How to survive a Sinking Ship in Silicon Valley

Sinking Ship Article

In my ten years working at tech companies in Silicon Valley, I’ve worked on a few projects that have been described as “sinking ships”. Usually, these projects have been stuck in managerial hell, with a revolving door of top leadership cycling through trying to “right the ship.” More often than not, some aspect of the product is simply not up to spec (the power consumption is too high, performance isn’t up to par, too much latency in a critical feature). The company is having trouble retaining employees, morale is low, and water cooler conversations revolve around what a mess everything is. Work itself has devolved into an endless cycle alternating between last minute pushes to reach newly defined milestones, and periods of complete inactivity while management is stuck in bureaucratic scrabbles. Sounds like a real bummer, huh?

That being said, you don’t have to work on a successful project to grow professionally. In fact, throughout my Silicon Valley career, prioritizing growth and opportunities has been much more valuable than whether the projects I worked on succeeded. When you’re stuck on a project that’s going nowhere, stop thinking about how to make the project work, and start thinking about how to make the project work for YOU. Here are five ways you can do that.

Hail Mary Cash Grab

The project is bleeding money for the company. After years of development, things still seem to be going nowhere. Senior management is on the chopping block if they can’t deliver by the end of the year. Everything seems completely hopeless. What does the company do?

Do they recognize everything they’ve invested as sunk costs, fold their losing hand, give up on the current project and try something new? Of course not! There’s still the belief that after so much research and development, the entire project’s just one more final push away from being a success. Plus there are egos to be managed, the huge team working on the project can’t all be laid off at once lest the company’s stock price suffer, and corporate executives are embarrassed they spent so much on a sinking ship and aren’t ready to admit it to their golf buddies yet. So what do they do?

Like every quarterback of a losing team with the clock running out, they throw a Hail Mary pass and hope for the best. And when corporate Silicon Valley throws a Hail Mary, they go ALL IN. Spend another $100 million to recruit new employees in a last ditch effort? Of course! The project isn’t failing because it’s unfeasible or doesn’t fit the market; no, it’s failing because the right talent hasn’t been there, and it takes a lot of compensation to put the right talent in place.

Plus, at this point, word has gotten out about how f*$ked the project is, and no one wants to work on it. To compound the problem, many of the existing employees are jumping ship. How does a company draw that valuable talent over and convince them to work on a raging dumpster fire of a project?

By offering them insanely above market rate salaries, of course. Joining a “sinking ship” project may be one of the easiest cash grabs in Silicon Valley. Your new job may not be around in 9 months, but by then they’ve already given you an insane upfront signing bonus, and that plus the severance is already enough to put you into a new tax bracket for the year. By the time you’re a few years into your career, this becomes one of the best reasons to join a sinking ship project. I know highly talented engineers who have a habit of joining sinking ship projects, locking in their signing bonus upfront, working for a few months before things go under and they get laid off, collecting a bit of severance, and immediately joining another sinking ship that offers yet another upfront signing bonus.

The two keys to successfully navigating the Hail Mary Cash Grab are: 1) don’t do it too often, or the stench of failure will start seeping into your bones and you’ll forget how to work on a successful tech project, and 2) like a high priced escort, always make sure you get that signing bonus upfront. Generally, the signing bonus comes with some stipulation stating that the entire amount must be paid back if the employee leaves voluntarily, but that won’t matter when they inevitably cancel the project a few months’ later. In some cases, if the signing bonus is high enough, instead of laying you off, the company will shift you onto their most successful product line that desperately needs more manpower. That ends up being a great backdoor way of getting onto the most visible projects.


Young engineers working at big tech companies are often stuck in a difficult Catch-22: in order to learn more skills and advance their career, they need to jump to a different company to be exposed to new technologies. However, no other company will hire them because they lack skills. Meanwhile, they’re stuck doing a limited amount of basic work, pigeonholed into a role with no growth and performing the same repetitive work everyday.

The good news is this often isn’t true on a sinking ship project. As engineers start to leave, they pass on their responsibilities to the remaining team members, often the junior engineers on the team. Before leaving, there’s usually a one week period when the departing engineers pass their knowledge on to the brave souls going down with the ship. That knowledge can be extremely valuable to young engineers just getting their start in the industry. After a few weeks’ taking on the new work, the young engineer suddenly has new skills to put on his or her resume.

Sometimes, things get so intense on a shipwrecked project that junior engineers are placed into a room with more senior employees to work in a “War Room,” where all sorts of gating obstacles are fixed. There’s often no better place for a young techie to learn new skills.

Failing Upwards

You might be a perfect fit for a management role, but at your current job there are a bunch of senior employees older than you. They’re next in line for any management openings, and you’ll just have to wait your turn. You start to investigate opportunities at other companies, but everywhere you look, there are older employees already queued up for management positions.

Why not join a sinking ship project and wait for the other managers to jump ship until the company has no choice but to let you lead things? Boom! Now you have management experience on your resume, and you’ve shown the senior executives in your company that you can handle a leadership role. I’ve seen this happen enough times to wonder if half the managers in Silicon Valley were promoted this way.

Foxhole Friends

Think about your closest friends. Chances are you didn’t meet them over oysters and caviar. In fact, they were probably the people who stayed up late studying for finals, sharing Instant Ramen, two dollar slices of pizza, and cheap beers with you. There’s something about facing adversity that bonds people together. Maybe that’s why folks in Silicon Valley make most of their close friends before they turn 30: by that age, they’ve already achieved some level of professional and financial success, and their lives don’t have enough adversity to help them bond with others.

Like the tribulations of eating ramen and drinking Natty Light, working on a failing tech project can bring people closer together. For younger employees, complaining about the shitty codebase, inept management, and desperate attempts by HR to convince everyone that everything’s fine is one of the quickest ways to make new friends (in fact, at my first job, one of my best friends and I first started socializing over these complaints). For older employees, complaining about the same leads to new opportunities as everyone leaves the sinking ship. There’s something about being in a “War Room” trying to hit a seemingly impossible deadline with a group of engineers that makes everyone seem better at their jobs than they really are. you can make a lot of deep professional connections and friendships in a sinking ship, leverage these benefits accordingly.

“What Happened”

Hillary Clinton’s mea culpa cum cathartic release about losing the Presidential election, “What Happened”, dominated bestselling book lists in 2017. Start-up founders around the country organize Fuck-Up Nights to discuss what went wrong at their failed business ventures. Talking about your most embarrassing moment over beers with friends is a surefire way to have some good laughs. Clearly, there’s a lot to be learned and even enjoyed from failure.

If nothing else, working on a sinking ship project will teach you what NOT to do, and give you some good stories to tell to your friends, future colleagues, and even solid talking points at future job interviews.

There’s no place in the world that embraces failure quite like Silicon Valley. The region’s ability to quickly move on from failure has allowed it to innovate faster than anywhere else. Failure is so accepted here that from time to time, it makes sense to go fail on purpose. Out here, even on a sinking ship, you can still feel like the king or queen of the world.

About the Writer: Leon D worked in technical, marketing and sales roles in various tech companies. Passionate about GPU design, Blockchain, and Machine Learning. Avid surfer. 6ers fan.

About the Editor: Jason Weber is a Director at Wiseflow Ventures. He’s built several profitable companies in SaaS, IT Consulting, and Corporate Housing, and has worked at top tech firms including Amazon, Hewlett-Packard, and Intel. He holds four issued patents and is passionate about practical Zen, the Flow State, high-tech, and the hustle.