Hello fellows. Let’s talk about dilemmas.
If you find yourself stuck in dilemmas on a regular basis, you are rarely “thinking deeply.” You usually use better vocabulary when you procrastinate. You postpone the decision into the future because a part of you is afraid that choosing a direction means losing all other directions, and with it, losing safety, approval, or control.
In leadership, that pattern is expensive. Not because every decision is critical, but because indecision becomes culture. Your team watches how you move, then copies your pace. If you freeze, they learn freezing is acceptable. If you move, they learn that movement is normal.
Here’s the uncomfortable truth: a dilemma is not a sign of sophistication. A dilemma is a stuck moment. It’s the moment where your current patterns don’t give you a clear answer, so you hesitate, you overanalyze, you seek more input than you need, you try to eliminate uncertainty that cannot be eliminated.
Stoicism has a clean lens for this. Control is small, outcomes are not. What you control is your judgment in the moment, your choice, your action, your reaction, and your willingness to learn. The rest is weather.
So the question is not, “How do I avoid wrong decisions?” The question is, “How do I stop treating normal decisions like irreversible life events?”
Why dilemmas are dangerous for leaders
A leader’s job is not to be right all the time. A leader’s job is to keep the system moving, to create clarity, to shorten feedback loops, to prevent paralysis from spreading.
When you get stuck, you also teach your nervous system a lesson: “This is scary.” The next time, it becomes scarier. That’s how a single hesitation becomes a habit.
You can see this everywhere in tech. Planning meetings that turn into debate marathons, not because the stakes are high, but because nobody wants to be the person who commits. Content creation is the same game in different clothes. You don’t post because you’re “optimizing timing,” you’re avoiding the discomfort of being seen. The dilemma is a disguise.
And the longer you sit in it, the more choices you imagine, the more drawbacks you discover, the harder it becomes to pick one. That’s the fallacy of choice at work; optionality feels safe until it becomes a cage.
My stance: avoid the dilemma state
My core idea is simple: a leader should avoid being stuck in a dilemma. Ideally, you enter the situation, you decide, you move on.
Not recklessly, not impulsively, not “gut feeling because I’m special,” but decisively within sensible guardrails.
Here are the guardrails I use:
If the decision does not severely harm you or others,
if it does not risk an unrecoverable financial hit,
if it does not create irreversible damage to trust, reputation, or safety,
Then it’s a decision you can make fast.
Make it, then learn.
This is where Stoicism becomes practical. Your control is the choice and your conduct, not the outcome. You cannot fully control the consequences; you cannot even meaningfully influence it. What you can control is how quickly you observe what happened, how honestly you reflect, and how cleanly you adjust the next time.
Decision, action, consequence, reflection, adaptation. That cycle never ends, and that’s good news, because it means you don’t need perfection; you need repetition.
Over time, repetition becomes pattern recognition. You build a mental library. “Ah, this type of call again.” What looked like a dilemma last year becomes obvious this year, not because you became magically smarter, but because you earned the pattern through decisions, including failures.
A Tony Robbins-flavored angle: decisions create identity
Tony Robbins has a very direct approach to this topic. His whole energy is built around one principle: your life changes when your standards change, and your standards show up in your decisions. He pushes people away from “let me think about it” and toward “decide who you are going to be.”
That’s why his style often sounds like, “Stop negotiating with yourself.” Not because nuance is bad, but because endless negotiation is a coping mechanism.
A simple Robbins-aligned example that fits leadership: imagine you’re debating whether to address a recurring delivery problem with a senior engineer who keeps missing expectations. You can call it a dilemma and spend three weeks collecting more “context,” or you can decide: “I’m the kind of leader who protects the team’s reality.” Then you schedule the conversation, you speak clearly, you keep it respectful, and you move.
The fear is rarely the conversation. The fear is the identity shift, from colleague-with-responsibility to leader-with-standards.
Robbins would say: you don’t wait for confidence, you build confidence by acting in alignment. Stoicism would say: do what is yours to do, then accept what follows. Same direction, different language.
Tech leadership example: sprint planning isn’t a life decision
Let’s ground this in a very boring, very real tech example: sprint planning.
(btw I don’t like sprints at all as a method; but I know many of you have those implemented 😀)
Even if you do it weekly, the decisions you make during sprint planning are usually not severe. It’s a one-week bet. On a long enough timeline, that first week disappears, and you adjust.
That’s the key. Many leadership decisions are reversible, or at least correctable. The earlier you get feedback, the earlier you can course-correct, and the less emotional weight the decision should carry.
If you treat a one-week planning call like a permanent tattoo, you’ll get stuck. If you treat it like an experiment with feedback, you’ll move.
The stoic move: focus on what you control, then move
Here’s the operating system I want you to practice:
Control your judgment, then choose.
Act, don’t ruminate.
Observe consequences without drama.
Accept the emotional wave (regret, irritation, doubt), without obeying it.
Reflect, extract the lesson, update your pattern.
Repeat.
This is what experienced CEOs and CTOs are doing when it looks like “easy decisions.” They aren’t lucky. They’re trained. Their experience is not passive observation; it’s active decision-making plus honest review over the years.
And because leadership is always watched, your decision speed becomes your team’s. Your calm becomes their calm. Your courage becomes their permission.
Takeaway
Avoid the dilemma state. If it’s not a severe, irreversible decision, decide and move.
If you want a rule of thumb, you can actually use tomorrow:
If it’s reversible, decide fast.
If it’s irreversible, slow down, get counsel, and still decide.
If you keep calling it a dilemma, ask yourself what you’re protecting: comfort, identity, approval, or control.
Your job is not to eliminate uncertainty; your job is to move the system forward under uncertainty.
See you next time. Goodbye everyone.
—Adrian
