Guest Post By Member Nick Armstrong

I took issue with last week’s blog post on How To Earn Paid Sick Days As a Self-Employed Entrepreneur.

Actually, it kinda made me want to take a sick day. Why? It’s just not that simple.

If you’re an entrepreneur focused in knowledge work like me, you probably have a reason that you work outside the 9-to-5 world. Two years after graduating from Colorado State University, 12 jobs and three firings later, I decided to escape the 9-to-5 for good and start my own business, WTF Marketing. If you want to know how I did it, here’s my origin story…

Knowledge workers, creative product workers, or businesses with unpredictable client streams (seasonal, cyclical, coincidental), you’ll have a hard time trying to “accrue” sick or vacation days as this post (and others like it) suggests.

The suggestion that you can accrue sick or vacation days as a freelancer just by “dividing what you need to earn by the number of days you want to work in a year” is disingenuous.

Accruing sick or vacation days as a freelancer requires three components:
emotional systems (covered in depth here)
contractual systems (I’ll cover this here)
financial systems (half-way covered in the articles I took issue with – I’ll cover what’s missing)

First, there’s Emotional Systems

The emotional component is simple enough. You have to think you deserve a sick or a vacation day in order to take one. When you’re the primary earner for your household, and what you do is directly tied to how much you earn, and what you earn is directly tied to how much and how long you work, it can feel *really* painful to turn down clients or delay clients.

This is a self-defeatist attitude; if you burn out, you can’t do your best work and you can’t land new clients because the old ones aren’t happy with your burnt-out level of quality.

Take the time you need, right? Easier said than done, but whatever – I’m not a shrink and can’t help you with the guilt aspect. What I can help you with is this: create an OMFG I’ve Got The Plague strategy. Here’s how:

Create a client notification plan. Inventory what you’re currently working on, notify every client that you’ve caught the plague, and ask for an extension on anything due within the next two weeks. Push any deadlines back and stagger your due dates so you have time to complete the work (don’t just put everything on the Monday two weeks out).

Create a “microscopic task list”. That is – one thing for each project you can complete in 5 minutes or less that will move the deliverable forward. Install WordPress? 5 minutes. Install theme? 5 minutes. Copy and paste content? 5 minutes. 5 minutes. Update your microscopic task list each time you finish a task.

Use Fancy Hands to get some research done, get soup delivered, get your groceries delivered (King Soopers delivers if you get the order in before 11 – there is a minimum). Use local coworkers, Fancy Hands, eLance, or oDesk to delegate anything to an hourly person that you’d feel comfortable isn’t the “core” of your work.

Create the expectation with your clients that when you’re sick, it’s time to heal by managing your responses correctly. When you’re resting, you need to rest. Do not take calls, do not respond to “urgent” emails, do not respond to texts. Turn the ringer off on your phone.

Know what your “sick time” budget is (we’ll talk about this in a bit). You won’t be able to do anything about it once you’re sick, but you’ll feel better for knowing the number.

Then there’s Contractual Systems

I have it built into my contract that if I get sick, if I get hit by a car, if someone dies, if anything that I didn’t directly cause does something to delay the project, I’m off the hook. The contract can’t be cancelled, I get the time I need, and I can come back when I’m able to do good work.

This has been utilized a whopping total of one time since I included it. Even so, the stress savings alone is worth including it in your next contract.

I make sure that the client is also protected the same way if something happens to them – it’s only fair. Beyond being fair, it also sets an expectation of humanity – I’m not just a cursor and a keyboard magically producing marketing plans. I’m a living, breathing, hard-working business owner who sometimes gets sick, has to go to a funeral, or gets his car totaled. A little bit of contractual wordsmithing can generate quite a bit of client consideration when things go wrong.

In that same vein, I also state my best working hours and my offline time – when clients shouldn’t expect a response. Because everybody has their email in their pocket 24/7, folks think they can get a hold of you 24/7 – and sometimes expect a response as soon as they send you something. Stating your “office hours” and contact policy makes it really clear when the client can expect a response – but it’s up to you to stick to it. If you waiver, the client will be “trained” to expect a response when you might not want to give one.

Finally, there’s Financial Systems

Financial systems take a while to put into place in your business. You have to make enough money to even think about having a financial system. Once you’re out of “bills only” mode, you should add a few systems to cover yourself:

An HSA or Insurance
A “Hidden” Savings Account
Income Balancing System

It took me three and a half years, but I finally snagged a Health Savings Account insurance plan for myself. HSAs allow you to sock money away for health care related expenses. An HSA gives you an automatic method of paying for the more expensive things related to being sick (doctor visit, hospitals, prescriptions, etc). I haven’t used mine yet (the benefit of an HSA is that it can also behave like an IRA retirement account).

In addition to that, I also take 10% of what I earn each time I get paid and put it into a “hidden” savings account. This account isn’t listed anywhere in my balance sheets, I don’t look at the totals more than once a month, I don’t withdraw money unless I get sick, I just know it’s there somewhere – prepped in case I need it. Think of it as a rainy day fund – this is my “sick time” budget.

Last – and this is something totally dependent on the type and style of your business – an income balancing system. Which is what those earlier articles were alluding to. “I need X per year and I only want to work Y days.”

The only trick here is knowing your business. Figuring out which are the fast months and slow months, knowing when you need to market and push for new clients, which networking events are crucial to your pipeline, and how to deal with variable income (if it applies to you).

Fine, so – how do I take a sick day?

To recap: be OK with taking it, plan to take it, and have a sick-time budget ready to go so you don’t have to sacrifice your financial wellbeing for your physical and emotional wellbeing.

Sounds super simple. In reality – achievable, if not more complicated than we’ve been led to believe.
Have your own system to take a sick day? Let me know in the comments below!

Photo Credit: RL Hyde
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Nick Armstrong is unapologetically awesome at explaining difficult-to-grasp marketing and technology concepts regarding the web. In his day-to-day work, he helps small business owners swear less and profit more through kick-ass marketing.

For the last 3.5 years, Nick’s business WTF Marketing has amassed a large number of happy clients, among them Fortune 100s, solopreneurs, and everything in between, including three distinct $2M+/year businesses. Leveraging over a decade of web design experience and eight years of hands-on, knee-deep community building and marketing. He founded the Digital Gunslingers in 2009, teaching $5 classes on social media and marketing concepts and donating all the proceeds to charities in Fort Collins, Colorado. Connect with him on Google+, Twitter, and Facebook.

Got something to say? The Cohere blog is always open to member contributions. Contact Angel or Kristin to pitch your idea.