5 Scary things I've Tackled Since Starting My Own Business


I'm often asked, "How do you come up with so many things that scare you?"

EASY. So many things freak me out!

Really, the dumbest, most mundane things. This was especially true when I left my 9-to-5 and started working for myself. From stupid computer stuff to legal junk, here's a smattering of what might give you a slight panic attack should you go into business for yourself.

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1. Setting up a printer

I was gifted not one, but TWO crappy printers in the past 10 years. But I never used them because I couldn't figure out how to get them to function without karate chopping the item nearest me. Dealing with junk technology is infuriating! My work around: printing nearly everything at my office.

However, when I quit my job last fall and started working from home, I needed  printer at home. I put off this purchase for months until I absolutely needed one. Eventually, I went to Costco in a huff, picked out the second cheapest printer and brought it home. 

After unboxing/unstyrofoaming/unpamphleting the printer, I took a deep breath and plugged the thing in. Then, I actually followed the instructions. Within twenty minutes. my printer was functioning AND somehow working wirelessly! Whoa!

Either printers have become easier to set up or reading the instructions are the key to technology success. Probably both.


2. Starting My Own LLC

When I quit my job to focus on freelance writing and building the 'Hey Eleanor brand' [barf], I was encouraged to start my own LLC. Apparently, it helps with taxes? And apparently, it means I'm not personally liable if I really screw up in some way (write a slanderous blog post?) and get sued?

I'm still not sure I really needed an LLC, but I decided to start one anyway. Because I am an adult! And then came the scary paperwork. You know, the government-pages of words that don't make any sense. What's the difference between an s corp and a c corp? Hell if I know! 

I was way overwhelmed. So much so that... wait for it... I put it off starting my LLC for months (you might be noticing a theme here)! I eventually sought the advice of an accountant who guided me through the paperwork. Wiz-bang-boom, Hey Eleanor LLC happened in 35 minutes! Wow, that was easier than I thought!

And then, last week, when I started working on my taxes, I really started questioning this whole LLC thing. It seemed to really make things more complicated. I still don't really get why I need an LLC, but I have one. I think I might pay less taxes or something.

I vow to figure this out one day. 


2. Invoices! Billing! Bank Accounts!

More nitty-gritty starting my own business stuff: I'm a creative type, so being responsible for all of my own accounting scares the ever-living crap out of me. It's so not my jam. I'm always afraid I'm doing it wrong, missing something or just straight up forgetting to get paid, son. I am hoping and praying that one day everything will suddenly gel.

Or I make enough money to hire an accountant.


4. Working Alone

Working alone is great for a lot of reasons (working in pjs, flexible schedule, eating lunch at 10am), but scary because you can only rely on yourself to get everything accomplished. While I have a great support team (family, friends, husband, dog), relying on these folks to proofread my stuff, give me feedback and support me in the way a coworker might... well, let's just say it's not ideal. I don't want to burn my husband out on editing posts, plus sometimes it's hard to hear honest feedback from the person you have to sleep next to every night. Why even put unnecessary stress on your relationship? 


5. Questioning My Decision 

Last weekend marked the first time I was like, "How am I really going to make this work?" I'm talking from a financial perspective. I just don't even know. All I know for sure is that I absolutely love Hey Eleanoring, writing every day and sharing stories about regular people doing scary (but worth it) things, which means I need to figure out a way to keep doing this. Potentially, forever. I guess I just need to rely on that same gut that told me to start working for myself in the first place, which is equal parts scary and exciting. 


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Oh, hey there! Ever wonder what it's like to be self-employed? I'm no expert, but here's how my first two months went. I've learned a lot (one major thing: I'm shockingly more productive!), mostly that I love the freedom, even though it means you really must be a self-starter. And PS, here's two other stories of people who went into business for themselves: Michelle, who started her own web design company and Jessica, who became an ass-kickin' Girl Friday.