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