Working at A Failing Startup

A Guide to Dealing With Professional Uncertainty

Patrick Karsh
5 min readAug 31, 2023

Throughout various junctures in my career as an engineer within startup environments, I have found myself situated in circumstances where the inevitable failure of the company was evident to all stakeholders. The question at hand was not whether the company would fail, but rather a matter of when this unfortunate outcome would transpire.

Undoubtedly, this is an unfavorable situation, and its professional implications can be significantly stressful. Below, you’ll find several strategies aimed at helping you maximize the utility of the time you have remaining within a company that is on the brink of failure.

In the dynamic world of startups, not all journeys end in triumph. Some startups find themselves sailing through stormy seas, their survival hanging by a thread. If you’re a mid-level to senior employee in a startup that seems destined for failure, your experience and leadership become invaluable assets. This article delves into the unique challenges of steering a ship that’s headed for troubled waters and provides actionable insights for senior employees to navigate the uncertain terrain.

The Weight of Leadership Amidst Uncertainty

As a mid-level to senior employee, you are not just a cog in the wheel but a pivotal force that can influence the startup’s trajectory. The burden of leadership during trying times is immense. Your actions and attitude set the tone for the entire team. It’s your responsibility to exemplify resilience, dedication, and a level-headed approach. As the storm clouds gather, your experience becomes a lighthouse guiding the team through the tempest.

Strategic Input as a Lifeline

The startup ship may be sailing into a storm, but that doesn’t mean it’s beyond rescue. Your experience positions you to provide a lifeline in the form of strategic input. Leverage your industry insights and familiarity with the startup’s operations to offer well-informed recommendations. In these critical moments, your guidance can chart a new course, suggesting potential pivots, optimizations, or shifts that might just steer the startup away from the brink.

Collaborative Survival: Navigating as a Team

Navigating a sinking ship requires all hands on deck. A senior employee’s role extends beyond their immediate team to fostering collaboration across the organization. Initiate cross-functional dialogues that encourage team members to share their perspectives and insights. In these collaborative discussions, innovative ideas often surface, providing a ray of hope. Your role is not just to offer solutions but to create an environment where collective problem-solving thrives, potentially unearthing the spark that reignites the startup’s journey.

Leveraging Strengths for a Lasting Impression

In the face of failure, it’s easy to lose sight of what the startup does best. Your insight as a senior employee can illuminate the startup’s core strengths and unique selling points. By focusing on these strengths, you can craft a survival strategy that capitalizes on what sets the startup apart. The goal is to leave a lasting impression on the market, even if the startup’s journey ultimately takes an unexpected turn.

Communicating Amidst the Turmoil

Effective communication becomes a lifeline in times of crisis. While uncertainty might cloud the horizon, transparency can provide clarity to the crew. As a senior employee, you play a crucial role in fostering an environment of open communication. Encourage leadership to share updates and plans with the team, building a foundation of trust that steadies nerves as the startup sails through choppy waters.

Allocation in the Face of Scarcity

The startup’s resources are limited, and your experience becomes instrumental in making the most of what’s available. Your role involves assessing the potential impact of various projects and initiatives and aligning them with the startup’s dwindling resources. Resource allocation becomes a strategic dance, ensuring that every move contributes to the startup’s survival and potentially sets the stage for a resurgence.

A Beacon of Hope in External Relationships

Networking isn’t just about career advancement; it can also be a lifeline for a startup on the brink. Leverage your professional connections to explore collaboration opportunities, partnerships, or alliances that could provide a much-needed infusion of support. As a senior employee, your relationships could offer a glimmer of hope when the startup’s future seems uncertain.

Strengthening Through Adaptation and Upskilling

When a startup is headed for failure, adaptation is often the only way to survive. Your role as a senior employee involves identifying skill gaps within the team as the startup pivots or shifts its strategy. Suggest reskilling or upskilling initiatives that equip the team with the tools needed for the new direction. This not only strengthens the startup’s chances but also showcases your commitment to your team’s growth.

Weathering the Storm and Personal Resilience

The storm isn’t just external; it affects you personally. The challenges you face as a senior employee navigating a startup’s likely failure can take a toll on your emotional and mental well-being. It’s paramount to prioritize self-care. By taking care of yourself, you ensure you’re equipped to guide the team with clarity, empathy, and resilience.

Navigating Uncharted Waters: A Heroic Journey

In the end, leading through a startup’s impending failure is nothing short of a heroic journey. As a mid-level to senior employee, your experience, strategic thinking, and leadership skills take center stage. The ship might be headed for rough waters, but your guidance can shape how the crew responds. By embracing the challenge, staying adaptable, and exemplifying unwavering determination, you might just be the force that guides the startup through uncharted waters and, against all odds, helps it find a way to chart a new course toward success.


Facing the prospect of a startup’s failure is a daunting challenge. However, as a mid-level to senior employee, you possess the qualities needed to navigate through these troubled waters. By providing strategic input, fostering collaboration, leveraging strengths, and communicating transparently, you can lead your team with purpose. The storm may rage on, but your experience can be the lighthouse that guides the startup to safer shores. Remember, your role isn’t just about managing through uncertainty; it’s about leaving an indelible mark on the startup’s journey, regardless of the final destination.



Patrick Karsh

NYC-based Ruby on Rails and Javascript Engineer leveraging AI to explore Engineering.