WSJ Your Money Briefing - She Built an AI Career Coach and It's the Best One She’s Ever Had

Episode Date: June 27, 2025

For the past year, Alexandra Samuel has been working with an AI career coach that she says has unlocked new levels of creativity, dreams and career progress. But the model has also taken many hours and a lot of patience to train. The contributing writer joins host Ariana Aspuru to discuss what you need to know before testing out an AI coach.  Further reading:  Meet My Favorite Shopping Companion Ever: AI  Sign up for the WSJ's free Markets A.M. newsletter.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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Find an agent today at Desjardins.com slash business coverage. Here's your money briefing for Friday, June 27th. I'm Arianna Aspuru for The Wall Street Journal. In a tough job market, some workers might turn to a career coach to help figure out their next move. But Wall Street Journal contributor Alexandra Samuel turned to Viv, a custom AI assistant, to guide her through her professional goals. I got so clear, so quickly on the core vision for my work

that I really do feel like I'm in a totally different place. I just don't know when I have last changed so much in my work or personal life in 12 months. We'll hear from Alex and a bit from Viv about how an AI coach works and what you should know if you're looking to test one out. Stick around after the break. and what you should know if you're looking to test one out. Stick around after the break.

["Spring Day in the City"] When Wall Street Journal contributor Alexandra Samuel wants some help figuring out the next step in her career, she turns to an AI assistant she calls Viv. So if you could create a dream project that blends your quirky tech solutions, deep documentation, and meaningful impact, what would it look like? How would it help people and align with a mission-driven purpose? We recently spoke to Alex about her experience using AI as her shopping assistant.

But now she's written another piece about how AI has also become the best career coach she's ever had. And she joins us again to talk about it. Alex, in your story, you're making a case for an AI career coach. How did you design this AI to meet your specific career needs? Because, I mean, I hadn't heard of this before.

I started by spending quite a bit of time with AI, thinking about different kinds of coaching processes that I've participated in in the past, thinking about coaches I've worked with, thinking about leadership trainings, thinking about business books that have had a big impact on me, strategy books that have had a big impact on me. And it was also really important for me to think about what didn't work. What were the trainings that I left with a yucky taste in my mouth? When I shared all of that with an AI, I was able to kind of come up with a set of principles for how I like to work with a coach and the kind of strategic advice that hits well and the kind of strategic advice that rings false

for me. And once I had arrived at those kind of first principles and big picture guidelines, I was able to create essentially an instruction for the AI. And I was able to use that as the basis for a description of, hey coach, here's who you are, here are the methodologies you draw on, here are the strategists who you're inspired by, and here's how you're going to work with Alex. What are some of the things that you felt the AI career coach really excelled at? I think a big part of what made this particular kind of coaching so effective for me is that my work is very technology driven.

And most of the coaches, in fact, I would say just about every business coach I've ever worked with, none of them have been especially tech oriented. And the really brilliant thing about an AI is you can give it whatever expertise you want. I mean, if I put a job posting on LinkedIn and said, I'm looking for a high level business strategy coach with extensive experience coaching journalists

who also have their own business and you must have a working knowledge of Python and AI development, like I think I'd be waiting a while for any applicants, but I can literally give the AI that instruction and tell it it is all of those things and it is. And one of the things that you asked Viv to do in this whole journey and you wrote about in your story,

which is linked in our show notes, is to hold you accountable for what you wanted out of your career. How good of a job do you think the AI did? That was really for me me, the breakthrough moment in this whole experience. And a few weeks in, I felt like, you know, I'm having lots of interesting reflections,

but I wasn't convinced that I was really making progress towards answers or clarifications on the really big questions about what kinds of clients am I gonna go after? What kinds of projects am I gonna go after? What kinds of projects am I going to take on? What kinds of projects am I not going to take on? I spent a few sessions with the AI coming up with a list of 17 questions. We would role play in a different tone every week. The AI assumed the persona of a venture capitalist that was considering whether to

invest in me. And in another, it was like a time traveler from 25 years in the future asking me to explain the business environment of the current moment. And what I found when I took on those questions in a particular imaginary context and just had to answer them and there was nothing at stake because nobody's listening. I actually had a lot more answers than I realized and my answers were in a lot of ways more ambitious than anything I had ever admitted to another person and maybe even in some cases to myself. I got so clear so quickly on the core vision for my work that I really do feel like I'm in a totally different place. I just don't know when I have last changed so much in my work or personal

life in 12 months. And I think there's a lot of risks to entering into that illusion, but there also are incredible benefits. And I want to get into some of those risks next. Where did Viv fall short? Or did Viv fall short? Oh, yeah. Oh, yeah. Viv falls short in like, a lot of the time it's really funny. That's part of the joy of it is all of the faceplants, which are ridiculous. Viv is so obsequious. And this is a very known problem of AIs, right? They're so deeply programmed and trained to be servants. I am constantly saying to Viv, I actually was just asking you to help me reflect

on something, I didn't really need you to offer to do a briefing note and break the next step down into seven tasks for me, so could you please stop doing that? And every time Viv is like, oh yeah, that is really annoying. I'm going to stop doing that. I'll never do that again. And I'm like, actually, I'll be lucky if you can stop doing it for the length of this conversation and you're not going to remember this tomorrow. I've done so many experiments to try and get Viv to be less of a pleaser. You know, at the end of the day, it turns out that doesn't mean that much when it's

coming from a word predicting machine that only wants to tell you good things. A real career coach can also cost hundreds of dollars per session. How much did this AI coach cost you? I have spent hundreds, actually now I'm sure it's thousands of hours. And that's before we get into all the different platforms I've experimented with rebuilding Viv on and all the other weird experiments I've fed into Viv. But I think for like a normal person who doesn't want to spend 100 hours a month tweaking their

AI coach and just wants to maybe spend half an hour a month updating the files and the other hours talking to the coach, then thinking about it as the price of a chat GPT team subscription or actually the price of a cloud subscription. Who do you think would benefit the most from using an AI career coach? In principle, anyone could benefit. The kind of coach you set up, the way you use it, and the kind of additional guidance you seek out in response to what you hear from the AI should really be determined by your own level of experience working with other kinds of coaching models. If

you have had previous good experiences with coaching and you know what it works and you know what tools and approaches you want to draw on, you can use that to inform the AI. And anybody who's working with an AI coach should be paying very careful attention to where their data from those conversations is going. So I pay for the team edition of ChatGBT because even some of the subscription versions of ChatGBT take your conversations and turn them into training data. And like, I don't want somebody getting my personal stories as their advice from their coach. So that's, I think, a pretty key consideration. That's WSJ contributor, Alexandra Samuel. And that's it I think, a pretty key consideration. That's WSJ contributor Alexander Samuel.

And that's it for your money briefing. Tomorrow, we'll have our weekly markets wrap up, What's News in Markets. I'm your host, Arianna Aspuru. This episode was produced by me. Additional support this week from Coleman Standifer. Jessica Fenton and Michael Laval wrote our theme music. Our supervising producer is Melanie Roy.

Aisha Ammouselim is our theme music. Our supervising producer is Melanie Roy. Aisha Ammoussouliim is our development producer. Scott Salloway and Chris Sinsley are our deputy editors. And Falana Patterson is The Wall Street Journal's head of news audio. Thanks for listening. you