Podcast
The Optimization Toolbox with Jenna Redfield
Hosted by Jenna · EN
How to optimize your life from the inside out! The tools, tactics & techniques to constantly improve your life, business and marketing.
Sharing extended interviews from the Jenna Redfield YouTube channel, this podcast will deep dive into systems and tools to help you organize your online life.
jennaredfield.substack.com
jennaredfield.substack.com
20episodes
Episodes
Newest firstAll episodes
How to Never Forget Someone's Name (The 3-Step System That Actually Works)
2w ago00:43:15Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.This episode is part of what I call this podcast the Optimization Toolbox — practical systems for neurodivergent brains.Because so many of us have the same frustrating experience: you meet someone, you have a genuinely great conversation… and then five minutes later you can’t remember their name.It’s not because you don’t care. It’s not because you’re “bad at networking.” It’s because names are basically the worst possible input for an ADHD brain: random, context-free information delivered while you’re also trying to manage eye contact, read social cues, and not black out from overstimulation.And I wanted to talk about it because I think remembering people is a branding skill — not in a fake, “personal brand” way, but in the real way: how people feel after they interact with you. Being remembered (and remembering others) builds trust faster than almost anything.My angle on “memory” usually lives in the world of messaging and marketing — making ideas memorable, making offers clear, making your brand easy to recognize.But today’s guest, Bob Miller — former magician, memory speaker, and author of Remember the Room — focuses on something even more human: memorizing people’s names.We recorded in person at the amazing PodcastCrewMN in Robbinsdale MN.And instead of giving me “try harder” advice, he gave me what I actually want: a system.It’s a skill, not a personality flawThe first thing Bob said when I called remembering names a “gift” — he corrected me immediately.“It’s a skill,” he said. “I can forget stuff as easily as anybody.”That matters because most of us have spent years training ourselves to say:“I’m bad at names.”“I’m awkward.”“I’m not a networking person.”“My brain just doesn’t do that.”But neurodivergence isn’t a character flaw. It’s an operating system.And what Bob gave me was essentially this reframe:If your brain won’t do it automatically, you don’t need more willpower. You need a workflow.The Look → Listen → Link framework (aka: giving your brain something it can actually hold)Here’s Bob’s system, and once you hear it, it’s almost annoyingly obvious in the best way.Look → Listen → LinkStep 1: LOOKWe think we look at people, but we don’t.When you meet someone, choose one striking feature — the thing that stands out most about their face.Not clothing. Clothing changes. Faces (mostly) don’t.This matters for ADHD brains because attention is selective. If you don’t choose a focus point on purpose, your brain will focus on whatever is loudest/fastest/newest — which is usually your own internal monologue.So: pick the anchor.Step 2: LISTENBob said something that made me laugh because it’s so true:Names are basically nonsense words.What is a Jenna? What is a Bob?Your brain can’t hold onto a random, abstract sound — especially when you’re also juggling social anxiety, overstimulation, or five competing thoughts.So the moment you hear a name, your job is to convert it into something visual:* Bob → a fishing bobber* Sally → a salad* Doug → a dogIs it logical? Not always.Is it sticky? Yes.And for a neurodivergent brain, “sticky” beats “proper” every time.Step 3: LINKNow connect the two.Take the image you made for the name and mentally attach it to their striking feature — in the most ridiculous, vivid way you can imagine.Bob’s rule: weird is memorable. Boring isn’t.This is so important, because a lot of us try to remember names by being serious about it.But ADHD brains don’t remember what’s serious.They remember what’s distinct.So make it strange on purpose.The 3 pre-event rituals (because your brain needs a runway)Before you even walk into a networking event, Bob recommends three things:Make the decision.Decide ahead of time: I’m going to work on remembering names today.Neurodivergent brains do better with intentional “modes.” (Otherwise your brain defaults to survival mode.)Use the name immediately.When someone tells you their name, say it back once or twice:“Nice to meet you, Jenna.”You’re creating a memory of saying it, not just hearing it.Review while you’re still there.Before you leave, scan the room and mentally recite the names of the people you met.ADHD brains need repetition closer to the moment or it evaporates.Memory is the tool. Connection is the goal. (And this is the part ND folks deeply get)This was the line that stuck with me most:“The memory is just the tool that allows you to make that connection.”Because if you’re neurodivergent, you probably don’t struggle with caring about people.You struggle with the mechanics:* recall* follow-up* consistency* the “admin work” of relationshipsYou can be warm and brilliant and genuine… and still forget someone’s name five minutes later.So the goal isn’t “be a person who always remembers names.”The goal is: build a system that makes people feel remembered.My Notion CRM “database move” (because I don’t want my brain to be the storage unit)Bob told me that after events he collects business cards and puts notes into a database:* name* striking feature* key facts they shared* any context for follow-upHe said:“I can forget it once it’s in my database.”And I felt personally called out, because… same.This is exactly why I use Notion as a CRM. Not because I’m trying to be “optimized,” but because I’m trying to be kind to my future self.Here’s what’s true for my ADHD brain:If it lives in my head, it will disappear.If it lives in a system, it becomes reliable.So after I meet someone, I do a quick “capture” inside Notion:* who they are* how we met* what they do* anything personal they shared* what I want to follow up about* and (this is key) when I want to follow upNotion becomes the second brain for my relationships — which means my relationships don’t have to depend on perfect memory.The part nobody tells you: follow-up is a neurodivergent superpower when it’s systemizedA lot of people think networking is about being charismatic.I think networking is about being consistent.And consistency is hard when your brain is:* time blind* novelty-seeking* easily overwhelmed* allergic to “I’ll do it later”So instead of trying to become a different person, I build systems that do the remembering for me.That’s what a CRM is supposed to be.Not “salesy.” Not corporate.Just: a way to continue the conversation like a human.Try this todayNext time you meet someone:* Convert their name into an image (Listen)* Anchor it to one feature (Look)* Make it weird (Link)Afterward: write one line somewhere external(your Notes app, a Post-it, Notion, whatever)Because the win isn’t “remember forever.”The win is: don’t lose the connection.Want my Notion setup for this?If you’ve been thinking, “Okay I love this… but I need the system,” that’s exactly why I built Tabstack — my Notion template for tracking content + follow-ups in a way that actually works for a neurodivergent brain.It’s designed to help you capture people + context quickly, keep your relationship momentum, and stop relying on your memory to do the heavy lifting.If you want to turn “I should follow up with them” into an actual workflow, check out Tabstack here: https://course.jennaredfield.com/life-tracker/The Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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What Is Fractional Work? (And Why It Matters for Solopreneurs in 2026)
