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Don’t Work in Your Underwear

What I’ve learned in the first few months of freelancing

One of the most interesting aspects of working full-time freelance is the struggle of trial-and-error learning — the mad scramble to handle all the varied aspects of running my own business. While the rush of developing new skills is exhilarating, it’s also unnerving to feel that I now know twice as much today about running my own business as I did just a month ago. Put another way, I only knew half as much when I started. Sheesh.

So far, I’ve been extremely lucky — I have a full plate of scheduled projects, and I’ve had the pleasure to work for some great clients in the last few months. Yet as I’ve settled into the reality of freelance work, there are a few things I’ve found very important to my day-to-day routine — suggestions that I think might be helpful for those who are starting out. Here goes:

Fix up, look sharp

While seemingly obvious, I can’t stress how vital it is to keep yourself “dressed for work,” every single day. Sure, you may only work from home but if it’s in boxers and a t-shirt with a “don’t touch me” beard, you’ll be far less productive than if you treat freelancing as a formal, professional routine.

What does this mean, specifically? Shower everyday (before 9am), and dress in clean clothes (in fact, a pressed shirt makes one feel incredibly powerful). That advice sounds exceedingly momish, but it’s sound — when you treat your appearance seriously, you’re in a much better fame of mind to focus on your work.

Reset your workspace

Aiding in focus is an absolute devotion to a clean work space. No wires, no pens, papers, business cards, or coffee mugs. Unless you’re actively using something, it just shouldn’t be on your desk. Every night, any accumulated clutter on my desk is removed, so the next day starts fresh.

This advice extends to your computer’s workspace as well. It’s a great idea to clean up and remove all the junk files and icons on your desktop every night as well. When you start the next day, you’ll be ready to dive into work and not tempted to start poking around yesterday’s links and mp3s.

Read at lunch

Blogs and tech sites are the true evils of freelancing. It’s very easy to mentally justify ‘keeping up on things’ as a worthwhile time sink — after all, you have to keep honing your skills, right?. While it’s important to stay connected to the internet at large, it’s just far too easy to let tube surfing burn huge holes in your daily schedule.

The fix is simple. Only read ‘before’ work in the morning, and for a half an hour at lunch. Any other time is off limits.

Log your time

Keeping track of nearly every minute you spend during the day is one of the most important, internal business variables you can measure. It’s easy to think of time tracking as a pain or something that feels exceedingly ‘corporate.’ But you are a business, and as such, every hour of your time is a limited resource. In fact, you’ll find that much of your week’s work won’t be billable design hours, so knowing what you’re spending time on helps you get an overview of what parts of your work you’re most inefficient at.

Take blog writing, for example. I knew it was taking me far too long to complete and publish my posts, but I didn’t understand the gravity of it, until I looked at my time log. My last post took over two hours to write. Knowing this made me realize I have to refine how I write, focus on easier topics, break up the work, and create shorter format pieces to keep things running smoothly.

Put everything in one place

Finding a great place to keep “all of your bits” is vital to keeping your mind clear and not letting any details slip. Honestly it doesn’t matter what system you use, as long as you focus your energy into going “all in” to whichever system you pick. A splintered digital dump file is useless.

I currently use 37signals’ Backpack because it’s flexible enough to give me both a great place to organize my information and share bits with clients. Honestly though, any system is good so long as you use it.

Always be selling

This tip needs more explanation, but the short of it is this — you must always be selling. Always. Sales isn’t something that you “do” at certain times of the day. Rather, it’s the ability understand the value of your own services and communicate how your work helps others.

Put bluntly, you need to be in command of what is it that you offer, and why anyone should care. It’s vital to feel confident about your work, processes and business, and exude that confidence to everyone you meet. Being “just a great web designer” will get you nowhere, running your own business. Plus, it just feels great to be assured and excited about your work, everyday.

Where was I?

These tips are, of course, just a small sliver of what I’ve learned running my design shop so far. I’m hoping that by writing this out, as I learn, I’ll have a better understanding of what works and what doesn’t. Also, here’s to hoping that it helps another freelancer going through the same process.

NOTE – This post is quite obviously indebted to Cameron Moll’s post “Full-time freelancing: 10 things learned in 180 days,” way back from good ole’ 2005. It was inspiring then, and it’s still refreshing to read today — an an open, honest appraisal of an often confusing, risky career choice. All his points still stand, so go re-read it.


3 Comments

  1. August 1, 2008 12:11 pm
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    I absolutely agree with the stuff you covered in this post. Especially about the ‘looking sharp’ bit as it hit a special note with me. I honestly can’t do design work if I’m not freshly showered, with clean clothes, and my shoes on. I think it has to do with self-confidence, but when I prepare like that, I am guaranteed a productive day at work, plus, when you’re done, you’re practically ready for a night out with the boys! :)

    Cheers Matt.

  2. August 1, 2008 2:03 pm
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    @Dragan

    I think all of your suggestions are spot on, especially your point that “working from home is all about boundaries and discipline.” Well said.

  3. August 12, 2008 8:28 pm
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    Great tips, Matt. By any chance would you be comfortable sharing how much of your time ends up bring billable each week? I’ve seen a handful of different target numbers and I’m always curious to hear how different people operate in that regard.

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