The "Why I want to leave" list
A Professional's guide to self-awareness
We've all been there - that moment when we realize our current professional situation isn't quite what we hoped for. As a seasoned professional, I've developed a practical approach to tracking my job satisfaction and organizational health: the "Why I want to leave" list.
Every time I join a new company, I start with a blank document titled "Why I Want to Leave." Counter-intuitive? Perhaps. But this list serves a dual purpose - it not only tracks potential issues but also becomes a powerful input for setting my objectives as an engineering manager. The list begins completely empty, a fresh canvas waiting to be filled. As I encounter issues that concern me or areas that could be improved, I document them one by one. The goal isn't to compile reasons to quit, but rather to build a backlog of problems that need solving and improvements to make. Each item becomes a potential objective I can tackle in my role. If I can address these issues faster than new ones arise, I know I'm making meaningful progress. However, if the list grows faster than solutions appear, it helps me prioritize where to focus my management efforts or indicates that a broader organizational change may be needed.
This list also serves as a barometer for measuring organizational health and improvement over time. In an ideal scenario, issues get resolved and the list maintains a manageable length as the company demonstrates its commitment to positive change. However, if the list grows uncontrollably despite efforts to address concerns, it might signal a fundamental misalignment between my values and the organization's direction, or indicate insufficient organizational will to tackle systemic problems. Even in such cases, the list remains valuable as it provides concrete talking points for exit interviews and helps articulate specific reasons for seeking new opportunities. This documentation can offer valuable insights to the organization about areas needing attention, potentially benefiting those who remain.
What Goes on the List?
There's no limit to what you can add to this list. It can include inefficiencies, behaviors that don't align with your values, tools/techniques/technologies you believe are hampering your team or company's progress, or really anything that gives you pause. The act of writing things down often brings clarity. You may find that some "issues" that seemed significant in your mind appear less important once documented, or that you were reacting emotionally rather than rationally to certain situations. This reflection process helps you filter the list to what truly matters.
Additionally, documenting concerns this way helps distinguish between issues within your sphere of influence versus those beyond your control. As a true stoic1, marking these separately is crucial. Focus your energy on what you can change, while maintaining perspective on what you cannot.
The list typically covers various aspects of organizational health. Here's what it might include:
Technical challenges
Architecture disagreements (monolith vs. micro-services)
Technology stack conflicts (Ruby vs Elixir)
Code quality issues
Technical debt
Test coverage problems
Cultural issues
Split culture
Lack of leadership clarity
Communication barriers
Accountability gaps
Team collaboration challenges
Process problems
Inadequate development practices
Poor deployment procedures
Insufficient quality controls
Unclear standards
Ineffective DevOps practices
Organizational concerns
Departmental silos
Inefficient communication channels
Unclear roles and responsibilities
Poor internal mobility management
Lack of ownership
Insufficient support systems
Making the List Work for You
The true value of this list lies in its nature as a living document that evolves with your journey:
Regular Grooming: Review and refine the list frequently, removing items that are no longer relevant
Personal Objectives: Transform applicable items into concrete goals you can work towards
Manager Discussions: Use selected items as conversation starters with leadership
Progress Migration: As you solve issues, move them to your brag document as accomplishments
Pattern Recognition: Look for recurring themes that might indicate systemic issues
Impact Assessment: Track which items you can influence versus those requiring organizational change
Success Measurement: Monitor how effectively items move from concerns to achievements
Conclusion
The "Why I Want to Leave" list isn't about finding reasons to quit - it's about maintaining professional self-awareness and driving positive change. When used correctly, it can be a powerful tool for both personal growth and organizational improvement. However, if you find yourself adding items faster than you or the company can address them, and your attempts to influence change are consistently blocked, it might be time to consider new opportunities.
Ready to start? Download our simple “Why I want to leave” template and begin documenting your journey to success!
Remember: The goal isn't to compile an exit strategy but to create a blueprint for improvement. Sometimes you can be the change agent your organization needs; other times, you need to recognize when it's time to move on to an environment more aligned with your professional values and aspirations.
What's your experience with tracking organizational challenges? How do you decide when to fight for change versus when to seek new opportunities?