We’re constantly told to respect our elders and learn from those who came before us. And we should. But there’s a crucial distinction we often miss: not all achievements are equally difficult, and not all advice reflects transferable wisdom.When someone older gives you advice based on their success, you need to ask a harder question than “Did they succeed?” You need to ask: “How hard was it for them to succeed?”
The Problem with Success-Based Authority
Our culture grants authority to successful people. The wealthy give financial advice. The employed give career advice. The homeowners give real estate advice.But success alone tells you almost nothing about the quality of someone’s strategy. You need to understand the difficulty setting they played on.Different Difficulty SettingsImagine two people giving you advice about buying a house:
Person A: Bought their first house in 1985 for $89,000 on a single income, 10% down payment, at age 25. The house is now worth $650,000. They tell you: “Just save up, work hard, and buy property young. It’s the best investment you’ll ever make.”
Person B: Bought their first house in 2022 for $485,000, required two incomes and help from family for the down payment, at age 34. They tell you: “It’s incredibly difficult and you’ll need to make serious sacrifices, delay other goals, and probably need some help. But if you can manage it, do it.”
Both succeeded in buying a house. But Person A succeeded on easy mode. Their advice reflects a world that no longer exists. Person B’s advice reflects the actual difficulty you’ll face.
Historical Context Matters
The problem isn’t that older people are wrong or lying. It’s that they often don’t realize how much easier their path was.Consider someone who:
Got a good job without a degree in 1975
Paid for college with a summer job in 1980
Bought a house on a single income in 1990
Retired comfortably with a pension in 2010
Each of these achievements was genuinely easier in their era. Not because they weren’t hardworking or capable, but because the structural conditions were different.
When they tell you “just work hard and it’ll work out,” they’re not being malicious. They’re generalizing from their own experience. But their experience was on a different difficulty setting than yours.
The Difficulty Discount
Here’s a useful framework: mentally apply a “difficulty discount” to advice based on achievement difficulty.
If someone accomplished something when it was:
Much easier: Their advice is worth 30% of face value
Somewhat easier: Their advice is worth 60% of face value
Similar difficulty: Their advice is worth 90% of face value
Harder than your situation: Their advice is worth 120% of face value
This isn’t about disrespecting them. It’s about correctly calibrating how much their success tells you about effective strategy versus lucky timing.
Red Flags That Someone Had It Easier
Watch for these signs that someone’s achievement was easier than they realize:
They can’t explain specific obstacles you’re facing: “Why is housing so expensive?” “Why do you need a degree for that?” “Why can’t you just walk in and ask for a job?”
Their timeline doesn’t match current reality: “I was married with kids by 25, why aren’t you?” When they got married, housing cost 3x annual income instead of 8x.
They attribute everything to personal virtue: “I succeeded because I worked hard” with no acknowledgment of structural advantages.
They get defensive when you mention different conditions: “You’re just making excuses” rather than engaging with changed circumstances.Their advice is suspiciously simple: “Just save 10% of your income and you’ll retire comfortably.”
This might have worked with pensions and affordable housing. It doesn’t work now.
When Older Advice IS Valuable
This isn’t a blanket dismissal of older generations. Some achievements remain difficult across eras, and advice about these is genuinely valuable:
Relationship wisdom: Human nature hasn’t changed. Someone who maintained a 40-year marriage likely has transferable insights.
Character and discipline: The challenges of self-control, perseverance, and integrity are timeless.
Creative and intellectual work: The difficulty of writing, creating, or thinking deeply hasn’t changed much.
Physical health: Basic principles of fitness and wellness remain consistent.Navigating human systems: Understanding politics, social dynamics, and institutional behavior.The key is whether the domain they succeeded in has remained similarly difficult.
The Reverse Also Applies
Interestingly, this works in reverse too. Some things are harder for older generations now.
A 70-year-old navigating modern technology and digital systems is playing on hard mode. Their struggle doesn’t make them stupid—the difficulty increased.If they tell you “this technology stuff is impossible,” that’s useful information about age-related challenges, but it doesn’t mean you’ll face the same difficulty at their age with technologies that are native to you.
How to Evaluate Advice Properly
When receiving advice from someone older:
Identify their achievement: What specifically did they accomplish?
Research the historical difficulty: What were conditions like when they did it? What did it cost relative to income? What were the barriers?
Compare to current difficulty: What are those same metrics today?
Calculate the difficulty ratio: Was it 2x easier? 5x easier? Actually harder?
Adjust your evaluation accordingly: Weight their advice based on how transferable their experience is.
Look for process over outcome: Did they succeed through a robust, replicable process? Or did they succeed because conditions were favorable?
The Hardest Conversations
The most difficult part of this is that pointing it out often goes poorly. Telling someone “your achievement was easier than you think” is rarely received well.
People are deeply invested in believing their success was earned through their own merit. And it was—but merit operates within structural conditions. Someone can be hardworking AND have benefited from easier conditions. These aren’t mutually exclusive.You don’t need to argue with them. You just need to privately calibrate how much weight to give their advice.
Find the Right Mentors
The most valuable mentors are often those who:
Achieved something recently under current conditions
Acknowledge when conditions were different
Can articulate specific obstacles and strategiesUpdate their worldview based on new information
Succeeded at something that remains similarly difficultThese people have actually solved the puzzle you’re facing, not a different, easier puzzle.
A Personal Test
Here’s a thought experiment: Would you trade places with your advisor?
If someone telling you to “just work hard and save money” had to restart their life today at your age with your conditions, would they achieve the same outcomes using their own advice?If not, their advice might be survivorship bias rather than wisdom.
Respecting your elders doesn’t mean accepting all their advice uncritically. Real respect means engaging seriously with their experience while also honestly evaluating how applicable it is to your situation.
Judge the climb, not just the summit. Someone who reached the top of a hill shouldn’t give the same advice as someone who climbed a mountain—even if both made it to “the top” of their respective challenges.The question isn’t just “Did they succeed?” but “How hard was their path, and is mine similar?”
This isn’t cynicism. It’s calibration. And proper calibration is how you find actually useful wisdom in a changing world.
