For years, retirement is something you look forward toโ€”a reward for decades of hard work. But as the moment approaches, have you stopped to consider what it will ๐˜ข๐˜ค๐˜ต๐˜ถ๐˜ข๐˜ญ๐˜ญ๐˜บ ๐˜ง๐˜ฆ๐˜ฆ๐˜ญ ๐˜ญ๐˜ช๐˜ฌ๐˜ฆ when the structure of work disappears?

I retired two and a half years ago, after three decades as a teacher. I was fortunateโ€”I had already been growing my coaching and training business, which helped me see myself as more than just โ€œRob the teacher.โ€ But even then, there were adjustments.

The first few months? They felt like a vacation. No schedule, no routine, just time. And while that was refreshing at first, I soon realized that without a clear sense of routine, time could easily slip away.

Thatโ€™s when I made some key shifts:

  • I joined a monthly literary group and started volunteeringโ€”meeting new people, giving back, and staying connected.
  • I designed a daily schedule that included fitness, learning, business, family, and even household tasksโ€”because structure matters.
  • I used my coaching background to reframe any fears or limiting beliefs before they took root.


Iโ€™ve seen time and again–that many new retirees struggle with:

  • ๐—Ÿ๐—ผ๐˜€๐˜€ ๐—ผ๐—ณ ๐—œ๐—ฑ๐—ฒ๐—ป๐˜๐—ถ๐˜๐˜† & ๐—ฃ๐˜‚๐—ฟ๐—ฝ๐—ผ๐˜€๐—ฒ โ€“ Who am I without my job title?
  • ๐—Ÿ๐—ฎ๐—ฐ๐—ธ ๐—ผ๐—ณ ๐—ฆ๐˜๐—ฟ๐˜‚๐—ฐ๐˜๐˜‚๐—ฟ๐—ฒ & ๐—ฅ๐—ผ๐˜‚๐˜๐—ถ๐—ป๐—ฒ โ€“ How will I create meaningful days?
  • ๐—ฆ๐—ผ๐—ฐ๐—ถ๐—ฎ๐—น ๐—œ๐˜€๐—ผ๐—น๐—ฎ๐˜๐—ถ๐—ผ๐—ป โ€“ Where will I find connection and belonging?
  • ๐—™๐—ฒ๐—ฎ๐—ฟ ๐—ผ๐—ณ ๐—–๐—ต๐—ฎ๐—ป๐—ด๐—ฒ โ€“ Am I ready for the unknown?
  • ๐—จ๐—ป๐—ฟ๐—ฒ๐—ฎ๐—น๐—ถ๐˜€๐˜๐—ถ๐—ฐ ๐—˜๐˜…๐—ฝ๐—ฒ๐—ฐ๐˜๐—ฎ๐˜๐—ถ๐—ผ๐—ป๐˜€ โ€“ Is my vision of retirement aligned with reality?


Retirement is a huge life transitionโ€”one that deserves as much ๐˜ฑ๐˜ฆ๐˜ณ๐˜ด๐˜ฐ๐˜ฏ๐˜ข๐˜ญ ๐˜ฑ๐˜ญ๐˜ข๐˜ฏ๐˜ฏ๐˜ช๐˜ฏ๐˜จ as financial planning.

Wondering how prepared you really are? I put together a simple Retirement Readiness Scorecardโ€”a short (16-question) self-assessment to help you reflect on these key areas. It might just give you the insight you need.ย 

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