part 1, part 2, part 3 (from 2007!)
“Career planning = career limiting”, instead think in terms of opportunities and skills
How to think about risk?
- A career is a portfolio of jobs/roles/opportunities; when presented with an opportunity, analyze its risk in the context of the lifetime portfolio
- There is no opportunity without risk
- Pay careful attention to opportunity cost
What industry?
- Choose an industry where the founders are still working; it will be vibrant and full of opportunities for young, determined people
Where to live?
- Go to the center of the industry (e.g., for technology, SF), but maybe also where the most change is happening (e.g., instead of NYC for fintech, go to Africa).
- International experience is also great to broaden perspective and become a better global operator
What skills are worth learning, and how do you learn them?
- Learning something hard and technical (via school or work)
- Communication (read, write, go to an improv class)
- Management (work under a great manager)
- Sales (spend a year as a salesperson)
- Finance (learn from others, read)
- International experience (work abroad)
How to be valuable?
- It’s rare that someone will be top 1% in a skill
- Instead, it’s a much higher likelihood to stack multiple skills (i.e., to be top 25% in 3–4 skills)—suddenly this person is qualified to be the CEO;
- Takeaway - Develop multiple skill sets
How to learn decision-making?
- Put skin in the game; put myself in situations where things can go wrong, and where I live and breathe by decision-making ability
- Contra the organization kid
How to learn from each industry / opportunity?
“Think strategically: how would I start a firm like this today?
Or, if I were starting a company in this industry today, how would it be different than this firm?
Why is this firm and other firms in this industry doing what they do? What are the assumptions underneath their behavior? Should those assumptions be changing?
How might this industry work differently? Which customers are being underserved? What new technologies might change things completely?
How were things working 10 years ago, versus today, versus 10 years from now?
And, my favorite: if the creators of this industry were starting out today, what would they be doing now?”