Are You Freelancing the SMART Way?

Smart Freelancing

Smart Freelancing

When graceful Elizabeth Fayle and I (and her partner Marc) shared a bottle of Chardonnay one day, little did I know that within one week, I’d hire her as my consultant. Hey – if she’s good enough for the federal government (and Marc), she’s good enough for me. She smartened me up but good – and I’m frankly glad she did.

So when Elizabeth said, “Mind if I write about this on your blog? I think your readers could use this,” I was all for it. Enjoy her intro post, and the first of a six-part freelancer business series about working smarter, not harder.

I’m going to teach you how to be SMART – and I can hear you all now:

“What? Teach us how to be smart?”
“Is that like saying we aren’t smart already?”
“Who is she to show up like this and call us a bunch of dummies?”
“Hey, this chick just called us a bunch of morons!”

Relax. I’ll let you in on a little secret. Before I joined the Men with Pens team, James wasn’t being all that SMART, either.

“Whoa, she just crossed the line!”
“She dissed James! Nobody disses James.”
“Joined the team? The woman’s going to get herself fired at this rate.”
“Wow, someone get me Twitter. She just trashed James!”

Oh, James is smart enough. Brilliant, in fact – which is why he asked me to help make all his business dealings SMART:

* Specific
* Measurable
* Agreed Upon
* Realistic
* Time-based

And now that I have, Men with Pens has gone from rockin’ to ROCKIN’!

The point of the post isn’t to brag, though. It’s to let you know that being SMART makes a big difference to business, from solo freelancer itty biz to big international corporation.

And for some businesses – specifically artistic ones involving writing, designing or marketing – being SMART can be critical to achieving success. Most artistic people and freelancers tend not to use SMART principles – that’s not their thing. It looks complex, mathematical, too rigid.

Artists like creative methods, free-flowing processes, a take-it-day-by-day style. Which is fine if you like floating through the world never knowing what’s coming next, but this is business, people.

If you aren’t being SMART, you’re losing out on success.

Over the next five weeks, I’m going to delve further into each of the element of being SMART, and I’m going to help you learn how to be a better freelancer, a better professional, and a better service provider – so that you can make more money while working less.

Here’s what we’ll cover:


Being specific is all about how you communicate with people. Most conflicts arise from miscommunication, be it with a customer, a supplier, or a team member.

Conflicts cost money, and if you aren’t being specific, chances are that something is going to blow up in your face.

And there will be weeping and wailing and gnashing of teeth.


No, I’m not referring to the scary world of statistics here. Seriously – has anyone passed a statistics course the first time around?

By measurable, I mean having criteria that you can measure against. You know when a task is truly done, or how much the task truly costs you. (You may be surprised.)

If you aren’t measuring, your freelance business might be leaking money all over the place, and you wouldn’t even know it.

Agreed Upon

It’s all very lovely to operate on good faith with your peers, your clients, your outsourcers, and whomever you work with!

But for every person that you can work with on a good-faith basis, you’ll find 10 more that find loopholes in the way you work and communicate, and they’ll jump right through them. Some people even get their jollies just looking for those loopholes to jump through!

You need to have all your agreements tightened up tightly to close those holes – and to protect yourself.


Have you ever underestimated the time takes to deliver and end up having to pull an all-nighter just to meet the deadline? That was fine when you were 20 and in college. Chances are that you don’t bounce back so quickly these days.

What about taking on two, three or even five projects, sure you can get them all done on time? Then you scramble around, realizing that while they claim to clone sheep, no one has yet figured out how to clone you.

Know where you’re headed if you aren’t being realistic? Burnout City!


Time is money. Your time is money! And if you aren’t tracking where your time goes, you might be shocked to discover that you’re really working for pennies per hour.

And you thought you were bringing in a decent salary… no wonder you aren’t rich yet!

Part of the joy of being a freelancer means working when you want to, how you want to and as much as you want to, but that doesn’t mean you can disregard time altogether.

How to SMARTen up

We can all stand to SMARTen up a little. (Yes, even James.) It doesn’t mean we’re a bunch of dummies. As a matter of fact, you wouldn’t be where you are today if you weren’t already smart and savvy.

But even the truly brilliant amongst you may be running your business in a way that costs you time, money and adds stress to your life.

Over the next five weeks, you’ll learn how to be SMART with your business (and maybe even your life), and you’ll discover ways you can achieve less stress and more enjoyment out of your business. Stay tuned.

In the meantime, think about your freelance business now. What causes you the most grief? What process is the most frustrating? Which task do you hate doing? Which situations stress you out or make you mutter?

Post by James Chartrand

James Chartrand is an expert copywriter and the owner of Men with Pens and Damn Fine Words, the game-changing writing course for business owners. She loves the color blue, her kids, Nike sneakers and ice skating.

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  1. SMART is normally used to describe an objective, not a business methodology, but how you’ve broken it down makes perfect sense. Good article
    .-= Freelance Total´s last blog ..Video: Following up invoices using the reminder system =-.


  1. […] If you’re not sure what each of those means, check out my first post in the series, the introduction to SMART freelancing. […]

  2. […] The intro to being SMART The first key: Specific The second key: Measurable The third key: Agreed Upon […]

  3. […] you missed the first three posts, you can find them here: The Grand Introduction, Step One: Being Specific, and Step Two: Getting […]

  4. […] can read more on that introduction to SMART freelancing by clicking here. It’s a good read; I even suggested that James needed some SMARTening […]

  5. […] The intro to SMART freelancing The first key: Specific The second key: Measurable The third key: Agreed Upon The fourth key: Realistic […]

  6. […] Over at Men With Pens James Chartrand starts a five part series called Are You Freelancing the SMART Way?. […]

  7. Social comments and analytics for this post…

    This post was mentioned on Twitter by bloggingtweets: New @menwithpens: Are You Freelancing the SMART Way?

  8. […] consultar el artículo Are You Freelancing the SMART Way?, publicado en Smart Men with […]

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