Every December I get some version of the same question: what should I do before the year closes? Usually the person asking already has an answer in mind, and usually it's a tax move. That's the problem right there.
I've been allocating capital across market cycles for over 20 years now, through Tempo Investments, and the pattern never really changes. Here's what I'd tell any accredited investor sitting down to plan before 2027.
1. Don't let taxes drive the bus
This is the one I see constantly. Someone finds an investment that reduces this year's tax bill and stops asking whether it's actually a good investment. I call it letting the tax tail wag the wealth dog. Tax treatment should be the bonus on a deal that already made sense. It's not supposed to be the reason you did the deal.
2. Today's tax savings can become next year's cash problem
A lot of heavily depreciated, heavily leveraged deals look great on paper in year one. Then year three or four shows up and there's an income tax liability with no cash sitting there to pay it. If you're chasing tax-efficient investment strategies, make sure the depreciation benefit is riding on a deal that can also cover its own bills later.
3. Tax-loss harvesting has a blind spot
Harvesting a loss means selling something that's down. Sometimes that something is down because the market's wrong about it, not because the business or asset is actually worse. Howard Marks has a line I come back to a lot: the lower the price, the lower the risk, and the higher the price, the higher the risk, all else equal. Selling your cheapest asset to harvest a loss can mean selling your safest one. Worth checking before you hit sell.
4. Year-end is when to rebalance, not just when to file
Taxes and rebalancing happen to land on the same calendar deadline, so use that. Sometimes the two goals pull against each other a little. But skip rebalancing altogether and you end up with a portfolio that's quietly gotten concentrated, more risk than you signed up for, and you won't notice until something corrects.
5. Check your 401(k) and IRA before the ball drops
Converting Traditional to Roth is one of the more underused moves out there, especially if you're holding anything illiquid, private real estate, private equity, that kind of thing. Illiquid assets often get valued at a discount for the conversion, sometimes ~50%+ off what you actually put in. That's a real benefit if you're thinking about self-directed IRA real estate investments. Talk to your tax advisor about timing it.
6. Too much cash isn't automatically a mistake
Cash is optionality. And right now, with rates where they've been, you're getting paid more to hold it than you were a few years ago. Pick a range, 10 to 20%, 20 to 30%, whatever fits how you sleep at night, and stay inside it. Don't let a volatile year push you way above your own ceiling, and don't let FOMO push you below your own floor.
7. Don't chase whatever won last year
Higher price, higher risk. That's it, that's the whole rule, all else equal. Whatever did best in 2026 is probably priced for it already, which means the fundamentals are playing catch-up to the price rather than the other way around. Nobody rings a bell when momentum breaks. It's the same momentum-versus-value argument it's always been.
8. Ignore the headlines
I'll say it plainly: don't make decisions based on predictions about 2027. Nobody's predictions are reliable enough to bet a portfolio on, including mine. One thing that actually helps: putting money into something illiquid, like private real estate funds, on a long enough time horizon that you can't panic-sell even if you wanted to. The lack of liquidity forces the discipline your willpower won't. If you're staying in public markets, same rule applies, fundamentals, not forecasts.
9. The small stuff that bites hardest
Forgetting an estimated tax payment. Forgetting an RMD. Leaving dividend reinvestment switched on without realizing it can trigger a wash sale. None of these are complicated. All of them are easy to miss, and all of them cost real money when they're missed.
10. One check before 2027
Does your allocation still match your actual goals, cash flow needs, time horizon, risk tolerance? If you only check one number, check your distribution yield. Started the year at 5%, now sitting at 3.5%? That gap is appreciation outrunning your distributions. Time to rebalance back toward the yield you actually wanted.
Year-end planning works better when it starts with the portfolio you have, not the tax bill you're trying to dodge. If you want the fuller framework behind how I think about this, the Endgame Portfolio guide covers goal-setting, capital allocation, and operator vetting in more depth. It's free.
Or just grab time on my calendar and we'll go through your year-end numbers together.
