Why Some Goals Feel Effortless (and others hurt) - Chris Bailey

Goals are really predictions in disguise about where your current actions will take you. The key to achieving them isn't making them SMART - research shows that framework is outdated and lacks scientific backing. Instead, align your goals with your core values (like self-direction, security, or achi

March 28, 2026 1h 9m
Modern Wisdom

Key Takeaway

Goals are really predictions in disguise about where your current actions will take you. The key to achieving them isn't making them SMART - research shows that framework is outdated and lacks scientific backing. Instead, align your goals with your core values (like self-direction, security, or achievement) to create natural motivation. When goals connect to what fundamentally drives you, they stop feeling like a chore and start feeling effortless. The magic happens when your daily intentions, plans, and goals all stack up toward expressing who you truly value being.

Episode Overview

Chris Bailey explores the science of intentionality and goal achievement, revealing why some goals feel effortless while others become abandoned. Drawing from academic research and conversations with Buddhist monks, he introduces the 'intention stack' - a hierarchy showing how daily tasks, plans, goals, priorities, and values interconnect. Bailey challenges conventional wisdom about SMART goals and New Year's resolutions, arguing that goals should be viewed as predictions we continuously edit rather than fixed targets. The conversation covers the difference between default (automatic/habitual) and deliberate intentions, the role of values in motivation, and how procrastination stems from the balance between desire and aversion.

Key Insights

Goals Are Predictions, Not Fixed Targets

Every goal is essentially a prediction about where your current and planned actions will take you. When we treat goals as fixed expectations rather than flexible predictions, we set ourselves up for disappointment. The future is inherently unpredictable, so goals need to be edited and adjusted continuously as circumstances change. This reframe helps us hold goals more loosely and adapt them to reality.

The Intention Stack Connects Daily Actions to Core Values

There's a hierarchy of intentions in our lives: present intentions (to-do items), plans (broader than single tasks), goals (medium-term intentions), priorities (what you focus on becoming), and values (fundamental motivations). When these layers align - when tying your shoelaces connects to a plan to run, which supports a marathon goal, which expresses a fitness priority, which reflects your security value - motivation becomes effortless.

Your Twelve Core Values Drive All Motivation

Research by Shalom Schwartz identifies 12 fundamental human values: self-direction, stimulation, hedonism/pleasure, achievement, power, face (how you appear to others), security, tradition, conformity, humility, benevolence, and universalism. Each person has a unique combination of these values at different strengths. Goals aligned with your highest values feel naturally motivating, while misaligned goals create constant headwinds.

Default vs. Deliberate Intentions Shape Your Life

We operate on two types of intentions: default (automatic habits and responses to external triggers) and deliberate (consciously chosen directions based on self-reflection). The gaps between activities - before and after meetings, during walks, in transition moments - are where deliberate intentions emerge if we don't immediately fill them with distractions. Creating space for mind-wandering allows us to tap into our self-reflective capacity.

SMART Goals Lack Scientific Support

Despite their popularity in business, SMART goals (Specific, Measurable, Attainable, Realistic, Time-bound) originated from a non-academic management article and have little research backing. The framework has inherent problems: 'realistic' goals often limit our potential (challenging goals drive better results), and there's redundancy (measurable goals are already specific). The framework survives through cultural momentum, not evidence.

Notable Quotes

"We all have a sort of graveyard of forgotten goals. Every single person on the planet does. And so what is it that actually separates the goals that we're able to achieve and follow through with from the ones that we're not?"

— Chris Bailey

"An intention is just a plan that we're going to do something. And so values are a type of intention. Priorities are a type of intention, right? Because there's something that we plan to be."

— Chris Bailey

"Every goal is a prediction at where you believe your current and your planned actions will take you, right? And so so often those predictions, those goals, which are really predictions in disguise, they turn into expectations for how things will go, which then turn into disappointment when we inevitably aren't predicting the future properly."

— Chris Bailey

"48% of the time that our mind is wandering, it's thinking about the future. So, you know, we're taking a shower, for example, or we're going for a run, we're going for a walk, and we're listening to classical music or something and with a notepad in our pocket and we always unearth ideas."

— Chris Bailey

"If you don't value face, that goal to look a certain way by a certain amount of time, that's not going to be motivating for you. And you're going to find that you have this headwind for the goal all throughout the process."

— Chris Bailey

Action Items

  • 1
    Identify Your Top 3 Core Values

    Review the 12 fundamental values (self-direction, stimulation, pleasure, achievement, power, face, security, tradition, conformity, humility, benevolence, universalism) and identify which 3 resonate most strongly with you. Then audit your current goals to see if they align with these values. Misaligned goals will always feel like a struggle.

  • 2
    Create Intentional Gaps in Your Schedule

    Before and after important activities (meetings, workouts, conversations), build in 5-10 minutes of unstructured time without your phone. Use these gaps to let your mind wander and naturally surface intentions about the upcoming or completed activity. This is when deliberate intentions emerge most easily.

  • 3
    Reframe Goals as Editable Predictions

    For each major goal, write 'This is my current prediction' at the top. Schedule monthly reviews to edit these predictions based on what you've learned and how circumstances have changed. Drop goals that no longer serve you without guilt - they were just predictions that didn't pan out.

  • 4
    Replace SMART Goals with Values-Aligned Challenging Goals

    Instead of making goals merely 'realistic,' make them challenging while ensuring they connect to your core values. For fitness goals, ask: 'Does this reflect my security value (longevity), achievement value (performance), or face value (appearance)?' Choose the frame that genuinely motivates you, then set the bar higher than feels comfortable.

  1. Podcasts
  2. Browse
  3. Why Some Goals Feel Effortless (and others hurt) - Chris Bailey