3w ago00:49:07Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.If you’ve been calling yourself a freelancer but it never quite felt right, there’s a good chance you’re actually doing something called fractional work — and there’s a real difference between the two.I recently recorded an episode of the Optimization Toolbox Podcast with John Arms , who runs Voyager University and is one of the leading voices on fractional work in the country. We talked for almost an hour about what fractional work actually is, why it’s growing fast, and what it means for people building solo businesses right now.Here’s what I took away.What is fractional work?Fractional work is permanent part-time. You work with a client on an ongoing basis — not as a full-time employee, not as a project-based consultant — but as their embedded expert for a set number of hours per week. Usually around 10 hours, sometimes across two or three clients at once.The key word is permanent. Unlike freelancing, which tends to be project-to-project, fractional relationships are long-term. You’re not just completing a deliverable — you’re functioning as a part-time version of a role the company needs but can’t justify hiring full-time.Common fractional roles include fractional CMO, fractional COO, fractional marketing director, and fractional operations lead.Fractional vs. freelancing: what’s the difference?This is the question I asked John right away because honestly the line felt blurry to me.The short version: freelancing is episodic, fractional is stable.Freelancers typically work on projects with a clear start and end. The work is done, you move on, you find the next client. It’s unpredictable by nature.Fractional work is ongoing. You’re not selling a project — you’re selling your expertise applied consistently over time. Companies get a senior-level person without the full-time cost. You get stable, recurring income without the 40-hour week.John describes it as fractional heaven vs. purgatory. Purgatory is the feast-or-famine cycle most freelancers know too well. Heaven is consistent clients, work in your zone of genius, and income that reflects your actual value.Why fractional work is growing in 2026A few things are driving this:Companies are realizing they don’t need 40 hours of your expertise. They need your sharpest thinking applied consistently. A startup doesn’t need a full-time CMO — they need someone senior-level guiding their marketing strategy for 10 hours a week. That’s fractional.The traditional job market is harder than ever for experienced professionals. John shared a stat that stopped me: only 24% of people over 50 who leave a job will find a new one at the same pay level. Fractional gives experienced professionals a direct path to monetize their expertise without competing in a difficult hiring market.AI is accelerating the shift. As AI handles more tactical work, what companies actually need is senior-level thinking, judgment, and relationships — exactly what fractional professionals provide.What this means if you’re a solopreneurHere’s the practical takeaway for anyone running a solo business:If you work with clients on an ongoing basis, apply your expertise in a specific area, and operate in a part-time capacity — you’re probably already doing fractional work. You just might not be packaging or pricing it that way.The difference between freelancing and fractional often comes down to how you position yourself. Fractional professionals aren’t selling hours or deliverables — they’re selling a role. That shift in framing tends to lead to longer client relationships, more stable income, and higher rates.John’s framework for building a fractional business starts with what he calls your inner nerd — your specific combination of fascinations, skills, and obsessions that make you the go-to person in your lane. The clearer you are on that, the easier it is to attract the right clients and charge what your expertise is worth.The biggest barrier to going fractionalSpoiler: it’s not skills or experience. According to John, the two biggest barriers are:* Health insurance — the lack of portable, affordable benefits keeps a lot of people tied to full-time employment even when they’d rather be independent. John is actively working on solutions in this space.* Mindset — specifically, unlearning the idea that your value is measured in hours worked. That’s a hard reset for a lot of people, but John says it’s faster than most expect once you’re in the right environment.Listen to the episode on Spotify or Apple Podcasts or above on Youtube or on this webpageWant to build better systems for your solo business? Join me Wednesday 👇If this resonated and you’re thinking about how to actually structure a solopreneur business that works with your brain — come to my workshop this Wednesday.Notion + Claude for ADHD Brains 📅 Wednesday, May 13th · 12:00–1:00 PM CT · ZoomWe’re going hands-on with how to use Notion and Claude together as a practical system for running your business — task management, client work, content, all of it. Built specifically for ADHD and neurodivergent solopreneurs.→ $10 general admission — grab your spot here→ Free for paid Substack subscribers — promo code is just below the paywall. $5/month gets you into every workshop and office hour going forward.The Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Claude & Notion for ADHD Workshop for Paid SubscribersMay 13th 12pm CSThttps://luma.com/u319x0l5?coupon=REDTOOLBOXDISCOUNT CODE: REDTOOLBOXSee you Wednesday.— Jenna Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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The Future of Online Business: What's Changing in 2026 (and How to Stay Ahead) w/ Cathy Olson of Funnel Gorgeous
