Three Upgrades Your Small Business Needs — And Fast

three small business upgradesBoxes.

They stack neatly. If you’re lucky, they have lids. If you’re super organized (groan), they have labels.

But regardless of what condition a box is in, it’s great at doing one thing: making you lazy.

We throw stuff in boxes all of the time to get stuff we don’t want to deal with out of sight. The problem is, we’re not dealing with the mess we created in the first place. Personally, I’m a fan of drawers. Holy hell, don’t open my desk drawers (I recently found a missing pair of black tights and $50 gift card in an unopened envelope). Whatever your container of choice, there’s a hard truth many small business owners have to face:

You’re treating your business like a box. It looks great on the outside, but if you crack that sucker open, it’s a bit (a lot) of a mess. We heave stuff into boxes and drawers and onto shelves, both physical and mental. Before long, we have boxes filled with shit we didn’t want to deal with stacked up everywhere. So let me ask you this:

Would you rather your business look like a storage unit or an Apple store?

Today, we’re going to look at three upgrades you can make to get all of that business shit out of those boxes and back where it belongs — organized in crisp, clean, Apple store fashion. The hard truth is that you’ll never get from where you are to F&*K YEAH if you’re shaping things up to be a storage unit.

Let’s upgrade.

Your Inbox

Your inbox is not a storage unit — it’s a shipping dock. It’s where things land before they’re sent to where they need to go. Get it cleaned up using these tactics:

  • Hire a virtual assistant: I was at inbox (ahem) 8000 or so about two years ago. I hired a virtual assistant who was a night owl to log into my computer remotely and file all of my emails in folders. After a week, I woke up to inbox 8 — only a few flagged items needing my attention remained. Tools like LogMeIn can facilitate this process.
  • Day-end routines: When I’m ready to close my computer for the day, I review all of the day’s emails remaining in my inbox. If it’s not flagged for pending action, it gets deleted or filed. No excuses.
  • OMFG AIRPLANES: Travel much? Skip buying the WiFi and take an hour to sort your inbox.

It’s time to get over the CFS (Can’t Find Shit) filing system where the search box in your mail program is your best friend.

Your Finances

Without fail, the number one question I’m asked from emerging (and often seasoned) small business owners is, “How can I improve my cash flow?” No lie — it’s a key goal for my business in 2013 as well. Improving cash flow comes down to two things: organization and accountability. If you don’t treat yourself like a client, you’ll never get your cash flow reined-in. Here are some upgrades your business needs:

  • Invoicing: First, PayPal isn’t a solution for small businesses — it’s a payment gateway. Smart small businesses know that they need a billing, invoicing, and payment system that shows the true history and future of a business. Here are three solutions to get your financial shit together:
    •  PaySimple’s Starter Program: I ran my business on Harvest (below) for years. I needed a more comprehensive solution. PaySimple lets me invoice, create recurring billing for retainer-based clients, and receive/reconcile payments in one system. Goodbye, Paypal. Hello $9.95/month smart run-my-business solution. I happened to be Customer #1 for this product and will be reporting more information on it as I learn more. Disclosure: they are also a client, but I pay full price for my account.
    • Harvest: I love them with all my heart. They are, in my opinion, one of the best invoicing and time tracking solutions for project-based professionals like beginning consultants, designers, and developers. A slick, clean interface, PayPal integration (along with a few other payment gateways), customizable invoices and more. It’s only $11/month.
    • Freshbooks: Many of my company’s contractors use Freshbooks and love it. They do have a completely free account, but their best product begins at $19.95 a month. I get way more from PaySimple’s Starter product and for only $9.95. However, they are huge champions of small business and this might be a great way to get you out of whatever lamesauce invoicing and money management system you’re using now. I’d still personally chose Harvest over Freshbooks.
  • Health Insurance: If you’re not pursuing a health insurance plan with an HSA (Health Savings Account), you might want to have a look at it. This was recommended to me by multiple colleagues as well as my CPA.
  • SEP-IRAs: If you think you don’t earn enough or can’t afford to contribute to a retirement account, rethink that, please. Most small business owners are eligible to open what is called a SEP-IRA (Self-Employed IRA). The contribution limits are higher than a Traditional or Roth IRA and you can drastically reduce your growing business’ taxable income at year-end using one. Speak with your tax professional about how one could be a smart decision for you and your business.
  • Tax and Bookkeeping Professionals: I’ve had a CPA forever. Not only have I actually started listening to him, but I got him a present this year: a bookkeeper. It’s a present for me, too. Now, I have two trusted professionals who love dealing with money (which I do not — even though I do love invoicing!) who tell me exactly where I’m at and can help my business grow. Need one or both? Ask for referrals from fellow business owners who have been in business at least three years — this way, you’ll be more likely to receive referrals based on true bottom-line experience and not just OMFGMYWIFEISACPA or THISGUYINMYNETWORKINGGROUPISABOOKKEEPER. Ew.
  • Your business structure: Why do you not have at least an LLC? Another reason you need a tax professional. Sure, it might cost you a ducket or two to get set up, but you should be protecting your personal assets from any business snafus that could occur. In most states, you can set one up yourself online. I do recommend consulting with a tax professional, however, as it will change the way the IRS requires you handle your business bank account and the flow of money in and out from your business.

