Why Your Team Hates New Softwares (And What to Do About It)

You know what needs doing. You have the ideas. So why is actually finishing the thing so hard?Jason Chatfield has written and drawn the syndicated comic strip Ginger Meggs for sixteen years, writes for The New Yorker, and built a career across cartooning, comedy, and writing. But he learned he cannot rely on his brain to generate ideas and execute them at the same time.Instead, Jason built physical systems that separate thinking from doing: external deadlines, index cards, a wall calendar, batching, and pairing difficult tasks with things he actually enjoys.In this episode, Jason breaks down the practical systems he uses to turn ideas into finished work without relying on willpower.What We Cover:Why Jason stopped planning and executing in the same blockThe index card system that makes finished work visibleHow external deadlines give his ADHD brain structureWhy his wall calendar beats another productivity appHow he pairs difficult tasks with things he enjoysThe first-thing, last-thing routine that separates planning from doingWhy it took three ADHD diagnoses before he believed itConnect With Jason Chatfieldhttps://www.jasonchatfield.com/https://www.instagram.com/newyorkcartoons/P.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

You built the business because you were good at the work. Nobody warned you that promoting it might be harder than doing it.New research on neurodivergent entrepreneurs found that maintaining a social media profile was the most commonly reported self-employment challenge. Ahead of work-life balance, unpredictability, and financial pressures.In this episode, Skye and Robert unpack why social media has become such a difficult part of running a business, what else neurodivergent entrepreneurs say they struggle with, and the support and habits they find most helpful.What We Cover:Why maintaining a social media profile topped the list of challengesHow work-life balance, unpredictability, and marketing comparedWhy peer support, professional networks, and mentorship matterWhat entrepreneurs said helped their wellbeing, from movement and sleep to boundariesP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

Carlos Gutierrez spent 25 years rising from sales representative to CEO of Kellogg, then served as U.S. Commerce Secretary. He did it all without knowing he had ADHD.When he was diagnosed later in life, Carlos began looking back at his career differently. The disorganization, procrastination and impulsivity he had treated as personal flaws finally had a name. So did some of the traits that helped him succeed, including intense hyperfocus, intuition and an ability to connect with people.In this conversation, Carlos and Skye unpack the role ADHD played at the highest levels of his career, from the projects he could not stop thinking about to the support that helped him perform at his best. They also talk honestly about the cost of that drive, particularly the work that followed him home and the family time he lost along the way.It is a fascinating look at what ADHD can actually look like at the top, and what Carlos understands about himself now that he wishes he had known earlier.What We CoverWhy Carlos saw his ADHD traits as personal flaws for decadesHow hyperfocus became one of his biggest career advantagesWhy the right support and structure changed how he performedThe impact his intense focus on work had on his family lifeHow ADHD shaped his intuition, empathy and leadership styleWhat changed when Carlos finally learned he had ADHDP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

Waking up exhausted after eight hours of sleep isn't just bad luck. In this Research Recap, Skye and Will break down a meta-analysis on hay fever and ADHD, including the finding that people with allergies are significantly more likely to also meet the criteria for ADHD. They talk through how swollen sinuses can disrupt sleep, how that can show up as brain fog and forgetfulness, and why the researchers still can't say which condition comes first. Want more of Will's work? Visit HackingYourADHD.com or subscribe on YouTube.What We Cover:The 1.83x risk finding from 18 studies covering 4.2 million peopleWhy poor sleep from allergies can look a lot like ADHD symptomsThe inflammation theory behind the connectionWhy correlation isn't causation, and why the finding still mattersWhat researchers still don't know about the ADHD–allergy linkWant more of Will's work? Visit HackingYourADHD.com or subscribe on YouTube.P.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

You hit a growth ceiling and your first instinct is to change what you're doing, not fix how you're doing it.Matt Verlaque has coached founders past a million in revenue and sees the same pattern over and over: something works, the novelty wears off, growth stalls, and suddenly a new marketing channel, AI tool, or strategy looks like the answer.Matt and Skye unpack the “pivot chaser” trap, how to tell when a strategy is genuinely broken versus when you've simply gotten bored of executing it. They also dig into AI mania, the dopamine hit of learning and building new things, and why constantly chasing the next skill can quietly keep you from scaling.Because as Matt puts it: “Beginners don't scale companies.”What We CoverHow to tell whether you have a strategy problem or an execution problemWhy ADHD founders abandon the thing that was actually driving their growthWhy skill acquisition feels productive even when it stalls your companyThe difference between “can I build this?” and “should I build this?”Why constantly chasing novelty keeps you a beginnerConnect With Matt Verlaquehttps://mattverlaque.com/Instagram: @mattverlaqueP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

