Good Careers at Bad Companies

Someone once asked me whether you can join a dysfunctional company and still have a good career.

The question 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:

• Companies that are going somewhere (or have gotten somewhere), and
• Companies that are going nowhere (or are going back to nowhere).

The trajectory of a company is important because it correlates with that company's impact on your career.

Companies that have gotten somewhere are the BigCo/FAANGs (or your industry equivalents) – brand names with good salaries and a reputation halo for your resume. Companies that are going somewhere are the ones you read about in the news – a small set of rockets with fast growth and fawning coverage. Both of these types of companies give your resume (and career) a pedigree and an opportunity to work alongside some of the top talent or top operational structures in an industry. They also offer great paychecks that compensate for whatever issues may be present.

But while these companies can end up massive (tens to hundreds of thousands of employees), they make up a small subset of all employment because there are fewer of them around – not everyone is the number one in their industry, or on track to be.

That means most companies are those that are going nowhere or those that are going back to nowhere. Because trajectory, management, and quality of operations are strongly correlated, zero or negative growth¹ typically signals that something is wrong or broken, and it isn't being fixed. There's 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 likely 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 (To note, "bad" doesn't have to be a judgement: some have been nice to work for because of great teammates. Some have made a small but personally meaningful dent in the grand scheme of things. Others have ranged from being just a 'desk and a paycheck' to psychologically awful environments I couldn't wait to leave.)

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 broadly useful and applicable to any company you work at.

The arc of working at a bad company looks like this:

• You arrive optimistically – it seems like a nice company from the outside!
• You notice the dysfunction.
• You try to fix things.
• You learn the limitations of what you can do and/or how intractable the problems are.
• You realize that a meaningful, successful tenure here will mean something different.
• You build skills, extract experiences, and build relationships.
• You move on. There's little reason to stay once you've learned 80% of what is available to be learned or practiced. If you stay, you will stagnate.

So can you build a good career in such an environment?

Yes, but not in the same way that you'd do it at an exceptional company. The only two things you are certain to take away from a bad company are (1) your personal reputation and (2) the experience, knowledge, and confidence in dealing with dysfunction and messiness. To be clear, those are valuable takeaways.

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 is 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.

But mostly, you first have to survive.

(First You Should Survive...)

Avoid Stepping on Rakes

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. 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. (Especially if the insights are incomplete – 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 works and is almost universally applicable:

1. Respect the Overton window for change management.
   Big changes at companies come when there is some sort of shock to the system: an important person is either joining or leaving, or the company is navigating some crisis. This is when someone can come in and say without much pushback that "we're doing things differently moving forward", or when a company can change its strategy 180 degrees to address a challenge. (As Rahm Emanuel put it: "Never let a serious crisis go to waste.") At all other times, companies, teams, and people will be resistant to any change that isn't at best a half-step forward.
   
2. Don't lead with ego.
   People typically don't want to work with brilliant jerks... because they're jerks. They also don't want to work with people who take up all the air in a room, or people who make them feel stupid, intentionally or not. And you don't want to be so smart that you discount the observations or thoughts of your colleagues because you think you've already figured things out. So have some humility, and listen more than you speak.
   
   I've put my foot in my mouth too many times to count by jumping in to finish other people's thoughts, only to later learn that not only was I wrong, but it also made them want to work with me less. Many situations can be worsened by opening your mouth inopportunely, and many situations can be improved by keeping it closed.
   
   You don't need to let everyone know how smart you are. Be curious about other people's perspectives. Help other people look good, let them take credit from time to time. Win allies. Success comes easier when you make friends, not enemies.
   
3. Over-communicate, and keep your word.
   Learning to communicate well – succinctly, clearly, and at the level of detail matched to your audience – is one of the most important skills you can work on. And for anything important, you need to over-communicate. Tell people what you're going to tell them, then tell them the thing, then tell them what you told them. Follow up on things. Never assume that someone understood or is on the same page as you or knows what the next steps are; you'll end up wrong far more often than right.
   
   And if you ever say you're going to do something – you better do it, and do it well. Keeping your promises is the foundation of your reputation and credibility. There are many times when I have gotten ahead simply because I was the only one who left a meeting, did what we had talked about, and brought it back to the team.
   
4. Periodically check the balance in your reputational bank.
   Reputation takes a long time to build and a short time to lose. All the usual wisdom applies: don't make promises you can't keep, don't over-promise and under-deliver, don't pursue high-risk, high-failure projects unless you have some reason to be confident in the outcomes you want.
   
