I hope you had a wonderful Thanksgiving filled with too much food, great conversation, and maybe a little guilt-free couch time.
Last week, I wrote about the importance of being intentional with your investment goals. So this week (and the accompanying long weekend) is the perfect time for the logical next step: checking whether your portfolio is actually built to deliver those goals.
Not just checking your account balances (though I’m sure you’ve done that at least once this week). I’m talking about answering a deeper question: Is what you’re invested in actually getting you where you want to go?
The Goal-Portfolio Gap
I see this disconnect all too often.
An investor tells me they want consistent passive income to eventually replace their W-2. But when we start talking through their portfolio, it’s stuffed with equity-growth plays that won’t pay a dime for years (if ever).
The goals are clear. The implemented strategy is...lacking, to say the least.
Sometimes this happens because life changes. Your goals shift, but your portfolio stays frozen in time.
More often though? You’ve just been asleep at the investing wheel. Deals come across your desk, they look good, you write the check.
No master plan. No periodic review. Just hoping it all works out.
It’s more passive neglect than passive investing.
The Long Weekend Review
Thankfully, fixing that doesn’t require some massive overhaul.
You don't need a spreadsheet with 47 tabs or a three-hour analysis session. Thirty to sixty minutes answering a handful of questions this weekend can tell you whether your portfolio and your goals are actually pointing in the same direction.
To jumpstart you, here are some of the questions I ask myself when doing my own portfolio reviews:
The Cash Flow Check
What percentage of your investable assets actually generate cash flow? And more importantly, what’s the total dollar amount of cash flow across the full year?
Could those investments sustain your lifestyle without your W-2 or active business income?
(That's Robert Kiyosaki's definition of wealth – worth checking against if building passive cash flow is your goal.)
The Concentration Question
How much of your wealth is concentrated in any particular area?
Maybe you’re stock-heavy and realize you own way too much Tesla. Or within real estate, maybe you’re overexposed to one asset class – apartments, self-storage, whatever.
Geography matters too. If all of your real estate deals are in Kansas City, what happens to your portfolio as a whole if that market underperforms?
The Gap Identification
Look at your written goals. Then look at your current portfolio composition.
What gaps do you see?
If you need more cash flow but you’re sitting on a bunch of equity plays, you’ve found your gap. If tax benefits are a priority but none of your investments offer meaningful write-offs, that’s another. If wealth preservation matters but you’re heavy in speculative development deals…you get the idea.
Once you’ve identified the gaps, you can start taking steps to fix them – which is where deployment planning comes in.
The Deployment Plan
Looking ahead to 2026: What will you realistically have to invest?
And then, do you know where that money is going? Is there a strategy behind it, or are you just going to invest in whatever sounds interesting when it hits your inbox?
If you identified gaps, now is the time to start building that deal pipeline. Get connected with sponsors who focus on what you need so you’re not scrambling when capital is ready to deploy.
Course Correction, Not Crisis Management
If you run through this exercise and find that things aren’t aligned, don’t beat yourself up.
The goal is clarity on where you are and where you’re going. And if those two things aren’t pointed in the same direction, that’s ok – you now know what needs to change.
The best investors I know do this at least twice a year. Some do it quarterly. Regardless of frequency, it doesn’t have to be heavy-handed or time-consuming.
Honestly, you could even throw these questions into ChatGPT, give it some details about your investments and goals, and let it help you think through the analysis.
This Weekend
Investing without a periodic review is like driving cross-country without ever checking your GPS – you might end up somewhere interesting, but probably not where you intended.
So as you’re working through leftovers and enjoying some downtime, consider carving out an hour for this. Sixty minutes now could save you years of compounding in the wrong direction.
You’ll go into 2026 with clarity and a plan – not just hoping things work out, but knowing you’re either on track or making the intentional changes to get there.