141: Do the Scary Thing: My Top 10 Side Hustle Fears

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It’s a special Friday-before-Halloween edition of The Side Hustle Show!

Today we’re diving into some of the scary moments in my business and some frightening tales from Side Hustle Show listeners.

Even though we’re told to “punch fear in the face,” I think it’s something that will be a constant in our lives. There’s always something to be afraid of.

This was also recorded as a live Periscope broadcast. For the occasional glimpse behind-the-scenes, follow me on Periscope here.

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My Top 10 Side Hustle Fears:

  1. Fear of strangers. Including cold callingMy introverted-self is slowly getting over this as I go to more and more events. 
  2. Fear of making bad decisions. Like for hiring or web development.
  3. Fear of embarrassment. 
  4. Fear of it all coming crashing down
  5. Fear of messing up.
  6. Fear of inadvertently breaking the rules and getting in trouble. 
  7. Fear of missing out. And there’s always something to miss out on!
  8. Fear of losing money.
  9. Fear of rejection. Check out Season 2 of Alex Barker’s 66 Day Experiment.
  10. Fear of wasting time. Is this activity my highest and best use? is this getting me where I want to go?

BIG thanks to these awesome entrepreneurs and side hustlers for answering the call to share their scary moments!

Tune in to hear their stories plus one of my most irrational fears.

Fear is something we’ll face every day, but I’ve found it’s often in confronting these scary moments that gives us a leap ahead in life and in business.

So what are you afraid of? Let me know in the comments below!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

6 thoughts on “141: Do the Scary Thing: My Top 10 Side Hustle Fears”

  1. Thank you Nick for sharing my audio clip! Starting was super scary. Maybe the next scariest thing has been moving forward one day at a time when sometimes you get mentally tired.

  2. Thanks for sharing your fears, Nick.

    I struggle with some of the very same ones (like 1, 3, 5, 8 & 9 ). Crazy as it is to recognize these fears they still find a way to stop me from picking up the phone or sending an email offering my service, which I’ve shown to make a major impact on sales and conversion rates.

    It is reassuring to hear others have similar struggles.

    • Some of these fears are pretty silly, right?

      In a book called The Top 10 Distinctions Between Millionaires and the Middle Class, the author frames a 3-part question as it relates to risk — but I think it applies to fear as well.

      He says when confronted with a [scary] situation, “millionaires” ask:

      -What’s the best thing that could happen?
      -What’s the worst thing that could happen?
      -What’s the most likely thing to happen?

      And goes on to explain if you can live with the worst thing, and the most likely thing is a positive, you might as well go ahead.

      The rest of the book is good too!

  3. Hello Nick,
    Fear is something that is synonymous with every human being but with different levels.

    I’m also afraid of some of the things you mentioned here especially the fear of rejection and the fear of missing out.

    But one thing I usually ask myself once awhile is What will I do if I weren’t afraid? I guess the answer is that I will take massive action on the things I want and that is how it should.

    Fear is always a normal feeling but what matters the most is how you handle yours.


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