The Former-Self Letter
Use distance from your younger self to uncover advice you need today.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 6
- Confidence
- 96%
Choose a specific former version of yourself and write from the perspective of your present life. Begin with what that younger person currently believes, fears, or expects, then recount the major setbacks, choices, relationships, and unexpected opportunities that followed. Rather than optimizing the past or listing everything that should have been done differently, identify how difficult events contributed to the life you now value. End with the reassurance and guidance that younger self most needed. The psychological distance created by addressing another version of yourself can bypass Solomon's paradox: advice becomes easier to articulate because the recipient feels separate. Finally, reread the letter as a message to your present self, looking for guidance that remains relevant now.
Origin
Jasmine Star completed this exercise after her Hampton facilitator asked a cohort of high-growth founders to write letters to their former selves. Extracted from The Jasmine Star Show.
Core principles
- 01Psychological distance makes honest advice easier to access.
- 02Past disappointments can reveal a coherent path in retrospect.
- 03Advice offered to a younger self may also serve the present self.
- 04Compassion creates insights that harsh self-judgment obscures.
- 05The goal is understanding the journey, not rewriting it.
How to run it
- 1
Choose the recipient
Select a precise age and life moment rather than addressing your past in general. Pick a point when your expectations, fears, or identity felt especially consequential.
Pro tip Anchor the letter to a concrete milestone such as starting senior year, changing careers, or facing a family crisis.
Watch out A vague recipient can produce generic advice.
- 2
Reconstruct their worldview
Describe what your younger self believed would happen and what felt like success or failure at the time. Preserve that person's limited perspective before introducing what you now know.
Pro tip Include period-specific details that make the younger self feel real.
Watch out Do not mock past fears simply because they appear smaller in hindsight.
- 3
Tell the unpolished journey
Trace the important disappointments, decisions, relationships, and opportunities that followed. Include emotional and practical costs instead of packaging the story as uninterrupted progress.
Pro tip Focus on turning points that changed the direction or meaning of the journey.
Watch out Avoid converting the letter into a polished résumé.
- 4
Reframe without rewriting
Acknowledge what you might wish had happened differently, then examine how the actual path shaped your present life. Seek meaning without pretending painful experiences were easy or desirable.
Pro tip Ask which apparent failures opened paths you could not see at the time.
Watch out Do not use hindsight to claim every decision was objectively correct.
- 5
Give compassionate advice
Tell your younger self what they most needed to hear in that moment. Make the guidance specific enough to influence how they would treat themselves.
Pro tip Use the tone you would offer a close friend facing the same situation.
Watch out Advice dominated by criticism defeats the distancing benefit of the exercise.
- 6
Return the message to today
Read the letter again and identify which lines your present self also needs. Convert those lines into one or two actions or reminders for current life.
Pro tip Notice repeated themes such as presence, trust, patience, or self-compassion.
Watch out Do not assume the exercise is only about resolving the past.
In the wild
Jasmine addressed herself at the start of senior year, when poor standardized-test performance felt like a defining failure. She traced the path through law school, her mother's cancer, depression, marriage, photography, entrepreneurship, motherhood, and building multiple companies. Although she could imagine giving tactical advice about investing, debt, technology, and risk, she instead emphasized dreaming, patience, presence, and trust.
→ The letter exposed a less packaged version of her story and produced guidance she realized her present self still needed.
A founder writes to the version of herself who had just launched a promising product. She recounts a failed expansion, painful layoffs, a smaller relaunch, and the healthier company that emerged. Instead of telling her younger self to avoid every mistake, she explains which assumptions to question and offers the patience she currently struggles to extend to herself.
→ She identifies a present-day need to separate slow progress from personal failure.
Common mistakes
Writing to an undefined past self
Without a specific age and moment, the letter tends to become a broad life summary rather than a psychologically useful conversation.
Turning the letter into optimization advice
A list of better investments, choices, or tactics can obscure the deeper perspective and compassion the exercise is designed to reveal.
Packaging the struggle
Presenting a flawless success narrative prevents the writer from examining the uncertainty, pain, and vulnerability that give the journey meaning.
Is it for you?
Best for
People navigating uncertainty, disappointment, founder pressure, or a major life transition.
Not ideal for
People seeking a tactical business plan, clinical mental-health treatment, or a purely factual autobiography.
From the transcript
“He said, in preparation of our next call, I want you to write a letter to your former self. Tell me what you would say…”
“So Solomon's paradox means we can give advice better than we could take it ourselves, but oftentimes we can give ourselves advice to our younger…”
“I wrote the letter to my former self, but the person who needs to hear it is my present self.”
From the episode
The Letter I Wrote to My Younger Self (And Why It Changed Everything)