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

By Brittany Taylor | Boss

Oct 17

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

Oct. 17, 2016 

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 (thanks, 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 bosses doesn't protect us; it hurts us. It prevents us from doing the hard 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, according to 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.

Most bosses are scared to death 97.2 percent of the time. Here are 99 absolutely normal business fears plus the resources you need to conquer each and every one of them.

The big list of fears for bosses

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 the big list of 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 headshots

  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 my 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.

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!

P.S. There’s a worksheet for that! And it’s free—bet you didn’t see that coming.

This worksheet will walk you through the steps in the last section. In one page, I’ll take you from terrified to pretty much OK about things. And if not quite OK, strong enough and ready enough to move forward anyway.

I know bossing it out is scary. But come on. Let’s do it together.

Start working through your fears instead of running from them. Sound good?

Download this worksheet and use it alongside the Big List of Business Fears in this post to get a head start on the hard work of being a boss, fears and all.

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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!

99 fears and working through 'em ain't one. Learn how to get 'er done in 3 steps.

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When it comes to being the boss you need to be to grow your biz, what scares you the most?

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You are 1 worksheet + 6 steps away from working w/ your fears to get shit done. Let's do this, boss.

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