I’ve been producing 2B Bolder for six years now, sitting down every other Tuesday with an accomplished woman in business or tech to talk about her career, the setbacks nobody sees from the outside, the breakthroughs that usually looked nothing like what she’d planned, and the advice she’d go back and give her younger self if she could. Over six years, that adds up to more than 150 conversations, and somewhere along the way, without me ever quite noticing it happen, some of those women became friends. Some of those conversations still surface in my head months later, unprompted, the way a good piece of advice or an unexpectedly honest moment about imposter syndrome settles in and stays there.

What’s funny, looking back, is that I never once thought of all of it as a library. It was just the show, the thing I loved doing every other Tuesday because I believed, and still believe, in the particular power of one woman hearing another woman’s story and recognizing something true about her own, and it made me a better listener and a better storyteller in the process. But I never sat back far enough to ask what six years of that, stacked up and recorded and sitting on a hard drive somewhere, actually amounted to. It was just work I loved, and that was enough.

Now that I’ve returned to work full time, I’ve been leaning on AI to help me automate some of the production and promotion side of the podcast, because 2B Bolder has always been a labor of love rather than a full-time job, and I wanted to find a way to protect what little time I had left for it without losing the momentum I’d built over the years, which felt like a reasonable, practical thing to ask for, nothing ambitious, just someone trying to work a little smarter with the hours I had. So I asked AI for the basics, a keyword strategy, a few ideas for social posts, some ways to get a bit more visibility for the show, small and sensible requests from someone trying to keep a beloved project alive during a busy season of life.

And AI pushed back on me.

It told me, more or less, that I was thinking too small, that 150 interviews isn’t just content sitting in a feed, it’s data, and most podcasters never stop long enough to see the difference. It pointed out that I was sitting on something rare, a structured, proprietary archive of career advice from more than a hundred accomplished women in business and technology, built one conversation at a time over six years, and it asked me a question I honestly hadn’t asked myself in all that time: not how do I promote my podcast, but what do I actually want 2B Bolder to become.

I sat with that question longer than I expected to. My first instinct, if I’m being honest, was almost defensive, a small voice in my head saying I’m not trying to build an empire here, I just wanted help writing a caption. But the longer I let the question breathe, the more I understood it was right, and that I’d been standing too close to my own work for too long to see the actual shape of it. Six years of showing up every other Tuesday will do that to you. You get so far inside a thing that you stop being able to see its outline.

That reframe changed something fundamental in how I think about all of this. I stopped seeing myself as a podcast host with a nice back catalog of episodes, and I started seeing myself as someone who owns a career intelligence company, where the podcast itself is simply the raw material and everything else, the searchable knowledge base, the coaching tools, the research reports, maybe someday a book, gets built up from that foundation. Six years of Tuesday conversations stopped being just episodes in my mind and became a dataset, a moat even, because nobody else has sat across from OVER 150 accomplished women in business and tech and has the transcripts, and the trust, to prove it.

I didn’t change a single thing about the interviews I’d already recorded, but I changed my understanding of what they were worth.

I’m still working through what this actually looks like in practice, and I want to be honest that it’s early days. I’m trying to partner with a cohort of students from an AI training program that matches people looking for real business problems to apply their skills to. The goal will be to scope out a searchable knowledge engine built from the transcripts, an editorial intelligence tool that could surface content ideas I’d never think to go looking for on my own, and further down the road, a coaching tool grounded in real advice from real women rather than generic AI output pulled from nowhere in particular. There are real questions still to work through, especially around consent, and what it means for a guest’s words to become training data for a product rather than simply an episode someone listens to once and moves on from. I don’t have all of that figured out yet, and I’m not going to pretend otherwise, but I’ll keep sharing how it unfolds as I get further into it.

What I really want to leave you with this week, though, isn’t the roadmap. It’s something simpler, and I think more useful: the quality of your thinking with AI depends almost entirely on the quality of what you’re willing to ask it. If I’d only ever asked for a caption or a handful of hashtags, I never would have come anywhere close to hearing that I was sitting on something bigger than I’d realized. I had to ask it to challenge me, and harder than that, I had to actually be willing to sit with the answer once it did.

A few things I’ve learned about prompting along the way, things that got me to that moment even though I didn’t know I was looking for it.