Jan 1300:41:00Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.The online business world is shifting faster than most entrepreneurs realize.In my latest podcast episode, I sat down with Cathy Olson—co-founder of Funnel Gorgeous and FG Funnels—to talk about what’s really happening in 2026. Full transparency: I’ve been learning from Cathy and her business partner Julie for years. In 2021, I became sales funnel certified through their program, FG Society, and their teachings completely transformed how I think about offers, messaging, and strategy. So this conversation was both an honor and a bit surreal—getting to interview someone who’s taught me so much.Cathy has been in the trenches for over 15 years, teaching design, copy, and marketing strategy. She’s a total expert in this space and has built a multi-million dollar business helping entrepreneurs create profitable funnels and courses. And she’s not sugarcoating what’s ahead.If you’ve been feeling like the ground is shifting under your feet, you’re not alone. Here’s what we covered—and what you need to know to stay relevant.BEFORE I FORGETJoin my next FREE Notion AI Workshop on Goal Setting on January 22 at 12pm CSTAI Isn’t the Enemy. Resistance Is.One of the first things Cathy said that caught me off guard: “Why are we so scared about AI doing our job? Isn’t that kind of a good thing?”Most of us panic when we think about AI replacing what we do. But Cathy flipped the script. If AI can handle the tedious, repetitive parts of your work—editing, drafting, research—doesn’t that free you up to do the higher-level thinking that actually moves the needle?The shift happening right now isn’t about AI replacing you. It’s about AI replacing the parts of your job you probably don’t want to do anyway.The question is: Are you ready to move up the ladder?Moving “Up the Ladder” to Stay RelevantCathy introduced a concept I haven’t stopped thinking about: the hierarchy of your skill.Let’s say you’re a video editor. At the bottom, you have the actual editing work. In the middle, you have the creative direction and storytelling. At the top, you have strategy—knowing why a video should exist, what the goal is, and how it fits into the bigger picture.AI can already handle the bottom. Soon, it’ll handle the middle.Your job is to get to the top.The same goes for designers, copywriters, coaches, and consultants. If you’re offering mediocre design or mediocre copy, AI can do that now. But if you’re the one making the decisions—the one who understands human psychology, brand strategy, and what will actually resonate—you’re irreplaceable.Think of AI like a VA or production assistant. You wouldn’t give them full creative control. You’d give them tasks and review the output. That’s the relationship you need with AI.The Trust Recession is RealHere’s a wild moment from the conversation: Cathy told me that during a live webinar for FG Funnels, people in the chat were asking, “Is this live? Are you real?”That’s where we are now. People can’t tell what’s real anymore.With AI-generated avatars, deepfakes, and synthetic voices, trust is eroding fast. Cathy called it a trust recession, and I think she’s spot on.That’s why faceless marketing is not going to last. People need to see you, hear you, and connect with you as a human. If you’ve been hiding behind stock images and templated captions, 2026 is the year to show up.This is also why I’m such a big advocate for consistent on-camera work. When you practice being on camera every week, you get better at speaking, presenting, and connecting. And when you need to go live, speak on stage, or show up in a sales call, you’re ready.Courses Are Evolving (and GPTs Are Taking Over)Cathy and I talked a lot about how courses are changing. People don’t just want information anymore. They want interaction.Static PDFs and pre-recorded videos aren’t cutting it. Students want to ask questions, get customized feedback, and apply what they’re learning to their specific situation.That’s where GPTs come in.Custom GPTs allow you to package your knowledge in a way that’s interactive and personalized. Instead of selling a course, you can create a trained AI assistant that answers questions based on your framework, your voice, and your expertise.Cathy’s team is building GPTs for their Metrics Muse subscription, and they’ve embedded AI into their course platform so students can ask questions about each module as they go.This is where education is headed. If you’re still thinking about courses the old way, you’re already behind.Clarity Over EverythingOne of the biggest shifts Cathy emphasized: You need to be known for ONE thing.I know, I know. If you’re a multi-passionate entrepreneur like me (and Cathy), this hurts to hear. But it’s true.People can’t remember 20 things you do. They can barely remember one.When I go to a networking event now, I don’t list everything I offer. I pick one thing I want them to walk away remembering. That’s it.Cathy said the same thing: Clarity of messaging is going to be critical in 2026. If people can’t explain what you do in one sentence, they can’t refer you. And referrals are everything right now.This ties directly into my Repeat Method framework—showing up consistently with the same message so people actually remember you.Outlasting is the Name of the GameHere’s the tough love part of the conversation: 2026 is a correction.Since 2020, a flood of new entrepreneurs entered the online space. Money was flowing, courses were selling, and it felt easy. But now? The market is stabilizing. A lot of people Cathy knew as entrepreneurs are back at regular jobs.If your revenue has stayed flat or dipped slightly, you’re not failing. You’re normal.The businesses that will thrive are the ones that outlast. The ones that stay agile, keep learning, and don’t hold onto strategies that stopped working two years ago.Cathy said something I’ll never forget: “Stable income is the new growth.”If you’re still here, still showing up, still making it work—you’re winning.AI and Health (a Personal Aside)One of my favorite parts of the conversation was when we talked about using AI for health.I’ve been on a three-year journey trying to figure out some health issues, and Notion AI literally helped me connect the dots. I uploaded all my blood tests into Notion, asked it to summarize patterns across years of data, and had a major breakthrough.Cathy shared a similar story—AI helped her identify a rare benign tumor before her doctors did. She uploaded her MRI results, and it broke down the medical jargon into plain language.This is the kind of stuff that makes AI genuinely useful. Not replacing humans, but helping us see things we couldn’t see on our own.What to Do NextIf you take one thing from this conversation, let it be this:Don’t stick your head in the sand.AI is here. The market is shifting. Trust is eroding. Courses are evolving.But that doesn’t mean you’re doomed. It means you need to adapt.* Move up the ladder in your skillset* Show up as a human (on camera, in writing, in person)* Get clear on the ONE thing you want to be known for* Make your content interactive and personalized* Focus on outlasting, not just growingIf you do those things, you’re not just surviving 2026. You’re setting yourself up to thrive.Want to go deeper?📘 Check out my Notion Foundations Course to build ADHD-friendly systems that actually work💡 Book a THREAD Clarity Call if you need 1:1 help cutting through the noiseConnect with Cathy:📍 Funnel Gorgeous (courses on offers, copy, and design)📍 FG Funnels (all-in-one software for funnels, email, and community)📍 Instagram: @funnelgorgeous Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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How Notion AI Just Replaced ChatGPT in My Business Workflow
