Money Matters Presented by Freshbooks: Financial Mistakes


Written by Shannon Wasden

Once upon a time, I was a professional business organizational assistant.  If you think that sounds boring, you’d be right. During those years, I assisted a lot of small business owners in the kind of detail you might see in a Hugh Grant movie-- minus the romance because these guys were definitely not Hugh Grant.  I helped them air out a LOT of their financial dirty laundry. Obviously, as a bystander, I’m no expert, but I have seen a lot of small business struggles and learned a bit about how to deal with them.

Let’s say it’s you and your business that are struggling.  Maybe there’s a royal screw-up going down in your business accounting.  Or maybe the suggestion of “money management” has made you cower in fear one too many times.  What do you do?

  1. Identify the problem and accept it.
    These things happen, and they happen to everyone.  Even Rockefeller made some major errors of judgement in his businesses.  Don’t assign blame, even though that might be your natural tendency. And don’t try to avoid the problem-- that always makes everything worse.  Just define the problem. Figure out exactly what happened, then calm down. Take a minute. Drink your favorite wine. Take a bath by candlelight.  Meditate. Namaste. Whatever.

  2. Don’t be afraid of your weaknesses.  Recognize them, then get help.
    If you need to hire out for tax season, DO IT.  Don’t be ashamed. I’ve helped organize the books for one guy’s taxes, three months overdue, and seen all kinds of mishmashed garbage in his accounting (side note: buying lingerie for someone is never, ever a marketing expense. I helped another guy with a similar problem, only he KNEW he was trash at accounting, so he employed the heavy use of software and a proper accountant’s steady hand. I know, especially when you’re just getting started, that hiring out can seem like an indulgence-- I mean, how hard is money management, really?  You kept your checking account out of the red during college, right?. But you need to set yourself up for success. Recognize where you need help and get it, girl.

  3. Find a way to prevent the problem going forward.  
    This part seems obvious, but it needs to be said. I worked for a man once who had run several businesses for ages, but he’d always struggled financially.  The reason? He had never done invoicing in his life. He was too soft on his clients, didn’t ask for money until he desperately needed it, and set himself up as a perpetual doormat.  When I got ahold of him, he was struggling to make ends meet with one enterprise, trying to invest in another, and attempting to keep a charitable organization afloat. When I left him, he had his businesses set up on a tablet so he could access them anywhere.  I helped him figure out how to use invoicing software to his advantage. Sadly, he didn’t follow my advice after I left. But you won’t be like that, will you? Hook yourself up with some incredible tools that can turn you and your business into its greatest potential.  This is 2018, people! There’s an app for that. Enter Freshbooks. Freshbooks is a mobile app (and website!) that helps you catalog your time, prepare and send invoices, set up budgets for specific projects for total transparency, track your work expenses (Taco Tuesday lunch meetups can count as a marketing expense), and, most importantly, all your info is recorded simply, professionally, and accurately, which will save your life in the long run.

  4. Stay in touch with your market and your customers.  
    I’m assuming you want to see your business through to the end.  So, find a way to stay connected (I once assisted a guy who made me read the Wall Street Journal and a bunch of other financial news sources for the duration of me helping him so that I’d understand all the ins and outs of accounting while I was there).  Make sure you’re pricing your goods or services appropriately, but don’t undercut yourself. As you get better at what you do, don’t be afraid to raise your prices. You are worth it! Also, make sure you stay relevant. You don’t want to be that person who’s selling Beanie Babies long after the bubble burst (wait a minute though, if the 90s are back, does that mean I can still make money on Patti the Platypus?).  Use social media to your advantage, and stay in touch with people who have similar business interests.

  5. Learn from your mistakes.  
    This should be the motto for your life: let your mistakes shape who you are, but don’t let them define you.  The same goes for your business. Your dreams are an incredible rainbow worthy of being chased. But sometimes you can’t jump into the pool without your floaties-- at least, not yet.  Go forward better organized, with a stronger backbone, and with a more relevant product-- then take the plunge again.

Unless you majored in business, you’re probably going to hit a few roadblocks in your professional pursuits when running your own company, however big or small.  Just remember that it isn’t the end of the world, and not even necessarily the end of your business. Hopefully these five tips will help you keep your head on straight and leave you coming out the other end on top.


Shannon Wasden is a serial project-starter who currently lives with her husband and two children near Galveston, Texas.  She has a degree in Archaeology but never uses it except to impress people.  She loves hiking, writing, photography, and baking.  Her current projects include a real-life food blog in its infant stages, transcribing letters for people's family history, too many house renovations, and attempting to keep her five-year-old daughter, three-year-old son, enthusiastic cattle dog, demanding cat, five dramatic chickens, and an array of assorted plants alive without prematurely reaching an advanced age.  Showering is out of the question.  She is an unabashed introvert, and her life goal is to make people laugh, as long as she doesn't have to talk to anyone in person.

This blog is sponsored by Freshbooks, though all the thoughts and opinions expressed in this post are those of the writer and approved by Pass/Fail. Freshbooks is a cloud based small business accounting software. Send invoices, track time, manage receipts, expenses, and accept credit cards. They make managing every aspect of your business easier, whether that’s project workflow, billing, or following up with clients who haven’t paid you yet. Pass/Fail readers can get two months free to give it a try by clicking here.

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