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3 Challenges That Will Teach You to Think Like an Entrepreneur

Challenges are certainly social media gold--just about everyone has had people trying to do planks or push-ups consistently for a month pop up on their feed. But do these challenges actually work? While experts warn against inflated expectations and pushing yourself too hard too fast, when it comes to the mental side, the verdict is largely positive. A limited timeline helps take some of the terror out of getting started on a new habit, the social aspect of sharing your progress reinforces your commitment, and the sheer repetition of these challenges helps habits stick (though scientists warn that, depending on the difficulty of a new habit, truly making a new behavior automatic can take well more than a month).

This means maybe your Facebook friend's month of planks isn't so silly. But can the same principle be used not just for building core strength but for more substantive change? Can a challenge help you develop the mindset and skills you need to be successful as an entrepreneur? Noah Kagan, for one, says yes. On his blog recently the startup veteran and AppSumo founder argue that simple but quirky challenges can help prep any would-be entrepreneur for what it really takes to run a successful business. "One of the most shocking things I've seen while helping 10,000+ people start businesses is fear. They're afraid of rejection and they're afraid of asking," Kagan writes. "But, there are very specific challenges that I've come up with to help thousands of people overcome that." He runs through seven such challenges in his detailed post but I'll just give three here to give you the flavor of his ideas.

1. The Coffee Challenge This challenge is a classic for a reason. To complete it you just ask for a small discount on your morning cup of coffee (or a similar small purchase) and see what happens. Just don't be a jerk to the no-doubt-harried service employee you're dealing with. To deepen the challenge, commit to doing it every day for a week. Sounds simple, but according to Kagan, the effects can be surprisingly profound. "Most people will make an excuse. 'Oh, I've already done sales for five years.' 'Oh, I'm not afraid of doing that.' 'Oh, I don't need a discount, I have money.' But if you go ahead and ask for 10 percent off coffee, I guarantee that you will learn something about yourself that will surprise you," Kagan explained on a podcast.

Those who have tried it report he's on to something. Asking for a discount is both surprisingly hard and surprisingly empowering. And not because you might manage to save a few cents on your latte. Instead, the benefit is proving to yourself that you can experience social anxiety and rejection and still be just fine.

"​​Overcoming the awkwardness and moving forward is how you succeed. Not by getting the discount," explains Kagan.

2. The Ask Challenge No one, no matter how smart or how experienced, starts a business entirely alone. Everyone leans on outside experts and trusted advisors for some part of the process. So it's best to get comfortable for reaching out for help right at the start, which is why Kagan advocated for what he calls "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," Kagan writes. He insists the response will be instructive. "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," he says. "People are willing to help you. They just don't know how to if you don't ask."

3. The Feedback Challenge Getting over the fear of rejection and learning to ask for help is key to entrepreneurial success. So is personal growth. If you want your business to succeed over the long haul you are going to need to become a better version of yourself in the process of building it. And the best way to improve is to ask for feedback.

"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," instructs Kagan. "It doesn't always feel good, but it's always a gift." If you find the experience useful, you could even commit to asking three or five people to get a range of feedback.

Research shows that it is possible to shift your personality over time, but the secret is action. Wishing you were the kind of person who is open and brave enough to start a business won't make it so. Actually putting yourself in situations that demand those attributes will. And the more relevant experiences you rack up, the more you will change. Which makes the challenges suggested by Kagan one great way to prepare yourself for a life of entrepreneurship.


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