What Changes When a Retirement Expert Finally Retires? With David Conti

Retirement writer David Conti shares his True Retirement Story of what it was like to go from writing about retirement to actually retiring himself.

Most people spend years preparing financially for retirement. They save consistently, invest wisely, pay down debt, and work toward the day when employment becomes optional. As financial advisors, we spend a great deal of time helping clients answer the question, “Can I afford to retire?”

But another question deserves just as much attention:

What happens after you get there?

On the Retire Today podcast, I sat down with David Conti, a longtime retirement writer, coach, and former Fidelity Investments executive who has spent decades helping people prepare for retirement. Recently, David experienced something new: he turned 65 and began navigating retirement for himself. His perspective is especially valuable because it combines years of professional expertise with firsthand experience, reminding us that retirement is something we continue to learn—even after we’ve spent a career teaching others about it.

Retirement Is About More Than Leaving Work

When I ask clients what they’re looking forward to in retirement, “freedom” is one of the most common answers.

David described retirement the same way. Freedom means having the flexibility to choose how you spend your time, pursue work that is personally meaningful, and reflect on questions that busy careers often leave unanswered. Who am I without my job? What relationships matter most? How can I use my experience to serve others?

Those questions rarely have financial answers.

Yet they often determine whether retirement feels fulfilling.

Saving for Retirement Is Different Than Spending in Retirement

One of the biggest emotional transitions retirees face is moving from accumulation to distribution.

For decades, we’ve conditioned ourselves to celebrate watching retirement accounts grow. Contributions increase. Account balances climb. Saving becomes a habit.

Retirement asks us to reverse that mindset.

David admitted that even after years of writing about retirement, it still felt strange to stop adding money to retirement accounts and begin thinking differently about income. Rather than relying on a single paycheck, he now thinks about retirement income as a collection of multiple streams—investment income, dividends, retirement accounts, and other resources working together to support the lifestyle he wants.

That shift is more psychological than mathematical.

A retirement income plan isn’t simply replacing a paycheck. It’s replacing decades of financial habits.

Simplicity Often Wins

Another lesson that resonated with me is the value of simplifying your financial life before retirement.

Over the course of a career, many investors accumulate accounts, individual stocks, specialty funds, and investments that made sense at one point but no longer serve a clear purpose.

Complexity can create unnecessary risk.

David explained that working with an advisor helped identify opportunities to improve tax efficiency and simplify his portfolio without sacrificing his long-term objectives.

I’ve found the same thing with many of my own clients.

The goal isn’t owning more investments.

It’s owning the right investments for the retirement you’re trying to create.

Medicare Is More Complicated Than Most People Expect

Many retirees assume that once they enroll in Medicare, the difficult decisions are behind them.

David’s experience demonstrates otherwise.

After carefully selecting a Medicare Advantage plan and establishing relationships with new healthcare providers, he learned only a few months later that his insurance company was leaving his state. Suddenly, he was back to evaluating plans, finding new physicians, and comparing coverage options all over again.

His experience highlights an important lesson: Medicare planning doesn’t end after enrollment.

Plans change.

Networks change.

Benefits change.

That’s one reason I encourage clients to review their Medicare coverage every year instead of assuming last year’s plan is still the best fit.

Retirement Creates New Opportunities to Give

Financial security often creates opportunities that extend beyond personal spending.

David shared how opening a donor-advised fund more than twenty years ago gradually transformed the way he thinks about charitable giving. Rather than making occasional donations, he became much more intentional about supporting organizations that reflected his family’s values, while also involving future generations in conversations about generosity.

I’ve seen something similar with many retirees.

As financial concerns become less pressing, people often begin asking a different question:

How can I use what I’ve built to make a difference?

For some, that’s volunteering.

For others, it’s mentoring.

For many, it’s charitable giving that reflects a lifetime of values.

Practice Retirement Before You Retire

Perhaps my favorite advice David shared had nothing to do with investments or taxes.

He recommended practicing retirement before making the transition.

If you’re still working, consider taking an extended period of time away from work—not as a vacation filled with activities, but as a chance to experience what everyday retirement might actually feel like. Teachers naturally experience something similar during summer breaks, but many professionals can create their own version through sabbaticals, unpaid leave, or simply taking additional time off before retirement.

One other suggestion stood out to me. Looking back, David wishes he had given himself more time to decompress after leaving his full-time career. Instead of immediately filling his calendar with new projects, he recommends taking several months to reset before deciding what comes next.

That advice reflects something I’ve observed as well.

Retirement isn’t a race.

Sometimes the best way to begin the next chapter is to create enough space to discover what you truly want from it.

Retirement Lessons from a Retirement Expert’ Experience

Preparing financially for retirement is essential.

Preparing personally is just as important.

Your investments, tax strategy, Social Security decisions, and Medicare coverage create the foundation for retirement. What you choose to do with the freedom those plans create is what ultimately shapes the experience.

The goal isn’t simply to retire from work.

It’s to retire to a life that’s meaningful, intentional, and worth looking forward to.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

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Additional Links:

• Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
• David Conti on LinkedIn
• RetireMentors.net

Connect With Jeremy Keil:

• Keil Financial Partners
• LinkedIn: Jeremy Keil
• Facebook: Jeremy Keil
• LinkedIn: Keil Financial Partners
• YouTube: Mr. Retirement
• Book an Intro Call with Jeremy’s Team

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