3 Retirement Experts Dish: My Dream Retirement—and My Plan for Getting There


Have you ever envisioned what your life will be like in 20, 30 or 40 years—in retirement? Will you travel the world? Start a side gig? Spend the winter months at your second home … right on the beach?

There’s no right or wrong answer. After all, dream retirements are a bit like snowflakes—no two are exactly alike.

There is, however, one thing that remains the same for everyone: fulfilling that wish list retirement requires some careful planning.

So whether you want to make homemade pasta in a Tuscan farmhouse or sail the Caribbean with your grandkids, you have to plot out how exactly you’ll get there well before you clock in those last hours on the job.

Of course, planning that far in advance can be daunting, especially if you’re still just trying to figure out how to balance all of your in-the-now financial priorities.

So we asked ourselves: Well, how do the pros do it—and what can we learn from them? And then we reached out to three well-known retirement experts for the skinny on their own goals for their golden years (spoiler alert: none of them plan to stop working completely), including the savings and investing strategies they’re using to get there.

Read on to see what savvy tips you can potentially glean from them to help bring you one step closer to your own retirement dreams.

RELATED: 6 Common Retirement Savings Mistakes to Avoid

  • Reality Check

    How about you show some REAL people with REAL lives for once! The majority of people with middle class jobs living paycheck to paycheck. That would mean your tinker bell dusted article wouldn’t have any magic to it, life isn’t a fairy tale for many. You want a great article, write with some integrity, some truth for the real people struggling, we are still in the recession. I still see many companies with mass layoffs and many people not getting rehired or if they do it’s not a fraction of what they had vested in their previous employment for 10+ years. Pasta in a Tuscan farmhouse or sailing in the Caribbean? Most people are hoping to have three square meals and enough sleep to put in another 9-10 hour shift with continuous added roles with no extra pay accrued for any of it. Write an article that’s for the real majority

    • Joehazard

      Agreed. I am 40, just started a 401k and frantically trying to save up for retirement and an emergency fund after ignoring retirement for most of my life. I would like a nuts and bolts article which might contain some suggested percentages of how much to go into each area; long term savings, short term and security.

      • AverageJo

        Yes, Learnvest does seem to skew toward people who have more going for them in their lives than most average Americans. I’ve also noticed that New York/the East Coast is featured in more articles than the rest of the country. I don’t care about New York or the crazy price to live there. There are 49 other states people live & work in!

  • ana

    Great article! I got a few pieces of advice I like from it. I think anyone can follow this advice, it’s not how much you make it’s what you do with it.

  • Anon

    This is one of my favorite Learnvest articles in a long time. I’ve saved quite a bit for retirement by age 31, and love hearing about ways to transition into a working retirement or more flexible plan rather than dropping work cold turkey in your 60s. I love the example of pie slices!

  • Lea

    I agree with some of the PP – these people are financially secure enough to max out their 401(k) every year and have other investments that have turned out well for them. They probably also all make a boatload of money every year. Sure is nice to hear how rich people are going to achieve their retirement dreams… this advice is not particularly helpful to me.

    • immigrantlivingthedream

      how old are you?

  • immigrantlivingthedream

    I can see some envy here. What these guys have in common is that they started young. It doesn’t matter if you are rich or middle class… you can always try to live with a budget and have a savings rate no matter how small. When times are good, save. When times are bad, you can use those savings (instead of getting into unmanageable debt).

  • mitchmiller

    Based on some of the advice here, I would be hesitant to call these people retirement experts. Advising one near retirement to over-allocate retirement savings to bonds requires a risk assessment of based on the duration of the bond. Some analysts are fearful the market in long term bonds could see unprecedented price declines within the next few years. Another piece of bad advice is to buy and forget. This strategy works well so long as you aren’t forced to retire and begin to draw down accounts in the midst of a financial decline. Most advisors suggest some type of strategy to protect the value of your portfolio, be it diversification (which lowers overall yields), using puts as “insurance” on stock portfolios, or stop losses.

  • Isaac

    The most effective investment plans always include real estate. If you’re not investing in low-risk real estate, you’re robbing yourself and making your investment company rich. I teach others how to invest in low-risk real estate without being a landlord. It’s absolutely free. No strings attached. http://www.RetireBetterWithRealEstate.com