Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLE

Episode Overview

• The hosts begin with a humorous discussion about the complexities of YAML and the proliferation of markup languages.
• They address a question from a long-tenured CTO at a small startup who feels stagnant, worries about the company's future, and is concerned their resume is becoming less valuable.
• The hosts tackle a second question from a developer who pursued a leadership role, found it unbearable, returned to an individual contributor (IC) position, and now feels lost about their career direction.
• The episode explores themes of career longevity, the difference between leadership aspirations and reality, and how to navigate career pivots and uncertainty.

Key Concepts

• Career Stagnation vs. Loyalty: The dilemma of staying at a single company for a long time (e.g., nine years) can be viewed as either loyalty and deep expertise or stagnation and a lack of diverse experience.
• The Founder Mindset vs. Employee Mindset: As a key early employee with significant equity, it's beneficial to think like a founder, which includes creating succession plans to de-risk the company, even if that plan is for your own departure.
• The Reality of Engineering Management: Many developers aspire to leadership roles for the perceived influence and impact, but the reality often involves tasks they dislike, such as performance reporting, managing team delivery, and pulling people off enjoyable technical work for business priorities.
• "Hyphen-Shaped" vs. "T-Shaped" Developers: The concept of a "hyphen-shaped" developer is introduced as someone with broad but not deep expertise across many areas, contrasting with the "T-shaped" developer who has broad knowledge and deep expertise in one area. This can be a career challenge if not framed correctly.
• Career Recalibration: After a failed career pivot (like moving to management and hating it), it's important to analyze the experience to understand what specific aspects were disliked and what parts of the previous role were fulfilling, in order to find a new, more suitable career path.

Quotes

• At 00:31 - "There's got to be a reason why YAML is so complicated, right?" - The hosts joke about the notorious complexity of YAML while discussing various markup languages.
• At 05:13 - "I don't believe this company will succeed in the long run." - A listener, who is the CTO and a 10% owner of a startup, expresses their concern about the company's viability, creating a core dilemma for their career.
• At 14:38 - "It has been hell. It has been like falling backwards out of a tree and hitting every branch on the way down." - A listener vividly describes their negative experience after being promoted to a team leader role they had long desired.
• At 21:16 - "I think one way to look at this is say... I might be a hyphen-shaped developer in terms of technical areas of expertise, but maybe my T-trunk is getting stuff done ability." - Jameson suggests reframing a broad but shallow skillset as a deep expertise in execution and project delivery.

Takeaways

• If you are a critical employee at a company you believe may fail, proactively create a succession plan for your role. This not only protects the company and your colleagues but also gives you a clear path to exit gracefully.
• When a desired career move, like a promotion to management, turns out to be a negative experience, treat it as a valuable learning opportunity. Analyze which specific responsibilities you disliked to better define what you truly want in your next role.
• Don't be afraid to try a new career path and "fail." Discovering what you don't want is a crucial part of figuring out what you do want, and it's better to find out sooner rather than later.