It's time to have the talk (about 1099s).

The blissfully uninitiated may ask, "What are 1099s?"

1099s are, essentially, a service vendor's version of the W-2s you'd file for an employee. The IRS mandates that you do them a favor by helping report the money you pay individuals and small businesses for services.

"Oh, I don't have any contractors, so I can't stop reading here." PLEASE DON'T.

Does your business pay for rent? Marketing? Legal help? These are all services.

If you spend money on anything that isn't a material good, via any method that isn't a credit card, 1099s need to be on your radar. There are multiple types of 1099 filings, but, in general, the one most people think of is Form 1099-NEC. This covers most of your cash and check payments for services to unincorporated vendors.

(There is often confusion here around what makes a vendor incorporated. Please note than having an LLC does not automatically mean that a company is incorporated, as an LLC acts as a legal designation, and not, necessarily a tax entity. There can be LLCs that are sole proprietorships and LLCs that are S-Corporations.)
Besides non-employee contractors (the "NEC" in "Form 1099-NEC"), there are special forms and rules for how you might record rent payments, or payments to attorneys. Rules also change frequently on how payments made by such sources as PayPal and Venmo are reported.
In short, 1099s are messy, complicated, and the government can punish you severely if you get them wrong. (Basically, just like the rest of the tax code.)

If this is a tax season thing, why are we talking about it now, in early October?

Like W-2s, 1099s are due by January 31st. They are though, in my opinion, more complicated than W-2s. With 1099s, if you have someone paid with both check and credit card, you wouldn't include the credit card payments. On the other side, if you have a vendor who has been paid under both their personal and business name, you want to be careful to combine those payments. Vendors are also notoriously bad for providing updated W-9s each year, which causes issues when addresses, or business forms change. In the event of error, it is the 1099-filer, not the recipient, who incurs penalties.
Given their importance and complexity, we find it vital to start preparing early. When the calendar flips over to a new year, we are on the clock to quickly close the books on the fiscal year, verify cash receipt totals, and get the forms filed by the end of the month. That is why we start discussing 1099s with clients now, and begin doing as much work as possible in advance. Penalties for late, ignored, or improperly filed 1099s can cost hundreds of dollar per form, so it is vital that they are done on-time, and correctly.

Can Your Business Run Without You? (Beta Test)

Perhaps the most cliched goal in the small business world is to structure your business so that it can run without you. It’s something many entrepreneurs run toward, but that few achieve. And, if it is achievable, it’s even harder to test. Sure, you can go on vacation and tell everyone not to bother you unless it’s an “emergency”. Or, if you’re like me, you might go backpacking off-grid for a long weekend. But that’s really not the same as your business running itself without you. After all, how often is a business owner ever in a position where they absolutely cannot, for an extended period, respond to an urgent need within their company?

I recently did get the chance to see how The Bookkeeper operates in my absence. After a concerning checkup in January, I went in for a lung biopsy and was diagnosed with cancer in February, then scheduled for surgery in March. (Spoiler alert: The surgery was successful and I’m going to be fine.)

However, this did mean I was going to be out-of-work for weeks, with some of that period including a 4-day hospitalization, where I could not be accessible for even the tiniest work question. (I’m fairly confident in my accounting skills, but doubt I could T-chart a transaction with a chest tube in.) We had to make some quick, difficult decisions about how my work would be divvyed up and if we could even keep all of the work at TBK.

I also had to have some hard conversations. Telling someone you have cancer isn’t easy but, what became burdensome was having to tell new people over-and-over. However, I wanted to be honest with clients about why I wouldn’t be available. Most people were great. There were some awkward questions, but I wasn’t offended. (“No, I wasn’t a smoker. Yes, you can get lung cancer without smoking.”)

But, overall, things went fine in my time away. I had the benefit of having a co-owner who could pick up the slack and, as mentioned, I had a couple of weeks in which to make decisions and prepare. Perhaps that’s not the exact same as having a unicorn business that can operate perfectly in your absence, but I was proud of how TBK weathered nonetheless.

The hard part was in coming back. My first week I only worked a few hours, but already felt like I was un-needed, or didn’t know my place in the company anymore. As I started feeling better and working more, I came to see this as a blessing in disguise. Suddenly there was time to work on those marketing initiatives I’d been putting off, or work proactively on some new forecasts for clients.

As I’ve been getting back to full-time, the second-hardest aspect has been not slipping into old bad habits. One of the things a lot of people don’t realize about cancer is that it’s rarely considered “cured” right-away. My medical team feels confident the surgery removed all the
cancer, but I won’t actually be considered cured until 5 years of clean scans. I’m currently considered “no evidence of disease” (or “NED”) and will have to have scans for the rest of my life. It’s important to keep the new structure we established while I was out, so my time is not bogged down with things I shouldn’t be doing. It’s also helpful to keep my time flexible so I can assist if an employee needs to be out unexpectedly; I know so well now that anyone could have to be gone from work at any time.


Working When Overwhelmed

There will frequently be times in your business when you feel overwhelmed. There will be days or weeks when setbacks pile upon themselves, when everything that can go wrong will go wrong, and all at once. And you'll fall behind.

The danger in being overwhelmed is that it can lead to two disastrous pathways: one in which you're paralyzed into inaction by the seemingly insurmountable mountain of tasks before you, or one where you fall prey to the temptation of "multitasking" and fall to pieces trying to do too much at once.

Fortunately, procrastination and busyness are really two sides of the same evil coin. Today we're going to discuss how to catch up on what you need to do, even when the sky is falling.

