2.5 Breaking Free from “Shoulds”

The Weight of “Should”

You’ve likely noticed a pattern of “shoulds” in your life—unspoken rules that can feel second nature, especially in Hong Kong’s high-pressure environment. They might look like:

• “You should buy property as soon as possible.”
• “You should only spend on absolute necessities.”
• “You should stick to a ‘stable job’ until you retire.”

Sound familiar? In a city where external validation often feels essential, these rules can go unquestioned for years. Yet blindly following them might not align with your personal values, goals, or life circumstances. It’s worth asking: “Whose life am I trying to live—mine, or someone else’s?”

Understanding the Power of “Shoulds”

1. Social and Familial Pressure

• Close-Knit Communities: Families that survived difficult times may push certain money habits they found essential—like buying a flat early or choosing a high-paying job. While this advice often stems from love and concern, it may not match your reality.
• Friend Circles: Peers may rave about their property investments or career paths, unintentionally nudging you toward choices that don’t truly excite you.

2. Fear of Disappointment

• Avoiding Judgment: Many of us obey “shoulds” to dodge criticism or disapproval. We worry about letting our parents down, or being perceived as irresponsible by peers.
• Long-Term Impact: Living under constant fear of disappointing others can trigger stress, guilt, or resentment—especially if you sacrifice personal growth or happiness.

3. Cultural Norms vs. Personal Values

• Prudence and Security: Hong Kong culture highly values stability—saving money, owning property, and working hard. These can be great virtues, but they might clash with your desire for exploration, career shifts, or self-care.
• Individual Mismatches: Recognizing when cultural expectations no longer serve you is the first step to challenging them.

4. Social Comparisons

• FOMO and Peer Pressure: Seeing friends land high-paying jobs, buy flats, or lead luxury lifestyles can intensify the urge to conform. It’s easy to think, “I should be doing that, too!”—even if it doesn’t align with your goals.

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Realizing You Have a Choice

You might think, “But everyone says I need to buy property. It’s Hong Kong!” Yet, consider the stories you’ve heard in the previous lessons about emotional baggage, generational conflict, and the push-pull of scarcity vs. opportunity. Yes, property might be right for some people. But what if it’s not the only path?

Key takeaway: You always have options—renting, investing, focusing on career or skill-building, exploring life overseas. Questioning the “shoulds” doesn’t mean you’re reckless; it means you’re exploring your personal reality before making big commitments.

Common “Shoulds” in Hong Kong—and Their Impact

1. “You Should Own Property to Be Secure”
   
   • Why It’s Appealing: Property ownership can feel like the ultimate badge of stability.
   • Reality Check: With sky-high prices, a hefty mortgage can lead to ongoing stress. Renting or exploring other investments might be more in tune with your lifestyle or future plans.
2. “You Should Save Every Dollar and Spend as Little as Possible”
   
   • Benefit: Frugality is a virtue—especially in uncertain economic times.
   • Downside: Extreme saving can stifle experiences like travel, skill-building, or entrepreneurial ventures.
3. “You Should Never Rent—It’s Throwing Money Into the Sea”
   
   • Older View: Renting feels “wasteful” because it doesn’t build home equity.
   • Counterpoint: Renting covers a necessity—just like food or utilities. Upfront homeownership costs (stamp duty, taxes, maintenance) can be draining; investing elsewhere might yield better returns, depending on your goals.
4. “You Should Stick to a Stable Job (Even If You Dislike It)”
   
   • Why It’s Common: Traditional stability can reduce risks; older generations value the “iron rice bowl.”
   • Potential Cost: You might miss out on more fulfilling or lucrative paths—like startups, creative ventures, or freelance work—especially relevant in today’s gig economy.
5. “You Should Listen to Elder Financial Advice Without Question”
   
   • Benefit: Family elders have invaluable experience.
   • Drawback: Times change, and markets evolve. Updating old advice is often necessary.
6. “You Should Prioritize Price Over Quality”
   
   • Rooted in Scarcity: Always buying the cheapest option can seem wise.
   • Long-Term Effect: Constantly replacing low-quality items or missing out on better experiences can cost you more in time, money, and satisfaction.
7. “You Should Follow the Traditional Timeline (Job, Marriage, Home, Kids)”
   
   • Cultural Norm: Many families expect these milestones in a neat order.
   • Impact: Rushing into major life decisions to “keep up” can lead to stress, regret, or mismatched commitments.

Think of It This Way

Imagine you’re wearing shoes your parents or society insisted on because they’re “practical.” They fit, but every step feels slightly off. Over time, your feet ache—but you continue wearing them, because “that’s what everyone does.” Breaking free from ‘shoulds’ is like removing those ill-fitting shoes and finding a pair that truly fits your lifestyle.