Nov 2501:13:17Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Let’s be honest: I wasn’t totally sold on Notion AI at first, especially after it launched. I’d been using ChatGPT religiously for content creation, brainstorming, scripting videos, and outlining newsletters. It had the context. It knew my tone. I’d built custom GPTs. I didn’t think I needed another AI tool.But then...I went to the Notion Conference and learned they spent the last 2 years rebuilding Notion AI from the ground up….and I was shocked at how useful it had become. At that conference I met so many people including fellow ambassador Val. Valeria Alfuzzi is a fellow Notion nerd (and Notion-certified consultant) who lives in Colombia, she is a full time Notion Consultant with 6 employees and we recently sat down on my podcast, The Optimization Toolbox, to talk all things Custom Personal AI Agents in Notion.You can find her on instagram and her Notion website And real talk? It kinda blew my mind. 💥Here’s why.🧠 What Are Custom Personal Agents in Notion?If you haven’t played with these yet, Custom Agents are basically little AI “team members” that live inside your Notion workspace. They’re like ChatGPT, but with memory, structure, and direct access to your workspace databases. They can be trained on your tone, style, workflow—and actually learn from the context inside your Notion setup.Val showed me her setup (yes, with naming conventions like Casper the newsletter ghost 👻 and Frankenstein the agent that builds other agents 😍). She’s built a whole team of AI helpers that write, format, and even organize her content pipeline.And I thought...wait, I could do this.🤯 Why I’m (Finally) Making the SwitchAfter that call, I started recreating my custom GPTs inside Notion. Here’s why I’m shifting away from ChatGPT for my day-to-day tasks:* Context lives in Notion: I’ve been using Notion for 4+ years. All my content ideas, client notes, health logs, even my book drafts live there. Why not let AI live there too?* Memory that matters: Notion’s agents don’t just remember stuff—you can tell them to update their memories based on what you’re teaching them. It’s like having an assistant who gets smarter over time.* Workflow integration: Val showed how she assigns specific agents to specific content types (newsletters, carousels, outlines), even grouping agents by project. It’s like building a team inside your digital brain.* It’s cheaper: Notion’s AI plan is $10–$20/month including workspace features. That’s a steal if you’re already paying for Notion + ChatGPT separately.* Privacy wins: Everything stays in your Notion workspace. That means more control and less worry about where your data is going.🎯 How I’m Starting SmallI’m not moving everything overnight. But here’s how I’m easing in:* Recreating my top-used GPTs (like my newsletter formatter and YouTube idea generator).* Cleaning up my old databases so AI can actually pull helpful info (Val even suggested creating an AI agent just to help clean old pages—genius).* Experimenting with workflows—like generating carousel copy from a YouTube script, or summarizing client call notes into next steps.* Tagging context-rich databases so the agents can pull smarter insights over time.This might not be for everyone—but if you’re already using Notion and feel spread thin between tools, I highly recommend giving it a try.🎥 Want to Watch the Full Interview?Check out my convo with Val on The Optimization Toolbox. We go deep on:* Her system for managing 10+ custom agents* How to structure your agent’s “personality”* Real use cases for newsletters, client reports, health logs, and more* What’s coming next with Notion AI (hint: custom workflows are about to get wild) Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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🧠 How to Build a Personal Brand That Converts Without Feeling Cringe (with Howie Chan)
Oct 2800:49:21Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Featuring Howie Chan on The Optimization ToolboxIf you’ve ever felt like building your “personal brand” makes you sound fake, braggy, or—let’s be honest—a little cringe… you’re not alone.This week, I sat down in person with Howie Chan at the Podcast Crew Online studio in Robbinsdale, Minnesota. (Seriously — shout-out to them. Their team makes the in-studio experience so easy and the quality so good. If you’re local and want to level up your podcast or video setup, check them out at podcastcrew.online.)💼 Meet Howie ChanHowie Chan is a founder and brand strategist helping individuals and companies go from unknown to unignorable.With over 20 years in healthcare, he’s helped launch multiple companies and products, including a multi-billion-dollar spinout from Merck. He continues to consult, speak, and serve as a change agent for organizations navigating transformation.Today, he also helps experts and leaders build personal and business brands through his coaching programs. As host of Influence Anyone podcast, he’s interviewed thought leaders like Henna Pryor (workplace performance), David Robson(science journalist), and Nir Eyal (habits expert), sharing actionable lessons on influence, attraction, and growth.With 100 K+ LinkedIn followers, Howie was named Top LinkedIn Creator in Branding & Positioning by Favikon in 2024. His mission?“To help 1 million people live their version of legendary by sharing their unique gifts with the world through the power of influence and brand.”💼 1. Stop Building a “Personal Brand.” Build aProfessional Brand.Howie’s biggest reframe? Stop calling it personal branding.“A professional brand,” he says, “is the story people tell about you when you’re not in the room.”Your professional brand isn’t about how often you post—it’s about credibility and clarity. It’s how people in your space describe what you do and why you matter.That clarity doesn’t come from fancy design—it comes from consistency. Your words, your work, and how you make people feel all need to line up.So if you hate “personal branding,” good news: You don’t have to sell yourself. You just have to make it easy for people to understand how you help.🌱 2. Howie’s LinkedIn Growth (and What Actually Works)When Howie was laid off in 2022, he started posting on LinkedIn—not with a strategy, but with curiosity.He didn’t chase trends or virality. Instead, he shared short, thoughtful posts about emotion, leadership, and brand psychology. And that honesty resonated.Over time, his visibility grew—not because he was loud, but because he was clear.He posted about what he knew deeply, not everything he could talk about.