Let's examine the Who, When, Where, and How of working when overwhelmed.

WhoDelegation

This seems obvious enough. You, right? Well, if you have employees, there might be some tasks you can delegate. The trick is to assign appropriate tasks in a manner which does not eat up your time or create more work for you. If an employee is already capable and available to take something off your to-do list, that's great. If you are going to have to expend time and energy in explaining the assignment, it is better, while you are behind, to go ahead and do the task quickly yourself. Training can come later when more time is available.

Also, asking an employee to assume additional or different duties is not a time for the two of you to hold a vent session on how busy and behind you are. It's nice to have someone in the business with whom to commiserate, but that will have to come after you're finally caught up.

Work EnvironmentWhen

Now! If you are behind on work, start with the first thing on your to-do list and get to it. Don't go make coffee, don't check Facebook "real quick", and don't cultivate your Pandora station. Give yourself little breaks to do those things as rewards for tasks completed. But if you're waiting until everything is "just perfect" to start, you'll never get ahead of the work.

Where

As mentioned before, don't spend too much time getting your environment ideal before you address your to-do list. However, it is imperative that your area be relatively distraction-free. Put your phone on silent; close your office door if you have one. Even if you're in a co-working space, you can put in headphones, or something else that sends the message that you're not available for small talk. Do not have social media tabs open in your browser.

HowTo-Do List

Start with taking a quick inventory of everything you need to get done. (No, don't make a complicated, color-coded Excel spreadsheet of your task list. That's just procrastinating with the illusion of working.) Personally, I love the Wunderlist app for keeping to-do lists, as it allows you to make categories and re-order your lists. See what assignments you need to complete first, and what can be put off. (Maybe have a to-do list for today, this week, etc.)

Block off time on your calendar for these tasks. Not only does it help you get in the mindset of, "I am scheduled to work on this, now", it sends a clear message to anyone you work with that you are busy. It particularly helps if you have the sort of business that includes frequent meetings, as it serves as a visual reminder to leave some time for solo work.

Get the first item on your list done as quickly as you can, with no breaks unless absolutely necessary. Check it off your list. Once you have made that first bit of progress, you'll be amazed at how much it motivates you to knock out the next item. Getting a few things out of the way can help you build momentum and feel accomplished. After that, you can battle that "overwhelmed" feeling and start to see that, though you are very busy right now, there is a light at the end of the tunnel and, when you get this backload of work completed, things will calm down for a while.

If work has piled up on you and you're feeling like you'll never be out from under it, try these steps. And stay tuned for our upcoming article on how to get organized and avoid becoming overwhelmed in the first place.


Maintaining Work/Life Balance (When You Work From Home)

With the increase of mobile technology and the high cost of office rentals, it is increasingly common for small business owners to work from home.  And since they’re their own bosses, those entrepreneurs can get left out of the discussion of how to achieve work-life balance.  After all, how do you “get away from work” when work is where you live?  In this article, we’ll discuss some steps that can be taken to maintain work-life balance when working from home.

1.  Have a separate space.

If possible, keep one room in your home dedicated exclusively to work.  Don’t do work anywhere else in the house, and don’t do leisure in that room.  It’s too easy to take a break from playing a game or watching a show to “answer a few work emails real quick”.  (Likewise, it’s too easy to check on Facebook mid-conference call.)  If you make a space just for working, it helps you to fully commit to what you are supposed to be doing at the time, whether that is working or relaxing.

On top of the mental and emotional benefits of having a dedicated workspace, there is a financial benefit.  A home office deduction can be a huge boon at tax time and, per the IRS, is defined as, “Exclusive and regular use as the main place in which you conduct your business...”

Of course, not everyone will have the option of having an entirely separate room for a home office.  If that’s the case for you, try to find a way to differentiate your “workspace” from your “living space”.  Make sure that, when you’re working, your area is free of distractions.  If you normally listen to Top 40, turn the radio to classical.  You can even have a picture or two you set up on your desk, as though you were working at an office away from home.  Just find a way, personal to you, to clarify in your mind that you’re currently “at work”.

2.  Have set work hours…

Now, this isn’t to say that you’re required to work a standard 9-5.  Many of us go into business for ourselves for the freedom and flexibility that comes along with being your own boss.  However, not having a particular time set specifically aside for work tasks can also make it easy to procrastinate.  Find a regular time, maybe daily or once a week, when you look at your schedule and map out exactly when you’re going to work on specific work tasks.  And stick to it.

3.  …And set leisure hours.

Again, this doesn’t mean you ignore a work emergency because you refuse to do business after 6.  However, it is imperative that you find times when you focus your energies on something besides work (even if it’s just to focus on a tv show you really enjoy).  Living and breathing work 24/7 is a good way to burn yourself out, and to forget what you enjoyed about your business in the first place.

4.  Have someone keeping you accountable.

Everything in life is easier with a partner.  Even if you are the sole employee of your company, you should have a friend or mentor who can give you the kick in the butt you need when you’re lacking motivation.  (Of course, the various benefits of having a mentor are a different article for a different day.)  Likewise, in your personal life, you need a friend who can make plans with you to have fun and relax, and who won’t let you off the hook if you try to bail for work reasons.  Find a friend who will hold you to dinner plans, and who will confiscate your cellphone if necessary.  (No work calls or emails at the table!)

Most of all, remember that, when you own your own business, you are in charge.  It’s doubtful that anyone starts a business with the dream of working 60+ hours a week and never having a night out again.  Remember what you’re working for, and go easy on yourself every once in a while.  Work to live; don’t live to work.