PDF Summary:Leveling Up, by Ryan Leak

Most people want to advance in their careers and grow as individuals, but many struggle to identify concrete steps toward improvement. In Leveling Up, Ryan Leak offers a framework for personal and professional growth centered on self-reflection and feedback from others. He presents twelve guiding questions designed to help you define success on your own terms and identify areas for development.

Leak explains how to build the internal foundations needed for growth, including self-awareness and intentional time management. He discusses why accepting change and taking calculated risks are essential for advancement, and he provides practical strategies for learning from failure. Throughout, Leak emphasizes the importance of seeking honest feedback from trusted advisors and aligning your daily actions with your long-term goals.

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(Shortform note: Choosing a word to describe who you want to become can help you elevate yourself because it gives your mind a simple cue to filter your experiences. For example, if you choose the word “supportive,” you’ll start to notice situations where you can be supportive. This happens because your brain is always looking for patterns and meaning. When you give it a word, it starts to see that word everywhere. Over time, you’ll start to treat situations that match your word as more important and worth acting on.)

Another key principle is to accept change and take risks. Leak explains that the planet is changing at an unprecedented pace. Those who thrive are those who adapt, take carefully assessed risks, and keep trying after failure. Change is exhausting, though it's less difficult when you acknowledge and confront it directly. To transition from your current position to your desired one, you'll have to take a risky step. Leak elaborates that risk-taking can result in failure. The severity of your failure depends on how risky the move you made was, so assess it before you jump in.

(Shortform note: In Scarcity, Sendhil Mullainathan and Eldar Shafir explain that people who live in chronic financial scarcity have little to no slack. This means that a small setback, like a fee, a loss of income, or an unexpected bill, can immediately threaten their ability to pay rent or buy food. For people in this situation, the advice that you “have to take a risky step” to move from your current position to your desired one may not apply. The potential downside of a risky move is too great.)

Record the most unfavorable outcome. If it seems manageable, what's stopping you from risking a positive outcome? If you fail, determine what didn't go as planned. Did you incorrectly evaluate the risk? Did you not execute it well? Were you missing a vital ability? What will you change going forward? Leak notes that our greatest risks and worst mistakes are often related to the people we choose to trust. But a single negative encounter mustn't prevent us from ever placing our faith in people again. People will let you down, yet they'll also surprise you. You’ll be sorrier for not supporting someone than for doing so. So, try something new and be willing to learn from the results. Failure occurs only if you fail to gain insight from your mistakes.

(Shortform note: While Leak encourages us to keep placing our faith in people, this can be dangerous in certain situations. For example, if you’re in a relationship with someone who repeatedly uses your trust to override your boundaries or dismiss your “no,” you may find yourself in a pattern of escalating emotional, financial, or physical harm. In these cases, treating each incident as a single negative encounter and continuing to “support someone” and “place your faith in people” can entrench you in a cycle of abuse.)

Let’s look at some internal foundations and the importance of intentional momentum.

Internal Foundations

Let's examine some internal foundations. Leak explains that being self-aware is a key internal foundation for success. This is the ability to recognize your strengths, weaknesses, and the effect you create for others. Being self-aware is rare because most people think they have it, though they actually don't. In fact, the more convinced you are of your self-awareness, the less likely you actually possess it. This understanding may assist you in improving your relationships and moving toward becoming your ideal self.

To become more self-aware, start by reflecting on what others experience in your presence. Consider this from different perspectives and accept that it won't necessarily be positive. Then, ask others for honest feedback about how it feels to engage with you.

When Feedback Backfires

Leak’s advice to ask others for honest feedback about how it feels to engage with you can be helpful, but it can also backfire if you’re in an unsafe environment. In Thanks for the Feedback, the authors explain that feedback is never just about you—it’s also about the person giving it. If you ask for feedback from someone who’s invested in keeping you small, or who’s abusive, you may end up internalizing their distorted view of you and moving further away from self-awareness. The authors suggest that your job is to sort feedback, not just accept it. If you’re in a situation where you can’t trust the feedback you’re getting, it may be more helpful to focus on your own self-reflection and seek out feedback from people who have your best interests at heart.

Intentional Momentum

Let's explore why intentional momentum matters. Leak explains that being intentional about how you use your time enables you to reach your goals. Failing to organize your schedule means you won't reach your objectives. If you fail to respect your time, others won't either. It's essential to be mindful about your use of time because it’s limited. Most people assume they'll carve out time for the important things, but life doesn't work that way. We often have lofty aims but an unmanageable schedule without room to accomplish them.

(Shortform note: The idea that you must organize your time to reach your goals is a relatively new one. In Pressed for Time, Judy Wajcman explains that the Industrial Revolution changed how we view time. Before the rise of factories, people worked at their own pace, but the industrial workplace required them to work at a set pace. This led to the idea that time is a limited resource that must be managed. The digital revolution has further changed how we view time. The rise of the internet and smartphones has made it possible to work from anywhere, at any time. This has led to the expectation that we should be available 24/7, and that we should be constantly productive.)

We must create space in our schedules for what we delay doing, for our education and self-growth, and for the individuals who matter most to us. We should also carve out time for ourselves. We need to prioritize our physical and mental well-being—and ensure our schedules align with this. To manage your time better, Leak suggests examining your calendar to see where you can cut back and identify priorities that need scheduling. Review your agenda for the previous month. Break down your time usage, then determine what wasn't needed. Which time-wasting activities were under your control? What could you discontinue? Next, determine what was absent. What do you wish you’d spent more time on? What actions could you start taking? The exercise aims to create a perfect schedule to help you achieve your objectives, taking into account what's feasible for you.

How Mental Contrasting Can Help You Stick to Your Schedule

In Rethinking Positive Thinking, Gabriele Oettingen explains that when we compare our current reality to our desired future, we’re more likely to take action to achieve our goals. This is because we’re more aware of the gap between where we are and where we want to be, which motivates us to bridge that gap. When you review your calendar and identify time-wasting activities, you’re engaging in a form of mental contrasting. You’re acknowledging the reality of how you currently spend your time and contrasting it with how you wish you spent your time. This process helps you become more aware of the obstacles that prevent you from achieving your goals, such as procrastination or poor time management. By identifying these obstacles and creating a plan to overcome them, you’re more likely to follow through with your new schedule. You’re not just indulging in positive fantasies about how you’d like to spend your time; you’re taking concrete steps to make those fantasies a reality. This approach is more effective than simply imagining a better future without considering the challenges you’ll face along the way.