   If you've been at a company for a while and 'can do no wrong', you've probably saved up enough reputation that you can cash in for a big initiative or gamble. And if you're not effective or sidelined at meetings, practice some introspection as to why you're not able to make things happen. Reputation is an external measure – it is a reflection of other people's views of you, and you may need to put in some effort to improve those.
   
   And lastly,
   
5. Don't try to apply philosophical approaches to management without catering them to your specific context.
   This is very specific advice, and what I mean is, don't try to apply blanket changes such as "We did X at my last place, so we'll also do it here" without figuring out how "here" and "my last place" are different. Every company has a flavor of processes that has been optimized for the specific context in which those processes exist. What works for one company may not work for another.
   
   When my teams and I evaluate processes and share blog posts about what other folks are doing, it is with a big asterisk that these are interesting solutions to challenges we're likely not facing. Unless we have those same variables, we're likely looking at a solution in search of a problem. We need to stay focused on our specific flavor of problems. This is what is meant by "Google's problems are not your problems."

All of these are simple in principle but rare and difficult in practice.

(... Then Learn to Navigate)

Dysfunction Scares Away Quality Candidates; That Creates Opportunities for Progression

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 imploded and no one wanted to lead that department for fear of getting failure on their hands. I volunteered to lead that team in addition to my then-current responsibility. Because I was able to turn the team around, it was the doorway I needed to move full-time into doing product and engineering work... a door that would have been hard to open otherwise.

In fact, much of my career growth has come from volunteering to do the work no one else wants or has time to do, and not expecting any additional compensation for it. (The compensation is the practical skills developed and the challenges you get to work on.) Being especially attuned to how opportunity windows open and close, I'm often the first one in to ask if I can help, or take on some adjacent responsibility when a window opens. But you need to be strategic about it: aim to take on opportunities you can learn from, tell a good story about, practice something new, or test a theory. Avoid work for the sake of extra work, and avoid taking on work that isn't valuable in some way. There's a fine line between being exploited and seizing a moment to make the most of your circumstances.

As a corollary, turning such 'dirt' into actual title progression is often easier when you're switching companies, not intra-company. When you're inside a company, a promotion is tied up in budget changes, title and staffing politics, seniority calculations, and ceilings on acceptable changes. But when you go to a new company, none of that baggage exists for you: it's a blank slate with comp and a title matched to the role's expectations, not anchored to your past. That's why jumps between companies result in quicker title and pay growth than waiting for internal promotions.

Recognize Unserious People

I've worked with enough people to notice that for nearly every problem someone has, there is a corresponding solution often within grasp. There are very few problems where a solution can't be reached within a few iterations.

But not every problem has the willpower or consensus around it to be solved, and not every solution will be pursued. Moreover, many people do not do anything to solve their problems (and some, whose responsibility is managing problems, have an incentive to keep problems around). They have reasons, excuses, committees. They have a lack of alignment, lack of confidence, too much risk. There is always too much other stuff on their plate.

You can tease out these people over time: folks who complain about how something is, but are unwilling to do anything about it. I think of them as "unserious" (think Logan Roy's quip to his kids in Succession: "I love you, but you are not serious people"). They may be wonderful humans full of good intent, but they are also black holes into which effort enters and nothing returns. They are often the piece of the puzzle that needs to change, and there is very little to be gained from helping them until they are ready to help themselves.

The flip side is: savor the serious people!

Even though they are unlikely to be successful in bad companies (because (a) their heads will get lopped off for repeatedly tipping over management's proverbial apple cart or (b) they get burnt out), these people Care with a capital-C and eventually they will find a place/company/team that values their contribution. There, they will be gasoline. Don't write them off. Care about them back. Build that bridge. Don't let them burn out. If you're a manager, clear the road for them to do their thing. If you're a teammate, support them.

(If you're reading this, perhaps they are you, or some past iteration of you.)

(... Then Contribute)

Bad companies are extraordinarily hard to fix, especially if you're not the CEO.

My experience has been that problems at companies almost always come from some form of executive dysfunction, because if the executive team was functional, they'd already be elbows-deep in implementing changes. Examples of such dysfunction include:

• Indecision and capriciousness,
• Lack of strategy, bad strategy, or uncorrected poor decisions,
• Lack of self-awareness,
• Uninformed micromanagement and a general disconnect from operational reality,
• Team misalignment or misdirection that leads to people working at cross-purposes,
• Unwillingness to address problems and a lack of accountability, and
• Various forms of nepotism that destroy morale and/or foster role-skill mismatch.

Most of these are human failings of unseriousness or incompetence, not tactical or operational failings. Where operational failings exist, they persist because of executive dysfunction, not in spite of it.

Human-shaped problems require human-shaped solutions. At non-executive levels, you’re not going to fix those issues because you can't make the personnel changes required. At best, you can work around the problems-in-charge; I'd go so far as to say that most poorly run companies survive in spite of poor leadership by having effective middle management that keeps the lights on.

You're not going to be a hero in those sorts of circumstances, especially if it isn't your company. The takeaway is gaining a working, close-up knowledge of how organizations and people fail, and adding that to your repertoire of rakes to not step on. As I mentioned earlier, understanding the variations of human failure is in itself a useful end; it is a broad, useful, and transferable skill.

At this point, you might remember my pitch that "eventually you'll find yourself in a position of both being able to make an impact and having the skills and wherewithal to do so". How do you reconcile that with the recognition that you're not going to be the hero and solve all of the problems?

I lied, sorry about that.

At best, you're going to be making local contributions: things within your circle of control, such as a project, a team, or a department. Enough of those kinds of contributions can roll up to something greater, but if it is not your company, you're always going to be limited in your total impact. Local pockets of positive change may not be broadly meaningful to the company, but they are meaningful to the people around you, and they're the "effective middle management that keeps the lights on". So expanding your circle of control is still a valuable goal because it increases your surface area for such impact.

"Personal success" at bad companies looks more like reputation and relationships than metrics and deliverables.

So how do you validate, verify, or showcase that you've done good work (or done anything meaningful) at a bad company when the company or product fails for reasons outside of your control? If you fixed a feature, turned around a department, or delivered an amazing new feature, but the company lacks product-market fit or otherwise can't capitalize on your contribution, what story can you tell?

Most resume advice tells you to focus on metrics and quantifiable impact (and if those metrics are about increasing profit/cutting costs, so much the better!). But in bad companies—or early in your career— the key metric might not have moved, or you might not have access to that data, or even be privy to the decision-making room. Even when you do, companies aren't solo endeavors. There are many reasons outside your control for why your work didn't translate into a compelling story.

An example: very early on, I led the product development and launch for a physician-focused professional network. As far as the product went, it was as good as it could have been. But (a) it was never something we should have built because there was no demand for it, and (b) when company leadership eventually realized that, they decided not to dedicate any promotional budget around it and the sales team had zero financial incentive for promoting it. The product was "pivoted away from" shortly after launch and never talked about again. It was a massive strategic blunder for the company... but I still gained a lot of hands on experience with product development, marketing, and positioning. That was useful even when the product amounted to nothing.⁵

But what I lost in marketable successes (it's tough to edit "led new product development from zero to stillbirth" into something that resonates with a resume review), I gained in relationships and reputation. Within my own realm of control, I did the best work I could, I advocated for things to be better, and I helped others make the most of their time assigned to a doomed project. And from that, I learned that most people within a bad company are generally well intentioned but take up a posture of learned helplessness when they see that they have limited impact. So showing up, caring about your work, and making quality of life changes are rewarding not just on their own, but they also fill up your reputation bank and build the relationships and networks that are critical for implementing bigger changes.

So this is a pitch for why management-path growth matters: you increase the area of impact that you can make, and in the small scheme of an individual life, making a local impact matters.

A successful stint in a bad company may look like that. You probably won't be able to measure yourself against the products you shipped or the metrics you hit—those may be out of your control. But within the areas you can impact, you should be able to look around and have confidence and certainty that the people with whom you have worked will advocate for you and bring you into future opportunities.

That part is quantifiable: you can count how many doors open for you, how many people would want to work with you again, how many useful learning experiences you had, and how many skills you were able to put into practice.

... And Then You Should Move On

Bad companies are not worth staying at long term for a reason (and often many reasons):

• If you're early in your career, you'll likely end up learning bad practices without realizing they're bad and internalizing dysfunctional patterns as normal.
• If you are looking for status games, you won't be rewarded (there's no pedigree from bad companies).
• You won’t learn from the top of the field or find too much opportunity to work on frontier projects.
• You'll be doing a lot of structurally similar things over and over again; without strong mentors or structural changes that come with growth, your skills development will eventually hit a ceiling and stagnate.
• Once you're a bit further in your career, you'll spend more time defusing situations and untangling knotty issues than moving things forward. That's a huge psychological hurdle for people who are not interested in management-track growth, though "being able to navigate the political landscape" is what separates a staff-level contributor from a regular individual contributor.
• And at otherwise "fine" companies that happen to be going nowhere, there's little career progression available.

