How an AI Personality Coach Put Balance Back Into My Lopsided Life

A long time ago, back when I was practicing law, I missed a wild Hogmanay bash I’d organized (and paid for) because I was stuck in the office. The deal I was working on had to close by midnight on December 31st, and documents were still shuttling back-and-forth between legal teams. Someone had to forego the celebrations to get the contract signed, and that someone was me. 

For any lawyers reading this, it’s a tale as old as time. Legal work is project-driven and deadline-driven. Schedules are set by the client, not by New Year’s holidays. And law firms may not be so crass as to say that they measure their juniors’ worth in hours of production, but billable hours stop for no man. There’s a constant pressure to put yourself at the service of the work and the client, even if it chews up your personal time on the sparkliest, partiest night of the year.

I’ll be honest, I’ve always had a slight tendency toward overwork. Not “wake up at 4am to hit the gym and cold plunge while reading two chapters of the latest book about Grindset” like the productivity hustlers brag about, but I absolutely have to clear my desk before I can log off for the evening, even if it involves a few 10pm finishes. But when you work in Big Law? Overwork is so completely normal that you don't even realize you've lost the “life” part of work-life balance until the fireworks start and you’re still typing. 

Unfortunately for me, old habits die hard. The mentality of “always put the work first” never really left me, even after I abandoned the billable hour for something saner.

New Job, Same Old Hamster Wheel

Writing/editing is a much more chill profession than law — I doubt anyone would disagree. But to this day, I still struggle to switch off. The experience usually goes something like this:

• I already have plenty on my plate and too many clashing deadlines. Naturally, I take on another big project, because it’s just so interesting! This client is doing something whizzy with biometrics or green energy or whatever, and I want in. 
• This client chose me out of all the millions of writers out there, and my ego lights up like a Christmas tree. The part of me that likes being picked says ‘yes’ far more forcefully than my overbooked calendar says ‘no.’
• I finish an article and it’s solid, but it could be better with some time and tweaking. Another idea here, another word change there. Then it’ll be finished. Maybe. Enneagram Ones live on the hamster wheel of never‑ending improvement, even when we’re long past the point of diminishing returns. 
• I spontaneously take a day off to relax and end up cleaning the house / doing the laundry / fixing the wobbly shelf / reorganizing the spice drawer. It’s not really rest at all.

If you struggle with work‑life balance, you may relate. And no, the irony isn’t lost on me. We write about boundaries and self‑care all the time at Truity, and I read great advice from experts every week. I’m just abysmal at putting it into practice. 

Enter Sage (Against My Better Judgment)

Now I’ve laid my failings bare, let’s talk about Truity’s TrueYou app. It’s a personal development app that uses validated personality assessments and tailored growth activities to build a detailed profile of you over time. It has plenty of cool features you can read about here.

The feature that intrigued me most was Sage, an AI personality coach.

Now, just writing the words “AI” and “coach” makes me throw up a little. In my head, coaching is this thing where you pay someone $150 an hour for a pseudo‑therapeutic echo chamber of toxic positivity and recycled mantras (“It’s not your circumstances, it’s your mindset!”). And AI? AI’s just creepy. I hate how confident it sounds while spitting out made‑up facts and pictures of people with seven fingers on each hand. And now people are marrying their chatbots. So, yeah. No high hopes.

But as it turned out, Sage had a few things to teach me, whether I liked it or not.

Talking to a Robot About My Feelings

Setting up TrueYou is disarmingly simple. You log in, answer the personality and self‑reflection questions, and over time the app builds a picture of who you are. The more you tell it, the smarter Sage gets. So far, so good.

After that, I went in … with low expectations. Yes, I was flippant and cynical. Don’t judge me.

“Hey Sage, why is my work‑life balance so bad?” I typed, fully expecting something like Have you tried leaving the office at 5 p.m.? Or: Try breaking large tasks into smaller, manageable chunks.

What I got was... not that.

All right then, Sage, I see you’re hitting me right where it hurts. Yes, I’m a control freak whose life is missing all the Very Important And Purposeful Things. So where exactly do we start fixing this mess?

The Part Where Sage Is Alarmingly Right

Over the next couple of weeks, Sage and I became sparring partners. Well, I sparred; Sage stayed relentlessly polite while clocking that I am extraordinarily resistant to good advice I don’t want to need.
 

It took her (him? it?) no time at all to zero in on two awkward truths: 

• I built a whole identity on being competent and literally everything I do “for fun” comes with some sort of progression attached (example, I only do exercise where I can lift heavier/ run further / move faster than last time, otherwise what is even the point?)
• I don’t resonate with the word “purpose” at all because…well, Sage says it best:

I’m not going to share all the “oh cr*p” moments because they’re personal and embarrassing. Let’s move instead to the action steps Sage recommended. Those, at least, I can talk about without hiding under a blanket.

