Podcast Summary: Hacking Your ADHD

Episode: Shrinking the Goal to Find the Win with Sharon Pope
Host: William Curb
Guest: Sharon Pope, Certified Habit Coach & CEO of Shelpful
Date: February 9, 2026

Overview

In this episode, William Curb welcomes back Sharon Pope, CEO of Shelpful and co-host of the ADHD Founders podcast, to discuss building systems, particularly AI-based tools, that help people with ADHD achieve their goals. The conversation focuses on using AI as a supportive “second brain,” the importance of shrinking goals to achievable micro-habits, and creative accountability strategies. Sharon shares her journey founding Shelpful, shifting from human-based support to an AI-driven accountability platform, and offers practical advice for managing ADHD with tech—including gamification, automation, and celebrating small wins.

Key Discussion Points & Insights

Sharon’s ADHD Journey and the Genesis of Shelpful

• Origin Story: Sharon created Shelpful out of a desire for a persistent, supportive presence to help manage daily self-care tasks (e.g., drinking water, getting fresh air).
  • “I just wish I could have something, someone sitting on my shoulder just reminding me to take care of myself.” – Sharon (03:25)
• Transition from Humans to AI: Shelpful began with “Shelpers”—actual humans serving as accountability partners via text. Over time (and due to cost/scale), it evolved into an affordable, AI-driven mobile app.
  • “We now have...an AI accountability system. Basically it’s an AI task manager and you chat with it throughout the day.” – Sharon (05:15)

How Shelpful’s AI Helps with ADHD

• Beyond Simple Reminders: The AI employs conversational nudges—sometimes with custom personalities (e.g., “drill sergeant” or “Chandler Bing”)—to break “notification immunity.”
  • “My eyes are immune to reminders oftentimes...it’s in a conversation. Like, it doesn’t feel like...just a notification.” – Sharon (07:00)
• Personalization for Dopamine & Accountability: Users can set the AI to interact in novel or playful ways, which increases engagement. Sharon mentions setting the AI to be sassy and even swear, which makes her smile and increases her likelihood of following through.
  • “When I get like a ‘hey, have you washed your bleeping face yet, Sharon?’ It makes me smile.” – Sharon (06:50)
• Energy-based Task Sorting: Favorite feature—‘magic sort’—lets users filter to-dos by current energy level instead of just due date, reducing overwhelm and task paralysis.
  • “You can pick a different way to view your list...like by location...or by vibe. By energy level is probably my favorite.” – Sharon (33:13)

On Goal Setting: The Power of Shrinking Goals

• Small Wins Build Momentum: Sharon and William emphasize the importance of intentionally lowering the bar (tiny, achievable steps) to ensure success and build positive neural pathways.
  • “The people...feeling success from the product are the ones who are allowing themselves to think small and then they’re able to have more successes.” – Sharon (25:45)
• Research Backing: Sharon cites BJ Fogg’s behavioral research: “If you can set a smaller goal, it’s always a better idea...with no exceptions.” – Sharon (27:54)
• Celebration as Reinforcement: Even small acts (“walk three steps outside”) get rewarded by the AI with celebratory messages. Acknowledgment and self-validation strengthen the habit loop.
  • “Just saying that to yourself...I didn’t think I was gonna do this, but I did it. That’s a celebration.” – Sharon (31:33)

Accountability: Human vs. AI

• AI Can’t Fully Replace Human Accountability: The emotional weight of letting down a machine isn’t equivalent to letting down a person. But AI can still nudge users, offer creative responses, and inject novelty/dopamine to overcome ADHD paralysis.
  • “You don’t feel true human-style accountability to an AI. I don’t think that’s possible...But I do think there’s a flavor of accountability that comes through that’s more than a to-do list.” – Sharon (18:10)
• Creative Use of Oppositional Defiance: Sometimes, disagreeing with the AI’s suggestions (“No, I don’t want to do that!”) helps users clarify their priorities and get motivated.
  • “Even just like disagreeing with it can be helpful in me getting clarity on what I should work on.” – Sharon (34:12)

Dealing with Negative Self-Talk and Shame

• AI as a Safe Space: The conversational, non-judgmental nature of the AI chat makes it safe to admit struggles (“I just don’t feel like paying my taxes today”). The AI meets users where they’re at without toxic positivity.
  • “It really is meeting you where you’re at...could you just try this? Like, it’s not gonna be fun, but could you just do a little?” – Sharon (11:00)
• Breaking Shame Loops: Open acknowledgment and celebration of small, “embarrassing” chores (one dish, basic hygiene) help challenge stigma and reinforce healthy habits.