Don't Burn Out

Bad companies are also guaranteed to have their own special brands of toxicity that drive good people towards burnout. Burnout is not good for your career! And if you don't get burned out, you might get "compassion fatigue", a close cousin. Burnout and compassion fatigue impact your professional, personal, and emotional life, and leave psychological scars that are tough to recover from. Burnout also compromises you: it leads to making obvious mistakes and compounds all friction that exists.

I can't stress it enough: avoid burnout. Take time off, and find the exit door from toxic environments whenever possible. There's a solid line between "this is an incredibly tough environment but I am going to win generational wealth from a few years of work" and "I hate my job and it makes me miserable and I don't get paid enough to do this".

Remember that this is not your company, this is not your life. This is one of many possible jobs you will hold. Your responsibility is to protect yourself, be a good human being, and get what you can before burning out. To keep playing, you first need to survive.

And to survive, you have to be at least semi-interested in political games of management.

Don't Lose Yourself

Being too involved with political games can result in a slow evaporation of many ethical or moral qualms you might hold. Don't be that person. People who sacrifice parts of themselves to get ahead are left with neither themselves nor success (of which there is never enough).

Conversely, holding on to strong ethical standards (or even having ethical standards) is a surefire way to play the game on hard mode, especially if your standards are inconvenient for your company or leadership. Yes, you can "care too much" if your standards are out of sync with what leadership cares about. I've worked with too many well-intentioned product managers, designers, and engineers who each believed in their own version that "good is the enemy of perfect" and became bottlenecks against forward progress. They failed to understand that perfection is a direction and not an end-state, and they did not want to recognize that the general direction of movement was, within the compromised environment we were operating in, the best match of what they wanted and what we could do as a team.

They were serious people and unfortunately, their uncompromising stances became the problem. They were perceived as being fixated and holding things up. Knowing which battles to skip is a skill, not a compromise. Political survival sometimes requires tolerating things you'd rather fix.

Find The Right Company-Role-Skills Match

Every company can be described as a microcosm in which certain behaviors and skills are rewarded, and others are punished.

Eventually, you'll notice that there are companies which reward unserious people and punish the serious ones. You'll notice details that suggest where certain types of dysfunction are addressable, and others are not. For example, you may be the specific new hire brought in as the personnel change, and given an Overton window through which to pull the company (as I have been, when asked to join a company to turn around a team and/or a product). You'll find, through conversations and behaviors, which companies value the skills and approach you bring to the table and which ones don't.

And sometimes, rather than contorting yourself to succeed in a new environment, you need to find the specific company, role, and skill match where you can thrive.

So as the saying goes, “You can spend your whole life climbing the ladder, only to find, once you reach the top, that the ladder is leaning against the wrong wall.” When you realize it's the wrong wall — learn what you can, practice what you're given space for, help others, and move on.

^{1 - Leaving aside companies that are intentionally going nowhere, such as lifestyle businesses, dying industries, and intentionally small shops (mom and pop, local, artisanal, etc.). These are typically not where 'careers' happen, though if they hold output to a very high standard, they can develop a sense of craft and be a launching pad for a future career.}

^{2 - To note, roles in wildly successful BigCos are not always a golden ticket to good careers either. Hiring processes for most companies sell a roses-and-sunshine version of who they are, not the warts versions. Even "great on the tin" companies may be disaster zones surviving on good press and duct tape, so it's hard to tell with a high level of accuracy exactly what you’re getting into. Some "going somewhere" rocket ships implode spectacularly before they leave the atmosphere; some "got somewhere" BigCos find themselves coasting on stupid amounts of recurring money from early successes, unable to re-achieve those heights and never succeeding. Your mileage, as with all advice, will vary.}

^{3 - Charlie Munger said it quite well too: “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”}

^{4 - Another important piece of advice I offer to ambitious folks is "always try to operate one level above your role". At all times, you're essentially auditioning for the next role up and practicing those skills. So when an opportunity for growth comes up, you're the most prepared and obvious candidate. It also forces you to expand your view of the organization and its challenges, and not hit a skills/perspective ceiling at your current level.}

^{5 - The flip side to this is resume inflation from good companies: if you’ve done a merely adequate or even subpar job at a stupidly successful company, does that broader success rub off on your work? (That's rhetorical – yes, yes it does.) As the saying goes, positive cash flow hides many failures... and yet so many teams still manage to snatch defeat from the jaws of victory!}