The Cost of Living Someone Else’s “Should”

• Stifled Personal Growth: Adhering to rules that don’t resonate can limit career pivots, educational opportunities, or lifestyle changes.
• Resentment and Stress: Constantly trying to satisfy others’ expectations can build frustration—both towards loved ones and yourself.
• Missed Financial Opportunities: If you cling to outdated rules (like “property is the only smart investment”), you might ignore alternative assets or personal ventures better suited to today’s market.

You’ve Probably Felt It

• Relatives wonder why you’re “just renting” instead of buying a flat.
• Friends post their latest stock or property gains, and you worry you’re “falling behind.”
• Colleagues praise someone pulling 80-hour weeks, and you question if you should do the same—despite valuing family or personal time.

I’ve been there, and it’s tempting to just follow the crowd. But each time, I try to pause and think: “Am I doing this because it truly aligns with my goals—or because I don’t want to face criticism?”

Shifting From “Should” to “Want”

It’s not about rebelling against tradition—it’s about choosing consciously which beliefs genuinely align with who you are today. Here’s how:

1. Identify Your Core Values
   
   • Security, freedom, creativity, health, family time—pinpoint what matters most. This clarity helps you see which “shoulds” deserve reevaluation.
2. Rewrite the Script
   
   • List your biggest “shoulds”—e.g., “I should buy a house by 30.” Ask, “Why do I feel this way? Whose voice is behind it?” Then decide if it still resonates with your present life.
3. Experiment With Small Steps
   
   • If you think you “should never invest” because it’s “too risky,” try a small, manageable investment to learn the ropes. If you believe you “should always save,” allow a modest fund for personal enjoyment or skill-building.
4. Communicate Your Choices
   
   • If loved ones expect certain milestones, calmly explain your reasoning. Show them it’s not about rejecting their wisdom—it’s about adapting it to modern realities and personal aspirations.

Real-Life Example: Alex’s Career Crossroads

• Background: Alex works at a reputable bank, fulfilling his parents’ dream of “job security.”
• Problem: He’s unhappy and passionate about technology. He wants to launch a fintech venture but fears disappointing his parents.
• Resolution: Alex starts building his fintech idea on weekends, testing the waters before leaving his banking job. While his parents remain cautious, they see he’s done his research. He’s choosing to break free from the “should” of a stable job, finding a path that balances risk and responsibility.

Key Questions to Ask Yourself

(Grab a notepad or open your notes app—writing solidifies insights!)

1. What financial ‘shoulds’ do I follow out of habit?
   
   • Buying property, overworking, or avoiding all “luxuries”? List them out.
2. Where did each ‘should’ come from?
   
   • Is it your parents’ voice, a friend’s advice, or social media influence?
3. Which ones serve me, and which feel outdated or burdensome?
   
   • Do they align with your top values—like freedom, creativity, or security?
4. Do I truly believe in this ‘should,’ or do I fear disappointing someone?
   
   • Self-awareness can reveal whether you’re motivated by genuine desire or avoidance of conflict.

Action Steps: Moving Toward Authentic Choices

(Commit to an action plan—actually note it down!)

1. Identify Your Top 3 “Shoulds”
   
   • Next to each, write whether you feel genuine agreement or just pressure to conform.
2. Question the Origin
   
   • Whose life experience shaped this rule? Are they living in the same economic and cultural climate you are?
3. Evaluate Pros and Cons
   
   • Could letting go of a certain “should” open up new financial or personal opportunities?
4. Test a Small Shift
   
   • If you “should always save,” budget a small portion for leisure or personal growth. See how it feels to break that rule on a small scale.

Bringing It All Together

Your “shoulds” might reflect cultural roots, family history, or social influences—and many come from a place of love or caution. But not all still fit you in modern Hong Kong. By examining these expectations and deciding which to keep, you’re taking control of your financial story.

• Acknowledge their origins—they shaped who you are.
• Question their relevance—do they align with your authentic goals?
• Navigate any tension with empathy—you’re not rejecting tradition blindly, you’re updating it for a new era.

Remember: letting go of a “should” doesn’t mean you’re being reckless or unfilial. It means you’re thoughtfully curating which rules help you thrive. In the next lesson, we’ll explore redefining success in a cultural context—turning away from one-size-fits-all measures like property or job title, and instead focusing on what truly matters to you. For now, reflect on which “shoulds” might be holding you back and envision the freedom that comes with choosing your path—rather than inheriting it unchallenged.