“People think visibility is about reach,” he told me. “It’s really about resonance.”His growth came from repeating consistent ideas, showing up with empathy, and building genuine connections—not optimizing for algorithms.That’s the model ADHD creators and solopreneurs can actually sustain: authentic repetition over performative variety.🧭 3. Start Narrow, Then Go WideIf you’re multi-passionate (hi, ADHD friends 👋), this one hits home.Howie explained that most people try to start wide—they want to talk about all their passions at once. But the best brands? They start narrow.“Be known for one thing first,” he says. “Then you earn the right to expand.”He compared it to restaurants: if you walk into a place that serves sushi, tacos, burgers, and pizza… you walk out. Because it’s confusing.Narrowing your focus doesn’t mean you can’t evolve later—it just means you’re easier to find right now.🧠 4. Branding = Behavioral ScienceThis is where Howie gets nerdy in the best way.He draws from thinkers like Daniel Kahneman, Robert Cialdini, and Melina Palmer to explain why humans don’t make purely rational decisions.We buy, follow, and trust based on ease and emotion.* Ease: If something feels hard to understand, we skip it. (Cialdini calls this pre-suasion.)* Emotion: We decide first, then justify later. (Kahneman’s “System 1 thinking.”)* Exposure: The more people see you, the more they like you. (The mere exposure effect.)“Make it easy for people to believe in you.”That means clarity over cleverness. Fewer choices. Simpler copy. More consistency.📚Books, Ideas & Resources Mentioned🧠 Psychology, Behavior & Influence* Thinking, Fast and Slow — Daniel KahnemanThe foundation of behavioral science — referenced when Howie talks about how 95% of decisions are subconscious.📘 Amazon* Influence: The Psychology of Persuasion — Dr. Robert CialdiniCore to Howie’s worldview on ethical persuasion and reciprocity.📘 Amazon* Pre-Suasion: A Revolutionary Way to Influence and Persuade — Dr. Robert CialdiniHow what happens before the message shapes the outcome.📘 Amazon* The Paradox of Choice — Barry SchwartzFewer choices = less friction. Referenced when discussing “making it easy.”📘 Amazon* What Your Customer Wants and Can’t Tell You — Melina PalmerBehavioral science meets marketing — why ease, framing, and emotion drive conversion.📘 Amazon💡Branding, Marketing & Entrepreneurship* How Brands Grow — Byron SharpWhy availability often beats differentiation.📘 Amazon* Start With Why — Simon SinekThe importance of people, purpose, and trust in business.📘 Amazon* Building a StoryBrand — Donald Miller“You’re not the hero — you’re the guide.” Discussed when Jenna mentions the StoryBrand framework.📘 Amazon* Made to Stick — Chip Heath & Dan HeathHow to craft memorable, sticky brand ideas that people remember.📘 Amazon🎧 Podcasts & Audio Resources* 🎙 Influence Anyone — Host: Howie ChanApple Podcasts* 💬 “Godfather of Influence” ft. Dr. Robert CialdiniEthical persuasion, the Unity principle, and Pre-Suasion.Episode Link • Apple Podcasts* 🎯 “Influence With Ease: Humans Are Lazy” (Solo Sesh)Howie’s solo deep dive on “make it easy” and behavioral friction.Episode Link* 🧭 “Building a Professional Brand That Gets You Noticed” (Solo Sesh)3-step framework for your professional brand.Episode Link Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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Time Management for Multi-Passionate Entrepreneurs: How to Plan Your Week and Stick to It
Sep 3000:32:35Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Why I Brought Erica On the PodcastHere’s the truth: my hardest struggle as an entrepreneur isn’t ideas (I’ve got plenty). It’s time management—deciding what actually matters today, tracking how long things take, and sticking with it when my brain wants to do anything else.Most ADHD entrepreneurs I know feel the same. Big visions, tons of passions—but structuring time? That’s where everything unravels.So when I met time management coach Erica Dirkes at a networking event, I knew instantly: she had to come on the podcast. Because this is the conversation we’re all craving.Why Time Management Feels ImpossibleErica summed it up perfectly: you can do anything, but not everything. The challenge isn’t laziness—it’s how our brains work:* Time blindness: no sense of how long tasks actually take* Resistance: procrastinating until the task feels scarier than it is* Dopamine chasing: scrolling instead of focusing* Overwhelm: trying to juggle big dreams and small firesErica’s ADHD-Friendly FrameworkInstead of forcing rigid schedules, Erica helps clients build systems that match their wiring. Her process is simple but game-changing:* Start with values: what actually matters to you* Plan just one week: no massive life overhaul* Self-care first: anchor your week with energy-boosting habits* Brain dump everything: get tasks out of your head* Calendarize priorities: block time for the big stuff* Batch + buffer: group tasks, leave margin for surprisesIt’s not about squeezing in more—it’s about choosing better.Handling Big Goals (Without Burning Out)Writing a book while also needing income? You can’t give both full attention at once. Erica’s advice: prioritize the urgent seasonally. If revenue matters most now, schedule income-generating work during prime hours and tuck book time into smaller blocks. The order can shift later—but clarity helps now.Tools to Beat ResistanceProcrastination isn’t just annoying—it steals mental energy all week. Here are some hacks Erica and I love:* Scary Hour: dedicate one block to all those avoided 15-min tasks* Anchors/pacts: make distractions harder to access (hide apps, grayscale phone)* Timers/lockboxes: build friction for tech habits* Parkinson’s Law: give tasks a time limit—ship “good enough”* Reality checks: log how long tasks actually take for next timePlan Ahead, Not In the MomentIf you only plan in the moment, your primitive brain votes for comfort (scrolling, snacks, couch). Planning ahead engages your strategic brain. Erica suggests a Friday Power Hour:* Review what worked (and what didn’t) this week* Brain dump → categorize → calendarize for next week* Pick the top 3 must-dos per dayThen do quick daily check-ins (5–10 minutes). Adjust without overhauling.Letting Go to Gain TimeErica also recommends Drop the Ball by Tiffany Dufu—especially for women. You can’t delegate what you refuse to release. Start small: decide what only you should do, and outsource the rest.Final ThoughtADHD brains crave freedom—but freedom without structure turns into chaos. The good news? You have more control than you think. Plan one week at a time, choose the tasks that matter most, and set yourself up to follow through even when you don’t feel like it.Work with Ericka: mindfultimecoaching.com • erica@mindfultimecoaching.comWant more ADHD-friendly systems? Subscribe to my newsletter + grab my Notion planning template: https://notion.jennaredfield.com/life-tracker Thanks for reading The Optimization Toolbox by Jenna Redfield! This post is public so feel free to share it. Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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Inside Make with Notion 2025: My Ambassador Experience & Favorite Updates
