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Category: Retirement Planning

When It’s Smart to Pay Capital Gains Taxes

When It’s Smart to Pay Capital Gains Taxes

Imagine for a moment that you are the coach of a Major League Baseball team and you’ve successfully coached your team to the World Series. You’re about to start the 9th inning of Game 7 and your team is up 3-1. You are just three outs away from being crowned World Champions. A life-changing opportunity for players and coaches alike. But before the 9th inning begins, you visit the opposing team’s dugout and ask their coach if they’d like to…

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Designing Your Days In Retirement

Designing Your Days In Retirement

A couple of weeks ago, I attended an industry conference in Arizona that was filled with the creme de la creme of advisors. Being around a group of high-flyers like that, it wasn’t surprising to learn that most of these advisors have big goals. Many want to build large organizations with lots of advisors and “own their market.” They manage billions of dollars and are actively onboarding as many clients as possible as quickly as possible. Further still, many of…

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Life’s Curveballs

Life’s Curveballs

Over the weekend, I went for a run as I often do. I time myself for every single run and I generally run the same route each time. Some might consider that boring, but I do it because it gives me a number to shoot for. If I run different routes, I can’t compete with myself to try to beat my best time. If you think that’s silly, I totally respect that. But all I did growing up was play…

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Retiring at Market Highs

Retiring at Market Highs

As we approach new all-time market highs, one fear I routinely hear is a concern over retiring at market highs. It makes sense given that sequence of returns risk is so prevalent early in retirement. If you experience a market meltdown during your first few years in retirement, that’s obviously not a good thing and most certainly not enjoyable. It’s the primary reason I advocate for pairing dividend growth investing with a bucket allocation strategy in an effort to stem…

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Talking About Childhood and Retirement

Talking About Childhood and Retirement

Last week, I was interviewed by my good friend and fellow advisor, Justin Castelli on his All About Your Benjamins podcast. I’m thankful for that opportunity, not because we discussed retirement (which we did), but because he wanted to chat about my childhood. Justin and I had previously shared an offline call where we happened to chat about how I grew up and he encouraged me to share my story as it’s probably relatively unique – or at least not…

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Finding Fulfillment in Retirement

Finding Fulfillment in Retirement

A couple of months back, I had a conversation with Fritz Gilbert, the writer and owner of the retirement blog, The Retirement Manifesto. I’ve been a reader of his for quite some time as his posts are always insightful and entertaining. His writing offers particularly useful perspectives for me thanks to his willingness to share all that he’s going through as he is going through it. I reached out to him via phone to gain some wisdom on a variety…

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Increasing Your Odds of Retirement Success

Increasing Your Odds of Retirement Success

Recently, I was asked a great question: “What is the #1 thing I can do to increase my odds of retirement success?” Most people are inclined to focus on the portfolio since it gets all the love and attention in retirement planning – how can you optimize your portfolio, pay less in taxes or squeeze out more return?? But when it comes to retirement planning, often the easiest way to increase your chance at retirement success is to concentrate on…

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How to Invest For a 30+ Year Retirement

How to Invest For a 30+ Year Retirement

A couple of weeks back, I had the pleasure of chatting with Taylor Schulte, CFP® on his retirement podcast, “Stay Wealthy.” Taylor is a highly respected retirement expert, so naturally, I was excited to have a public chat about a topic we are both passionate about. On the podcast, we discuss my post, A Portfolio Strategy for 30-Year Retirements, to include the following topics: Why living longer should be a goal to strive for and why you’ll probably live much…

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A Retirement Trial Run

A Retirement Trial Run

I’m on vacation in the Outer Banks this week and I was planning to skip a week of writing the blog, but I couldn’t help myself. Something surprised me prior to leaving for our trip. Before we started the long drive, my wife informed me that I haven’t taken a full week off since my youngest son was born – he is almost three. Before I get emails about needing more work/life balance, anyone who knows me well knows it’s…

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Why I Prefer Dividend Income Over Total Return in Retirement

Why I Prefer Dividend Income Over Total Return in Retirement

The one constructive response I received on the article, A Portfolio Strategy for 30-Year Retirements, was the preference for total return versus dividend income. If you haven’t read it, I’d encourage you to do so now as what follows will make much more sense. Before we dive in, let’s first define total return investing. Total return investing is the idea that there is no preference for investment gains, whether via dividends or growth of underlying capital. The thought process here…

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