Good Careers at Bad Companies

Published on May 31, 2026 | 17 min read | | How To Business Someone once asked me whether you can join a dysfunctional company and still have a good career. They assumed dysfunction is rare—something you'd see in advance and choose to join or avoid. But my experience is that most companies are dysfunctional in some significant and non-immediately obvious way, so a better question is: how do you build a meaningful career when those kinds of companies are the norm, not the exception? There are, broadly speaking, two types of companies: Trajectory is important because it correlates with that company's impact on your career. Companies that have gotten somewhere (such as the BigCos, FAANGs, and industry equivalents) and companies going somewhere (rocket ships with fast growth and fawning coverage) offer a pedigree, a reputation halo for your resume, and an opportunity to work alongside some of the top talent or top operational structures in an industry. They also have great pay packages that compensate for whatever issues you'll experience working there. These companies can end up massive (tens to hundreds of thousands of employees) but they make up a small subset of all employment. Not everyone is the number one in their industry, or on track to be. Good for you if you work for them! The remaining majority of companies are those that are going nowhere or those that are sliding back in that direction. Because trajectory, management, and quality of operations are strongly correlated, zero or negative growth typically signals that something is wrong or broken at a company, and it isn't being fixed.1 The company has some disconnect in the feedback loop between performance and accountability. These companies are not at the top of their game and the toughest challenges you'll encounter at them are navigating the dysfunction without becoming jaded or burning out. That's what makes them, in common parlance, "bad companies". Most people work for these kinds of companies, or will work for a company like this at some point in their career. And most companies I have worked with, in that regard, have been "bad" companies.2 That's why I'm writing this. To flip Tolstoy's wisdom, great companies are all contextually unique and idiosyncratic outliers, while bad companies are bad in mostly similar ways. Because of those similarities, there are takeaways from working at bad companies that are useful and applicable to any company you work at. The arc of working at a bad company looks like this: So can you build a good career across such environments? Yes, but not in the same way that you'd do it at a company with a great trajectory. Two things you're certain to take away from a bad company are (1) your reputation and (2) the experience, knowledge, and confidence in dealing with dysfunction and messiness. And so career growth at a bad company comes from learning to survive, navigate, and then solve mostly human-caused problems without burning out. In many ways, that's also your career arc: with survival comes learning; with learning comes experimentation, experience, and growth; and eventually you'll find yourself both in the position of being able to make an impact and having the skills and wherewithal to do so. Being right is often extremely context-specific while being wrong is often pretty universal.3 So learning what the universal mistakes look like and subsequently avoiding them has been more effective for me than trying to be overly clever, innovative, and correct. Being clever, innovative, and correct is especially tough early on in your career because you likely lack the experience to distinguish between superficial similarities and significant differences (and vice versa) between situations. And what passes for early-career innovation is often a rediscovery of existing techniques, principles, and observations, that when presented as novel insights is read by the rest of the room as inexperience and chutzpah. (That's been me, in many rooms). That's not to dissuade you from trying. There is no learning without risk of failure, and you don't know what you don't know; that's the essence of inexperience. So as a corollary to avoiding stepping on known and obvious rakes along your path, here's my kit of heuristics for what does work: All of these are simple in principle but rare and difficult in practice. If you’re willing to “eat dirt” (take on additional responsibility without additional compensation), especially early in your career, you’ll be given opportunities to take on increasingly bigger challenges which lead to operating above your title.4 As an example, early in my career I was able to take on responsibilities in data work and user research because I was volunteering for them without asking for anything in return (early enough, being hands-on and learning was reward enough). Similarly, I was afforded a lateral career move from marketing into product management because a company's product team had

Good Careers at Bad Companies

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