Have you ever sat in a room, completely exhausted, pretending to be “on” because that is what everyone expects from you? As an introvert with ADHD, I know that feeling all too well. We push ourselves to perform, to make eye contact, and to smile until our social battery hits zero. But what happens when we stop pretending?

In this episode, I sit down with my friend Chester Gregory. You might know him as a Broadway legend who originated the role of Sweaty Eddie in Sister Act: The Musical and played Berry Gordy in Motown. Today, we are talking about the man behind the curtain. Chester recently opened up about his late adult ADHD diagnosis, dyslexia, and navigating profound grief while in the public eye.

Before we get into the conversation, I want to thank our sponsor for this season, Sucreabeille. They collaborated with me to create a custom fragrance called “Why Did I Walk Into This Room”. With notes of cherry pie, cinnamon, and acceptance, it is a gender-neutral love letter to the ADHD community. Check them out at https://sucreabeille.com/.

Masking ADHD on Broadway

Chester spent years in an industry that demands high energy. Looking back through his new ADHD lens, he realized how much of his life was spent masking to fit into a neurotypical world.

For example, Chester explains that he listens best by folding his arms or looking away. To the rest of the world, this looks like he is tuning out. He spent years forcing eye contact and nodding to perform active listening. According to ADDitude Magazine, ADHD masking involves intentionally shifting your behavior to hide your differences, which causes extreme exhaustion and burnout.

  • Chester told me:

“I’m not performing to show you that I’m listening. I’m taking the information in on a much deeper level now.”

The Truth About High Functioning Burnout

We hear the phrase “high functioning” all the time. But let us be honest: it usually means you are suffering quietly so you do not inconvenience anyone else.

  • Chester’s definition hits hard:

“High functioning for me is me not taking the time that I need to rest.”

Chester admitted that ignoring his limits led to his body shutting down. We have to intentionally slow down before our bodies force us to.

The Difference Between Grief and Mourning

Chester experienced deep personal loss while still having to show up publicly. He shared a profound lesson about navigating this heavy season.

  • He learned a vital distinction:

“I started to learn the difference between grief and mourning.”

This aligns with the American Psychological Association, which defines grief as the internal anguish experienced after a loss, whereas mourning is the outward, active expression of that sorrow. By separating the two, Chester found a way to process his pain privately while managing his public presence.

Building The Cypher and Honoring Your Moon Phase

Instead of getting trapped in a cycle of executive dysfunction, Chester built a wellness community called The Cypher to help adults find alignment and self reflection. He encourages people to stop asking what is wrong with them.

  • He poses a different question entirely:

“What is this season asking of me?”

He refers to times of isolation and deep reflection as a “Moon Phase”. Rather than fighting it, we should honor it, take a step back, and sit with our feelings.

    Guest Resources

    People Also Ask

    Q: What does ADHD masking look like in adults? A: Masking involves hiding neurodivergent traits to appear neurotypical. This includes forcing eye contact, suppressing the need to fidget, or pretending to pay attention when overwhelmed. It is an exhausting survival strategy that leads straight to burnout.

    Q: How do you cope with grieving while working? A: Grieving while maintaining a job requires separating your internal feelings from your outward mourning. It is vital to set boundaries, ask for accommodations, and find safe spaces to process your emotions without the pressure of performing for others.

    Actionable Conclusion

    Try This: The next time you feel overwhelmed by executive dysfunction or burnout, pause and reframe your thoughts. Stop asking what is broken. Ask yourself what this season requires of you. Give yourself permission to rest.

    Disclaimer: I am not a licensed mental health professional. I am a guy sharing my story. Please seek professional help if you are struggling.

    Much love. Good vibes. – Ky