Sep 2300:18:48Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Last week I packed my bags and flew out to San Francisco for Make with Notion 2025—a mix of community summit, product showcase, and the biggest gathering of Notion fans you could imagine. Over 1,700 people came together at Fort Mason (with the Golden Gate Bridge literally in the background) to celebrate how we’re all building with blocks.I went not just as a creator, but as a Notion Ambassador. That meant extra behind-the-scenes time at Notion HQ, a chance to connect with other Ambassadors from around the world, and a front-row seat to some of the biggest product updates since Notion AI first launched.To give you a real feel for the trip, I’m breaking this recap down day by day—so you can follow along with my journey, and I can drop in photos from each part of the experience.How I Became a Notion AmbassadorBefore we get into San Francisco, let me rewind a bit. I’ve been creating content since 2014, but it wasn’t until around 2020 that Notion really clicked for me. I had tried all the tools—Trello, Asana, ClickUp, Airtable—but none of them fully stuck. Then I started hearing about Notion from creators like August Bradley and Ali Abdaal, and I decided to give it a real shot.Once I did, everything changed. I began sharing tutorials, grew a Facebook group (which is now over 5,000 members!), built the ADHD Life Tracker, and eventually launched my Notion Foundations course. That momentum helped me apply and get accepted as a Notion Ambassador in 2022. Fast forward to today—and that’s what led me to Make with Notion 2025 in San Francisco.Day 1: Flying In + Ambassador DinnerI flew into San Francisco excited (and a little nervous). First stop was dinner with fellow Ambassadors—a mix of people I’d met online and brand-new faces. Afterwards, I stopped by a networking event and even got to take my very first ride in a Waymo self-driving car (so surreal). It felt like the perfect kickoff—techy, future-focused, and community-oriented.Day 2: Notion Ambassador Summit at HQThe next day was our Ambassador Summit, hosted right at Notion HQ. The space itself felt so “on brand”—minimal, warm, thoughtful. We got tours, insider sneak peeks, and time to connect with the team.This was also when I met so many creators I’ve admired for years. We swapped stories, compared workflows, and geeked out about systems (the kind of stuff only Notion nerds love).It honestly felt like a family reunion, even though many of us were meeting in person for the first time.Day 3: The Conference at Fort MasonThen came the big day: the Make with Notion conference itself, hosted at Fort Mason with over 1,700 people attending. The setting was gorgeous—right on the water, with seagulls flying overhead.The keynote walked us through the latest Notion updates, including:* Notion AI Agents — rebuilt to actually do things inside your workspace, not just generate text.* Database Column Permissions — finally, granular control so teammates (or clients) can’t accidentally break formulas or edit fields.* Consultant + Marketplace Updates — certifications through the Academy, and the Marketplace now includes consulting services.If you missed the conference and want to watch, go to https://makewithnotion.comThroughout the day, I attended sessions (all of which are available as replays if you missed them), built custom LEGOs (such a fun metaphor for Notion’s building blocks), and got to chat with consultants offering free office hours. We ended with a massive Ambassador photo and after-hours networking.Day 4: Sightseeing + CoworkingBefore heading home, I squeezed in a little sightseeing. I hopped on one of those double-decker bus tours and saw the Painted Ladies, the “Full House” house, and even crossed the Golden Gate Bridge with my new friend Steph from Spain. Definitely a bucket-list moment.We later caught up with those coworking at Notion HQ and wrapped the trip with a relaxed game night. It was the perfect balance of productivity + play before flying back to Minneapolis.Final ThoughtsMake with Notion wasn’t just about product updates—it was about community. Meeting other Ambassadors, seeing the scale of the conference, and getting to experience the culture at HQ made me even more excited about where Notion is headed.And as an ADHD entrepreneur, these updates mean more ways to keep my systems inside one tool instead of juggling a million apps. I’ll be diving deeper into Notion AI Agents in an upcoming post/video—because that’s the feature I think will change the most for creators like us.If you want to see more Notion tips, systems breakdowns, and behind-the-scenes recaps, subscribe here. You’ll also get access to my templates, workshops, and weekly YouTube videos.The Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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How to Build a Personal Brand AI Will Notice (and Humans Will Remember)
Sep 900:47:31Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.What happens when people stop Googling and start asking ChatGPT instead?In this week’s episode of The Optimization Toolbox, I sat down with AI trainer and personal branding queen Princess Paula to explore exactly that. We covered what it takes to stand out in today’s AI-driven world—where showing up online isn’t just about being searchable, it’s about being findable by both people and platforms.Whether you’re an ADHD entrepreneur, solopreneur, or creative professional trying to figure out how to get noticed, this conversation is your guide.In this episode/blog, we cover:* Why traditional SEO is dying and AEO (Answer Engine Optimization) is the future* How AI tools like ChatGPT "find" people and why conversational content matters* Real-life tips to get your name (literally!) to show up in AI searches* Why your Google Business Profile and social media matter more than your website* How to build a memorable personal brand using color, props, and even your name tag* The origin story behind "Princess Paula" and "Red Thread Studios"* Jenna's daily LinkedIn posting strategy & content capture tips* How to use ChatGPT to test style, branding, and clothing choices* Using color and body type analysis to craft your visual brand identity (Check out my episode on this)* How to repurpose personal passions (like saunas!) to create sticky brand associations* Why "universal advice" doesn’t work in marketing anymore* How to stop getting "should-ed on" and start trusting your gut* Substack as a multi-platform content hub and monetization tool (Check out more on Substack) The biggest takeaway? You are your brand. And in a world where AI is helping people choose what to click, buy, or watch, your brand needs to be both authentic and algorithm-friendly.If you want to show up in AI searches, you need to:* Speak conversationally online* Post consistently on smart platforms like LinkedIn* Make sure your digital footprint is