7 Mistakes I Made in My First Year of Owning a Business

Happy HUMP, yo! If you’re subscribed to the CURation (if not, you should be! Get in the loop here), you might’ve caught this past Sunday’s chit chat on dreams etc…it was a goodie. In it, I also mentioned how we had had a *hella* productive day in the Gwynn casa. Part of that productivity was reconciling for Q3 (bit late on that one…) + getting my financial ish in order, which is not my favorite to-do on the list. But, it’s gotta happen, and sometimes, we’ve just gotta MAKE it happen in order for it to get done at all, let alone in a timely-ish manner. That’s a biggie lesson I’ve learned since having my own business – that just making it happen yourself is the #1 way to ensure something gets done, and gets done right.

But, that being said, we can’t do it all alone. So I’ve teamed up with my friends at Allstate to share 7 mistakes I made in my first year of owning my own business.

  • Disorganized invoices

When you’re your own boss and doing anything close to to resembling freelancing (ie. blogging, photography, actual freelancing, etc.), oftentimes there is no set salary. There is no biweekly direct deposit. Each + every transaction comes from a specific exchange of service or deliverable. With that, that means each + every transaction comes with an accompanying invoice, and any other appropriate paperwork (the important government ish, like a W9). A mistake I made early on was not having a system in place for collecting + organizing invoices. It was all just floating around in my inbox – not even in folders! – with the naive mindset that I wouldn’t have issues with anyone paying me on time. HA. Now, I have a Drive folder just for invoices, as well as a system in place for collecting any sorta late payments. Heck, we’re even bringing help on board to help serve as the collection agency at the end o’ the month! 😉

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7 Mistakes I Made in My First Year of Running my Own Business

  • Having only one bank account/mixing accounts

For the longest time, I didn’t have a bank account for my business exclusively. I would use PayPal, and I’d try to mentally keep track of any directly deposited money in my personal checking account. No bueno! Things got hella confusing hella quickly when it all started growing, and funds were all over the place. That makes it super hard, especially in just setting a working budget for your biz, since you’re not even sure at the end of the day what was a work payment (and if so, for what) or what was a birthday check from grandma.

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  • Not having set hours/Not having effective time control

This one comes with a grain of salt. When I first took CUR full time, I had hope in the back of my head that I’d have set working hours. When we got our house, I had this cutesy vision in my head of going into my office in the morning, coming out for coffee/snacks/to quick throw a load of laundry in, and then leaving the office at a specific time at night and closing the door behind me. LOL, E. I don’t think that’s happened *once* yet. In doing this for a living, it’s really freaking hard to have set work hours. Everyone and their mom says this, but really, everyday is oh so different. Yesterday is a perfect example. I had my day all planned out, ready to go. I got an email at 10 am from a brand saying CHANGE OF PLANS, they need content drafts by end of day. Except…I still had to shoot the content. And I had to shoot it about an hour from my house. So there went the day’s plans, and instead I had to adjust + adapt ASAP to get it all done (and of course, the day’s hours were altered accordingly, since I still had all of my other responsibilities of that day to finish, too!). Oftentimes, it feels impossible to have set hours. Hence the grain of salt.

The addendum to this is just not having more control over my time.

It’s easy for me to get in the habit of waking up + checking my email before I’m even actually functioning. And then I drop my phone on my face and it’s a bad day for all. 😉 So moreso, the big mistake here is ALLOWING other circumstances and/or third parties to control my time. One of the most amazing benefits of my job is usually that there are NOT set hours – that I can hypothetically work when it best fits my schedule, and play puzzle-master to make the pieces all fit. But sometimes, folks come in with expectations that you can just do whatever they need done, whenever they need it done, forgetting how the nature of your business actually works. So I wish I had learned sooner that it’s A-OK to put the brakes on someone and/or something when it completely conflicts with your life.

Do you need to take that work call at 7:30 pm because at 7:15 pm they emailed you asking for that? No.

Do you have to drop everything and rearrange your entire calendar because someone wants something sooner justbecause, even though it’s not in line with your contract? Nope.

