SSS #62: 11 Questions I Ask Myself


In today's email, I want to share the 11 questions I ask myself most often.

But before we get to that...

Livin' La Vida Luna


Luna and her great-grandmother sharing a laugh this weekend at my parent's house.

I'm so grateful Luna has her great-grandmother. 3 of my 4 grandparents passed away before I was born.

11 Questions I Ask Myself

1. How am I complicit in creating the conditions I say I don’t want?

More often than we'd like to admit, we are taking part in the things that make us mad, sad or unhappy.

Here's a silly example. You eat an entire bag of Oreos in one night. You tell yourself you can't let that happen again. You promise not to bring them into the house anymore. Next time you're at the grocery store, Oreos magically make their way into the shopping cart. 🤷🏽‍♂️

Here's a less silly example: You feel undervalued at work, yet stay the course. You don't further your education, seek training, or look for other opportunities.

2. Do my actions map towards my ambitions?

One of the most common things I see in the real estate investor / entrepreneurial market place is people with a million dollar dream, but dollar menu work ethic.

Figuring out the key action(s) that will ultimately lead you to the life you want is critical.

For me, it's CRM (Client Relationship Management). I'm constantly contacting my network for one reason. I want to be their first call when they are considering a new deal.

3. What am I afraid of?

Spiders. No, but really.

Asking yourself this question when you're considering the next move can be super powerful.

In late 2017, I found myself coming off a business failure. I was afraid to immediately step back into the ring.

I thought I was afraid of the game, but losing investor money again was the deeper fear. There are few worse feelings than someone betting on you to produce and then failing to deliver.

So I changed my approach. I didn't take on any ventures I couldn't fund myself. I started small and used a snowball approach. Today, I'm happy to say I take outside capital again, but it took a major mindset shift and a long track record of wins to get to this point again.

4. What is the basis of this belief?

Limiting beliefs are a motherfucker.

There's an old adage about a baby elephant being tied to a stake in the ground. The baby elephant repeatedly tries to tug and pull itself away, but ultimately fails. Eventually, it gives up and learns helplessness. That baby elephant is then controlled for the rest of its life by being tied to a weak little stake in the ground.

Identify the stakes in the ground that are holding you back and break free from the ropes tying you to them.

Two limiting beliefs I've "conquered" are:

  1. I'm not good at writing
  2. I'm not good at reading

Growing up, I didn't do too well in Literature or English class. I'm also comparing myself to my smart-ass asian friends who outscored me on everything.

In college, I completely avoided any class that had a writing component. I think the longest paper I ever wrote at University was 5 or 6 pages.

When it came to any reading assignments, my first stop was and my last stop was

If the book wasn't summarized on those sites, I just winged it.

But then I learned two incredibly important things:

  1. Writing is the antidote to confusion
  2. Reading books that are relevant to what you want to achieve eliminates any chance of boredom

5. What would I do even if I knew I would fail?

This is a twist on the more popular question: What would you do if you knew you wouldn't fail?

Answering this question gets you thinking about what you love to do regardless of the result. For me it happens to be writing right now.

Will this newsletter amount to anything? Will the book I'm working on sell a million copies? Probably not. But I write anyway.

6. How am I serving those around me?

Whenever I'm feeling down, the act of helping someone else will catapult me out of my woes.

Many times it's as simple as making a connection between two people who have complimentary skill sets.

Being useful to other people is a great feeling. Be careful not to confuse this with being used by other people.

7. How can I remove tasks that don't require judgment?

"Judgment comes from clear thinking. Clear thinking comes from having time to reflect and to pursue your genuine intellectual curiosity. A lot of the great investors, like Warren Buffet for example, just sit around reading most of the time."

"We’re living in an age of infinite leverage and your judgment just gets multiplied through this massive force multiplier through code, capital, community, labor, what have you"

8. What's the cost of being wrong?

A few weeks ago someone asked me if it was a good idea to sell their home today, rent an apartment for a little while, and then buy again when the housing market inevitably collapses from an abundance of foreclosures.

Their logic makes sense on paper. But what's the cost of being wrong? Not just monetary, but mentally. Moving an entire family two times in the near future seems like an impossible task given the current Coronavirus climate.

Also, are they potentially stepping over dollars to make cents? The transaction costs of purchasing and selling a home are sometimes 10% of the home's price.

9, 10, & 11. What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing?

When Dia and I hit a rough patch, I try to ask myself these three questions.

A successful relationship is built on open communication. I think we often bite our tongues to avoid conflict. Or we let things we don't agree with go in one ear and out the other.

Which Questions Do You Ask Yourself?