5 Crazy Things You Can Do To Overcome Your Fear Of Rejection


This post is going to be very different than anything else I've put out. 

It's going to challenge you, push you, make you uncomfortable and hopefully inspire you. It starts with a story about dealing with success barriers and follows with 5 crazy things I did to overcome my fear of rejection. 

Some of them are obvious, others are downright silly and they all can help you (if you actually do them). 

My hope is that you can learn from my experience and complete at least one of the five challenges. If you do, I'd love to hear about your experience. You can either post in the comments section or send me a email.


Here's the story: 

The email glowed in my inbox. It softly whispered my name and pulled me in.

The title read:  let’s partner together? 

I clicked. Inside there was an application to be a part of a very exclusive 12 person mastermind meeting of industry leaders. The type of thing that NEVER happens. 

The potential rewards were huge and the downsides were minimal. If I got accepted, it could skyrocket the success of Stop. Start. Do. 

To say I was excited, would be an understatement. Visions of success, money, and fame entered my mind. I saw myself hanging out at the pool with industry titans, sipping on mojitos, laughing, and building life long relationships with millionaires.

Then, like a series of lightning bolts, negative thoughts started flashing in my head. 

I don’t have a chance.
Why would they choose me?
I'm not qualified.
I'm not the right person.
I don't deserve this yet.
I'm an impostor.

Like anything important, I procrastinated for 3 FULL DAYS before filling out the application. 

I was nervous. My heart pounded and I could feel the insides of my veins expanding. My cursor hovered over the green Submit Button for a few minutes - my eyes fixated on the black text.

A few more minutes passed...  

The pressure was really building now. My body told me to get up, drink a glass of water, go the bathroom, and check my email... ANYTHING TO RELIEVE THE TENSION! 

I recognized what was happening, took a deep breath, said my prayers and clicked Submit. It was no longer in my hands.

Then, the unexpected happened. At 7:01 PM that night, I got the call.


Going though this process forced me to re-learn ONE very valuable lesson:


The world puts enough limitations on you, why limit yourself more?  

If you want to overcome your fear of rejection, smash your success barriers, push your limits, and turn off those annoying voices in your head, there's only one solution - Stop Thinking, Start Doing. 

Below are 5 exercises which helped me overcome my irrational fear of rejection - all took less than 5 minutes. It took a little peer pressure and some arm twisting, but I'm glad I did them.

I'm challenging you to do the same. Pick one that scares you and do it today.


Challenge #1: Reach Out To A VIP.

Is there someone you admire? Someone whose work has changed your life? An actor, star, writer, blogger, influencer, entrepreneur, or president?

Who is this person for you? Get the picture him/her in your mind... Got it?

Your Challenge: Reach out to him/her and try to get a response. Call them, write them, tweet them, message them. Tell them exactly how much their work has changed your life.

It's the only way you can offer of value. Don't be needy. Just Give.

If you actually do this, you'll be surprised at how many of them will respond to you (like this one or this one or this one).

Please return my tweets Sir Richard!

Please return my tweets Sir Richard!

Ben's Note: I've tried to get a response from Richard Branson several times (at least 2). If someone can get a response from him, send me a screenshot because that would be awesome.




Challenge #2: Ask Your Family And Friends.

This one is powerful. It even made me cry.  

Credit goes to my mastermind partners Martin and Raj, who made me do it. There's no way I would have done it on my own. It shifted my perspective about how the world sees me and helped me figure out the person I wanted to become. 

I hope it does the same for you. 

Here's how to do it: Pick 5 People. It can be your best friend, coworker, peer, teammate, lover, spouse, mistress, boy toy, bae etc. Preferably, someone who knows you well.

And Send them THIS EMAIL:


Hi [Their NAME],
I am taking part in a personal development exercise, and I need your help. 

Could you please answer the questions below? It would really help me a lot. 


  • What am I great at?
  • What other people come to mind when you think of me? 
  • What’s one word that best describes me?

Thanks’ for your help! I appreciate your support.

-[Insert Your Name]


I guarantee their responses will surprise you. It just might make you cry. 


Challenge #3. Allow Yourself To Be Vulnerable (In Public).

It's strange... We are a world connected like never before, yet everyone feels so ignored. We want to be seen, to be heard, and to feel like someone cares. Yet we avoid putting ourselves out there at all costs. 

This is why everyone at singles bars gets completely wasted. If they get turned down or rejected they can blame it on the alcohol. This way they don't challenge their self-image and their ego's stay intact. It's easier. 

Fuck That. 

Your friends, family, fans, followers and tribe want to hear your story, read your words, see your face, and hear your voice. They want to connect with the real part of you. They don't care about the picture you post on Facebook of your dinner. They want to know the real you.

The Rap duo  Atmosphere  is a great example of vulnerability. Check them out. 

The Rap duo Atmosphere is a great example of vulnerability. Check them out. 

How to do it: Tell your story (this may take more than 5 minutes). Tell the world about a defining moment which changed your life. Post it to Facebook, Instagram, your blog, this blog, whatever. The medium doesn't matter. Just word vomit, proof it and post it.

If you are an inspiring musician, artist, writer or creator, just put your work out there! Show us who you are. 

Remember... You are enough as is. This exercise will give you proof. 





Challenge #4. Call A Friend Who Changed Your Life.

Is there someone who you haven't seen in a while? Do you wonder what they are up to? Is there a good reason why you haven't hung out? Other than it it's been a while and feels ackward?

I can almost guarantee, they are wondering the same thing. 

How to do it: Pick up the phone, call them, and ask to meet for coffee. Don't email. Don't text. Call and ask. If they don't answer, leave a message.

That's me walking across the stage at my 6th Grade Graduation... The peak of my academic achievement. 

That's me walking across the stage at my 6th Grade Graduation... The peak of my academic achievement. 

Ben's Note: After writing this I immediately called my elementary school teacher. She taught me how to follow my curiosity and let my natural interests lead me down new paths. Buying her a cup of coffee and letting her know how much she impacted me, is the least I can do for her.

Who is this person for you?



Challenge #5. Ask For 10% Off Of Your Next Cup Of Coffee.

In order to get what you want out of life, sometimes you need to ask.

App Sumo's Noah Kagan challenged me to do this 2 years ago and I still vividly remember it.

How to do it: You walk up to the barista, order your drink and then ask for 10% off. Then you smile and wait.

Let them speak first.  

If they ask why? You say you're taking a course in leadership and this is your homework. Then you smile and wait.

Doing this teaches you 3 things:

Your coffee will be happy you asked for 10% off!

Your coffee will be happy you asked for 10% off!

  • 1st. It's OK to ask for what you want.
  • 2nd. The worst that happens is they say "No" (which really isn't bad).
  • 3rd. If you ask, you may get what you want.





Your Challenge

Your comfort zone where all the learning happens

Pick one of these and do it today. If you wait until tomorrow, you won't follow through. After you have completed one of items, let me know what happened in the comments section below. Or, if posting on public websites isn't your thing, email me (see below). I want to hear your success barrier smashing story! 

Remember... You become a better leader when you challenge yourself each and every day.  It begins with dumb little challenges like this and then grows into all areas of your life.