I picked up Lives of the Stoics by Ryan Holiday during one of the most intense stretches of my career — three concurrent projects, midnight deploys, and the kind of scope creep that makes you question every life decision that led you to engineering.
The book was not a self-help manual. It was a collection of biographies — real people who lived through war, exile, political chaos, and personal tragedy — and still managed to show up, do the work, and act with integrity. Reading about Epictetus writing philosophy while enslaved, or Marcus Aurelius governing an empire during a plague, made my production hotfix at 2 AM feel remarkably manageable.
Here is what stuck with me, and how I apply it to building software in startup environments every day.
1. The Dichotomy of Control
"We cannot choose our external circumstances, but we can always choose how we respond to them." — Epictetus
In a startup, the list of things you cannot control is endless:
- The founder pivoting the product direction mid-sprint
- A critical dependency releasing a breaking change
- The client changing requirements after you have already shipped
- AWS having an outage on your launch day
Early in my career, I wasted enormous energy being frustrated by these events. I would vent in Slack, argue in retrospectives, and carry the stress home.
Stoicism taught me a cleaner approach: separate what you control from what you do not, and pour your energy only into the first category.
I cannot control that the requirements changed. I can control how quickly I adapt the architecture. I cannot control that the deploy failed. I can control how thorough my rollback plan is. I cannot control the timeline pressure. I can control the quality of what I ship within that timeline.
This is not passive acceptance — it is strategic energy management. Every minute spent being frustrated about things outside your control is a minute stolen from things within it.
2. Amor Fati — Love Your Fate
"A blazing fire makes flame and brightness out of everything that is thrown into it." — Marcus Aurelius
Holiday writes extensively about amor fati — not just accepting your circumstances, but loving them. Using them as fuel.
The hardest bugs I have ever fixed taught me the most. The ugliest legacy codebases forced me to become a better architect. The tightest deadlines sharpened my ability to cut scope without cutting quality.
In startup engineering, you will inherit terrible code. You will work with incomplete specs. You will deploy on Fridays because the client needs it live by Monday. These are not obstacles to your growth — they are your growth.
Every production incident is a lesson in observability. Every impossible deadline is a lesson in prioritization. Every miscommunication is a lesson in documentation.
The engineer who treats adversity as the curriculum will always outgrow the one who treats it as an interruption.
3. Memento Mori — Remember Your Mortality
"You could leave life right now. Let that determine what you do and say and think." — Marcus Aurelius
This sounds morbid, but in practice it is the ultimate productivity hack. Holiday describes how the Stoics used the awareness of death not to create anxiety, but to create urgency and clarity.
Applied to engineering:
- That refactor you have been postponing for six months? Start it today. You will never have a "perfect" window.
- That junior developer who asked for help? Stop and teach them now. Your knowledge compounds through others.
- That side project collecting dust? Ship it imperfect or kill it. Half-built ideas are just guilt with a GitHub URL.
Memento mori strips away the trivial. It makes you ask: "If this was my last sprint, would I spend it bikeshedding this PR review, or would I ship something that matters?"
4. Premeditatio Malorum — The Premeditation of Evils
"We should project our thoughts ahead of us at every turn and have in mind every possible eventuality instead of only the usual course of events." — Seneca
The Stoics practiced negative visualization — imagining what could go wrong before it happens. Not to create fear, but to create preparedness.
This is the philosophical foundation of every good engineering practice I follow:
- Chaos engineering: What if this service goes down? Let us find out now, not at 3 AM on a Saturday.
- Rollback plans: What if this migration corrupts data? Have the rollback script written and tested before you start.
- Incident runbooks: What if the on-call engineer has never seen this failure mode? Document it before it happens.
- Load testing: What if we get 10x the expected traffic? Let us break it in staging, not in production.
The best engineers I know are not optimists. They are prepared pessimists — people who have already imagined the failure and built the safety net.
5. Sympatheia — We Are All Connected
"What injures the hive injures the bee." — Marcus Aurelius
Holiday highlights how the Stoics valued community and contribution above individual achievement. Marcus Aurelius, the most powerful man in the world, spent his evenings writing reminders to himself about serving others.
In startup engineering, this translates directly:
- Code reviews are not gatekeeping — they are mentorship. Every review is a chance to teach and to learn.
- Documentation is not overhead — it is empathy. You are writing for the engineer who will maintain this at 2 AM, six months from now. That engineer might be you.
- Helping a teammate unblock is not a distraction — it is leverage. A team that ships together outperforms a collection of individual contributors every time.
When I set up CI/CD pipelines and automated testing at Metric, the goal was never just technical improvement. It was about removing friction for the entire team — so everyone could deploy with confidence, not just the senior engineers.
The Daily Practice
Stoicism is not something you read once and absorb. It is a daily practice. Here is what mine looks like as an engineer:
Morning: Before opening Slack, I spend five minutes identifying what I can and cannot control about today's tasks. I write down the one thing that matters most.
During work: When something breaks or plans change, I pause and ask: "Is this within my control? If yes, act. If no, adapt."
End of day: I review what I shipped, what I learned, and what I would do differently. Not with judgment — with curiosity.
On hard days: I remind myself that Epictetus built an entire school of philosophy while physically disabled and formerly enslaved. My deployment pipeline can wait.
Why This Matters for Engineers
Startup engineering is not just a technical challenge — it is a psychological one. The stress, the ambiguity, the constant context-switching — these break engineers long before the code does.
Stoicism does not eliminate the stress. It gives you a framework for operating within it — for making clear decisions when everything is on fire, for staying grounded when the roadmap changes for the third time this quarter, and for finding meaning in work that sometimes feels like an endless cycle of tickets.
Ryan Holiday's Lives of the Stoics showed me that the greatest minds in history faced far worse circumstances than a startup engineering environment — and they did not just survive, they thrived. Not by avoiding difficulty, but by meeting it with discipline, purpose, and an unshakable commitment to doing their work well.
That is the kind of engineer I want to be.