Leverage Maps: Mental Models For Making Systems Move
Chapter 2 – Playing the Right Game
Most career advice focuses on building skills, optimizing tactics, or working harder. But what if the real advantage comes from choosing the right arena in the first place? Your struggles may not be about your innate capability or lack of domain experience. Your struggles might be related to the poor environments that you put yourself in. This chapter explores honest assessments, strategic positioning, and transferrable skills that come from varied work experiences.
Don't Lie to People (or Yourself)
I once worked with a colleague who led a project I was on. There were missed deadlines, confused stakeholders, and our manager became increasingly frustrated. Everyone could see it, but no one said anything because we all hoped that it would resolve itself. After a delayed feature deployment, I privately asked him if he wanted honest feedback. I told him that we kept doing more and more rework because the project requirements were unclear. It was uncomfortable. But three months later, he thanked me after he adjusted his client communication approach and rebuilt trust with the stakeholders.
Leverage Map 2.1: Act on reality to avoid self-deception.
Self-deception operates like a slow leak in your cognitive system. You might function day-to-day even though the distorted information gradually undermines your decision-making. Eventually, small problems become catastrophic failures. If we modify our behavior after confronting uncomfortable truths, we avoid the costs of self-deception.
Three Lies We Tell Ourselves
Engineers blame 'unrealistic timelines' for delays when the real issue is estimation skills they haven't developed. They blame open offices for inability to focus while scheduling their hardest work during low-energy afternoons. They label coworkers 'difficult' instead of examining their own impatience with different communication styles.
Patterns of self-deception are tough to see, but you can spot them in yourself by using question/answer loops (LM 1.3): Ask what role you played in past frustrating situations, and watch for recurring themes.
How To Effectively Give Constructive Feedback
Clarity is kindness. The same honesty you need with yourself applies to others, but giving feedback externally requires reading the situation. Once you decide to give feedback to another person, here is how to do it more effectively:
Assess capacity for feedback: Is this person in learning mode or survival mode? Someone overwhelmed with deadlines can't process developmental feedback effectively.
Consider your relationship: Do you have enough trust built up to weather potential defensiveness?
Frame for growth and not criticism: "I think your analytical skills could have more impact if you presented findings differently" works better than "Your presentations are confusing."
Choose your moments: Right after a success, people are more open to improving further. Right after a failure, they're often too defensive to hear clearly.
Follow through with support: Offer to help with solutions instead of just pointing out problems. "Would it help if we practiced your next presentation together?"
People remember who gave them useful feedback when it mattered. Years later, they'll bring you into bigger conversations precisely because they trust you to tell them the truth.
Play the Right Game
Where does your combination of strengths create disproportionate value? You may have met a subject matter expert that can debug complex systems faster than anyone. But that person gets frustrated when non-technical stakeholders ask “basic” questions. On the other hand, you may know an engineer that struggles with the more advanced technical work but thrives in the ambiguous space that is requirements engineering and anticipating business needs. Neither is better. They've just found the right game for their own strengths.
Finding Your Optimal Game Environment
Leverage Map 2.2: Find your optimal game environment.
To find your optimal environment, consider your energy patterns, flow states, friction points, and source of results. Notice the work that feels effortless and the work that requires willpower. Observe the kinds of problems that consume your attention. Reveal misalignment by finding what consistently drains you. Pinpoint the specific actions that bring you the most results and the portion of the time you spend doing them.
Burnout And Mismatched Environments
Leverage Map 2.3: Burnout warning signs due to a mismatched environment.
A bad environmental fit makes burnout more likely to occur. When you’re in an environment that does not play to your strengths, watch out for some of the following burnout warning signs. Your results may decline even if you are working harder. Your clarity of mind and attention span decreases. You need coffee and hard deadlines to get work done that used to feel enjoyable. Your workplace relationships require significant effort to maintain. Although burnout isn’t always caused by a bad environment, it can be a triggering factor. If you are noticing burnout symptoms, gradually work towards making your job more aligned with your strengths as possible.
Valuable Nonlinear Experience
Leverage Map 2.4: Accumulate transferable skills.
The standard career advice is to follow a linear progression: pick a field, build expertise, climb the ladder. But this model breaks down when industries shift rapidly and interdisciplinary skills become valuable. For example, my work history spans everything from manual labor to financial markets to embedded systems to blockchain development. On paper, it can look chaotic. In practice, it's been building something that’s hard to replicate: an interdisciplinary perspective on how systems actually work.
The value of nonlinear experience varies, but frequent areas of value include system literacy from working across different domains. You learn to spot dysfunction, identify leverage points in your role, and navigate organizational dynamics that specialists would miss. Moving between contexts develops communication skills that allow you to explain complex ideas to different audiences, which can bridge communication gaps. Frequently changing contexts forces you to develop efficient learning strategies and quickly identify what matters most in your work. Also, diverse experience builds your self-confidence in that you can figure things out even when you feel you are a bit out of your depth. To identify the value in your experiences, you can do the following. Consider all of your past experiences, note any skills or talents that you gained, and look for recurring themes or patterns that are common across industries.
To identify the value in your own experiences: inventory every significant role without filtering, extract the meta-skills you developed about how systems and people actually work, then look for recurring themes that transcend specific industries.
📘 Leverage Summary
Chapter 2 – Playing the Right Game
Key Insight: Your advantage compounds when you choose the right environment. Either change your environment accordingly or improve your environmental fit over time.
System Maps:
Leverage Map 2.1: Act on reality to avoid self-deception.
Leverage Map 2.2: Find your optimal game environment.
Leverage Map 2.3: Burnout warning signs due to a mismatched environment.
Leverage Map 2.4: Accumulate transferable skills.
Diagnostic Questions:
- What feedback would I or others around me benefit from hearing?
- When did effort feel effortless and results compound naturally?
- What patterns do I see across my "failed" or frustrating experiences?
- Am I honest with myself about what energizes versus drains me?
- How does my unique combination of experience create value that others can't replicate?
- If you could snap your fingers, what role would make the most out of your unique combination of work experiences?
Action Steps:
- Identify one area where you've been avoiding an uncomfortable truth about your situation, skills, or environment. Ensure you have emotional distance from recent events before doing this assessment
- Do an energy and results audit on yourself for two weeks. Consider what is realistically changeable.
- Practice articulating the value of your diverse work experience in different contexts: