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Welcome to the WINDERMERE blog

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Stay the course. How many times have I given that message to clients (and myself), both in these weekly posts and in general conversation? Thousands of times I am sure! And a large majority of those have come in the past three years as all investors have been thru a lifetime’s worth of challenges. Truth […]

Trendlines move in both directions

June 15, 2023

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I’d imagine whatever professional field you are in, you have a certain vernacular that has become second nature to you. So much so that you don’t even realize when you’re using terms that those outside your profession may not immediately understand. This is certainly true for me and the terminology that accompanies a career in […]

Client Question: What do birds have to do with the Federal Reserve?

June 15, 2023

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I received a question from a client this week, sparked by a recent job change. He has a 401k plan (at his now former employer) and was wondering what to do with that account. With today’s job market strength and the tendency of people to change jobs more frequently, this is a relatively common question […]

Client Question: Former 401k Plan

June 8, 2023

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It’s been a relatively quiet week in the markets (finally!). With a return to action next week (an inflation print and a meeting of the Federal Reserve), I thought this was a great chance to write about a non-investment topic this week…habits. A few weeks back, I was reading James Clear’s weekly 3-2-1 email and […]

Happy (Belated) 1st Birthday to The Friday Five

June 8, 2023

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If you’ve been reading my articles for a while, you know I’ve written about a tetter totter (or see saw if you prefer) in the past when explaining any number of market dynamics. I’ll risk repeating myself this week as it is such a good visual. It works especially well when thinking about investor sentiment. […]

The Sentiment Teeter Totter

June 1, 2023

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When it comes to income taxes, there is no shortage of rules, acronyms, and best practices. One such “tax term” came up this week as I worked thru a retirement plan distribution for a client. Find out what “safe harbor” means in terms of estimated income tax payments and why it’s a strategy you should […]

Client Question: Safe Harbor

June 1, 2023

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2023 is quickly becoming the year in which I discuss topics I never imagined would come up with such frequency, if at all… topics such as bank failures (see March 2023 publications) and now the potential of a US default. But in life it seems we should expect the unexpected! The United States is a […]

Debt Ceiling Considerations

May 25, 2023

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Undoubtedly, our clients are free to do what they choose with their invested funds. However, it is not uncommon for them to seek my advice when it comes to withdrawals – especially those that are above and beyond their planned/recurring distributions. Taking funds out of savings runs contrary to what our actions have been most […]

Client Question: Evaluating Withdrawals

May 24, 2023

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I onboarded a new client this week, and within minutes of looking at his pre-existing Roth IRA and tax returns for the given years, I realized he had made improper contributions to his account (due to exceeding the income limit). While he had an advisor helping him, that individual did not confirm my new client’s […]

Client Question: Improper Roth Contribution

May 18, 2023

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I receive a weekly newsletter from Jesse Itzler, a serial entrepreneur and speaker who has a unique and compelling take on many topics. In a recent newsletter, he took readers thru a quick exercise to illustrate an innate human instinct. I’m about to put my own spin on this same exercise to reiterate the point […]

Change Exercise

May 18, 2023

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