What is The Skip?
The Skip is a newsletter focused on helping you build a career that both has a positive impact and brings you joy. For many, a career is one of the most critical parts of identity. Yet most people don’t have a clear sense of how to maximize their current position, navigate job transitions, or invest in the right long-term skills to optimize their professional life. Unfortunately, if you work at a company, your manager is rarely capable or incentivized to help you develop the necessary skills or think through transitions. And most self-help books and articles focus on your current role, not on the next one or on any sort of long-term career roadmap.
I coach nearly a hundred leaders on their tech careers. I am certain, however, there are many others also looking to become more intentional about their career choices — which has led me to publish this newsletter. Each edition, I dive into some of the common questions I receive and the advice I provide with the hope of reaching as many people as possible. Though I mostly work with product managers, I think the themes apply to anyone looking to shape a fulfilling career.
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Here is how I organize my content with key resources in bold.
Choosing a new job
Product management leadership
Maximizing a job transition
Getting the most out of my existing job
I grew up in Kansas, did my undergrad and grad work in computer science from Stanford, then did four startups out of college. One I joined, one I founded (which failed), and two I founded as CEO. Cast Iron Systems was acquired by IBM, and SayNow became Google, and that started chapter 2 of my career. During my four years at Google, I became a product manager and got to launch Hangouts and pivot Google Photos. Then I joined Credit Karma as chief product officer, helping to expand the business from offering free credit scores to adding the money button on the phone in the US, with over 90 million members. And I now work at Facebook, supporting the News Feed. I’m settled in the San Francisco Bay Area with my wife, two kids, and two white fluffy doggies.