4 Fun Challenges That Will Force You To Grow As An Entrepreneur

So you want to be an entrepreneur— or you want to be a better one. The beauty of entrepreneurship is that it’s a choice. You can choose to be one, and you can choose to get better at it, every single day. You can choose to do the things that raise your skill level. You can choose to challenge yourself in ways that make you grow. You can choose to never settle for just “ok.”

There are specific things you can do to build the skills and attitudes needed to succeed in business. There are exercises, like the ones I’ll outline here, that will build your ability and your confidence. They may seem odd. They may even seem ridiculous. But if you do them, you will come away a better entrepreneur.

These four exercises aren’t meant to be mulled over or filed away for later. They’re meant to be implemented now, as in today. They’re listed from least challenging to most challenging, but they’re all achievable within the next 24 hours. I challenge you to choose any one of them, and accomplish it now. It’s not a dare. It’s a call to action, and one that can have a surprising impact.

Challenge #1: The Coffee Challenge

This one comes from seasoned entrepreneur and friend of the $100 MBA Noah Kagan. The coffee challenge is very simple, but it takes some guts to try! You go to a coffee shop (or any business, really), and you make a simple purchase. Whether you’re buying a cup of coffee, a cup of tea, a donut, or a ratchet set, you ask for one thing: a 10% discount.

You don’t have a coupon. Nothing is damaged. You have no particular reason to expect this discount. You’re just going to ask for it. You might get it. You might not. What matters is that you develop the confidence, the people skills, and the sheer “what the hell” to try. As an entrepreneur, you will constantly have to ask for things. You’ll ask for sales. You’ll ask for deals. You’ll ask for partnerships and trust. Salesmanship is about asking, usually for a chance.

If you can face possible (or likely) rejection, revel in the awkwardness, and smile in the face of risk, you can entrepreneur. If you meet this challenge, you’ll know you can ask for anything— even when it’s time to convince someone to give you a shot in a business context. This is a necessary skill. It’s a freedom of attitude that will serve you well.

Challenge #2: Hire Someone

Anyone. Literally. To do whatever. Just pay a stranger to do something you need done. It can be a small task like writing some copy or designing a logo. It can be cheap; use sites like Fiverr or The point is to get comfortable finding someone, entrusting them with a task, and following up. The point is to know that you can delegate.

If you already have people working for you, this may seem like a pointless exercise— but it’s not. It’s important to exercise the skills you need in order to deal with (and occasionally rely on) outsiders and total strangers. Being able to choose who does things for you is the most important factor in freeing yourself up to be a true leader. Being comfortable with hiring out— even outside your trusted team— opens up a whole world of possibilities.

Challenge #3: Creating Content

Produce one— just one— high-quality piece of content, today. Right now. Before you go to bed tonight, write a great blog or shoot a great video. Create a nifty infographic or convenient pocket how-to guide. Whatever it is, design it, produce it, and put it out there. Put it on your website or social media. Email it to your list. But do it before your head hits the pillow tonight.

You’ll be shocked at your ability to create genuine value at a moment’s notice. What’s already in your head is worth having, and ultimately worth paying for. With a looming deadline and some pressure, you can create something excellent. Once you do, you’ll realize you’re capable of doing it every day. And you should!

Challenge #4: Put Something Up

For sale, that is— in the next 24 hours. Whatever it is; service, product, ebook, whatever, sell something. All you need is a one-page website with a “buy” button. You can use social media or other third party platforms, but offer something in exchange for money within the next 24 hours.

Again, the point is to see what you’re capable of. You may find out you’re capable of more than you thought.

It doesn’t matter how much money you make, or if you make any at all. Sell something for a dollar if that’s a fair price. You won’t be able to spend too much in the next 24 hours, so you won’t be operating at a loss. No matter what you actually sell, you’ll learn something that matters. You’ll learn that you can sell, even a random product on short notice.

Whichever of these challenges you choose, you’ll be glad you did. You’re capable of all of them, and they’ll show you that you’re capable of more. Challenge yourself, grow, and see what you can accomplish. The great entrepreneur Pat Flynn once told an audience of his to raise their hands “as high as they could.” With everyone’s hands in the air, he told them to raise them two inches higher. Every hand in the room went up, despite their supposedly being at their limit.

You never know what you can do until you try.