Hullo

Welcome to Dear Sam: Advice on Retiring Early, a newsletter for anyone curious about what happens after you close the work chapter of your life and step into something new.

I’m Trent, and I retired early at 43 after building and selling two businesses. What I didn’t anticipate was how complex life after work could be—losing routine, identity, and connection while searching for meaning. This newsletter is my honest, personal exploration of the challenges, joys, and possibilities of early retirement.

Each week, I’ll share practical advice, personal stories, and reflections on topics like redefining identity, building meaningful routines, maintaining health and relationships, and rediscovering purpose. Whether you’re considering retiring early, already there, or just curious, you’ll find ideas, inspiration, and a sense of community here.

Here are a few posts to get you started and set the scene:

• “What do you say when people ask, ‘What do you do?’”

• First, Some Context

• Early Retirement Is Harder Than It Looks

Join me as we figure this stuff out together. Early retirement isn’t the end of the story—it’s the start of a new adventure.

New posts drop every week, at least to begin with, so subscribe to follow along.