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.

* * *

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.

* * *

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.

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Comments (8)

  • Diana 6 years ago Reply

    LMK if you ever want a proofreader! You should know I’m Team Oxford Comma, though.

    Hopefully this doesn’t happen to you, but…I thought I had a handle on my printer. Then I had to change the toner. That’s a lie. Bil eventually did it. I still don’t know how.

    molly mogren katt 6 years ago Reply

    My blog must drive you bananas ’cause I don’t do the Oxford Comma! It’s more about leaving entire words out. Oopsies! I’ll let you know if I ever need another set of eyes.

    And see, it’s good to live with a tech-savvy person. Or at least a person who has more patience than you do.

  • Ellie 6 years ago Reply

    Love your blog, lady!
    Have you heard of Braid Creative? Kathleen did the design work for Well Fed and now runs a business coaching creative entrepreneurs. Lots of cool stuff over there!

    molly mogren katt 6 years ago Reply

    Yes, I have checked them out, but just in a cursory glance kind of way. Thanks for the reminder (and for reading!)

  • Audrey 6 years ago Reply

    Hey Molly! I love listening to your podcast and hearing about your latest adventures. Which is what my question for you is about. How do you turn a to do list into exciting memorable moments? I have a lot of flexibility and freedom in my life but can’t seem to take advantage of it, being weighed down by so many tasks (e.g. getting and setting up a printer and paying bills). How can I find freedom and spontaneity in my life when I’m trying to be responsible all the time?

    molly mogren katt 6 years ago Reply

    This is a great question!

    First and foremost, you need to making having "adventures" a priority. Which is to say that you have to own up to the fact that those experiences are important to you. And guess what– it turns out having fun & playing as an adult is actually really good for your health. You can read about that here:

    Additionally, I think we’ve all been shamed just a little into thinking that if we’re not being "responsible adults" all of the time, we’re doing it wrong. Wasting time, being a load, whatever. We all need to cut ourselves a little more slack. You’re allowed spend your Saturday doing something new/fun/exciting. It’s not irresponsible. In fact, I’d argue that you’ll be less resentful of your ‘responsible’ tasks if you inject some fun stuff here and there.

    I do find that the more crammed my schedule gets with fun things (meeting friends for coffee, trying a new workout class, going to a movie), the more EFFICIENT I get at the boring, responsible stuff. I like to crank it out so I can move on with my life!

    Hope that answered your question. I think I’m going to dig into this one a little more in the next few weeks. Stay tuned! (and thanks for reading and listening to the podcast!)

  • Kyle Jeffrey Kranz 6 years ago Reply

    I just started using Quickbooks, and I think I should have started using it a long time ago. If you don’t use any accounting program, it may be worth looking into 🙂

    Kyle @ SKORA

    molly mogren katt 6 years ago Reply

    In my mind, my business isn’t "real" enough to use Quickbooks. Hahaha! Maybe I should give it a whirl.

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