If you’re reading this, chances are you’re at least somewhat interested in alternative investments (I’m making a big leap here, I know).
Maybe you’ve invested in a couple of deals. Maybe you’ve been at this for a decade (or longer) and have invested a dozen (or more).
But if you’ve been interested for a while and haven’t pulled the trigger yet, have you stopped to ask why? You might be falling for a common trap among high-achievers.
I’ve watched this play out enough times to recognize the pattern. You do the research. You understand the case for investing outside the stock market. You review investment decks, run the numbers, even jump on due diligence calls with sponsors and ask smart questions.
And then...
You wait. One more data point. One more conversation. One more comparison.
I wrote a while back about the opportunity cost of waiting to invest – discussing the dollars-and-cents problem of continually sitting on the sidelines.
But today, I want to talk about the psychology behind why intelligent, successful people get stuck in this pattern – and why your strengths as a high-achiever might actually be working against you.
Why high-achievers struggle
If you’ve built a career in tech, consulting, finance, or any analytical field, you’ve been rewarded your entire professional life for one thing: making the right decision based on complete information.
You analyze the data. You build the model. You test the assumptions. You derisk the variables. And then you execute.
This approach works brilliantly when you’re solving engineering problems or optimizing business processes. But it often becomes a liability when applied to investing.
Because in investing, you never have complete information. You can’t A/B test a real estate deal. You can’t run controlled experiments on market cycles. No amount of analysis will give you certainty about what happens five years from now.
So you keep digging, convinced that if you just study one more market report or stress-test one more scenario, clarity will emerge.
It won’t.
A spreadsheet as a security blanket
I've seen passive investors choose deals primarily because “the model is so thorough” rather than focusing on fundamentals that actually matter.
Detailed financial models create a sense of precision that feels reassuring. There’s something deeply satisfying about a complex spreadsheet with dozens of inputs and outputs all working together.
But that level of detail often creates a false sense of certainty.
One of the most successful real estate investors I know says that if he can’t do the math for a deal on the back of a napkin, it’s probably not a good enough deal.
Complexity shouldn’t create confidence. A fancier spreadsheet doesn’t reduce real-world uncertainty.
The trap many technical-minded investors fall into is over-scrutinizing specific details in the underwriting while missing the big picture – what I call the “overarching story” of a deal.
What drives the hesitation?
When I dig deeper with investors who are stuck, the conversation almost always starts around “needing more information.” But that’s rarely what's actually happening.
More often than not, hesitation is driven by an attempt to completely de-risk the investment.
You’re looking for the data point that will guarantee you’re making the right choice. The analysis that eliminates all uncertainty. The signal that confirms this is the one.
And because that level of certainty simply doesn’t exist in investing, you stay stuck.
The endless research becomes a way to avoid confronting an uncomfortable truth: you’re afraid of being wrong.
Not afraid of losing money, necessarily. Afraid of what it would mean if you, someone who’s built a career on making smart decisions, chose poorly.
That fear keeps six figures sitting in cash, disguised as prudence.
Approaching it differently
Now, I’m not suggesting you should stop doing due diligence or throw money at the next deal you see. Thoughtful analysis absolutely matters.
But recognize that at some point, more research doesn’t reduce risk – it just delays action.
A few mindset shifts that help:
Stop looking for the “perfect” deal. It doesn’t exist. Every investment has trade-offs. Your job is to find acceptable risk-adjusted returns that align with your goals.
Focus on the operator, not just the deal. The sponsor’s track record and operational competence matter far more than the projected IRR on their pro forma.
Remember that not deciding is still a decision. Sitting in cash waiting for perfection means you’re choosing the guaranteed loss of inflation and opportunity cost over the uncertain outcomes of actual investing.
One more thing to consider
I've worked with enough passive investors to recognize the people who build meaningful wealth through passive real estate aren’t necessarily the smartest people in the room.
But they have tolerance for uncertainty, can make smart decisions with incomplete information, and stay committed to a strategy.
Your analytical skills are an asset. But only if you know when to use them... and when to stop.