Confessions of a Creative Leader

What a year April was. Here’s what happened.

21 min · 3. touko 2026
jakson What a year April was. Here’s what happened. kansikuva

Kuvaus

Note: This post is a quick recap of the episode. The podcast is richer — more stories, more texture, more of the real stuff. It’s about 10 minutes at 1.5x speed and worth the listen. After a month away and a year and a half as Confessions of a Facilitation Artist, this show has a new name, Confessions of a Creative Leader. Why “Confessions” stays: It traces back to my Catholic roots — my dad is a deacon, confessions before Sunday mass, vulnerability as practice. It fits what I do here. Why “Facilitation Artist” is gone: It was always an experiment. A conversation with my friend and fellow facilitator Chloe Temple [https://substack.com/profile/152347872-chloe-temple] reframed things for me — she described me as a model of self-leadership, and I thought: yes, that’s actually what this is. Lifelong learning, taking responsibility for my own growth so I can show up in service to others. Facilitation is part of that. So is product leadership, entrepreneurship, and figuring out motherhood. Creative Leader is just more honest about the full territory. What April Actually Was Intense. Good-intense, not overwhelmed-bad. A few things made it one of the fuller months I can remember: Work: I went back full-time to build a zero-to-one AI-native product. April was mostly a multi-week design sprint — interviewing higher ed leaders, evolving prototypes, testing them, and this past week, finally starting to build. I was also deep in Claude Code doing POC (that means proof of concept) work to test feasibility, and using Claude Projects and Cowork heavily for context documents and requirements. (Claude is my second husband it seems.) Weekends: Sixteen garden beds don’t prep themselves. Hard physical work, completely restorative after a week at a screen. Health: I’m 47 and perimenopausal (I’m a woman and I’m not hiding from that) — noticing that shift and taking it seriously. Consistent exercise, more intentional eating, and the small delights: fresh eggs from our neighbor’s chickens, kimchi, the occasional fresh-squeezed grapefruit juice. My Sister For new listeners & readers: in October, my sister was diagnosed with terminal stage four cancer across multiple sites. It was really scary. Mid-April, we had the appointment — the one to find out if her treatment was working. The oncologist, who is normally very measured, walked in with unmistakable joy. The news: treatment is working well, some tumors have actually shrunk, and based on the data, this typically holds for up to two years. We thought we might be down to months. She’s doing well. We’re celebrating. The emotions are complicated — relief and sadness at the same time — but the news is good. If My Response to You Was Short — Here’s Why A lot of you reached out during the break. Thank you. If I didn’t respond well, or at all: it wasn’t personal, it was capacity. Maxed out at work, exhausted at night, in the garden on weekends. I’m behind on a lot of conversations and I’m working on it. What’s Coming I’m not turning this into an AI or product podcast — there are better ones for that (Lenny's Newsletter [https://open.substack.com/pub/lenny] - Lenny Rachitsky [https://substack.com/profile/1849774-lenny-rachitsky], Prompt-Led Product | For PMs Building in the AI Era [https://open.substack.com/pub/promptledproduct] with Elena | AI Product Leader [https://substack.com/profile/31598723-elena-ai-product-leader] , Product Management IRL [https://open.substack.com/pub/amycmitchell] with Amy Mitchell [https://substack.com/profile/23488597-amy-mitchell] ). But I have real experiments to share over the next few episodes: * AI + facilitation — specific tools and prompts for foundation sprints and design sprints, beyond basic brainstorming * AI in product discovery — how I’ve been using it in zero-to-one work * Tactical leadership uses — including Cowork for general tasks and, yes, researching summer camps for my kids * My first vibe-coded app — a facilitation timer I built for myself, and what that experience was actually like Episodes may be biweekly for a while. I’d rather show up with something real than force a cadence. Reach out on LinkedIn, Substack, or text. I read everything — I’m just slow to respond. Love you all. Good to be back. — Monica Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe [https://creativeleaderconfessions.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

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jakson Life at the Speed of Play - Chapter 1: Book of Life kansikuva