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7 Mistakes I Made in My First Year of Running my Own Business

  • Not reconciling regularly

You would think I would enjoy accounting. Or finance, or math, or at least numbers. It’s not like I went to Wharton or anything. 😉 HAHAHA no. I think my body has a visceral reaction to anything with “reconcile” in it. What I’ve learned time + time again, though, (heck, I learned it AGAIN last weekend) is that reconciling regularly is goooooood. The worst idea is waiting until it’s tax time, and then collecting receipts from purses and expenses from your bank statement to make heads + tails of what went down. It used to take me *hours* to reconcile, ’cause I’d be using a hand-written list of “expenses” and “earnings” and a pile of paper receipts to then add to a spreadsheet and OY. Too many headaches. Reconcile once a week, as you go.

  • Waiting until the last minute to do taxes

My body ALSO has a visceral reaction to anything with “quarterly” in the title, unless it’s a quarterly sale. 😉 I swear quarterly taxes sneak up on me every. single. quarter. But waiting until the day before they’re due (or day of…whoops) is a recipe for disaster. Chances are, you’re going to miss something or need extra time to figure something out. Or, in my case, chances are you’re not going to have enough money in your bank account to pay taxes, and you need an extra day or two to transfer money to the right place from the right account that does have enough $$$ inside (and isn’t depleted from Starbucks, Target, + Chickfila runs…).

7 Mistakes I Made in My First Year of Running my Own Business

  • Not preparing ahead for taxes

This ties the previous two points together with a nice lil’ bow. Make sure you’re reconciling regularly. Make sure you’ve got money in the right account to PAY taxes (since there’s no government stepping on paychecks to handle it for ya!). Make sure you’ve got the right help! I’m #blessed with a financially-savvy (*ahem* nerdy) husband who doesn’t mind helping me figure everything out – he even made a bombdotcom spreadsheet for me to keep everything in order + automatically calculate tax payments (if ya want it, it’s in this post for ya to download!)

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  • Being too sensitive

When I first started my business, I cared waaaaaaay too much about what other people thought of it. And me. Granted, I am and always have been a super emotive, expressive, empathetic person. I crave connection. I lovelovelove talking to people, and – just like anyone else and their mom – I want to feel accepted by others. I’m not the type that lives + breathes for others’ approval (just my mom’s 😉 ), but I do care. I mean, I created CUR in the first place as a place to connect with other likeminded girls – to provide a hub of inspiration, fun, + good ol’ talk. If I don’t listen to what you guys think/say/want/need, then I’m not doing my job. So I HAVE to care about what people think! But especially first starting out, I was glued to opinions, forgetting that everyone has one (and they’re not all good, or equal). And it became toxic when it became just too much. I’d find myself completely unproductive for an *entire day*, just trying to please one hard-to-please person (read: a jerk) or prove myself to a doubter (read: an a$$hole).

Especially when it came to partnerships behind-the-scenes, I was always bending over backwards – usually at my own mental or actual expense – to be the best, and to overperform at all costs. I was too sensitive to the needs of others instead of my own needs and the needs of my family.

That being said, I will ALWAYS be the girl that overperforms. That’s just what I like to do. 😉 But I had to learn how to put my foot down in necessary circumstances to protect my own time, my own resources, my own everything.

Good things come to those who…persevere

7 Mistakes I Made in My First Year of Running my Own Business

PHEW. That quickly became about 750 words longer than anticipated. 😉 If you’re still with us, THANK YOU for reading, and thank you for being a part of this journey for the past year + beyond. (Heck, thankyouthankyouthankyou if you’re one of the folks that’s been around since the very beginning, 4+ years ago!) I hope you can take my mistakes + learn from ’em. That’s the whole point, after all. 😉

For more on small biz talk, I highly recommend Allstate’s Small Business Barometer – it’s this awesome tool that provides a peek into the world of small business across the whole USA.

Do you have your own business? Would you WANT to have a business someday, if not?

P.S. Didja enter to win $725 to Nordstrom yet?

Happy HUMP.signature blog

*This post was written as part of the Allstate Influencer Program and sponsored by Allstate. As always, all thoughts and opinions presented are entirely my own. As the nation’s largest publicly held personal lines insurer, Allstate is dedicated not only to protecting what matters most–but to guiding people to live the Good Life, every day. Thank you for supporting the brands that support Coming Up Roses!

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