Ask it what it would do if it were you. Not give me ideas, which tends to produce a safe, neutral list, but if you were me, what would you actually do, which seems to unlock something more opinionated and higher stakes, an answer with a point of view behind it rather than a menu.

Ask what you might be missing, or where you’re not thinking big enough. Most of us default to asking AI to execute a task we’ve already fully defined in our own heads, when the more interesting move is asking it to question the task itself, before you’ve even decided what the task should be.

Push back on the first answer you get. My best insight didn’t come from the first exchange; it came from the third or fourth, once I’d stopped treating the conversation like a vending machine where you put in a request and walk away with a final answer, and started treating it more like a real conversation with a sharp, honest business partner sitting across the table.

Give it real context, not just a task. The more AI understood about my actual business, my history, my constraints, the six years, the 150 interviews, the fact that I’d just gone back to work and was stretched thin, the sharper and more specific its thinking became, because a prompt with no context behind it will always give you back something generic enough to apply to anyone, which means it applies to no one in particular.

Ask it to rank and prioritize instead of simply listing. Ten ideas is useful, but it can also be overwhelming and a little hollow, while ten ideas followed by which four you’d actually pursue first and why is where the real thinking begins, because now the AI has to defend a point of view instead of just brainstorming into the void.

And maybe most importantly, let it disagree with you. The moment that actually moved me forward wasn’t AI agreeing with my small idea, it was AI telling me, respectfully but clearly, that my small idea was smaller than what I actually had in front of me. That’s an uncomfortable thing to hear in the moment, but it’s also, I’ve come to think, the entire point of asking in the first place.

AI didn’t hand me a finished business plan, and I don’t think that was ever really the goal. What it handed me was a better question than the one I’d walked in with. The plan is still mine to build, one Tuesday, one conversation, one chapter at a time, the same way it’s always been.

The lesson: AI is at its most valuable not when it hands you answers, but when it challenges the size of the question you walked in with. Prompt it like a business partner sitting across the table from you, not a search engine, and be willing to actually hear it when it tells you that you’re thinking too small. Six years of work can hide in plain sight until someone, or something, finally asks you to see it differently.

Still becoming, one Sunday at a time. 🖤

Subscribe now

Raising children is one of the hardest jobs there is. I think, as a society, we under-articulate not just the sacrifices you make as a parent, but the sheer responsibility of successfully raising a person. People often say, “well, they’re 18, I’ve done my job,” but children don’t come with an expiration date. Or at least, not in my book. The love and hope you carry for them, that they’ll be safe, that they’ll find happiness and joy, that’s something that keeps you up at night for the rest of your life.

And when you do see them find that happiness, real success, real joy, it brings a kind of gratification that’s hard to put into words. Achieving your own success feels good. But watching your children experience theirs is on a different level entirely. It’s a peaceful, fulfilling feeling that washes over you like a sweet summer breeze on a hot day.

I'm entering a new phase now. I have so many memories from raising both of my girls: learning to ride big wheels, then bikes, cheering from the sidelines at every sporting event, college visits, graduation day. I've loved every phase, though I'll admit the early years are mostly a blur (sheer exhaustion will do that to your memory). But life has slowed down now. My girls are young women now, one working as an event coordinator for a tech event company, the other as an assistant manager at a retail brand, and I get to soak them in differently than I could back then.

This past weekend gave me exactly that kind of moment. My oldest was visiting with her boyfriend from California, and Saturday night the whole family ended up sitting out back after takeout sushi, half-watching the World Cup wind down, playing a few rounds of Rummikub as the evening cooled off. Nothing was planned. Nothing was special, on paper. But I remember sitting there wanting to freeze it: the five of us, easy and unhurried, nowhere else anyone needed to be. That’s the moment that told me this chapter is real.

Both of my daughters have a sense of self-confidence I didn’t have at their age. They each have a sense of style, too, one I’d like to think they got from me. Watching them move through the world as fully themselves, without asking permission for it, is its own quiet kind of pride.

I have friends whose kids are getting married now, becoming grandparents. I know that day is coming for me too. But for now, I’m not rushing toward it. I’m enjoying exactly where we are: this version of our relationship, this particular chapter, this Saturday night with sushi containers still on the table and the cards still in our hands.

