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.
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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:
- 1Quitting your full-time job
- 2Sharing your Big Dream with your person
- 3Sending your first marketing email
- 4Paying for a monthly service
- 5Securing a domain name
- 6Introducing yourself in a Facebook group of bosses
- 7Joining a networking meet-up
- 8Setting up your website solo
- 9Launching an ad
- 10Asking for feedback from other business owners
- 11Publishing your first blog post
- 12Going live on Facebook
- 13Sharing personal stories on Instagram
- 14Deciding what to do about haters and trolls on social media
- 15Sending your biggest proposal yet
- 16Following up on an unpaid invoice
- 17Enforcing your contract terms
- 18Taking down your website’s “under construction” page
- 19Settling on a color palette
- 20Raising your prices
- 21Putting your first product up for sale
- 22Making an estimated tax payment
- 23Choosing a self-employed insurance plan
- 24Signing a contract with a fellow boss
- 25Taking an unpopular stand online
- 26Pitching a guest post
- 27Ordering nicer-than-budget-paper business cards
- 28Losing a long-time client
- 29Requesting a testimonial or recommendation
- 30Proposing a collaboration with another business owner
- 31Stepping onstage at a speaking gig
- 32Selecting a niche
- 33Asking your target audience to fill out a survey
- 34Automating your business processes
- 35Hiring an employee
- 36Taking a vacation
- 37Turning down a full-time job offer
- 38Bailing on a client project when you’re over your head
- 39Launching a product that’s expensive enough to justify a payment plan
- 40Skyping with a boss who is way more successful than you are
- 41Being a podcast guest
- 42Accidentally copying someone else
- 43Starting an enormous project with a new program
- 44Checking your Google Analytics after a couple of months
- 45Signing a lease without a steady income
- 46Meeting a new client face-to-face
- 47Attending a conference
- 48Explaining what you do to somebody new
- 49Deciding to rebrand your business
- 50Firing someone you hired
- 51Filing your business with your state
- 52Hiring a professional, like a lawyer or an accountant
- 53Picking the social media networks you’re going to use
- 54Taking someone to small claims court
- 55Making a plan for what happens with your projects and clients in case you die
- 56Collaborating on a joint venture
- 57Writing your about page
- 58Pitching your services
- 59Not being taken seriously
- 60Sending a cold email to a dreamy client
- 61Deleting old, irrelevant blog posts
- 62Taking a break from social media
- 63Working with a business coach
- 64Updating your financial spreadsheets
- 65Filing your taxes as a self-employed business owner
- 66Your competition is better at what you do that you are
- 67Dealing with a plagiarist
- 68Responding to hate mail
- 69Discovering an inquiry you missed from a few months back
- 70Deciding what to do with your stuff when you need to pee while working at Starbucks
- 71Missing out on a project you’d be perfect for
- 72Forgetting about an important call
- 73Someone else launching an idea that you were too scared to run with
- 74Losing your phone (and your calendar with it)
- 75Your website crashing on a really, really important day
- 76Being hacked
- 77Not syncing your opt-in forms with your email server properly…and losing heaps of sign-ups
- 78Crafting a longform sales page
- 79Calculating how much you “invested” in courses and e-books that you still haven’t started
- 80Snapping your own headshot
- 81Celebrating a small win in a public space
- 82Someone realizing you’re not the expert you said you were
- 83Doing something illegal without realizing it
- 84Updating your plugins in the wrong order and breaking your website
- 85Firing a client
- 86Sending your favorite brand your media kit
- 87Wasting time DIYing graphics that aren’t even the right size
- 88Missing a stupid, obvious typo in something you’re otherwise super proud of
- 89Losing the motivation to be your own boss
- 90Including your home address on your email newsletters
- 91Giving someone else, like a developer or VA, the passwords to your business accounts
- 92A lead telling you you’re too expensive
- 93Not meeting your earnings goals for the quarter
- 94Your webinar tech not working, even though you triple-checked everything
- 95Only selling products when you discount them
- 96Waking up to fewer followers than you had when you went to bed
- 97Moving your established website from one platform to another
- 98Neglecting another important part of your life for the sake of your business
- 99Your 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.
Grab the free worksheet that will help your conquer your fears!
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:
- 1Craft a mission statement. (For more on that, click here)
- 2Brainstorm 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.
- 3Write 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.”
- 4Put 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!
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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