Life at the Speed of Play - Chapter 1: Book of Life

Life at the Speed of Play, Chapter One: The Book of LifeHow creating a Book of Life makes your life worth living, and scaffolds you as a strategic leader Continuing our summer read-along of https://www.amazon.com/s?k=life%2Bat%2Bthe%2Bspeed%2Bof%2Bplay&adgrpid=184262060617&channelId=4&clpRedir=Y&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&tag=googhydr-20&ref=pd_sl_4i7cfmd53g_eLife at the Speed of Play [https://www.amazon.com/s?k=life%2Bat%2Bthe%2Bspeed%2Bof%2Bplay&adgrpid=184262060617&channelId=4&clpRedir=Y&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&tag=googhydr-20&ref=pd_sl_4i7cfmd53g_e] by Zynga founder Mark Pincus [https://www.amazon.com/s?k=life%2Bat%2Bthe%2Bspeed%2Bof%2Bplay&adgrpid=184262060617&channelId=4&clpRedir=Y&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&tag=googhydr-20&ref=pd_sl_4i7cfmd53g_e], this week I’m digging into Chapter One: The Book of Life. Pincus’s core idea, “know your goal or suffer death by 1,000 compromises,” comes from his own annual ritual of writing in the same physical book every year during the Jewish high holidays. I’m curating the insights I found most useful for anyone building a strategic practice, not just product folks. What you’ll learn: * Why Pincus’s “Book of Life” ritual, taking stock, reviewing the past year against goals, and setting intentions for the next, works as a personal North Star practice. I’m adopting a version of it even though I currently just journal and burn my notebooks every few months * His framework for choosing two types of yearly goals: something fully in your control, like a daily habit, paired with something bigger and less certain. Proving you can control the small thing builds belief you can pull off the big one * The “abyss” concept, the disorienting, unproductive-feeling space before and after a big venture or job. He argues it’s where real instincts, pattern recognition, and taste actually get built. I connected this back to my own five years of feeling lost before landing back in product * The “imagination chessboard” exercise, starting strategy conversations by asking “what if everything goes right?” instead of leading with constraints. He notes that AI can now help you build that exercise out in minutes Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe [https://creativeleaderconfessions.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

19. heinä 202627 min
jakson Let's Read Life at the Speed of Play kansikuva

Let's Read Life at the Speed of Play

Let’s get started with our new book series. I’m kicking off the Life at the Speed of Play [https://www.amazon.com/s?k=life%2Bat%2Bthe%2Bspeed%2Bof%2Bplay&adgrpid=184262060617&channelId=4&clpRedir=Y&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&tag=googhydr-20&ref=pd_sl_4i7cfmd53g_e] https://www.amazon.com/s?k=life%2Bat%2Bthe%2Bspeed%2Bof%2Bplay&adgrpid=184262060617&channelId=4&clpRedir=Y&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&tag=googhydr-20&ref=pd_sl_4i7cfmd53g_eread-along, starting with Reid Hoffman’s foreword and Mark Pincus’s introduction. This is a short intro episode to help you decide if you want to journey through the book with me. I’ll be doing roughly one chapter a week through the end of September. What you’ll learn: * Why I’m anchoring this next stretch of episodes in Mark Pincus’s book, and my loose reading cadence (about one chapter a week, wrapped by end of Q3) * Reid Hoffman’s foreword idea of “what game are you playing” and “what’s your theory of the game,” and why that framing hit home for me as both a product leader and a recovering serial idea-generator * Why generating ideas isn’t the hard part for me… killing them is, and why I think that’s the real skill this book is going to help me build * My take on Pincus’s line that “corporate” really means “lack of thought or intent,” and why I push back on that a little, because being intentional and thoughtful in a corporate role is exactly what I get paid to do Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe [https://creativeleaderconfessions.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

15. heinä 202626 min
jakson How my entrepreneur journey has made me a better leader! kansikuva

How my entrepreneur journey has made me a better leader!

