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7 Challenges To Help You Start A Business

If you desperately want to start your own company, but for some reason you just can’t get yourself to take action — this post is for YOU.

In this post, I share some challenges with you that you can complete in a weekend that will help you get over your fear of getting started with a business and asking for money from customers.

This stuff’s powerful, so don’t try these challenges if you don’t want to start a business.

7 Challenges To Help You Start A Business

PS: Check out this video we made to see our marketing guy, George, try all of the challenges in real life.

Btw — Sign up for my newsletter. It’s FREE, and you’ll get my best business tips.

One of the most shocking things I’ve seen while helping 10,000+ people start businesses is fear.

And that’s just the straight truth.

They’re afraid of rejection and they’re afraid of asking.

But, there are very specific challenges that I’ve come up with to help thousands of people overcome that.

Let’s dive in.

Warning: These challenges might seem stupid. But, they work.

Challenge #1: The Push-up Challenge

I do 205 push-ups a day — and sometimes I do them in awkward places just because it makes me uncomfortable.

I do them at the airport, I do them in a parking lot, I do them at restaurants, etc. And when I do them, I always ask myself why I care so much about what everyone around me (who I don’t even know) thinks.

Part of the beauty is just going out and putting yourself out there. If you want to have a normal life and be employed at a company you might not like or do things you don’t really want to do, then just keep doing what you’re doing.

But if you’re not getting what you want and you want to try something new, then give these challenges a try for yourself.

When I’m doing pushups, the best part is that no one else cares.

It’s only in us. It’s only in our own minds that we’re afraid.

No one else gives a sh*t. They’re worried about their own problems. Just like you. You’re worried about your own stuff.

Challenge #2: The Coffee Challenge

And my most famous challenge of them all, the Coffee Challenge.

All you’ve gotta do is walk into a coffee shop (or tea shop, or just next time you buy anything) and ask for 10% off your purchase.

And then just wait for a reaction.

I find this challenge to be the most powerful because it’s deceptively simple.

Some people are like, “I’ve done sales for years, this is nothing!” and I’m like, well then just do it because it’s so easy.

Others are terrified to try this.

And what’s amazing about this is that you have to pre-commit before you do it. You can’t chicken out.

There’s also a lot of people that say they don’t want to do the challenge at a place they’re a local at… Of course you don’t! Because that’ll make it more awkward.

But that’s exactly where you should do it.

About a month ago, I went to the local bakery by my house and asked for 10% off. They asked why I wanted it, and I just said, “I don’t know. Do you want to give it to me?

They said no.

And I survived!

The whole point is not to create other excuses or make it softer. It’s fine if it’s a little bit uncomfortable, that’s part of the challenge. Overcoming the awkwardness and moving forward is how you succeed. Not by getting the discount.

Challenge #3: Asking a Stranger to Take a Photo of You

For this challenge, all you’ve gotta do is ask a stranger on the street or at a restaurant or wherever you are to take a photo of you.

Yeah, it might seem silly, but it’s a way to practice dealing with your fear of discomfort and your fear of rejection.

Yes, it’s small. But doing these smaller challenges where there’s no stakes will help you when you’re an entrepreneur and there’s bigger stakes. You get used to being uncomfortable and doing it anyway.

Plus you get to meet cool people and have a nice photo.

Challenge #4: The Dollar Challenge

Next up, ask for a dollar from a friend.

This is something I call velocity $1.

As you’re getting a business going, a lot of it is about momentum. It’s honestly just about increasing your self worth and knowing that you’re working on something else other people want to value, too.

It seems really trivial, but I’ve seen this literally happen thousands of times when someone gets the first dollar they’re like, “Wow, someone else believes in me?! I believe in me!

This is something you can do right now. Call up your homies or your brother or sister or whoever and ask them for $1. Again, don’t make up an explanation to soften it. Just exercise your ask muscle. And ask them to Venmo you or PayPal or get that old-school paper money from them.

And actually try it out! It’s easy to read this post and stay behind the screen, but actually get out in front of the screen and try it in real life.

You’ll probably have that “Oh.” moment that entrepreneurs usually have when someone gives them money for the first time. That realization that “Oh, someone actually wants to give me money for solving their problem or providing them with a service!”

Which is an amazing feeling and becomes something that entrepreneurs start to chase.

Challenge #5: The Borrow Challenge

This challenge is about asking someone you don’t know for their newspaper or something that they’re using.

The point isn’t to take something from others — again, it’s more about overcoming the awkwardness of asking.

I love reading newspapers in airports, so that’s where I go up to people and do this.

And the point is actually to get rejected. So if you go up to someone and you just ask them what time it is and then run away after they tell you, that’s not really overcoming the fear. That’s just skipping out on it, and it’s the awkwardness part you’ve got to lean into.

Which is hard! But rewarding.

Challenge #6: The Ask Challenge

If you have a Twitter, Instagram, TikTok or Facebook — post something right now that you need help with. Ideally, you haven’t posted about it before and you may be a tad uncomfortable posting about it.

That’s where the good stuff lives.

There are a lot of people out there that want to see you succeed but I see a lot of entrepreneurs who are afraid to ask anyone for help, or they’ll only ask people who they don’t know.

They’ll post about something on Craigslist or TikTok or Facebook groups where people don’t know them, so if they get rejected, it doesn’t really matter. But really what they’re doing is they’re avoiding the hard/easier part of asking all of the people in their workgroup, friend group, or social group who probably actually want to see them succeed!

Go ask them.

People are willing to help you. They just don’t know how to if you don’t ask.

Challenge #7: The Feedback Challenge

The last challenge we’re going to talk about is the Feedback Challenge.

Ask for feedback about yourself — that may be negative — but will help you improve some areas of your life.

It doesn’t always feel good, but it’s always a gift.

And it helps you keep improving as a person.

Find someone that you’re interacting with on a regular basis that can give you some feedback that will be challenging and help you improve.

Feedback is literally the best way you can keep improving yourself — either in relationships or work — and it will tell you what to work on so you can keep having a more interesting life.

Key Takeaways

Give these challenges a try!

They might not seem like a big deal, but you’ll probably learn something about yourself, and you’ll likely feel more empowered to be able to do bigger and bolder things in other areas of your life.

The thing is just putting in the reps so that when you actually get in the game, it’s a lot easier.


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