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updated 1/25/2013 10:24:08 AM ET 2013-01-25T15:24:08

Great entrepreneurs often talk about persistence -- pushing past ridicule and doubt to achieve success that no one believed possible. But successful leaders have another skill that often slips under the radar: the wisdom to let go of ideas that fail or lose their luster.

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As an entrepreneur, how do you know when it’s time to let go?

Sadly, there's no formula for making that decision. "Many successful people have had success because they pivot and others because they persevere," says Jason Calacanis, a serial entrepreneur, angel investor, and founder of Mahalo.com. The choice depends on the leader and the situation.

Learning to make that choice for yourself is about gaining the self-awareness to sense when your effort is productive and when it’s not. "People with a sense of commitment and loyalty sometimes feel like they need to fight the battle until the last dying breath," Calacanis says. "That's honorable, but naive."

Related: How to Sharpen Your Decision-Making Skills

To help you decide if it's time to move on, try these four tips: 

1. Make sure you still love it. If you're having doubts, then ask yourself, are you still driven to create this product? Do you talk about it constantly, get excited about using it, and blog about your ideas? Your enthusiasm is the heartbeat of your company. "If the founder comes to work every day and it's a struggle, that permeates the whole organization," Calacanis says. 

Use your team as a benchmark as well. Notice if they use the product, talk about it with friends, and promote it on social media. "If they're really proud of their work, they're going to crow about it," Calacanis says. If you or your team sees the work as a chore, it's time to reassess.

2. Give yourself an expiration date. Entrepreneurship is riddled with challenges, so you want to make sure that you don't let go too soon. "To get your head around the opportunity, you have to soak in it for a little bit," Calacanis says. He recommends giving yourself a cutoff date -- about one to three years, depending on your business -- at which point you’ll move on if it’s not working.

At the same time, you want to set shorter deadlines -- a few weeks or months -- to test shorter term projects or meet your growth goals. Benchmarks will tell you when your implementation needs to be adjusted, while the overall expiration date will tell you when the concept itself is flawed.

3. Talk to peers and mentors. When you're considering letting go, explain the situation to more successful entrepreneurs who've been around the block. Clarity comes from the process of explaining your situation and hearing their reaction. "You're going to figure it out real quick," Calacanis says.

Admitting hardship or doubt seems threatening at first, but it's a fear to overcome. "[Young entrepreneurs] worry that their teams will leave or panic, and that investors won’t believe in them," Calacanis says. “The opposite is true: They're going to respect you more."

4. Look five years ahead. If you're debating whether to let go of an idea, turn to your competitors -- similar companies that have already achieved success. "Look at the best case scenario and see if you want that," Calacanis says.

For example, when Calacanis was deciding whether to continue his popular podcast, "This Week in Startups," he saw that his most successful competitor was worth about $5 million, a number unlikely to grow in the current radio market. He wanted a bigger opportunity, so he chose to pivot and moved into video, launching Inside.com, a soon-to-be-launched site producing serial internet television shows.

Related: 5 Ways to Learn to Trust Your Instincts

Copyright © 2013 Entrepreneur.com, Inc.


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