Shrinking the Goal to Find the Win with Sharon Pope

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Feb 9, 2026

Sharon Pope, certified habit coach and CEO of Shelpful who builds AI accountability tools for neurodivergent brains. They talk about using AI as a second brain, conversational nudges that beat notification fatigue, and sorting tasks by energy level with Shelfful’s Magic Sort. Also covered: tiny, win-focused goals, automations like NFC and location triggers, and gamifying habit support.

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ADVICE

Shrink Goals To Guarantee Wins

Start with tiny, specific goals instead of giant, vague ones to build consistent wins.
Celebrate micro-successes to strengthen neural pathways and make habits stick.

ANECDOTE

Founder’s Origin: From Human Check‑Ins To AI

Sharon built Shelpful after struggling with basic self-care despite professional success.
The service started as human text check-ins and evolved into an AI accountability app.

INSIGHT

AI As A Conversational Second Brain

AI can act as a low-stakes conversational second brain rather than just a static to-do list.
Novelty and personality in prompts break through notification immunity and increase engagement.

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Hey Team!

Today I'm talking with Sharon Pope, a certified habit coach and the CEO of Shelpful. Sharon has an extensive background in the tech world, having served as a CMO for multiple companies and as an advisor for the startup accelerator Y Combinator. After her own ADHD diagnosis, she pivoted her career to focus on building tools that help neurodivergent brains get more done.

Sharon also runs the ADHD Founders Podcast with Jesse J. Anderson and Marie Ng, where they talk about the unique challenges of having ADHD and building a business.

I actually had Sharon on the show a number of years ago and thought it would be fun to have her on again after running into her at the 2025 ADHD Conference. And one of the big changes that has happened at her company. Shelpful, since we last talked, is the shift to using AI, so we spend a good portion of this episode discussing how to use AI as a "second brain" rather than just another static to-do list. Sharon explains how they've integrated personality and novelty into their system to break through our natural notification immunity. We also explore some of her favorite "Magic Sort" features that help you pick tasks based on your current energy level rather than just due dates, because we all know that looking at a massive, unsorted list is a one-way ticket to Task Paralysis.

But we are also talking about accountability, automation, and how to gamify our habits. I had a lot of fun with this one.

If you'd life to follow along on the show notes page you can find that at HackingYourADHD.com/271

YouTube: https://tinyurl.com/y835cnrk

Patreon: https://www.patreon.com/HackingYourADHD

This Episode's Top Tips

1. Try sorting your to-do list by energy level. Instead of looking at a stressful, long list, you can sort your tasks by "vibe" or energy (low, medium, high) to find a task that matches your current capacity.
2. When we're setting goals, we want to intentionally lower the bar to ensure a win and strengthen neural pathways. Often our inclination is to overdo whatever it is we're trying to do in an effort to catch up, but by lowering the bar instead, we can often create more sustainable habits.
3. A fun way to get into automation can be to try out cheap NFC stickers around your house to trigger specific automations, like reminders to move the laundry or start a playlist, with a single tap of your phone.