Oct 7, 2026

The first six months of retirement may be the easy part.

At first, there may be travel, projects, and long-awaited plans to fill the time. But once the dust settles, retirement can begin to feel very different.

Psychotherapist Austin Dowling joins me again on Chapter X to talk about what can surface after the initial transition. We explore loneliness, identity, self-reliance, and the challenge of adjusting habits that may have served us well throughout our careers.

We covered:

• Why loneliness often appears after the first few months of retirement 
• How senior roles can make relationships feel increasingly transactional 
• Why successful people may struggle to ask for help 
• How over-scheduling can become another way to avoid discomfort 
• How to adapt your career strengths instead of leaving them behind

Resources

Website: www.insighstudiotherapy.com
Email: austindowlingpsychotherapy@gmail.com
Phone: 347-454-2799

About Austin:
Austin Dowling is a New York-based psychotherapist and executive coach who helps professionals navigate career and personal roadblocks, anxiety, and lack of motivation. Originally from Ireland, he previously worked as a corporate attorney in Australia and China and held senior executive roles, including Global Head of Talent for an international investment bank.