“I Wish I Had Taken More Risks”: A Career Reflection That Changed How I Think About Work
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“I built a safe career. But not an exciting one.”
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Yesterday, I had a heartfelt conversation with someone who recently retired at 60.
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A respected name in his field.
nA well-paid professional with a solid track record.
nSomeone many would consider “successful.”
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But what he said left a lasting impact on me.
“I wish I had taken more risks.”
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Not “I wish I had earned more.”
nNot “I wish I had worked longer.”
nJust… more risks.
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That one sentence cracked open an entirely new way of thinking about careers.
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A Familiar Beginning: The Allure of Stability
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He began his career at 25 with a good job.
nNot a dream job, but a “safe” one
“Stability first, passion can wait,” he thought.
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So he worked hard. Got promoted. Bought a house.
nFrom the outside, life looked sorted.
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But internally?
nHe was often curious about other possibilities.
nDifferent roles. New industries. Starting something of his own.
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Every time he thought of trying something new, fear crept in:
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“What if I fail?”
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“Maybe next year.”
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“Let me wait till I’m more settled.”
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And like that, years slipped by.
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Seniority Without Satisfaction
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By his mid-40s, he had reached a leadership role.
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But something had changed.
nHe was no longer learning. No longer growing.
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“I became comfortable… but not content,” he admitted.
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Meanwhile, younger colleagues were adapting faster—mastering new tools and systems.
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He stuck to what he knew.
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Because it felt safe. Predictable.
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But also, limiting.
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Regret at 60: Time, Money, and a List of “Never Tried”
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Now at 60, he has:
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Time
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Money
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Experience
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But also… a list.
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A list of things he never tried.
nA list of “What ifs.”
nA list of unlived dreams.
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“I built a safe career. But not an exciting one.”
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So What Can We Learn?
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His story isn’t unique.
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Many of us follow a similar path:
nChoose stability. Postpone passion. Avoid discomfort.
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But what if we could do it differently?
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4 Principles to Design a Career Without Regrets
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✅ Take Calculated Risks
n→ Not reckless jumps, but informed leaps that stretch your potential.
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✅ Reskill Every 3–5 Years
n→ Stay relevant. Stay curious. Stay in demand.
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✅ Say Yes to What Scares You (a Little)
n→ Growth lives just outside your comfort zone.
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✅ Don’t Just Chase Safety—Chase Growth
n→ A career should not just pay the bills—it should light you up.
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Think in Career Seasons
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Reframe how you plan your career:
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Early Career (20s-30s): Learn. Experiment. Build foundations.
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Mid Career (30s-40s): Lead. Take bold steps. Find your edge.
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Late Career (50s-60s): Mentor. Give back. Create lasting impact.
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Don’t Wait Till 60 to Ask, “What If?”
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Don’t build a career that’s only rich in pay slips.
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Build one rich in stories, risks, failures, wins, and impact.
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Because at the end of the road, what you’ll remember most…
n…isn’t the comfort you stayed in.
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It’s the courage you acted on.
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Final Thought
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Start today.
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Take one step that feels bold.
nOne course. One conversation. One decision.
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Because a career well-lived is a story worth telling.