Theodore Roosevelt
Adventure Leader
adventure"Do what you can, with what you have, where you are"
This is Chris, 28, software engineer. He's been texting Theodore for 16 days.
What Theodore remembers
- Wants to quit his job and freelance
- Has been 'thinking about it' for 8 months
- Savings can cover 6 months of expenses
- Best friend Jake went freelance last year successfully
Patterns noticed
- Researches freelancing for hours but never contacts potential clients
- Analysis paralysis hits hardest on Sunday nights
Active reminders
- 7:00 AM The man in the arena
- 6:00 PM What bold thing did you do today?
Text Theodore yourself
Pick your platform. Theodore texts first.
Free trial, then $25/mo
How it works
Text Theodore
Send a message on Signal, Telegram, or iMessage. No app to download.
Theodore learns about you
Your goals, struggles, and patterns. The more you talk, the more useful Theodore gets.
Theodore texts you first
Morning check-ins. Pattern callouts. Accountability when you need it — not when you remember to ask.
About Theodore
The president who charged up San Juan Hill helps you embrace the strenuous life, take bold action, and live fully.
Style: Direct, energetic, and passionate—speaking in declarative statements with vivid imagery, challengingly inspirational, using metaphors from nature, combat, and athletics.
Theodore's philosophy
The strenuous life of action, effort, and courage defines character. Inaction is the greatest sin, and failure while daring greatly is far nobler than living safely. Moral integrity matters above success, and nothing worth having comes without effort, pain, and difficulty.
It is not the critic who counts; not the man who points out how the strong man stumbles. The credit belongs to the man who is actually in the arena.
Do what you can, with what you have, where you are.
Far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure, than to rank with those poor spirits who neither enjoy nor suffer much.
What Theodore tracks
- Action vs. hesitation—how quickly you move from decision to action
- Effort quality—giving full effort or coasting
- Response to failure—quitting or learning and trying again
- Moral consistency—living up to stated ideals
- Courage moments—facing fear and acting anyway