The lesson: Parenthood doesn’t end at 18. The worry doesn’t, and neither does the joy. The ordinary nights, the ones with no occasion attached, are often the ones worth freezing in time. Don’t wait for a milestone to soak it in.

Still becoming, one Sunday at a time. 🖤

Subscribe now

Yes, I dye my hair. Yes, I work out, get my nails done, keep up with what’s current. But I do all of it because I have free will, not because I’m running from a number. I make no apologies for wanting to feel beautiful, fit, and attractive. Age is just a number. What matters is the story you’re writing with it.

And that’s the thing — I don’t think of life in “seasons.” Seasons happen to you. I think of life as a book, and you are the author. That distinction matters. It means you stop waiting for some magical moment to arrive, and you stop blaming the universe when it doesn’t. You pick up the pen.

I’ve actually been living that metaphor pretty literally this week. I’m reading a book called Theo from Golden — I’m only on chapter 57 with 5 more chapters to go, and I already can’t put it down. It follows an old man named Theo who visits a town called Golden, and the whole book is quietly making a case for something I think I already believed but needed reminding of: one person, filled with kindness, can ripple out and change a great number of lives. Not through some grand gesture. Just through daily intention, being present, seeing people, actually valuing them. It’s a first-time author, and honestly, I’m blown away by the writing. If you haven’t read it, I highly recommend it.

It’s part of what’s nudging me into this next chapter I’m optimistic about. I feel grounded in a new way; I like my job, my kids are in good places, my husband is happy in his own chapter. That’s not something I take for granted, and I won’t pretend it’s always been this way.

I’ve also been watching Your Friends and Neighbors on Netflix (John Hamm, Amanda Peet), and between that and Theo, something’s being amplified for me right now: we were sold a false blueprint for happiness. Find the spouse. Buy the house. White picket fence, the dog, the two kids, both of you with good jobs. Smile. Post the vacation photos. Let everyone envy the highlight reel.

I’ll be honest, I have a complicated relationship with this. I love social media. I love writing here on Substack, which is its own strange, semi-public act. But I’m also not going into debt to chase a vacation that keeps up with the Joneses. Both things are true. And Theo would probably say the ripple effect I want to leave behind has nothing to do with either extreme; it’s just about showing up for the people in front of me.

This birthday has me landing somewhere I like: grateful, and more comfortable in my own life than I’ve ever been. I’m not in a rush to be somewhere else, or someone else. I’m slowing down and taking in the moments, valuing time with friends and real conversations with family way more than I used to.

I think that’s what comes with age, not less curiosity, but more confidence. I still want to learn, to grow, to try new things. But now I also know I have something to offer the world because of what I’ve already lived. Maybe that’s the whole point of the ripple: you don’t need to have it all figured out to still be worth learning from.

The lesson: You don't have to wait for permission to be proud of where you are. Age isn't something happening to you; it's a chapter you're writing. And kindness, offered daily and without fanfare, ripples further than you'll ever get to see. Pick up the pen and own your own story.

Still becoming, one Sunday at a time. 🖤

Four weeks into my new job, I’m still learning the rhythm of it — when to push, when to breathe, how to be fully on without burning out by Friday. Work demands a kind of constant readiness that’s exhilarating and exhausting in equal measure.

So this week, I’ve been thinking about what I reach for when I need to come back to myself. And the answer, as it turns out, has always been the same: a table, some people I love, and a good game.

My mom loved to play cards. Some of my earliest and best memories are sitting across from her, learning the rules, watching her face when she had a good hand. When I had my own daughters, I taught them all the favorite card games I grew up on. I just love that particular kind of closeness that happens when you’re playing something together. Now that my girls are grown, my husband and I find ourselves returning to it. A quiet evening, Rummikub on the table, the news off, the chaotic world outside. It’s one of the simplest ways we know how to connect.

So when friends suggested Pinochle on the Oregon coast last weekend, I didn't hesitate.

Rummikub is one of those games that looks deceptively simple. You’re laying tiles, building runs and groups of numbers, racing to clear your rack before anyone else. But the moment someone disrupts your perfectly planned set and you have to rethink everything on the fly — that’s where the real fun lives. It’s fast, it’s strategic, and it rewards the kind of focused attention that’s hard to come by these days.

