I rarely write about specific tax rulings, particularly private letter rulings, but this one is just too packed with lessons to pass up. In this situation, a lifetime of accumulation winds up being unnecessarily whacked with taxes simply because of procedural errors and lack of planning or good advice.
While this is part of the "Lessons I Learned" category of this blog, this crisis is ongoing so I thought I would do this one in the midst of the event. I have spent the last three weeks reaching out to clients offering perspective, advice, portfolio updates and planning opportunities. Now I'll take a pause to review the big picture and hopefully provide some therapy along the way.
I want to address a common investment strategy (“income/yield investing”) and a related spending rule of thumb (“don’t spend your principal”). Despite the superficial attractiveness and a certain forced discipline, neither of these are good strategies. At the end, I’ll offer improved versions of both of those ideas...
I recently read of summary of poker champion turned business consultant Annie Duke's book, Thinking in Bets. Duke describes one of the more common mistakes amateurs make is the tendency to equate the quality of a decision with the quality of its outcome. Poker players call this trait “resulting.”
One comment I’ve received over the years when working with a new client is, “I want to spend all of my money before I die.” Or said another way by the character Saul Bloom in the movie Ocean’s Twelve, “I want the last check I write to bounce.” This idea sounds very simple and elegant, but the reality is more like the unpredictable, all-over-the-place capers of the Ocean’s gang.
Last month marked the 30th anniversary of Black Monday, October 19th, 1987, when the Dow Jones Industrial Average fell 508 points and the S&P 500 saw a one-day loss of -20.5%. The market has certainly come a long way since then, having weathered two more bear markets and continuing to reach all-time highs.
I recently wrote about why I Hate Predicting Investment Returns. As I continue to meet with clients and potential clients, the reality of return expectations continues to be a necessary part of the discussion. Toward the end of the previous post, I made the statement, “This (lower return) expectation is being baked into my discussions with clients and the planning projections we do.” Here is what that means in practice using an example.
I generally spend little time talking about investments, investment returns and the outlook for the markets. Instead, my focus tends to be more on planning, be it investment, financial, estate, risk management, etc.