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

By Brittany Taylor

Work + Life

The big list of running-your-own business fears

99 scary things and how to conquer them as a creative entrepreneur


by Brittany Taylor

published October 17, 2016

updated June 5, 2018


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.

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.

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
    Introducing yourself in a Facebook group of bosses
  • 7
    Joining a networking meet-up
  • 8
    Setting up your website solo
  • 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
    Sending your favorite brand your media kit
  • 87
    Wasting time DIYing graphics that aren’t even the right size
  • 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.

How to get over your business fears

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.

Step 1. Pick a scary thing

Let’s go with No. 57: writing your about page.

Step 2. Break the scary thing down 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.
Step 3. Add baby step No. 1 to your to-do list

Do it today. Then, celebrate how good you feel about getting it done.

Step 4. Add baby step No. 2 to your to-do list

Do it 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 merits, after all.

Step 5. Work your way down the list
Step 6. Cross this fear off your list. Good work, boss!

About me

Brittany Taylor

My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.

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