Home Blog Real Estate Business

What One NYT Bestseller Says About Traps That Hold Ambitious People Back

Philip Michael
4 min read
What One NYT Bestseller Says About Traps That Hold Ambitious People Back

Since 2004, New York Times bestseller Ramit Sethi has built an almost cult following of success chasers with I Will Teach You to Be Rich, a personal lifestyle blog, “which I started from my dorm room in 2004 as a hobby.”

What started as a hobby has since—get this—done some radical numbers across the board, including 500,000 newsletter subscribers, one million monthly readers, and 23 million lifetime readers.

As the name suggests, Sethi specializes in, well, teaching people how to get rich.

Ramit’s also the same guy behind the $5 million week (1)—as in, he built a product and grossed $5,524,714 over the span of 6 days. (2)

On the blog, Sethi breaks down the three success traps that hold people back, including the very factor Harvard Business Review called the “No. 1 enemy of creativity”:

“It’s scary to decide what you want for yourself. Fear of failure is a very real problem, especially for ambitious people. We’re talented, we’ve been told how smart we are our whole lives, and now we’re supposed to ‘prove’ it by achieving our goals. Gulp.”

In reality, fear of failure is one of the biggest stiflers of success the world has ever seen. (This Forbes piece actually has five solid pieces of advice on how to deal with fear of failure.)


Fear of Failure

Any business is entrepreneurship, real estate included, and fear of failure will find a way to rear its ugly head, even for seasoned BiggerPockets contributor-investors.

Another big enemy against action is analysis paralysis. Here’s what Harvard Business Review had to say about that:

“Instead of feeling comfortable with the unknown, humans crave information that will make the ambiguous less so. The problem is that seeking more information sometimes feels like forward movement, when in reality, we’re delaying taking action because the information we need doesn’t exist or is so hard to find that we won’t get it in time.”

We all know the feeling. I’m sure we all fall victim to it at times. Getting caught up in “busy work” (lawyers are notorious for this), creating the illusion that we’re actually getting sh*t done—when in reality, we’re not. It’s just sophisticated procrastination.

Related: 5 Steps to Harness Your Fear of Real Estate Investing (& Use it to Motivate You!)

What Can Be Done Right Now?

Not sure if this is a strength or a weakness, but one of my idiosyncrasies is that I batch things into what can be done now, today, as opposed to a few irrelevant knowledge gaps that hypothetically could get in the way at some undefined point in the future.

Off the top of my head, I can list two or three paralyzingly frightening scenarios from my personal life where I had “deferred” factors that could trap me in analysis paralysis hell like it was a 1031 exchange.

I somehow got a gig to host a show on national TV (3) on a network in 80 million homes, directed by some guy named Benny Boom. He also happens to be the guy who did the Tupac Shakur summer blockbuster. (4)

I had no idea who Benny was at the time or what we were doing; I just knew I was going to be on TV. And that was probably a good thing—the mind tends to play tricks on us once we start thinking of all the things that can go wrong.

I was coming off a run as a host on SiriusXM with Randy Gordon, a mentor of mine, who put me on the show despite having zero experience and no idea what I was doing. I had accepted the gig on the condition Randy would be a co-host (at least I could look to him and not be totally lost).

Now, I figured it was going be taped. I thought I’d be on for 10 minutes, then I’d be out of there.

Instead, they told me 30 minutes before showtime that I was hosting for three hours alongside Showtime’s Al Bernstein, a Hall of Fame broadcaster with little patience for incompetence.


Related: Fear Could Be Costing You Millions: Here’s How to Overcome It

Just Be You

I was scared to death. I had no idea what I was doing. I kept botching my lines during prep. My stubborn pride superseded my cowardice, which is the only reason I didn’t throw the headset across the room and get out of dodge.

I asked Randy, “What the hell do I say? What can I do right now to not look like an idiot?”

“Just be you.”

“Commish, what the **** does that even mean?!”

“You’re fine, Shadow.”

You can literally see me tremble on the tape. However, after a few minutes of realizing I wasn’t going to die, it somehow became business as usual.

And once you actually confront the fear, power through and escape alive, it triggers this addictive feeling of supreme confidence that just snowballs into this feeling of invincibility. It’s pretty awesome.

I’m an Idiot 90% of the Time

Here’s a real estate-related example: We once raised money for a second, but smaller, real estate fund with less restrictive terms that allowed me to chase deals with more liberty.

There was so much I still didn’t know. I remember a call with an equity partner with an affinity for space asking about dimensions, natural light, and zoning variances. My attitude was, “I have no idea, but we’ll figure it out.”

I told my attorney outright, “I am from another country, I grew up with a different legal, business, and cultural system, so I will ask you questions at times like a two-year-old.”

And I do. And I ask. And I get on his nerves. And I don’t care. (No offense, Champ.)

This is the honest truth. At the time of this writing, we owned just over 100 units, and I still didn’t know dimensions or square feet or acres. I didn’t know Fahrenheit, and I didn’t understand miles, either.

The point is, I’m pretty sure people think I’m an idiot 90 percent of the time. Whatever.

You can’t have success without failure. I’ve had to learn how to get over my own fear of failure as I’ve built my business. You absolutely can, too.


  1. https://thehustle.co/ramit-sethi-5-million-dollar-week
  2. http://tim.blog/2016/03/04/5-million-week/
  3. http://goo.gl/ou5PXX
  4. https://www.gq.com/story/all-eyez-on-me-benny-boom-tupac-biopic

Premium 2

How have you tackled your fear of failure on your investing journey?

Weigh in below!

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.