updated and optimized* Share the things you're passionate about — even if they feel unrelated to your businessBecause in an AI-first world, the humans behind the brand matter more than ever.Follow Paula on Instagramhttps://www.instagram.com/princess_paula_consultingAnd LinkedIn https://www.linkedin.com/in/paulaskoviera🔗 Want to go deeper into the personal branding side of this convo and other marketing topics?Check out my sister Substack, Red Thread Report—it’s where I go deeper into storytelling, color analysis, name branding, and the psychology of being memorable online.A quick personal note to end the episode:I'm so excited that this is the direction my book is headed—all about branding, visibility, and how to thrive in this new AI-powered world. This topic lights me up, and I hope it got your wheels turning too.I also wanted to share a bit more about my business name: Red Thread Studios. It's a nod to the concept of finding your "red thread"—the unique through-line that ties everything together in your brand and business. And yes, it connects to my last name (Redfield), which makes it even more personal.I'm also heading to San Francisco next week for the Notion Conference, and I'm so pumped. Expect updates, behind-the-scenes peeks, and fresh ideas from that coming soon.If you have questions, thoughts, or just want to chat about your brand and visibility strategy—DM me or reply to this post. I'm always here for it.Thanks for being here. ❤️Thanks for reading The Optimization Toolbox by Jenna Redfield! This post is public so feel free to share it. Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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Why Attachment Styles Hit Different When You’re Neurodivergent
Aug 2600:35:51Tap to summarize✨ Big Update: I’m Splitting This Newsletter into TwoOver the past year, I’ve realized something important: my content actually lives in two different lanes.* Neurodivergence + Systems + Digital Organization → This is what The Optimization Toolbox will continue to focus on: ADHD, Notion, content systems, and the behind-the-scenes tools that help us get organized and stay consistent.* Marketing + Personal Branding + Video Strategy → This is the focus of my brand-new Substack: The Red Thread Report.You’re welcome to subscribe to one or both depending on what you’re most interested in:* 🧠 The Optimization Toolbox (this one) → Digital systems, Notion, ADHD-friendly tools* 🎥 The Red Thread Report → Marketing, video strategy, personal brandingI wanted to kick things off by sharing this update here so you know what’s changing — and what’s staying the same. The Optimization Toolbox will remain the place where I write and share podcasts about Notion, Neurodivergence, and building systems. But when I talk about video, messaging, or marketing strategy, that content will now live inside The Red Thread Report.The Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Most of the time, The Optimization Toolbox is where I share tools and systems for neurodivergence, Notion, digital organization, and creating structures that make life easier. That’s the heart of this newsletter — and it will stay that way moving forward.But every so often, I come across a topic that doesn’t fit neatly into productivity or organization — yet feels too important not to explore. Usually it’s because I go searching for answers myself and can’t find anything that goes deep enough.That’s exactly what happened with attachment styles.When I started digging into how attachment theory intersects with ADHD and autism, I couldn’t find much beyond surface-level psychology posts. Nothing that answered the questions I had as a neurodivergent person trying to make sense of my own patterns in relationships and self-esteem.So I decided to create the conversation I was looking for.This episode with Dr. Ellen Hansa is for anyone who’s ever wondered how being neurodivergent shapes their attachment style — and why relationships, belonging, and even self-compassion can feel so much more complicated than they “should.”Why This Conversation MattersWe live in a culture that loves quick-fix advice: “Set boundaries.” “Practice self-care.” “Communicate better.”But what happens when you’ve done all the things and you still end up in the same cycle — anxious when someone doesn’t text back, shutting down when things get too vulnerable, or people-pleasing your way into exhaustion?That’s where attachment styles matter. They help us see that these aren’t random bad habits. They’re predictable nervous system responses built over years of reinforcement.And when you layer on neurodivergence, it gets even more complicated:* Kids with ADHD are often criticized or labeled as “bad,” leading to anxious or avoidant attachment.* Autistic kids may grow up feeling othered, excluded, or misunderstood — which can mirror disorganized attachment dynamics.* Trauma can look like ADHD. ADHD can look like trauma. The overlap can be confusing unless you dig deeper.This isn’t about labeling yourself. It’s about having a framework for understanding why you might keep ending up in the same patterns.If you haven’t heard it yet, I actually recorded a full episode about my diagnosis journey — you can listen to it belowA Quick Walkthrough of the Four Attachment StylesBefore we dive deeper, it helps to understand the basics. Psychologists typically identify four main attachment styles — patterns that shape how we relate to others and ourselves:1. Secure AttachmentThis is the “gold standard.” People with secure attachment feel comfortable giving and receiving support. They can handle conflict without internalizing it as rejection. Secure attachment doesn’t mean being perfect — it means being resilient and able to bounce back when relationships hit bumps.2. Anxious AttachmentPeople with anxious attachment often fear abandonment. A late text reply can feel like rejection. They may people-please, overgive, or constantly seek reassurance. On the outside, they often look like high achievers — but underneath, they carry a deep fear of being left behind.3. Avoidant AttachmentAvoidant attachment looks like independence but often hides discomfort with vulnerability. These are the people who shut down or “ghost” when things get too close. It’s not that they don’t care — it’s that connection has historically felt unsafe, so pulling away feels protective.4. Disorganized AttachmentThe rarest but often the most difficult, disorganized attachment combines anxious and avoidant patterns. It’s the push-pull dynamic: “I want closeness, but I’m also terrified of it.” This often develops when caregivers were both a source of love and of fear, creating inner conflict.What Stood Out in This EpisodeHere are a few moments that stuck with me from my conversation with Dr. Hansa:* Attachment styles as survival strategies. What once helped you get love, safety, or protection as a child may be sabotaging you now.* Secure attachment isn’t about being less sensitive. It’s about finding people who can hold your intensity without making you feel wrong for it.