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Why “What I’d Tell My Younger Self” Is Often Bad Advice

"Every man takes the limits of his own field of vision for the limits of the world." — Arthur Schopenhauer

Every few months, a new listicle goes viral: "30 things I wish I knew at 20," "What every 40-year-old should do before it’s too late," or "Advice from 80-year-olds on how to live a meaningful life."

These pieces are often earnest, even well-meaning. But they carry a hidden danger: the illusion that there is one way to live well, if only we follow the right script, take the right risks, or apply the distilled wisdom of others to our own lives.

The problem is, life doesn’t unfold in copy-paste format. Each of us is living a different season. And not all advice is timeless. In fact, some of it can derail you entirely.

Life Comes in Seasons. Your Choices Should Too.

There is no universal roadmap. Each decade of life asks different questions of us — and demands different answers.

Your 20s: Exploration, Curiosity, Failure

This is often the season of trial and error. You have time, relative freedom, and space to experiment.

But today’s culture rushes young people into decisions they can’t yet make with clarity: "Build your personal brand," "Buy land early," "Start a business before 25." Yet many 20-year-olds barely know themselves, let alone what problem they want to solve.

Advice like "travel while you're young" may sound inspiring, but it ignores economic realities, visa restrictions, discriminatory border policies, weak currency, and inflexible work environments. In Kenya, taking a sabbatical is often a luxury only a handful can afford — and there is no guarantee your job will be waiting for you.

The push to "invest early" or "start a side hustle in your dorm room" also ignores the deeper issue: without proper financial literacy, mentorship, or capital, early investments can lead to poor decisions, burnout, and long-term regret. Many young Kenyans pour money into trends without research or strategy, only to lose what little they had.

Your 30s: Building, Focus, Trade-Offs

This is a decade of narrowing. You begin to understand that saying yes to one thing means saying no to many others. Whether it's building a career, nurturing a relationship, or raising children, your decisions now have compounding effects.

You will hear: "Pursue your passions," "Marry before 35 or it’s too late," or "Have children before your clock runs out." But these directives ignore reality. Not every passion is monetizable. Not everyone is ready for marriage. And some cannot or do not want to have children. These should be considered choices, not moral achievements.

The passion narrative in Kenya has encouraged many to abandon stable, meaningful jobs in search of something vague. But as Thomas Merton reminds us:

"People may spend their whole lives climbing the ladder of success only to find, once they reach the top, that the ladder is leaning against the wrong wall."

This is also when your body may begin to whisper reminders: sleep matters, sugar lingers, knees don’t bounce back. A lesson many ignore until it's too loud to dismiss.

Your 40s & 50s: Reflection, Shifts, Rebalancing

You start asking different questions: Is this it?, What have I lost?, What must I reclaim? It is a dangerous season for those still chasing the illusions of their 20s.

Advice like "Reinvent yourself, go back to school, start a new career" may sound thrilling, but if taken blindly, it can result in deep financial strain, identity confusion, or burnout. Reinvention is not rebellion. It must be rooted in wisdom and grounded assessment.

Your health might now be calling for discipline. A 20-year-old can skip meals and bounce back. At 45, poor habits become chronic issues. Eating vegetables is wonderful, but let’s not ignore the silent influence of genes, access to care, and social support. You don’t look good at 70 just because you eat greens. Let’s stop guilt-tripping those who don’t "age well."

Your 60s and Beyond: Stillness, Legacy, Stewardship

In a world obsessed with youth, aging is seen as decline. But this season can offer the richest wisdom — not because of what you've done, but because of what you've learned to release.

Advice like "Stay young at heart, travel the world, start over" can be tone-deaf. Not everyone wants or can afford a globe-trotting retirement. For many, this season is about healing old wounds, mentoring, or simply savoring the quiet.

Your body demands care, but not shame. Your pace slows, but your presence deepens. Don’t let youth culture rush you into irrelevant ambitions.

Why Bad Advice Hurts Good People

Much of the recycled life advice we hear does more than annoy — it misleads. It:

  • Pressures people into making choices that don’t align with their season

  • Creates shame and regret for things they couldn’t do

  • Distracts from the wisdom their current life is offering

As Kenyans, we often follow advice tailored to other economies, other family structures, other timelines. The "take a sabbatical and travel the world" narrative assumes visas, money, and time off that most don’t have. The "just do it" startup culture ignores our infrastructure gaps, financial limitations, and systemic hurdles.

Even the idea of "marry early" often becomes a race rather than a relationship. "Start a business" becomes the new pressure point, even when one is ill-prepared or lacking a safety net.

What Does It Mean to Honor Your Season?

  • To ask, not assume: What matters most to me now?

  • To make peace with limits, rather than escape them

  • To recognize that some advice is only helpful when filtered through the lens of your reality

Ask Yourself:

  • What is this season asking of me that no other season has?

  • What am I trying to prove — and to whom?

  • Is this advice energizing or exhausting me?

  • Who benefits if I follow this narrative?

  • What must I stop romanticizing?

Parting Thought

"He who has a why to live can bear almost any how." — Friedrich Nietzsche

Instead of obsessing over what you should have done by now, ask what your season is asking now. Live in tune with your life, not in reaction to someone else's highlight reel.

Because the wisest thing you can do might not be to travel, start a business, or reinvent yourself. It might be to rest. To listen. To choose peace. And to trust that your becoming is on time.

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