Career links: ladder-climbing vs bet-placing

Disclaimer: Not advice, consult a professional!

Software engineers (like anyone) often want a structured framework for thinking about career progression and growth. Many companies provide this in the form of a career ladder, and there are a wide variety of resources for learning more about developing skills and achieving milestones corresponding to different levels of the ladder. The simplicity of this approach can under-emphasize more strategic dimensions of personal development. For example, how can you cultivate some specialization, depth, or versatility that distinguishes you from a replacement-level Google L5? We can consider other non-ladder frameworks that place more emphasis on these aspects by viewing career development through the lens of startups, investing, or product development.


This post is a “Don’t Repeat Yourself” (DRY) attempt to capture links and other resources on these topics that I’ve by now shared with people individually more than three times. My intention here is to assemble and briefly describe a collection of ideas from which the reader can take or leave what they like. Everyone’s personal situations and trade-offs vary considerably, and even a specific individual’s context, objectives, and constraints will be dynamic over time - caveat lector!

Get enough sleep, exercise, eat your vegetables

Certain guidance is well-worn or cliché for good reason (ie, it is basically true): invest in your communication skills, follow through on your commitments, seek out learning opportunities, develop your craft, and try to understand the broader context. There is no shortage of excellent books and articles covering these topics. But once you are already investing in these foundations, what’s next?

Beyond the ladder

As mentioned earlier, many tech companies have some version of a career ladder: a linear (vertical, even!) progression of increasing impact, expertise, and responsibility. More sophisticated versions may strain the metaphor by forking into different tracks of growth such as technical leadership or people management. These ladders are a popular tool for good reasons, as they encapsulate a useful consensus bundle of information, structure, and shared vocabulary.


However, there is room in the toolkit for more than one tool. Alternatively we might think of a career as a sequential process of making investments of effort and attention into uncertain endeavors over time. Instead of a diligent climber making cumulative progress up a ladder, imagine a calculating gambler (or investor, if you like), continuously allocating a scarce portfolio of skills, time, and other capital to solving problems, identifying and evaluating opportunities, and gathering additional information. Variations on this theme include thinking of a career as a startup or product, spending capital to carve out a lucrative niche. Viewed from this perspective, tidy questions about the next rung of the ladder are replaced by more open-ended questions around differentiation and decision-making under limited information or uncertainty.


“…don’t enter the rat race unless you’re the fastest rat!” -Erik Torenberg, “Build Personal Moats”

The writings of business theorist Michael Porter contain strong warnings against companies simply trying to be “the best,” as any gains will inevitably be competed away by equally determined and capable competitors. The opposite of the naive “battle to be the best” is the careful formulation and execution of a well-chosen strategy that charts a course towards a unique and defensible position in the marketplace. One example from the book is that IKEA doesn’t necessarily make the world’s best furniture in some absolute sense, but they have a very attractive value proposition for a particular customer segment, and their entire business commits wholly to going after this market via an interlocking set of difficult-to-replicate trade-offs.

Analogously, a career plan premised on being the smartest, most talented, or hardest working is, by definition, a dicey proposition for all but a few individuals. The same pitfalls also apply to highly competitive tournaments such as exclusive university admissions or selective employers. Indeed, the odds become even more dire if you believe that the internet has created a global marketplace for talent, or that advances in technology are tending to create “winner take all” outcomes. The thoughtful development of some rare and valuable skill (or combination of skills) is one way to, at least somewhat, sidestep the costly and unwinnable “battle to be the best (employee).” Some links to thought-provoking writing on this topic are below, and many of these articles themselves have links to further reading materials:



One challenge around trying to build some differentiated personal value proposition is that, by definition, there must be some “moat” preventing others from doing so, or doing it as effectively as you can. Going again to the startup analogy, a trio of fascinating blog posts (links below) from Jerry Neumann propose that startups fundamentally take on the risk of attacking uncertain opportunities, and that this uncertainty acts as a temporary moat keeping competitors from entering. During this window of time, the startup is in a race to exploit that buffer to build some other, more durable advantage(s) before the opportunity is sufficiently de-risked in the eyes of other better-resourced entrants. Jumping back to personal skillsets, an example of this could be becoming an expert in some emerging but as yet unproven technology, process, or domain.

This approach requires you to take on some risk that your bet doesn’t pay off (eg, the tech you chose doesn’t take off). If it were a sure thing, everyone would already be piling into it and it would be difficult to stand out from the crowd. Hopefully you have some insider information or domain expertise to formulate a better assessment of the odds than the general public, but there will still be an element of uncertainty to be evaluated and managed. Joining an early-stage startup can also be interpreted in this way. You are quite definitely placing a bet where the potential payoffs include both direct financial rewards as well as exposure to different kinds of growth and learning opportunities than you might get elsewhere.

Therefore, to effectively execute on your career strategy, it would be helpful to get comfortable incorporating the unknown and the uncertain into your decision processes. Below are some interesting links on this theme, many of which are unsurprisingly concerned with the problem setting of financial investment:

Putting it all together: what’s your edge?

If you find any of the above even remotely compelling, it could be a worthwhile exercise to try and explicitly work through an inventory of your worldview, skills, interests, and goals in these terms: how are you (or could you be) uniquely well-positioned to create exceptional value or solve important problems?

Put another way, if you were positioning yourself in a job interview: what is your “edge” or “secret weapon”? Remember, all the candidates will (at least claim to) be proactive problem-solvers with cutting-edge technical skills, excellent collaboration habits, and a strong track record! At least once in a while, you may want to look “sideways” from the ladder and try to think about things a bit differently.


Thanks to my PhD co-advisor Mark Craven for the “secret weapon” framing and introduction to Hamming’s You and your research. Also many thanks to Cedric Chin, Jerry Neumann, and Erik Torenberg for “thinking in public” via blogs, Twitter, newsletters, etc!