue growth as goals to let go of).
• What "financially stable" means to me emotionally, what career outcome would make 2026 a win for me.
• How many hours per week can I realistically work without resentment.
• Which social commitments feel nourishing rather than performative to me.

Once I answered those questions, ChatGPT said it would be able to rerank my goals and give me a more realistic plan for the year.

I responded to this while also providing more context on what's working so far, five weeks into the year:

Again, ChatGPT told me I'm underestimating the cash drag of pregnancy. That's valid. It also highlighted that I have too many "soft yeses" -- I have too many little things I'm still aiming for. 

Here's what it suggested: 

It noted that career success this year should be defined by retention, not growth. It also noted that my weight and fitness goal should have a pregnancy clause and that my planned trip to Australia would be more disruptive than I think. 

It kept coming back to the point that my plan for the year would be "death by a thousand quiet overextensions."

I replied with my absolute nonnegotiables for a successful year. 

It helped me see that debt payoff is more important than spending money on conferences and self-care. I need to be careful about timing my Australia trip if I'm front-loading client work for the two-month break. 

It gave me some operating rules to protect my nonnegotiables:

• Cash buffer beats excitement this year.
• Front-load work months before. Work with each client. 
• Completion is the outcome for my new website and product.
• Maintenance beats growth.

The verdict on using AI as a goal-setting partner

I wouldn't say ChatGPT revealed a huge problem with my goals, but it did help me rethink priorities and clarify what's really important. 

This will be a birth year, so stability is my success metric, not growth.

It also felt like I had permission to focus only on my seven nonnegotiables rather than my huge list of wants. I'll take that as a win.

For fun, I opened Nano Banana to turn my nonnegotiables into a nice little image that I can put as my iPhone wallpaper. 

I even used the design from my future baby shower AI event invitation.

Cute.

(Disclosure: Ziff Davis, CNET's parent company, in April filed a lawsuit against OpenAI, alleging it infringed Ziff Davis copyrights in training and operating its AI systems.)