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The Startup of You: Executive Summary
Instructor Guide

Chapter 3: Plan to Adapt

How to articulate a plan for flexible persistance.
Chapter Summary
Popular career planning advice says you should decide where you want to be in 10 years and then develop a plan for getting there. Popular career advice says you should find your passion and then pursue it. These philosophies have serious strengths, but also huge drawbacks.
It presumes a static world. In fact, you change, the competition changes, and the world changes. It presumes that fixed, accurate self-knowledge can be easily attained through introspection. In fact, you identity is not found through introspection but rather emerges through experimentation.
Entrepreneurial career planning and adapting is about being flexibly persistent: always ready to adapt, but also persistent in driving towards set goals. Flickr and PayPal are two companies that adapted significantly, and Sheryl Sandberg’s adaptive career are examples of flexible persistence.
Make explicit the assumptions and hypotheses in your plan. You’ll never have complete certainty; identify areas of incomplete knowledge about yourself or your industry and make plans that will help you fill those gaps.
Prioritize learning. Just as start-ups in the early days prioritize learning over profitability, so should you prioritize learning (soft assets) over cash salary (hard assets) for the majority of your career. In the long run, you’ll likely lead a more meaningful life, as well as make more money.
Learn by doing. Actions, not plans, will generate the lessons that help you adapt to the next phase of your journey.
Think two steps ahead. What next move will maximize the quantity and quality of follow-on opportunities?
Then craft an experimental Plan A, an alternative Plan B, and an unchanging, certain Plan Z.
Plan A: What you’re doing now. Your current implementation of your competitive advantage.
Plan B: You pivot to B when your plan isn’t working or when you discover a better way toward your goal.
Plan Z: You shift to Z if something goes seriously wrong. It’s the lifeboat you can jump in if your plan fails and you need to re-load before getting back in the game.
Key Concepts
Understand and be able to articulate a Plan A, Plan B, and Plan Z in your career.
Understand that modern careers are adaptive and require “flexible persistence.”
Learn the importance of experimentation over introspection.
Discussion Questions
Add topic questions to discuss during class and take notes in the Notes column.
Add a topic
What conventional career advice have you been told?
How do you determine how much learning potential a career path offers?
What are the uncertainties, doubts, and questions you have about your career at the present moment?
How do you know when to pivot from Plan A to Plan B? When is it time to change divisions, change jobs, or even change the industry you work in?
What are other examples of first steps with high option value?
How do you know when to pivot into a new industry niche? Where should you pivot to and how?
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In-Class Activities
ABZ Consultants. Students will be divided into small groups. One student will be chosen, and the group will create an ABZ Plan for that person’s career.
Freeze Tag Theater. An improv game involving two in an introductory scene, who to an extent may wish to exaggerate gestures and physical actions. At any point an outside participant can shout "freeze," at which point all action and dialogue ceases (bodies frozen in place) and the person can then go and tag whichever player he wishes to replace. What ensues is up to the literal scene stealer, as he must resume where it all left off, though redirecting the scene however he chooses. The idea is that the newcomer will inevitably make use of the last line spoken or pose assumed for a humorous effect. This game demonstrates the surprising possibilities of constant adaptation.
Take-Home Assignments
Personal Brand. Students will establish an identity independent of your employer, city, industry; reserve a personal domain name (; print up a second set of business cards with just their name on it and no company name.
Side Project. Students will set aside time to work on something that could lead to a Plan B. Students should orient it around a skill or experience that is different but related to what they’re doing now. Perhaps they have a business idea they want to pursue, or a skill they want to learn, or a relationship they want to form, or some other curiosity or aspiration.
Coffee Meeting. Students will schedule a coffee meeting with someone who used to work in their professional niche who has pivoted to a new career plan. How did he or she make the shift? Why? What were the signs that the time was right? Or, students will reach out to five people who work in adjacent niches and ask them to coffee. Keep up this relationship over time so you can access diverse information and so you’re in a better position to potentially pivot to those niches when necessary.
Skills Investment Plan. Students will make a plan to develop more transferrable skills, those skills and experiences that are more broadly useful beyond what it takes to thrive in their Plan A. Writing skills, general management experience, technical and computer skills, people smarts, and international experience or language skills are examples of skills with high option value; i.e. they are transferable to a wide range of possible Plan B’s. Once they’ve figured out which transferrable skills to invest in, they should make a concrete action plan they can stick to, whether by signing up for a course or conference, or simply pledging to spend one hour each week self-learning.
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