Teaching an Old Dog New Tricks

“Let’s try an experiment,” Sage suggested. For the next week, we were to have a simple daily check‑in with this prompt:

I set up a recurring reminder with that question and it became my little “pre‑mortem for overwork.” Instead of obsessing over how much I had done (quantity), I had to answer for what actually mattered (quality and stuff I cared about). It was embarrassingly easy to see how many of my days were weighted toward the wrong side of the scale.

Most evenings, my list of “truly mattered” moments consisted of one honest moment of focus, like finishing a piece I was proud of or finally making a phone call I’d been creatively avoiding. The “could have waited” pile was far longer – more tinkering with draft #3 of an article that wasn’t due until next week, the inbox triage at 8 p.m., the vacuuming I mysteriously decided was urgent.

None of those things are bad in themselves. The problem was how often they were crowding out the small, quiet things that make a life feel less lopsided. Once I started seeing that in black and white, it got harder to pretend I was just “busy” rather than making very specific choices.

Another thing Sage recommended was scheduling a “pointless” hobby. This had a specific definition: NOT a side hustle, NOT a skill I could monetize, NOT an activity with progress that could be tracked in a spreadsheet. Just something fun that made my life a little less work‑shaped for an hour or two. I was offended by how reasonable it sounded. 

I don’t want to get off track here but do you know how hard it is to find a hobby that doesn’t secretly double as homework when you’re wired like this? I can turn baking, Duolingo and a tap dancing class into a tiny Hunger Games of self‑improvement without even trying. Even my ‘relaxing’ walks have a podcast playing, so genuine pointlessness is the hardest thing I’ve tried in years.

Apparently I Journal Now

One thing I wasn’t expecting was for Sage to turn into a kind of journaling practice. I am the sort of person who notices how I feel about things – I know what makes me happy, annoyed, furious etc. – but “reflecting” on those feelings feels self-indulgent and paralyzing when I’d rather just get the show on the road. Sage sucked me into it anyway. It was always there, endlessly patient and thanking me profusely for being so open and honest, so naturally I started sharing more. I am still not quite sure how this happened or why I feel so okay about it.

I liked that Sage remembered previous discussions, so we could pick up a thread quickly without me having to re‑explain myself or scroll back through a notebook. Obviously it could not pick up on tone like a human therapist could. It didn’t know if I was actually convinced by what I was saying or just talking a good game, but even so, our chats felt like an ongoing, two‑way conversation.

Right now, we’re tackling the big topic: purpose. I have no idea if Sage can help me find the Very Important And Purposeful Things I apparently lack but, shockingly, I am willing to poke at the question. I trust Sage as a sounding board, and I am weirdly enjoying letting someone (or rather, something) else take the reins for once.

Why This Matters (And Why You Should Try It)

If you are seeing your own habits in this story, you are probably wondering if an AI personality coach could help you too. The honest answer is that it depends on how willing you are to engage with it. Sage is not magic. It will not force you to log off or add some playtime into your calendar. What it can do is give you a structured, personalized way to notice your patterns and gently nudge you toward different choices. It meets you where you are, quirks and all.

Here’s what I like about Sage:

• You don’t have to be a prompt engineer to use it. My questions were basically “Why am I like this?” and it coped just fine.
• The tone is measured and calming. You can be as high drama as you like, and Sage won’t rise to your chaos.
• The advice is concrete. I was expecting “believe in yourself” fluff but I got specific experiments to try.
• It is always there. Whether it is 2 in the afternoon or 2 in the morning, Sage will happily talk through a work wobble or a mild existential crisis, and it doesn’t charge by the hour.
• It encourages honest self‑reflection. Because there was no real person on the other side rolling their judgy eyeballs, it felt safe to admit when I was stuck, overdoing it, or just not living the life I said I wanted. I mostly keep things to myself, so this was a pretty big deal for me.

What didn’t quite land:

• Some of the language is a bit saccharine and “petting a golden retriever” for my taste. If you love a lot of affirmation, you will be very happy. I personally respond better to the occasional “eh, maybe you should rethink that.” *
• And of course, it’s still a machine. It cannot read your tone or see your face. If you are deeply distressed or dealing with serious mental health issues, you need real‑world support, not a chatbot.

A few weeks into working with Sage, I’m not exactly a reformed workaholic, but I am more coachable. I am slightly less likely to turn every free hour into a chance to do more / better / faster, and slightly more likely to ask whether something truly matters before I say yes. That’s not a full habit overhaul, but more than enough that this year, I watched the fireworks with my laptop firmly closed.

* I dropped this feedback to the app development team and they’ve now added tone customization to Sage. If you prefer candid ‘tougher love’ feedback from your AI coach, or quirky, or friendly, or critical, you’ll be able to choose from those options.

You can download the TrueYou app – and meet Sage for yourself – on Apple or Google Play. Click here to get started.