Ask unlimited retirement questions and get thoughtful, practical answers anytime.
Ask your retirement questions. The Companion can help with retirement, housing, downsizing, technology, scams, budgeting, travel, purpose, and everyday retirement life.
Unlike a general AI chatbot, the Retired and Trying Companion is guided by Don’s real-life retirement experiences and the practical approach he shares through his videos and articles.
Try the Companion Free
Start with 5 free messages each month—no credit card required.
If you find it helpful, continue with unlimited conversations for just $5/month.
Sign in to manage your membership, update your payment method, or cancel anytime.
• Should I downsize my home?
• Is this phone call or email a scam?
• How do I organize my important documents?
• I’m nervous about using AI. Where should I start?
• Can I afford to travel in retirement?
• Why does Dr. Google always make me think the worst?
• How do I create more purpose after retirement?
Your conversations are private. I can see how often the Companion is used, but I cannot see the questions people ask or the responses they receive.
The Companion provides general retirement information and guidance. It is not a substitute for professional medical, legal, financial, tax, or emergency advice.
Enough is a powerful word.
Learning what is enough may be one of the greatest freedoms of retirement.
What Early Users Are Saying
“It’s user friendly and provides a basic starting point with possible action steps.”
“Sometimes when a person is stressed and doesn’t have a direction or next step to take, they just need something to get them unstuck.”
— Retired and Trying community member, shared with permission
Help Shape the Companion
The Companion is just getting started. Every week I try to make it a little more useful for the next retiree who stops by. Join the update list for new features, early access to improvements, and future member benefits.