Your Attitude

You have to treat your small business like a business. It’s not a piggy bank. It’s a tool that allows you to live the life you’ve always imagined. It also requires that you admit one important thing: you cannot do everything yourself. Every successful business you see of any size taps into the power of other people.

Changing your life and business requires an attitude change.

You run a business, not a free clinic.

You don’t want to be a whiny little freelancer.

There will always be something you wish you had known when you started your business.

You are a small business owner. You are smart and understand that people and the relationships you have with them are the only reason anything gets done. So why not start with changing the relationship you have with your business by changing your attitude?

Get organized. Rein-in that inbox. And while you’re at it, set some work hours and be sure to make time to LIVE.

Get your financial shit together. I got tired about bitching about money so now, I never have reason to bitch about it again.

But you’re the only one who can make these changes. YOU are the only reason your business is going to stop looking like a neatly (or not so) arranged pile of boxes you never want to open out of fear of finding what’s inside…

Or the Apple store-style brilliance of knowing exactly where everything is at every moment. And you can skip the quips about Apple’s stock price fluctuations. I’d rather own that stock than a pile of boxes filled with shit any day.

Now, I ask you: do you have hacks you want to share with your fellow readers? Leave them in the comments and we’ll all be smarter for it.




First. love you. your work. your words. your bitch slaps. and that you're a cussing redhead from Texas for God's sake! And Second. does anyone have any recommendations for reliable, trustworthy virtual assistance? I've been saying I need help with my damn inbox for 6 months! And accounting. And accountability. And time management. And insomnia. Thanks Erika for all your sound advice and kicks in the ass!

Brian Cobb
Brian Cobb

this was posted on my birthday, so I figured there HAD to be something good in it for me! Im seeking a career change, but deep down my goal is to establish a business of my own and I have learned FAR more from Erika than from any of my employers or instructors!


Great post Erika! Thanks for these great tips! Just want I needed!


Great advice! I need to apply many of them myself. I'd love to share this - why no sharing buttons?? (I'll still cut and paste but clicking is so much easier for the lazy in us) Thanks!


Spot on, Erika. Great comparison to the Apple Store. And thanks for reminding me to set boundaries in my business.


I heart you for this article. Specifically the accounting side of my business is all over. I keep trying new things but they never cover everything I need. Can't wait to try PaySimple. Also, I feel fancy commenting on your new design. 


Ah the Apple Store, would that my office were so neat. Despite my attempts at going paperless, all electronic and green, those boxes do fill up. Biggest thing here for any business owner/manager - the business won't run itself. It's why you hire consultants, virtual assistants, tax pros and the like - so they can do what they do best, freeing you to do the same.. and hell, maybe even have a life while you're at it.

One organizational change I'm making this year: better time management. Keeping closer eye on clock, being smarter about my multitasking, setting limits; new Friday hours are 9-1pm.. so hopefully no more weekend creep. All about running the biz, not letting it run you. FWIW.

John Suder
John Suder

Great advice, especially when it comes to finances. 

Creative people (myself especially) tend to cringe when it comes to managing their money. In the end, playing loose ends up costing you in time, money and anxiety. 

Get your financial house in order, you'll be happier all around.



First, congrats on the new look and launch. Love the fresh design.

As always, terrific advice, though I'd extend it with: outsource the drudgery. Most aggressive and successful entrepreneurs I know are best when they're creating and building, not when they're filling out forms or tracking down an insurance dispute. Hire people who can do the little tasks well and remove them entirely from your plate. It's less expensive than you think - you don't have to hire them full-time - and removes stress letting you focus on the things that matter most to you and your clients. 

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