Best Practices for Making the Most of AI Tools

• Shrink the Goal: Always start smaller than you think necessary (“three steps outside” instead of a one-hour walk).
• Customize and Gamify: Use features like custom personalities, playful celebrations, or real-life gamification tricks (e.g., clicking a tally counter, using sound effects) to make checking off tasks more rewarding.
  • “You can just do that for like, I answered an email...it feels good to click something or cross something off or push a button.” – William (32:15)
• Automation and Integrations: Shelpful connects with Apple’s Shortcuts app—users can trigger reminders based on context (like connecting to Wi-Fi, arriving home), or automate reminders using cheap NFC tags.
  • “Once I arrive home, it will ping my AI task manager saying, hey, I just got home, check in with me in 10 minutes to see if I have water at my desk.” – Sharon (35:56)

Navigating AI Limitations

• AI Hallucination: The team is aware that AI sometimes “makes up” answers or misinterprets intent (e.g., duplicating tasks). Sharon recommends always double-checking outputs, just like you would with an intern.
  • “I always like to compare using chatGPT to having like an intern who’s really green...you’d probably check some of their research!” – Sharon (17:15)
• AI and Mental Health: Shelpful is not a therapy or companionship service. The team monitors for unhealthy use and emphasizes that it’s a productivity/support tool, not a human relationship substitute.

Notable Quotes & Fun Moments

• On Notification Immunity:
  “My eyes are immune to reminders oftentimes...notification sounds for people with ADHD is very...easy to ignore them.”
  — Sharon (06:50)

• On Custom AI Personalities:
  “I tell it to swear at me because I think it’s fun. Like when I get like, ‘hey, have you washed your bleeping face yet, Sharon?’ It makes me smile.”
  — Sharon (06:54)

• On Small Wins:
  “Washing one dish is a huge freaking accomplishment. I spent a lot of my life hiding that...To have a bare minimum goal and hit that goal...is an amazing feeling.”
  — Sharon (26:00)

• On Accountability:
  “You don’t feel true human-style accountability to an AI...But there’s a flavor of accountability that comes through that’s more than a to-do list...it can give you a little spike of dopamine.”
  — Sharon (18:10)

• On Oppositional Defiance:
  “My AI will say...‘why don’t you do the product plan?’ and in my head I’m like, ‘no, that’s not what I should do!’...Even just disagreeing with it can be helpful.”
  — Sharon (34:12)

• On Task Initiation:
  “My AI says...‘what do you think about opening the browser? Like, just go to the URL, flipping it off and walking away.’ And I’m like, well, I could maybe do that.”
  — Sharon (11:00)

Timestamps for Key Segments

• [03:25] Sharon describes the origin of Shelpful and her ADHD “micro-care” insight.
• [06:50] On AI nudges, customizable personalities, and notification immunity.
• [10:20] Addressing the ADHD financial “tax” and lowering Shelpful’s costs with pay-what-you-can pricing.
• [11:00] Tackling negative self-talk and the importance of a supportive accountability framework.
• [13:05] How Shelpful’s AI keeps errors low, and advice on checking AI outputs.
• [17:15] Comparing AI to a “really green intern” and the importance of fact-checking.
• [18:10] Human vs. AI accountability and motivating users with novelty.
• [25:09] The best practice: Shrink your goals to guarantee wins and satisfaction.
• [27:54] Citing behavioral science—“smaller is better.”
• [33:13] Introduction of energy-based task sorting (‘magic sort’) for lists.
• [35:56] Using automation and Shortcuts app to drive context-aware reminders.

Final Takeaways

• Shrinking goals and celebrating micro-wins are crucial for building habits and combating ADHD paralysis.
• AI tools, when custom-tailored and gamified, can help “break through” the typical resistance and notification fatigue experienced by people with ADHD.
• Automation and contextual cues (via shortcuts, location, NFC tags) can free up mental energy and reduce the shame/overwhelm cycle.
• Accountability from AI isn’t a true substitute for human accountability, but it offers a novel layer of support, especially when invested with humor and personality.
• Shelpful is committed to affordability, accessibility, and user feedback, recognizing the unique challenges of ADHDers.

Resources & Links

• Shelpful – Sharon’s AI accountability platform
• Hacking Your ADHD Show Notes – Ep. 271
• BJ Fogg, Tiny Habits Method (Referenced in episode)

For further engagement, check show notes, the Hacking Your ADHD newsletter, and the ADHD Founders podcast.