Tom Reber built successful businesses while privately believing he wasn't smart enough to fight for his own ideas. That belief followed him from childhood special ed into business ownership, where he went bankrupt once and later sold another business for far less than he believed it was worth.Tom, founder of The Contractor Fight and a former Marine, explains where that belief came from, how it affected the decisions he made, and what changed when he finally stopped confusing not knowing something with being stupid.What We Cover:Why Tom stopped fighting for decisions he knew were rightHow childhood special ed shaped his self-image for decadesThe conversation with his mom that changed how he understood his pastThe bankruptcy and business buyout he connects to that beliefHow he learned to trust his own judgment againWhy he now sees his ADHD focus as an advantageWhat "strong you, strong home, strong business" means in practiceConnect With Tom Reberhttps://thecontractorfight.com/https://www.instagram.com/fightwithtom/?hl=enP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

You spent real money on a system nobody uses.Skye and Robert Waterson see this problem regularly working as fractional COOs with ADHD business owners. The owner gets excited about a new system, the team agrees to the change, and a few weeks later everyone quietly slips back into the old way of doing things.The problem usually isn’t the software. It’s how the change was handled.In this episode, Skye and Robert break down the six phases they use to move a team onto better systems without losing people halfway through. It starts with getting genuine buy-in before anything gets built, then prototyping the process, slowing down the rollout, and documenting it once it actually works.What We Cover:Why telling your team to “just use it” creates quiet noncomplianceWhy previous failed software changes make teams reluctant to try againGetting real buy-in before building the new systemWhy a rough prototype can beat an expensive polished platformHow ADHD founders can move faster than their team can realistically followKnowing when to stop adding features and let the new process settleWhy documentation matters once the system is actually workingIf you run a business with ADHD and keep finding yourself at the centre of the systems, decisions, and implementation, this one will probably feel familiar.P.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

Most people don't struggle to put themselves out there because they lack ideas. They struggle because they're afraid of what people will think once they see the real version of them.So they post the safe version instead. The version nobody remembers.Chris Do, Emmy-winning designer and founder of The Futur, has spent more than 20 years helping creatives build businesses by becoming more visible. He believes a brand people care about isn't built on sharper positioning. It's built on being willing to be seen. That means getting comfortable with the parts of yourself you've been editing out.He explains why fear of judgment (not a lack of confidence) is what keeps people editing, how radical self-acceptance changes what you're willing to say publicly, and the simple exercise he uses to help people work through it.If you're a creator, founder, or anyone building in public who has overthought a post, softened an opinion, or caught yourself over-explaining, this episode gives you a practical place to start.What We CoverWhy fear of judgment, not low confidence, is what keeps your work genericHow hidden fear leaks out as over-explaining and nervous energyChris's radical self-acceptance exercise, step by stepWhy confidence is built through exposure, not positive thinkingWhat changes in how people respond once you let yourself be seen accuratelyListen to the full conversation, then try Chris's exercise and tell me what came up in the comments.Connect With Chris DoInstagram @thechrisdoYouTube @ChrisDo/@thefuturP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

Most ADHD interventions only work if you actually stick with them. So what happens when the intervention is something your brain actually wants to do?Skye joins Will to unpack a systematic review of 22 studies on virtual reality interventions for ADHD. They look at surprisingly high adherence rates, what the research suggests about attention and working memory, and whether improvements inside VR actually carry over into everyday life.They also dig into the different ways VR is being used, from cognitive games and movement-based training to simulated real-world scenarios, plus where the evidence is still too thin to draw firm conclusions.Want more of Will's work? Visit HackingYourADHD.com or subscribe on YouTube.What We Cover:Why adherence rates of 85 percent or higher caught their attentionThree different ways researchers are using VR for ADHDWhat the studies suggest about attention and working memoryWhy VR is being studied alongside existing ADHD treatmentsThe big question of whether improvements transfer to real lifeReported side effects and the limitations of the current researchP.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407

You’re guessing how long things take.That guess feels reasonable.It’s just wrong, over and over again.In the last episode, we broke down why ADHD time blindness happens. This one is about what to do about it.Because the real problem isn’t planning. It’s relying on estimation at all.In this episode, Skye and Robert walk through how to replace your internal clock with systems that actually hold up in real work:why you can’t “get better” at estimating timehow to use past projects instead of guessinghow teams quietly adjust for you (and why that creates tension)why buffers and “extra time” don’t workhow to build timelines that don’t collapse halfway throughIf you’re tired of missing deadlines you genuinely thought were realistic, this will show you what’s actually going wrong, and what works instead.P.S. If you’re a founder who’s tired of the mad scramble of disorganized systems and stressful HR, and you want a business that feels as easy as plugging your headphones into an iPod shuffle, I’ve got something for you.Want to grow your business? My Focused Balanced Growth Program has everything you need to build consistent ADHD-friendly routines and processes to grow. Click here to learn more.https://www.unconventionalorganisation.com/clear-balanced-daysLooking for a coach who's also an operator who'll turn your business into a finely-tuned profit and peace machine designed for your brain? I work with one company a month as a fractional consultant and COO, learning about your business and implementing systems that allow both trust & transparency with your team. Click here to book a call and discuss.https://unconventionalorganisation.as.me/schedule/1153d1ef/appointment/71643407/calendar/7186455?appointmentTypeIds[]=71643407