I’m back after an unplanned couple-months break, and I wanted to catch you up on life! I’m talking about what I’ve brought back into my full-time Senior Director of Product Growth role after my stint as a part-time entrepreneur. I’m in throws of building a new AI-native product, and about to soft launch it next week. Also, the new book I’m picking up as my next read-along is Life at the Speed of Play [https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=sr_1_1?adgrpid=184262060617&channelId=4&clpRedir=Y&dib=eyJ2IjoiMSJ9.Evb_U93AoaMtG-9HvyMOmIeM15G58V7h2s5vY4xTZbvLalI69y33s4EM6oZYf9V0yLUAriCKvxYkFAALgxnDCwkQypgN8KmYuSWtsDQXZtKUxuYt_EEff-0P4bkO28F8OotMQZD76lV-We8EhbHTmEvBnwTU0-Arzpn1EEst0WhKqUwNBwOB4gWrCugPTCbZSBCAyeOD0eVmEPiHcn03uIFbpU7RXl1abL4in6e4eNE.wE61fD8bp8v9ZWUF4z4NlkT8ynogqst8dvO30UWh6ZU&dib_tag=se&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&keywords=life+at+the+speed+of+play&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&qid=1783814167&sr=8-1] by Zynga founder Mark Pincus [https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=sr_1_1?adgrpid=184262060617&channelId=4&clpRedir=Y&dib=eyJ2IjoiMSJ9.Evb_U93AoaMtG-9HvyMOmIeM15G58V7h2s5vY4xTZbvLalI69y33s4EM6oZYf9V0yLUAriCKvxYkFAALgxnDCwkQypgN8KmYuSWtsDQXZtKUxuYt_EEff-0P4bkO28F8OotMQZD76lV-We8EhbHTmEvBnwTU0-Arzpn1EEst0WhKqUwNBwOB4gWrCugPTCbZSBCAyeOD0eVmEPiHcn03uIFbpU7RXl1abL4in6e4eNE.wE61fD8bp8v9ZWUF4z4NlkT8ynogqst8dvO30UWh6ZU&dib_tag=se&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&keywords=life+at+the+speed+of+play&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&qid=1783814167&sr=8-1]. I also get into some personal updates about my family, health, the whole mess of it. What you’ll learn: * How I’m bringing product-led growth strategy (Wes Bush’s “bowling alley” framework) into a B2B SaaS environment that’s used to long sales cycles * The Russell Brunson-style webinar format I used for both an internal team training and an upcoming external product pre-launch webinar * Why I picked Life at the Speed of Play [https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=sr_1_1?adgrpid=184262060617&channelId=4&clpRedir=Y&dib=eyJ2IjoiMSJ9.Evb_U93AoaMtG-9HvyMOmIeM15G58V7h2s5vY4xTZbvLalI69y33s4EM6oZYf9V0yLUAriCKvxYkFAALgxnDCwkQypgN8KmYuSWtsDQXZtKUxuYt_EEff-0P4bkO28F8OotMQZD76lV-We8EhbHTmEvBnwTU0-Arzpn1EEst0WhKqUwNBwOB4gWrCugPTCbZSBCAyeOD0eVmEPiHcn03uIFbpU7RXl1abL4in6e4eNE.wE61fD8bp8v9ZWUF4z4NlkT8ynogqst8dvO30UWh6ZU&dib_tag=se&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&keywords=life+at+the+speed+of+play&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&qid=1783814167&sr=8-1] https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=sr_1_1?adgrpid=184262060617&channelId=4&clpRedir=Y&dib=eyJ2IjoiMSJ9.Evb_U93AoaMtG-9HvyMOmIeM15G58V7h2s5vY4xTZbvLalI69y33s4EM6oZYf9V0yLUAriCKvxYkFAALgxnDCwkQypgN8KmYuSWtsDQXZtKUxuYt_EEff-0P4bkO28F8OotMQZD76lV-We8EhbHTmEvBnwTU0-Arzpn1EEst0WhKqUwNBwOB4gWrCugPTCbZSBCAyeOD0eVmEPiHcn03uIFbpU7RXl1abL4in6e4eNE.wE61fD8bp8v9ZWUF4z4NlkT8ynogqst8dvO30UWh6ZU&dib_tag=se&hvadid=779578873675&hvdev=c&hvexpln=0&hvlocphy=9017427&hvnetw=g&hvocijid=15260571418118184131--&hvqmt=e&hvrand=15260571418118184131&hvtargid=kwd-2478764662973&hydadcr=22565_13531269_8697&keywords=life+at+the+speed+of+play&mcid=81c6351bed083c7ba8616557cb4b8507&plpRedirect=mhFallback&qid=1783814167&sr=8-1as my next read-along, and what I’m hoping to pull from it for facilitation and self-development * A candid life update: my family, my health, a summer with two kids underfoot, and how I’m protecting my own energy (daily walks, more fiction, less guilt about the podcast schedule) Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe [https://creativeleaderconfessions.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

12. heinä 202618 min
jakson I Have an Addiction...and it's not what you think kansikuva

I Have an Addiction...and it's not what you think

This week I’m showing up without a plan, and that’s kind of the whole point. I was supposed to continue the AI in facilitation series, but I wasn’t feeling it. And rather than not show up at all, I decided to just tell you what’s actually on my mind right now. In this episode I talk about: * Why I’ve scaled way back on how much time I spend preparing these episodes — and why that’s intentional, not lazy * The difference between consumption addiction and creation addiction — and why I think the second one is sneaking up on a lot of us right now * How I’m using a Claude Project to support this podcast (quick peek behind the curtain for the AI-curious) * And honestly — a little permission slip to say no to the things that aren’t high-leverage for your season of life right now Short one this week. Real one this week. Hope you find yourself in it somewhere. Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe [https://creativeleaderconfessions.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

17. touko 202617 min