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The Startup of You: Executive Summary
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Instructor Guide

Chapter 5: Pursue Breakout Opportunities

The two habits of breakout careers.
Chapter Summary
The trajectories of remarkable careers are not slow and steady and up to the right. Rather, they are marked by breakout opportunities—career experiences that lead to unusual rapid gains. For George Clooney, being cast in ER was his breakout opportunity.
You can develop habits of behavior that increase the likelihood you find great career opportunities:
Be in motion and court selective randomness. When you do something, you stir the pot and introduce the possibility that seemingly random ideas, people, and places will collide and form new combinations and opportunities.
Tap the networks and associations of people. If you’re looking for an opportunity, you’re really looking for people. Historical figures like Joseph Priestly and Benjamin Franklin, or modern figures like Steve Wozniak, all tapped networks of people when they discovered oxygen, invented the modern university, and founded Apple Computer. Join conferences and clubs. Better yet, start your own.
There will be times when your back’s against the wall, when you’re low on resources or time, and when you’ll have to get scrappy and hustle for opportunities. Constraints can be a blessing in disguise: it’s amazing how resourceful one can get when one has no choice but to be resourceful. Recall the entrepreneurial stories of Airbnb and Pandora—entrepreneurs are the kings of hustle.
Key Concepts
Understand that today’s remarkable careers are punctuated by breakout opportunities.
Learn how to develop habits of behavior to increase the likelihood of finding breakout opportunities.
Discussion Questions
Add topic questions to discuss during class and take notes in the Notes column.
Add a topic
Topic
Notes
1
Whose careers do you admire? What do their career paths actually look like?
2
When has being low on resources and time caused you to get something done when you didn’t think it was possible?
3
What are the best job opportunities and how do you exploit them?
4
What are ways that students can court selective randomness?
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In-Class Activities
1. Student Organization Consultants. Divide students into groups and have them pick an organization on campus — student activities, student union, health center, residence life, recreation center or other campus centers. Suggest reading student newspapers to get ideas of which organizations have issues in need of change they can explore. Brainstorm in their teams about how the operation works, gathering information on services offered, thinking about what their problems are, and what opportunities for change exist. Teams will prepare a paper and presentation to share their findings.
Take-Home Assignments
Day Experiments.
Budget Time for Randomness. Students will deliberately underschedule themself for a day to do something they don’t normally do — read a book they wouldn’t otherwise read, take a coworker out for lunch who works in a different department, or attend a speech or seminar in a different but related field.
Yes Day. Students will set aside one full day to be a “yes day.” They will say yes all day and mark down what they said yes to and what serendipity comes of it.
Curiosity Lunch. Students will ask the most curious person they know out to lunch and write about it.
Attend Industry Event. Students will find an industry event or conference to attend and write about it.
Network Dinner. Students will invite three friends to a dinner and ask each of them to invite one additional person whom they don’t already know.
Start A Group. Students will bring a group of people together for an in-person meeting or online (using LinkedIn Groups, for example). They should try to convene friends to share ideas and resources. Suggest setting up a simple wiki to organize and share the details.
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