Pinochle, I learned for the first time this weekend, huddled around a table with salt air and good people. It’s a classic trick-taking card game played in partnerships — part strategy, part bidding, part reading your partner without saying a word. You bid on what you think your team can score, name a trump suit, lay down your melds, then play out the tricks. It takes a few rounds to find your footing, but once it clicks, it really clicks.

We played for hours. We made mistakes. We laughed a lot.

What strikes me about both games is that they require you to think — to have a strategy, adapt it, and stay in it even when the cards (or tiles) don’t cooperate. There’s a challenge there that I love. But more than that, they require presence. You can’t half-pay attention and expect to win. You can’t drift.

In a world designed to pull us away from wherever we are, there’s something quietly radical about a game that holds you exactly where you are.

This Week’s Lesson

Play is not a break from real life — it's one of the most present things you can do in it. Find your game. Sit down. Stay there.

Thanks for being here — whoever you are. I’m planning to show up on Sundays with something short, honest, and worth your five minutes. If this resonated, I’d love to have you along for the ride. Please, share it with someone who might need it.

Subscribe now

About the author: I’m a marketer and enterprise storyteller at a tech company, host of the 2B Bolder podcast — a show featuring women in business and tech — and a mother, introvert, and lifelong work in progress. I started this newsletter because I wanted to write, and because I believe the most interesting chapter is always the one you’re still in the middle of. Glad you found me.

Still becoming, one Sunday at a time. 🖤

— Mary

I was sitting at my desk this week when I heard a group of colleagues laughing down the hall. Not at anything in particular — just that easy, mid-afternoon kind of laughter that happens when people are comfortable around each other. I stopped what I was doing and smiled.

I had forgotten what that felt like.

The Long Way Back

A year and a half ago, I stepped away from traditional work to try something I’d always wanted to do — build something of my own. I poured everything into it: time, energy, late nights, early mornings, and more tabs open on my browser than any person should legally be allowed.

It was a gift. I genuinely mean that. But the math eventually stopped working. The dream hadn’t grown to the point where it could replace what I needed it to replace, and reality — the good, grounding kind — reminded me it was time to make a move.

So I went back. Back to my old employer, actually, with a clearer sense of what I bring, a renewed desire to contribute, and — I’ll be honest — even a willingness to commute.

Four days a week in the office. And honestly? It’s not bad.

I think I’d had enough time alone to understand that working remotely, while it sounds like the dream, can quietly become its own kind of trap. When you’re tied to your computer trying to crack some magic code to make a buck, the romance fades fast. The isolation creeps in. The walls get closer.

Now someone stops by my desk to make small talk, and I realize — oh, right, this is nice.

The commute has even become something I look forward to. I’ve started an audiobook list, beginning with Theo of Golden by Allen Levi. That drive time is mine — no emails, no pressure, just a story or some music I’ve been meaning to get back to. I missed that more than I knew.

Stepping Into Something Familiar (That Still Feels New)

Returning to a place you know doesn’t mean everything is easy. A new role brings new challenges, new things to learn, new moments where the technical side of something feels like it’s written in a foreign language.

But I keep coming back to this: mindset is everything.

When something feels overwhelming, I remind myself — I can figure this out. I’ve figured things out before. And I was born to be bolder.

This Week’s Lesson

The thing you were running toward might have been right behind you.

Entrepreneurship taught me more about myself than any job ever has. But it also made me realize that collaboration, community, and even the structure of a workplace aren’t things to escape — they’re things that actually help some of us thrive.

Going back isn’t giving up. Sometimes it’s just growing up.

Thanks for being here — whoever you are. I’m planning to show up on Sundays with something short, honest, and worth your five minutes. If this resonated, share it with someone who might need it.

Still becoming, one Sunday at a time. 🖤

About the author: I’m a marketer and enterprise storyteller at a tech company, host of the 2B Bolder podcast — a show featuring women in business and tech — and a mother, introvert, and lifelong work in progress. I started this newsletter because I wanted to write, and because I believe the most interesting chapter is always the one you’re still in the middle of. Glad you found me.

Going back isn’t giving up. Sometimes it’s just growing up.

Still becoming, one Sunday at a time. 🖤

— Mary

If this resonated, I’d love to have you along for the ride.

Subscribe now