The big list of running-your-own-business fears (+ how to do scary shit anyway)

By Brittany Taylor

Truth: Most bosses are scared to death 97.2 percent of the time. This blog post is loaded with 99 absolutely normal business fears plus the resources you need to conquer each and every one of them. How boss is that?!

Also: According to the Bureau of Made-Up Statistics​, 93 percent of all quoted statistics are made up on the spot. File that under #funfact with a sprinkling of flaky sea salt, please.

What the fudge is fear, anyway?

Fear is unpleasant—that’s what Oxford and Merriam-Webster say. It intimately entwined with anxiety. The difference between the two is that fear is rooted in a present situation or stimulus, while anxiety deals with the future—something that hasn’t happened yet and may, indeed, never happen (more on that in The New York Times).

Fear is what protects us from danger. It’s an evolutionary emotional response that keeps us safe. Except, as bosses, we tend to experience fear about situations that are more awkward or uncomfortable than physically harmful.

The fear we feel as creative entrepreneurs doesn't protect us. It prevents us from doing the work.

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So, why are we scared of things that aren’t a legitimate threat? Often, it’s a result of past trauma, per Psychology Today​. It might seem trivial to our ancestors, but dealing with a bad boss or an online troll sticks in our psyches far longer than the physical fall-out.

The line between the two is hairline thin and wayyy too easy to cross. For online bosses like you and me, the digital world is so essential and our relationships with the people we meet there are so vibrant that the internet feels tangible. Our anxieties over these online what-ifs are very real.

They are true-blue fears.

Needless to say, fear is a big-time bitch. But bitches are everywhere. It’s time to confront this B and persevere in spite of her.

the big list

99 business fears

The best way to not think about what you’re currently terrified of? Reading an enormous list of things you’ve been scared of in the past and will probably be scared of in the future. I mean, obvi, right? Lucky you, kiddo!

Hold on to your teddy bear, boss. Here's that big list of boss fears:

  1. Quitting your full-time job
  2. Sharing your Big Dream with your person
  3. Sending your first marketing email
  4. Paying for a monthly service
  5. Securing a domain name
  6. Setting up your website solo
  7. Introducing yourself in a Facebook group of bosses
  8. Joining a networking meet-up
  9. Launching an ad
  10. Asking for feedback from other business owners
  11. Publishing your first blog post
  12. Going live on Facebook
  13. Sharing personal stories on Instagram
  14. Deciding what to do about haters and trolls on social media
  15. Sending your biggest proposal yet
  16. Following up on an unpaid invoice
  17. Enforcing your contract terms
  18. Taking down your website’s “under construction” page
  19. Settling on a color palette
  20. Raising your prices
  21. Putting your first product up for sale
  22. Making an estimated tax payment
  23. Choosing a self-employed insurance plan
  24. Signing a contract with a fellow boss
  25. Taking an unpopular stand online
  26. Pitching a guest post
  27. Ordering nicer-than-budget-paper business cards
  28. Losing a long-time client
  29. Requesting a testimonial or recommendation
  30. Proposing a collaboration with another business owner
  31. Stepping onstage at a speaking gig
  32. Selecting a niche
  33. Asking your target audience to fill out a survey
  34. Automating your business processes
  35. Hiring an employee
  36. Taking a vacation
  37. Turning down a full-time job offer
  38. Bailing on a client project when you’re over your head
  39. Launching a product that’s expensive enough to justify a payment plan
  40. Skyping with a boss who is way more successful than you are
  41. Being a podcast guest
  42. Accidentally copying someone else
  43. Starting an enormous project with a new program
  44. Checking your Google Analytics after a couple of months
  45. Signing a lease without a steady income
  46. Meeting a new client face-to-face
  47. Attending a conference
  48. Explaining what you do to somebody new
  49. Deciding to rebrand your business
  50. Firing someone you hired
  51. Filing your business with your state
  52. Hiring a professional, like a lawyer or an accountant
  53. Picking the social media networks you’re going to use
  54. Taking someone to small claims court
  55. Making a plan for what happens with your projects and clients in case you die
  56. Collaborating on a joint venture
  57. Writing your about page
  58. Pitching your services
  59. Not being taken seriously
  60. Sending a cold email to a dreamy client
  61. Deleting old, irrelevant blog posts
  62. Taking a break from social media
  63. Working with a business coach
  64. Updating your financial spreadsheets
  65. Filing your taxes as a self-employed business owner
  66. Your competition is better at what you do that you are
  67. Dealing with a plagiarist
  68. Responding to hate mail
  69. Discovering an inquiry you missed from a few months back
  70. Deciding what to do with your stuff when you need to pee while working at Starbucks
  71. Missing out on a project you’d be perfect for
  72. Forgetting about an important call
  73. Someone else launching an idea that you were too scared to run with
  74. Losing your phone (and your calendar with it)
  75. Your website crashing on a really, really important day
  76. Being hacked
  77. Not syncing your opt-in forms with your email server properly…and losing heaps of sign-ups
  78. Crafting a longform sales page
  79. Calculating how much you “invested” in courses and e-books that you still haven’t started
  80. Snapping your own headshot
  81. Celebrating a small win in a public space
  82. Someone realizing you’re not the expert you said you were
  83. Doing something illegal without realizing it
  84. Updating your plugins in the wrong order and breaking your website
  85. Firing a client
  86. Wasting time DIYing graphics that aren’t even the right size
  87. Sending your favorite brand your media kit
  88. Missing a stupid, obvious typo in something you’re otherwise super proud of
  89. Losing the motivation to be your own boss
  90. Including your home address on your email newsletters
  91. Giving someone else, like a developer or VA, the passwords to your business accounts
  92. A lead telling you you’re too expensive
  93. Not meeting your earnings goals for the quarter
  94. Your webinar tech not working, even though you triple-checked everything
  95. Only selling products when you discount them
  96. Waking up to fewer followers than you had when you went to bed
  97. Moving your established website from one platform to another
  98. Neglecting another important part of your life for the sake of your business
  99. Your last great idea was really your last great idea. That’s it. No more.

Boom, baby. Fear in the flesh...or, at the very least, fear in all its black-and-white pixelated glory.

action plan

Pick a scary thing and do it. Here's how.

Just do it. Sure, you could do that. But since I procrastinate my way to hell and back before I do the scary thing, I figured I’d tell you what I do, instead. It’s pretty simple.

First, you pick your scary thing. Let’s go with No. 57: writing your about page.

Second, you break that big, scary thing into baby steps. (I know, baby steps. I told you it was simple.) For No. 57, your baby steps might look like this:

  1. Craft a mission statement. (For more on that, click here)
  2. Brainstorm all the qualifications you have to do whatever it is you do. What are your pluses? What can you do that other people can’t? Be a braggart. Go on, do it.
  3. Write a one-paragraph biography that includes a few quirky, endearing details about you as a person, outside of your business. If you intend to get personal on your business’ Instagram account, try to incorporate a few themes you’ll share there, too. Consistency is key. I, for example, am “Brittany, the writer with the Goldendoodle from Charleston, S.C.”
  4. Put it all together. Write your about page. Do that shiz.

Third, you add baby step No. 1 to your to-do list today. And you do it. And you feel good about doing it.

Fourth, you add baby step No. 2 to your to-do list sometime in the next week. It could be tomorrow, or it could be next Monday. I vote for sooner rather than later. “Just do it” does have its uses, after all.

Fifth, keep working your way down the list of baby steps until you reach the very last one.

Sixth, cross this fear off your list. Move forward. Good work, boss!


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I see you, boss. I see you here, on this website, and I see you on social. If this post touched you, helped you, landed in your bookmarks, please consider sharing it with your friends and followers. Pay it forward!

- Brittany Taylor

#99fears and working through 'em ain't one. Learn how to get 'er done in 6 very do-able steps

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When it comes to being the boss you need to be to grow your business, what scares you the most? #99fears

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