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Why So Many People Play Small All Their Lives

I move a lot.

That could have multiple meanings; for me it’s accurate two ways.

The Activity app on my Apple Watch says I’m averaging over 10,000 steps per day in 2019. And my Sleep Cycle app says that the quality of my sleep is considerably higher the more physically active I am.

That’s not what I’m talking about though, for this post. When I say I move, I mean calling moving companies, ending and starting leases, rearranging furniture moving.

In ten plus years in Miami, I’ve lived in ten different places.

Blame some of this on the uncertainty of an overseas basketball career.

Blame some on the roach-infested place I got out of quickly.

Blame the hotel I stayed in for a couple of weeks, while all my stuff was in storage, while I searched for the condo that ended up being that roach motel.

Blame some on meeting a girl and basically living at her place while still paying rent on my previous place in South Beach.

Blame some on moving to a place, realizing that we don’t really like it, and subsequently moving again.

Anyhow, I was thinking about my most recent realtor (have had a lot of those, too) and got to wondering: why do some realtors choose to work in the rental market, or is smaller-sized homes, while other realtors sell million dollar mansions?

I’ve known a lot of realtors since I’ve been in Miami; it’s the go-to career out here (amongst a few other professions that I won’t address today). As far as I can tell, a realtor has free choice as to what to specialize in the same way, say, lawyers do. You can rent $1,100 apartments just as easily as you could be a public defender; you can sell million dollar mansions just as easily as you could be lead defender for OJ Simpson.

I’d assume that very few realtors, like lawyers, choose their profession out of love for the job, but for the income and status potential (though I have crossed paths with some public defenders who genuinely want to keep innocent-yet-underfunded people out of jail).

Knowing this, then, why would a lawyer play a smaller money game than he/she could play?

This article confirmed my original hypothesis.

The reason is simple. In my experience, the No. 1 reason real estate agents don’t try to work in the luxury market is fear.

Most real estate agents sell homes in areas where they’re most comfortable. If you’re comfortable selling $200,000 homes, then those are the customers that you will find easiest to attract.

Because agents are not used to living in, visiting or selling expensive homes — and working with wealthy people — there’s a fear of the unknown.

In other words, many (not all) realtors play a small game due to their fear of failing at a bigger game. They see more realistic possibilities in staying where they are, where it’s comfortable and realistic.

And they’re right: staying where they are is their destiny.

This isn’t about real estate. The previous paragraph could be applied to any cross section of humans in any profession and still be accurate. It’s about the targets we aim at, and the consequences of hitting those targets.

I’m always looking for ways to explain and understand how some people “crack the code:” why some people “make it” while others don’t, even when they are nearly equal in skill, opportunity and effort. I gave a talk about it last week in Miami. Luck matters, yes. But I believe you have to at least be aiming for something to even luckily get to it. I may have sat next to a powerful music executive on a plane last week, for instance, but if I’m not thinking about getting myself known through music, this “luck” doesn’t even dawn on me.

More and more, here’s the simple-but-not-so-simple conclusion I’ve found.

It’s the questions we ask ourselves.

There are other things, I know —


— they all stem from the questions. Thoughts are nothing more than the questions we ask ourselves and the answers we come up with for those questions.

Low level questions — how can I make a living being a ________? — lead to low-level results.

Different questions — how can I be the highest-earning ______ in the industry/city/world? — lead to different results.

Too basic? Too simple? Yes, it is too basic. Which is why it escapes many smart people's attention.

Jay-Z is the first billionaire rapper, according to reports. Jay is a very talented rapper, but probably not the most talented ever, though. So, how and why did Jay-Z get so far ahead of every other rapper who’s also rapping about money and cars and homes and being rich? Jay summed up my argument succinctly on his 2001 song You Don’t Know:

I’ll tell you the difference between me and them

They trying to get their ones — I’m trying to get them Ms

One million, two million, three million, four…

Jay-Z never claimed to have the most talent. There are probably several musicians who work harder and spend more time in the studio. Maybe you don’t think much of Jay-Z yourself; music is art, after all. The main difference for Jay-Z is what he is/was aiming for. Nothing else.

So, the not-so-simple part: you might fail.

Real estate is a tough business. I’ve had a single realtor show me ten potential living spaces over the course of two months… and I ultimately decided to re-up the lease at my current place. That’s two months of gas money, parking fees, time spent traveling, and opportunity cost of all the other clients the realtor wasn’t dealing with while tending to me. All of those expenses are out-of-pocket for the realtor. Multiply that by ten or twenty, combined with the fact that you don’t know who or when you’ll make a sale (or rental), and the fact that it’s damn near impossible to be a part-time realtor…

Swap our real estate for professional basketball. Or rapping. Or writing books. Or building houses. There’s a ton of uncertainty in the game even for the low-level players. At the higher levels? All the same uncertainty — plus you’re dealing with a smaller base of potential clients, who may or may not accept your presence in the game, and your expenses are probably higher simply due to the type of people you’re now engaging with and their expectations…

Bottom Line

The fear that you will play for high stakes and lose is not without merit — there’s a good chance that you will lose.


There’s uncertainty and risk involved in any game. This is not the question you should be asking, because that risk is not going away no matter how you look at it.

The reason so many of us play small is because we never ask ourselves how we can play big… while accepting the fact that we may not initially have the answers.

Actually, check that — we DO ask ourselves, but we quickly come up with an answer: it requires this and this and that — all of which I don’t have — so perish the thought. Then we pick back up where we left off on the small game from yesterday.

It’s OK to not have answers to really good questions. These really good questions are also known as insights. An insight’s purpose is not to make the heavens part. It exists to make you think.


I'm not mad at the rental property realtors. I’m not looking to buy a 6 bedroom mansion just yet. I like moving every year or two. I need those realtors to stick around for me.

Business is a numbers game, though: if you leave the small game to participate in the bigger game, ten fresh applicants will gladly take your vacated spot at the bottom of the pyramid.

The small game will never run out of players.

#1148: Making The Leap From “Good” To “Great”


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