How to Use ChatGPT to Set Ambitious Goals

I’ve been writing about how ChatGPT has changed how I see myself for about a year and a half. I think it’s the most important, broadly distributed tool for making psychological progress since the invention of the journal. Dr. Gena Gorlin agrees. She’s a clinical psychologist who co-teaches a course with me on how to use ChatGPT for psychological growth. Recently she was a guest on my podcast, where we discussed how she uses ChatGPT for goal setting.

This is the first piece in a new series in which we share actionable, tactical ways that some of the smartest people in technology are using ChatGPT and other AI tools. Every contributor Rhea Purohit will be breaking down the conversations from my podcast and pulling out the prompts and responses—complete with screenshots—for you to replicate. Read on to learn exactly how Gena uses ChatGPT, with specific prompts you can use to set and achieve ambitious goals. —Dan Shipper

---

I’ve never been consistent about setting goals for myself.

Even the prospect of sitting to write about my goals is mildly terrifying. I feel self-important and silly.

Besides, the few nuggets of valuable insight I have about myself, I’ve stumbled upon in conversations—warm, free-flowing dialogues with people I trust. Exchanges like these prompt candid, honest self-reflection I’ve never found on a blank Google Doc.

Instead of staring at a blinking cursor every December, when everyone around me seems to be deep in self-assessment, I just wait for one of these conversations to come along—maybe at a holiday party, a friend’s home, or a family gathering. The process is unstructured, disorganized, and entirely unpredictable. But it works.

This year, February rolled around and I was still waiting to have that conversation. But inspired by Dan Shipper’s interview with Dr. Gena Gorlin, I grabbed my laptop, filled up an oversized mug with coffee, and took matters into my own hands.

Gorlin is a clinical psychologist at the University of Texas at Austin who focuses on the psychological needs of startup founders. In the interview, Gorlin uses ChatGPT to conduct an incisive and systematic annual review and goal-setting session. She feeds ChatGPT her old journal entries, and it writes a year-by-year personal biography of her life, helps her set goals for the year ahead, and points out blind spots she might’ve missed in the half-decade of entries. It’s something out of a dream.

Testing this out myself, I entered the ChatGPT prompts that Gorlin used and—to my astonishment—found the conversation I had been waiting for. It was warm, free-flowing, and unlike the sporadic nature of the conversations with my human counterparts, I could talk to ChatGPT whenever I wanted to. It was an empowering exercise in radical self-betterment—a cause Gorlin fiercely swears by. 

Would you like to give it a try?

A couple of quick notes before you dive in:

• Gorlin offers psychological coaching to startup founders. She uses a custom version of ChatGPT that she’s instructed to talk to her like a busy founder who doesn’t have time for small talk and gives it to her straight. The custom GPT is also programmed to refer to a framework Gorlin has developed.
• Before starting the annual review, Gorlin published her journal entries over the last five years as a Notion page, and used that link in her first prompt. This is a trick she uses when she wants to feed ChatGPT a large amount of information.

Okay, let’s begin. First, we’ll give you Gorlin’s prompts, followed by screenshots from ChatGPT. Our comments are peppered in using italics.

Gorlin: I'm working on my 2023 “year in review” and “intention-setting for 2024,” and I'm having trouble figuring out the best way to proceed with it. Here's a journal that includes my year-in-review and intention-setting entries for the past few years, as well as some miscellaneous journal entries in between: [link to Gorlin’s Notion]. Could you read through this journal, including my laundry list of highlights from 2024, and then suggest some ways to organize my thoughts from there?

ChatGPT categorized the significant themes from Gorlin’s journal and listed a few suggestions on how she could move forward. Here’s a slice of what it said.

All screenshots courtesy of Dr. Gena Gorlin.

Gorlin likes ChatGPT’s approach but notices that it’s reading only about the first 20 percent of the journal entry she gave it. She decides to troubleshoot. 

Gorlin: Sounds like you don’t have access to the full journal I’ve published on that page. Could you please tell me what’s the last line you can read on that page?

ChatGPT:

Gorlin asks ChatGPT how she can help it get around this limitation—in effect, how they can create a solution together.

Gorlin: How do I make it so you can read the whole journal? Should I publish it on separate pages with a short excerpt in each, or can you think of another way?

Very helpful, ChatGPT! 

