At 57, most people are thinking about winding down, planning for retirement, or at least staying put in a stable, predictable environment. I did the opposite. I quit my corporate job—a position I had held for over three decades—without a clear plan for what came next.

Friends were shocked. Colleagues were incredulous. Even family members questioned whether I was being reckless. But the truth is, after years of navigating office politics, endless meetings, and projects that no longer excited me, I realized that staying put was riskier than leaving.

This article is both a reflection and a guide. I share what led me to resign, how I prepared (or failed to), the challenges I encountered, and the advice I wish someone had given me before walking out the door.

Understanding Why I Left

Corporate life has rewards: stability, benefits, social status. But it also comes with compromises: a rigid hierarchy, a constant pressure to perform, and the slow erosion of personal autonomy.

For me, the tipping point was subtle, yet undeniable:

Loss of engagement: Tasks that once felt meaningful became routine, repetitive, and draining.

Physical and mental toll: Long hours, commuting stress, and constant deadlines impacted my health.

Misalignment of values: The company’s direction shifted in ways that didn’t align with my ethics or priorities.

Desire for growth beyond the office: I wanted to explore interests that had been dormant for decades.

It wasn’t a single dramatic event that prompted my resignation—it was an accumulation of small signs pointing toward a need for change.

Preparing for the Leap

One of the biggest misconceptions about leaving a career at 57 is that you must have everything figured out. In truth, preparation is both practical and psychological.

Financial Readiness

Before resigning, I audited my finances rigorously:

Assessed retirement savings, emergency funds, and investments

Considered health insurance options, especially since Medicare wouldn’t kick in for several years

Calculated monthly living expenses and identified areas to reduce costs

Having a clear financial picture gave me confidence. I knew I could survive—and even thrive—without a steady paycheck while exploring new opportunities.

Emotional Readiness

Leaving a long-term career is emotionally taxing:

Identity loss: For decades, my professional role defined my sense of self.

Social shifts: Colleagues, office friends, and daily routines suddenly disappeared.

Fear of judgment: There’s a cultural expectation to “stay put until retirement,” and breaking that norm invites criticism.

I spent months processing these feelings, talking to mentors, and journaling. Emotional preparation was just as crucial as financial preparation.

Skill Assessment

Contrary to popular belief, age is not a barrier if you’re willing to learn. I reviewed my skills objectively:

What transferable skills did I have? Leadership, project management, client relations.

Which skills needed updating? Digital tools, social media proficiency, modern marketing trends.

Which personal passions could translate into income? Writing, consulting, speaking engagements.

By mapping my capabilities to potential opportunities, I reduced uncertainty and gained clarity.

The First 90 Days Post-Resignation

Leaving the corporate world is liberating, but the initial period is also the most challenging. Here’s what I encountered:

A sudden abundance of time: At first, the unstructured hours were exhilarating. Soon, boredom and restlessness crept in.

Rebuilding daily structure: Without meetings and deadlines, I had to create my own schedule, balancing productivity with rest.

Facing societal expectations: Casual questions like “So, what are you doing now?” felt loaded with judgment.

During these first months, I learned the importance of structure, community, and intentionality.

Finding New Purpose

One of the most important lessons was that leaving a job does not mean leaving work altogether. Purpose can be found in different forms:

Consulting: I began taking short-term consulting projects that leveraged my expertise without committing full-time.

Volunteering and mentorship: Sharing knowledge with younger professionals provided fulfillment and connection.

Personal projects: Writing, public speaking, and creative endeavors became central to my daily life.

Purpose, I realized, doesn’t have an age limit—it just requires a willingness to explore.

Common Misconceptions About Quitting Late

Many people hesitate to leave their corporate careers because of myths about age, risk, and opportunity:

You’re too old to start over.” Reality: Skills and experience are valuable; adaptability matters more than age.

You’ll run out of money.” Reality: With careful planning and small steps, financial sustainability is achievable.

You’ll regret leaving.” Reality: Regret usually stems from staying in a misaligned environment, not from leaving.

No one will hire you now.” Reality: Freelance, consulting, and part-time roles often value experience more than youth.

Confronting these misconceptions early helps reduce fear and empowers decision-making.

Advice for Those Considering a Leap

Here’s the advice I wish someone had given me:

Do a Self-Audit

Evaluate your motivations, strengths, weaknesses, and passions. Write them down. Clarity reduces anxiety and helps chart a realistic path forward.

Plan Financially, But Not Perfectly

Save and budget strategically, but don’t wait for the “perfect” financial moment. Flexibility and frugality can bridge gaps as you transition.

Build a Support System

Friends, mentors, and professional networks are essential. Share your plans and challenges. Emotional and practical support make the journey manageable.

Experiment First

Before fully resigning, test side projects, freelancing, or consulting. Early experimentation reduces the shock of transition and provides confidence.

Accept the Emotional Rollercoaster

Leaving a long-term career triggers doubt, fear, and occasional loneliness. Accept these feelings as part of the process rather than barriers.

Embrace Lifelong Learning

Stay curious. Take courses, attend seminars, or learn new technology. Growth doesn’t stop at 50, 60, or beyond.

Define Your Own Success

Success is not the title, salary, or corporate prestige. It’s autonomy, alignment with values, and satisfaction with how you spend your time.

Lessons Learned After One Year

After a full year away from my corporate job, the lessons are profound:

Freedom is exhilarating, but discipline creates fulfillment.

Risk feels bigger than it is until you take the leap.

Your professional identity doesn’t disappear—it evolves.

Connection with others becomes intentional rather than incidental.

Time becomes your most precious resource; spending it wisely is empowering.

These insights reinforce that leaving a career late in life can be transformative, not destructive.

Broader Perspective: Changing Work Norms

My experience reflects larger trends in today’s workforce:

People are retiring later but redefining “retirement.” Full cessation of work is no longer universal; many pursue second careers or entrepreneurial ventures.

Experience is increasingly valued in consulting and mentorship roles. Corporations and startups alike recognize the benefit of mature perspectives.

Mental and emotional well-being are priorities. Many professionals realize staying in unfulfilling work has hidden costs.
These trends suggest that leaving a corporate career at 57—or later—is not reckless; it is increasingly normalized.

Conclusion: Courage, Clarity, and Commitment

Quitting a corporate job at 57 is not about rejecting work—it’s about choosing life intentionally. It’s about assessing priorities, risks, and possibilities, and making a deliberate choice to align your daily reality with your values and aspirations.

To anyone contemplating this leap:

Take stock of your resources—financial, emotional, and social.

Plan carefully, but accept uncertainty.

Start small if needed, but don’t delay indefinitely.

Remember that fulfillment and growth don’t have an expiration date.

Leaving my corporate job at 57 was one of the most challenging decisions I’ve ever made. But it also became one of the most liberating. The transition tested me, stretched me, and ultimately revealed that life beyond the office—at any age—can be rich, meaningful, and deeply rewarding.

Sometimes, the best advice you can give yourself is simply to take the first step.