* ADHD vs trauma. The two can look nearly identical on the surface — but trauma-based symptoms often improve when safety is restored, while ADHD is lifelong and consistent across contexts.* Proprioceptive interventions. Small daily movements (walking, weighted blankets, stretching) help regulate your nervous system so you don’t swing between overdrive and burnout.* Body doubling. Sometimes the best hack isn’t a productivity app — it’s another human being in the room.Why I’m Talking About This HereThe Optimization Toolbox isn’t just about apps, Notion dashboards, or time-blocking hacks. It’s about understanding the systems behind the systems.You can have the best task manager in the world, but if your nervous system is locked in an anxious or avoidant cycle, it’s going to bleed into your work, your relationships, and your self-worth.That’s why conversations like this matter. Because optimizing your life doesn’t start with a better calendar. It starts with understanding your wiring.And if you’re neurodivergent, it’s not about fixing yourself. It’s about giving yourself permission to see your patterns clearly — and learning the tools that actually work for your brain and body.Final ThoughtHere’s the truth: you’re not broken.Attachment styles aren’t flaws. They’re echoes of the strategies you once needed to survive. The work isn’t to erase them. It’s to recognize them, understand them, and slowly rewrite the story.That’s why I believe talking about attachment styles — especially at the intersection of ADHD and autism — is so important. Because once you see the pattern, you can finally begin to change it.👉 Listen to the full episode with Dr. Ellen Hansa above.🔗 Dr. Ellen Hansa Links* Private Practice: Priority Mental Health* Instagram: @DrEllenHansa🌍 Availability* In-person: Minneapolis, MN (central office)* Virtual & In-home therapy: Available throughout Minnesota* PsyPact License: Can provide testing and therapy virtually in 46 U.S. statesMake sure to check out my new Substack! https://redthreadstudio.substack.com Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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How to Overcome Fear and Self-Doubt to Create Real, Authentic Content with the C.A.N.D.I.D. Content Framework
Aug 1200:35:59Tap to summarizeThe Optimization Toolbox by Jenna Redfield is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Over the years of working with clients on their marketing and content, I’ve noticed a pattern: so many people have the same hang-ups when it comes to visibility. They want to grow their brand, they know they should be putting themselves out there — but fear, self-doubt, and a desire to “play it safe” get in the way.For me, visibility feels natural. I’ve been showing up online for years, experimenting with video, sharing stories, and making connections. But I’ve learned that for a lot of people, this is really hard.That’s why this conversation with Tami Enfield of Brand Yourself Consulting was so interesting to me. Tami approaches the challenge from the angle of authenticity — helping people show up in a way that feels real and human, instead of polished and performative.I wanted to bring our two perspectives together — visibility and authenticity — because when you combine them, you get content that not only reaches people but resonates.From StoryBrand to Candid ContentTami’s background includes certification in the popular StoryBrand framework, but over time, she shifted toward a more human-centered approach. She noticed that while frameworks like StoryBrand help clarify messaging, they don’t always address the creator’s experience making the content.Why So Many People Struggle to Show Up AuthenticallyFrom Tami’s work with clients, three big fears keep people from creating real, memorable content:* Fear of judgment – Worrying about how they’ll be perceived.* Thinking they have nothing interesting to say – Underestimating their own story.* Fear of seeming unprofessional – Especially when blending personal and professional topics.These fears lead to “safe” content — posts that check the box but don’t connect.Performative vs. Authentic ContentWe talked about “performative” posts — the kind that look polished but don’t show the real human behind them. Signs your content might be performative:* Only sharing highlight reels* Posting on certain causes just when it’s trending (and disappearing the rest of the year)* Avoiding any signs of struggleAuthentic content, on the other hand, can be imperfect, but it resonates because it’s real.Sharing from the Scar, Not the WoundOne of my favorite takeaways from Tami: share vulnerable stories from the scar, not the wound.* From the wound: You’re still raw, triggered, or processing.* From the scar: You’ve processed the experience and can focus on the lessons learned.This keeps your content from becoming “trauma dumping” while still allowing your audience to connect with your humanity.Why Not Everyone Should Like Your ContentIf you’re trying to make posts that everyone agrees with, you’ll water down your voice until it’s forgettable. As Tami said, “If nobody hates your content, you’re probably not saying much.”Leaning into your unique perspective and niche means some people will love you and others won’t — and that’s okay.The Candid Content FrameworkTami’s framework blends audience-focused and creator-focused content creation:Audience-Focused (CAN)* Connection – Align with your core values and show empathy.* Alignment – Make sure your content fits your brand values.* Narrative – Tell a story that connects.Creator-Focused (DID)* Daring – Push your comfort zone just a little.* Inspired – Post content you’re genuinely excited about.* Delighted – Share things that make you happy to hit publish.Links & Resources Mentioned* Brand Yourself Consulting* Tami on Instagram* Tami on LinkedIn* The Candid Content Revolution PodcastCheckout our first episode back in 2019 aboveReady to Show Up Authentically Yourself?If this conversation with Tami got you thinking about how you’re showing up online—and maybe realizing you’re ready to step into more visibility—that’s exactly the work I do with my clients.Through my Untangle Clarity Calls, we take all the ideas, content, and messaging that feel scattered and simplify them into a clear, actionable visibility plan. It’s about untangling the noise so you can focus on showing up in a way that feels like you.And if you want to create a lot of on-brand content in one go, my VIP Video Days are perfect for batch-filming high-quality videos in person, so you can show up consistently without the stress of figuring it out week to week.You can check out all the details and book your spot here: https://redthreadstudiomn.com/Thanks for reading The Optimization Toolbox by Jenna Redfield! This post is public so feel free to share it. Get full access to The Optimization Toolbox by Jenna Redfield at jennaredfield.substack.com/subscribe
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