BOOK / SOURCE
What I Wish I Knew When I Was 20
- Material reviewed for this piece
- Both scans of the summary notebook were fully reviewed: 16 and 18 PDF pages. Comparison identified 16 distinct notebook pages; the longer scan contains one repeated page and one blank page. This synthesis uses the clearer scan and develops selected notebook themes; it does not claim a reading of the complete book.
Summary and application draft · awaiting review
AI-assisted draft based on a handwritten notebook. Book ideas are credited to Tina Seelig; the notes also include summary wording and emphasis whose exact origins are not always marked. The failure-résumé exercise was verified through Stanford. The fictional example, test questions and boundaries are new editorial adaptations awaiting Shachar’s approval. No personal success story or business outcome is claimed.
1. Start with the need, not the familiar solution
The notebook opens with seeing problems as opportunities and the danger of defining them too narrowly. If the problem is framed as “We need a system,” a whole family of solutions has already been selected. Return to what people struggle to do before deciding what to build or buy.
Consider a fictional team whose new members cannot find the information needed for their first task. Instead of “How do we build a portal?” ask “What needs to be clear for someone to complete that task?” Perhaps a short document, a contact person or consistent instructions are missing. Reframing guarantees no solution; it keeps more than one possibility open.
2. Put the assumptions on the page
The notebook suggests identifying conventions and reversing them as a thinking exercise. The point is not originality at any price, but noticing where habit has already shaped the solution. In our example, assumptions might include keeping all information together, teaching everything on day one or giving everyone identical instructions.
Beside each assumption, record its support, what changing it might reveal and what must remain protected. Safety, privacy and commitments are not merely conventions to discard for an interesting idea. An awkward rule may protect a need we have not understood. Testing an assumption starts by investigating its purpose, not breaking it.
3. Separate generating options from choosing an action
The brainstorming notes invite space for ideas and building on other people’s suggestions. Separate the stage of expanding possibilities from the stage of choosing a trial. Testing every unfinished sentence against cost, risk and schedules can send a group straight back to its familiar answer. But an idea that survives brainstorming has not thereby been shown to be good.
The fictional team might propose a short starting guide, guided practice or a peer partner. Then compare: which option tests the most important question, uses few resources and can be stopped without harm? This comparison is an editorial application, not a formula quoted from the book.
4. Initiative is not an unlimited commitment
The notebook emphasizes finding unmet needs rather than waiting for someone to offer the right role. It also warns against taking on so much that important commitments suffer. Those ideas belong together. Initiative needs room in the calendar and agreement when it involves other people or resources we do not control.
Define what is included, what is excluded and whose approval is needed. The team could propose testing one introductory task with willing participants rather than redesigning the entire onboarding process. Identify what will be deferred to make time. A clear boundary does not contradict responsibility; it makes the responsibility understandable.
5. A failure résumé with a lesson you can examine
One explicit tool in the notebook is the failure résumé. In a Stanford publication, Seelig describes recording personal, professional and academic mistakes together with the lesson from each. The useful emphasis is not a long inventory of disappointments, but the move from event to learning.
For the adaptation here, record one event, what you expected, what happened and a change worth testing next time. Distinguish an examined cause from an explanation that merely sounds convincing afterwards. If a new guide did not help, it may have been overloaded—or missing information may never have been the problem.
Not every failure is justified by learning, and not every lesson is correct. Account for the cost and the obligation to repair, while learning from successful attempts too.
SOURCES / FURTHER READING
SEE THE IDEA
Not just what failed—what will we check next?
A fictional record from the team-onboarding example. This newly applies the idea of learning from a mistake; it is not a book form or a client story.
- AttemptA short guide for one task
- ExpectationClearer information for newcomers
- What happened?Questions remain—which ones?
- Next checkInvestigate the barrier before another change
Possibility A: the guide is overloaded
Ask a willing participant to show where they lost the thread. If that is the problem, shortening the explanation may help. Do not assume it is the barrier merely because it sounds plausible.
Possibility B: information was not the missing piece
A contact person, practice or consistent instructions may be missing instead. Before adding text, check what the participant tried to do and what stopped them. Both possibilities are hypotheses, not diagnoses.
6. Personal interest needs to meet a real need
Later notes bring together personal interest, skills and a need other people have. This is a useful way to examine a professional direction without assuming enthusiasm is sufficient. Attention to opportunities, listening and appreciation for others recur too. Relationships need not become instruments for achieving a goal; a conversation can simply reveal what is missing and for whom.
Rather than concluding “I enjoy explaining, so I should build a course,” ask whom an explanation would help and with which task. Learning and experimentation do not erase differences in resources, access or chance. Responsibility for an available action is not responsibility for everything that happens; initiative is no proof that unsuccessful people failed to try.
7. Leave with a small test, not a lifelong decision
A new closing practice: choose one recurring difficulty, describe it without naming a solution and mark one assumption to investigate. Decide what you can do within existing permissions and resources, what you will record and when you will continue, change direction or stop.
In our example, trial a short guide for one task and ask willing participants where they got stuck and what remained unclear. Afterwards, write one lesson, including what is still unknown. This does not establish demand for a product or suitability for every team. It provides a better basis for the next step: attention before an idea, inquiry before commitment and learning after action.
SOURCES / FURTHER READING
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