The Strategic Art of Half-Assing (And Why Your Team Needs It)
When to deliberately take the quick path && how to do it without career damage
Perfection is the enemy of progress. In fast-paced engineering environments, the pursuit of perfection will bury you under a mountain of unmade decisions and unshipped features.
Here's an uncomfortable truth: sometimes you need to do a half-assed job. Contrary to popular belief, half-assing something should not indicate that you're lazy or incompetent. I see half-assing as a tool. And like any tool, it's about knowing when and how to use it.
The Two-Step Rule for Strategic Shortcuts
When you deliberately choose the quick-and-dirty path, you must do exactly two things:
Document the 'why' - Capture your reasoning, constraints, and trade-offs. Write down why you chose the expedient solution over the perfect one. Include what you would have done with more time and resources. Heck, even add the ‘ideal’ approach - what if you had unlimited time and resources? What would you do differently?
Socialize the 'why' - Share this context with your team. Make sure people understand this was a conscious choice, not an oversight. Your future self will thank you when someone asks why you built it ‘this way’ instead of the ‘best way’.
That's it. Two simple post-actions that transform a potentially career-limiting shortcut into a conscious engineering decision that speaks about your ability to make pragmatic engineering choices in an imperfect world full of constraints and hindrances.
Real-World Examples That Work
In my decade+ experience I can recall many occasions where I, or my colleagues, have made such decisions. Here are a few:
Email Monitoring for System Health. In my early days when it wasn’t that easy to just plug in some observability library (e.g. Datadog), building monitoring was a big lift and we didn’t have the time to engineer a proper solution. So, we built a nascent monitoring system: via email. Email isn't the best tool for monitoring – OK, it’s horrible! – but it got the job done while we focussed on building core features. On advice of an experienced colleague, we documented our plans to evolve this into proper tooling later. That allowed others, who joined the project later, to consider us not that crazy.
Shallow Performance Investigation. Due to customer complaints, a colleague had just two days to investigate performance issues. Due to external factors, setting up comprehensive profiling was not viable, so instead she focused on some obvious bottlenecks (i.e. database N+1 queries, lack of indices, data (de)serialization). She found three quick wins that improved the response time by ~30%. This way we showed our customer that we are able to act with urgency, which made them happy and bought us time to invest in proper performance optimizations. Later, when other colleagues jumped on, there was no FUD on the unorthodox way of approaching the performance analysis – they understood the constraints that the original engineer worked within and yet delivered measurable customer impact.
Hardcoded Configuration Values. We hardcoded API endpoints and feature flags directly in the code instead of building a configuration management system. For a very early-stage system this eliminated unnecessary complexity. It was key that we documented which values should become configurable as the system matures, so future colleagues (or ourselves) did not have to lose their minds to figure this out by themselves. .
The Documentation Template That Saves You
When you take a shortcut, use this format to capture context:
Decision: [Brief description of what you built]
Constraint: [Time/resource limitation that drove the decision]
Trade-off: [What you sacrificed for speed]
Evolution Path: [How this could be improved with more resources]
Threshold: [What would trigger an upgrade to the proper solution]
Date: [When this decision was made]
An example:
Decision: Implemented email-based error alerts
Constraint: Two-day deadline to ship monitoring before launch
Trade-off: No real-time alerts, manual email checking required
Evolution Path: Move to Slack/PagerDuty integration with proper alert routing
Threshold: When we have >10 errors/day or need 24/7 response
Date: March 15, 2024The Socialization Playbook
Documentation is not enough – it must be socialized.
Immediate Team Communication need not be fancy. Just share your decision in the next standup or team sync. Use this script: "I implemented [solution] for [problem]. I chose the quick path because [constraint]. Here's how we could improve it later: [evolution path]."
Slack/Team Chat Updates can take the same format, just post in your team channel: "Shipped the monitoring solution using email alerts. Quick context: [constraint] led me to choose this over [ideal solution]. Planning to upgrade when [threshold]. Questions welcome!"
In the codebase you can add comments directly in the code. I would suggest adding them near the top of the file so it’s easy for others to gain the context when opening the file:
# STRATEGIC_SHORTCUT: Using hardcoded values for v1 launch
# Context: 3-day deadline, 5 total config values
# Evolution: Move to config service when we have >20 values
# Decision date: 2024-03-15
API_ENDPOINT = "https://api.example.com"Another very solid alternative is to actually use the Git history of the project. A good approach that I like to point people to is The Linux Kernel’s guideilnes on how to submit patches, which includes a guide on how to use Git commit messages to share context on the changes. It’s a perfect and extremely cheap way to keep the context of how the code evolves, without needing any supporting documentation or software.
ADR (Architecture Decision Record)
For bigger shortcuts, write a brief ADR:
ADR-042: Email-based monitoring for MVP
Status: Active
Context
Need monitoring for launch in 2 days. Full observability stack would take 2 weeks.
Decision
Implement email alerts for critical errors. Check inbox twice daily.
Consequences
Pros: Unblocks launch, catches critical issues
Cons: No real-time response, manual process
Evolution: Migrate to proper alerting when team grows to 5+ engineers
When NOT to Half-Ass
Strategic shortcuts aren't appropriate everywhere. Avoid them for:
Security implementations - Never cut corners on authentication, authorization, or data protection. Security debt compounds dangerously. Security issues have a wide blast radius – when it explodes it can be fatal to the business.
Data integrity systems - Database schemas, backup procedures, and data validation logic need careful design. Recovery from data corruption is always more expensive than prevention.
Public APIs - External interfaces become contracts. Half-assed API design creates permanent technical debt that affects every consumer. I always like saying “APIs are forever, once it’s out in the wild you can’t bring it back home”.
Critical path dependencies - If other teams depend on your component, invest in proper implementation. Your shortcuts become their blockers.
The Communication That Makes It Work
When you ship the quick solution, be explicit about your trade-offs. Tell your team: "I had two days to solve this monitoring problem, so I built an email-based solution. Here's how we could improve it with more time, and here's why the current approach is sufficient for now."
This transparency prevents future confusion and demonstrates thoughtful decision-making under pressure. It shows you understand the difference between optimal solutions and practical ones.
Create a shared document or wiki page tracking these decisions. Include the threshold conditions that would trigger upgrades. This becomes a living roadmap of technical improvements tied to business metrics.
Remember: your future self is part of your team too. Document decisions so you can remember your reasoning six months later when the constraints have changed and the quick solution needs evolution.
Making Shortcuts Strategic
The difference between strategic half-assing and poor engineering is intentionality. Strategic shortcuts advance your goals within real constraints. Poor engineering ignores constraints and creates unnecessary technical debt.
Before taking a shortcut, ask: "What would I build with unlimited time?" Then ask: "What's the minimum that solves the current problem?" The gap between these answers is your strategic shortcut.
Strategic half-assing isn't about lowering standards. It's about being honest about trade-offs and communicating context so your team can make informed decisions about when to improve, iterate, or leave things as they are.
Engineering leadership means making tough calls about resource allocation and technical trade-offs. I share frameworks for navigating these decisions every week—practical approaches that work in real engineering environments, not theoretical perfection.
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