Gorlin:

ChatGPT puts the events in Gorlin’s journal in chronological order by year. It also suggests a framework for how she can organize her thoughts moving forward. Here’s a bit of what it said:



Gorlin starts asking ChatGPT questions she would typically ask herself. 

Gorlin: Are there any major themes you anticipate emerging for me in the coming year given the patterns you see in my entries to date?

Gorlin is impressed. She’s also curious to see what else she can get ChatGPT to do. 

Gorlin: What do you think might be different about this year compared to prior years?

Now, Gorlin wants to see what ChatGPT can find that she would’ve otherwise missed. 

Gorlin: What are my blind spots most likely to be in the coming year?

Gorlin thinks these insights are very helpful. But she also wants ChatGPT to fill in the other side of the puzzle: Is it just that she’ll be too ambitious? Or is it possible that she might not be ambitious enough?

Gorlin: What would you suggest as the highest-leverage goals and intentions for me to set for the coming year?

Gorlin wants to prompt ChatGPT to uncover her blind spots. 

Gorlin: What are some goals I maybe SHOULDN’T set for the coming year

She gives ChatGPT a little more context.

Gorlin: Another salient aspect of the coming year that’s not yet reflected in my journal entry is that Matt (my husband) will be between jobs at least for a while and so will be helping me part-time. Given his acknowledged difficulties with collaboration and my residual insecurities/attachment patterns (which sometimes push me toward trying to get too much or the wrong kinds of help from him), what are some principles and practices that would be good to keep in mind?

Gorlin wants to use ChatGPT to dig even deeper.

Gorlin: Based on the sum of my journal entries to date, what are the hard-won insights I’m most likely to lose sight of in the coming year?

Gorlin notices that ChatGPT seems focused on making sure she doesn’t overextend herself. She knows that these are important points, but a big part of her personality is maximizing ambition. Gorlin wants to probe ChatGPT further by giving it more pointed direction.

Gorlin: I don’t actually like the phrase “work-life balance.” What insights have I in fact articulated about this in my journals, and what’s my distinct perspective on it, if you can tell? 

Gorlin: Yeah, that sounds right. So then how am I specifically likely to mess up on this in the coming year, given my stated approach to it? 

ChatGPT’s first point reminds Gorlin of moments when she’s talking to a friend and isn’t sure if she’s wearing her “therapist hat” or her “friend hat.” She also agrees that neglecting her personal needs is something she’s prone to doing. But “over-integration” is a new concept to Gorlin, and she’s eager to understand what it means.

Gorlin: Can you give a specific example of what “over-integration” might look like for me?

Gorlin thinks that ChatGPT’s example probed something she wouldn’t have thought about otherwise. For the next step of her review process, she wants tactical advice from ChatGPT about some of the broader themes it had previously surfaced.

Gorlin: What are the most high-leverage activities for me to be engaging in toward my goal of selective client expansion (i.e., attracting and retaining high-profile founder clients)?

Gorlin goes on to use ChatGPT as an organizational tool of sorts to help her operationalize the goals it had surfaced.

Gorlin: How would you rank these in terms of likely impact on my client base? 

Gorlin questions ChatGPT further about specific goals.

Gorlin: One of the projects I’m currently facing some ambivalence about is the “builder’s mindset” book for which I signed a contract with an agency this fall (and for which they’re currently waiting on me to write a book proposal). Thoughts on how this goal aligns with my overall mission and with the selective client expansion strategies above. 

To conclude her annual self-review, Gorlin turns to ChatGPT to chart a roadmap for the coming year.

Gorlin: Could you now summarize and consolidate everything we’ve talked about by writing up a “roadmap of 2024” for me?

Gorlin acknowledges that nothing in ChatGPT’s roadmap is exactly new to her—either something it summarized from her journals or an insight they arrived at collaboratively. However, she thinks it’s incredibly valuable to have access to a tool that organizes her thoughts coherently and allows her to interact with them. 

I agree. I’ve always articulated my thoughts through conversations. As a writer, that typically means I sit someone down and bore them with the tiniest details of what I’m thinking about before I even start a piece. (Friends and family have been known to take cover when I approach with laptop in hand.) To have a tool like ChatGPT that talks back to me—that I can actually engage in conversation on demand—is priceless.

---

Rhea Purohit is a contributing writer for Every. You can follow her on X at @RheaPurohit1 and on LinkedIn, and Every on X at @every and on LinkedIn.