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5 Empowering Questions You Should Ask About Your Most Recent Failure

Everyone fails.

Every successful real estate investor on the planet has made a bad investment, hired someone who wasn’t a fit, chosen the wrong market, or lost a big deal to the competition.

Contrary to popular belief, it isn’t failing that determines whether you’re successful or not, it’s how you perceive that failure.

Do you perceive it as an end-all to your dreams, as the final nail in the coffin of your hoped-for reality? Or do you perceive it as a minor speedbump on the road of life, as a single bad moment amidst millions of moments just brimming with opportunity?

Your answer to that question is everything.

How you perceive failure will determine, in the end, how happy and successful you are in your personal and professional life. It’ll determine whether you stick with it til’ it works or quit “3 feet from gold.”

Of course, changing your perception is easier said than done. So to help, here are 5 questions you can ask yourself  in the midst of or after a “crippling” failure. Making these questions instinctual and habitual can, I believe, completely change the way you perceive setbacks and thus, how little power those setbacks have over you.

We answer the phone for hundreds of top investors around the U.S. — Do you want to be next?

1. What is great about this?

I know.

It’s the last thing you think of asking yourself when an A-player just quit, when a big investment fell through, or when your high-ticket ad campaign isn’t generating leads.

But it’s also the most important question you can ask yourself for re-framing the way that you perceive problems and setbacks in your life.

What is great about this problem?

At first, you’re going to think, Nothing!! Nothing is great about this problem. 

But hold on for a second and ask yourself that question until you come up with a different answer. Maybe that A-player quitting gives you an exciting opportunity to find someone new who can really help you take your business to the next level. Or maybe that bad investment falling through is just the kick in the rear you needed to finally hone in on your due diligence process. Or maybe your failing high-ticket ad investment that you’re stuck with for an entire year gives you the motivation to finally fix your website’s conversion rate.

The point is, every setback has a silver lining (even if it’s a really thin silver lining). And you can remind yourself of that by asking this question the moment something bad happens.

2. What can I do to make this more enjoyable?

Sometimes, a setback or failure will involve doing something you really don’t want to do. Going to court, sitting through long negotiations, cold calling, fixing your website, or learning about social media are a few examples.

But ask yourself… What can I do to make this more enjoyable?

You might find that it’s just your perception that’s out of whack and with a quick “Oh — it might actually be fun to learn how to be a better cold caller,” you can create more positivity and motivation.

Or you might find that you do need to change something to make it more fun. I like to drink coffee every morning while I work because I associate coffee with pleasure and when I drink coffee with work, I associate pleasure with work. It might mean changing your work environment, sitting in the hot tub while you make phone calls, or getting physical activity in between 30 minute stints of doing whatever it is you need to do.

Whatever you can do to make the process more enjoyable, do it. You’ll do a better job of it and you’ll be less miserable.

3. What can I learn from this experience?

Every failure is an opportunity to learn something new about yourself, your business, and the way the world works.

So embrace that; what can you learn from your most recent failure?

When you allow curiosity to dominate your thoughts in the midst of a difficult situation, you are suddenly less concerned about the consequences of your setback, you are empowered to make meaningful changes, and you are working toward solving the problem rather than wallowing in it.

4. What did I do to make this happen?

You and I have far more control over the current state of things then we give ourselves credit for.

When you make a bad investment, a bad hire, or when you’re not generating leads or closing deals, it’s easy to blame the other person — whoever that is. A lot of times, that scapegoat is an employee you hired or a lead you spent too much time working with that never converted.

But did you catch that?

You hired them. You trained them. You spent too much time with a half-committed lead.

So… what did you do to make your situation the way it is? Own it, don’t wallow in it, and resolve to do things differently in the future. While you have to accept that you’ve made some bad decisions, knowing that you made those decisions empowers you to make different decisions in the future.

5. From a bird’s eye view, is this really a big deal?

We tend to make too big a deal of things.

We think that one season of bad investments means we’ll never succeed. We think that one key employee quitting means we’re always going to be a bad boss.

But that isn’t true.

In the scheme of things, your one failure is just a single blip in the night sky — insignificant, unimportant, and unrelated to your own success and happiness. If you ask this question more often, you’ll realize that, from a bird’s eye view, your failure really isn’t that big of a deal.

Do what you can to fix it and move on.


Failing is a part of life. And it’s a part of business.

You’re going to fail.

But how you deal with those failures is far more impactful than how often you make mistakes. And by asking the five questions above, you can rewire your brain to view failure as the opportunity that it is.

And with so many opportunities before you, success ought to be just around the corner!

We answer the phone for hundreds of top investors around the U.S. — Do you want to be next?