Do as I say, not as I do: On my failings as an investor

If a knowledgeable observer trained his or her sights on my choices, what are the trouble spots they would identify? Here are some of the biggies.

I understand the tax implications of this, so I might as well sell each lot of restricted stock units as soon as it vests because there’s no tax benefit to hanging on longer. And it’s not like I think I possess some inside knowledge that the shares are likely to outperform the broad market.

Instead, the key culprit here is inertia. There’s a little bit of tax dread mixed in, too, as selling them would trigger a big tax bill. I’ve been in the process of divesting from company stock for the past several years, but the allocation is still high.

Even when cash yields are higher, as they are today, inflation still gobbles up most of the interest.

Cash has stacked up in our account following bonuses or other windfalls, or during fallow spending periods like 2020. And it just never feels like an especially great time to move the money into long-term investments.

Perhaps most important, having cash on hand confers valuable peace of mind. I like knowing that almost anything could happen, and we’d be able to cover it without touching our long-term investments. I think of cash as one of my luxury goods.

My husband and I should have a good slug of retirement assets in fixed-income investments at our life stage. But our portfolio is oddly barbelled, with a healthy dose of cash alongside a long-term portfolio that’smainly invested in equities.

In a way, I think the cash and the equities work together from a psychological perspective, with the liquid assets giving us peace of mind to stay the course with stocks.

But the lack of bonds isn’t really deliberate. Instead, inertia is probably the main reason. We set up our long-term portfolios with heavy equity allocations in our 30s, and we’ve never really wavered. But this is something that I’d like to address as retirement approaches.

There’s a fantastic fund I own-but in our taxable brokerage account. If I could do it again, I’d buy this fund in a tax-sheltered account, because it has made some significant capital gains distributions over the years, which have boosted our household’s annual tax bills.

Asset-location problems can be difficult to fix. Even though our reinvested capital gains have helped boost our cost basis, we would still owe a big tax bill if we liquidated the position because of the fund’s gains.

Ideally, IRA contributions would go in right around the first of the year, to benefit from tax-sheltered compounding for a longer period. And our IRAs sit right alongside our taxable brokerage account, so transferring funds from the brokerage account to the IRA and converting them to Roth is simple.

But I’ve sometimes made those IRA contributions right before the deadline, a full 15 months later than when we were first eligible to make them. I’ve also been slow to make the conversions to Roth, periodically letting a few years’ worth of contributions stack up in our IRAs before converting.

The baby bear market of March 2020 provided a good opportunity to convert all the traditional IRA assets to Roth with no tax repercussions. I’ve been walking the straight and narrow-with timely contributions and conversions -ever since.