The biggest freelancing “do.”

[photo credit]

June marked the two-year anniversary of my freelance writing work. Not of my official declaration of freelancerness, but of the first time I agreed to write on a contractual basis for a legitimate company hiring my services.

In these two years of freelancing, I’ve been both painfully idle and gainfully employed. I’ve made mistakes, and I’ve had  successes. So, although this isn’t a “how to” blog in the least, I’ve decided to put together a list of some of the most important steps to success I’ve picked up along the way.

#1 Biggest DO: Be dependable.

For us anxious types, maybe this comes naturally — after all, the fear of disappointing someone far outweighs the inclination to skirt by on the bare minimum. But I will say this has been the number one reason I’ve stayed employed, and it’s been the most consistently offered praise from my clients and subcontracting higher-ups. Being dependable basically means doing work well and finishing it on time, although there are other subtleties. To be dependable, you need to start with the following three steps:

Stay organized

Your schedule, calendar, task list, inbox and billings resources HAVE to be kept up. I’ve mentioned the apps I use most — Sparrow, iCal synced with my Google Calendar, Wunderlist and Billings — in other posts. Here are a couple notes on my methods:

  • • I essentially use my own sort of inbox zero method to control my emails. Before I label and archive messages, I add tasks to Wunderlist and due dates to iCal, and I keep a list of notes and items to revisit. I also don’t archive anything that needs a response until I send that response. I star emails that pertain to current projects, and unstar them when the projects are complete. My inbox stays clear and I never worry about losing little details or ignoring peoples’ correspondence.
  • • Time-tracking and invoicing are way too important to mess up. Your clients should never have to worry about you under-billing and asking for more money, or over-billing, which makes you look dishonest. Pay for an app that does what you need it to.  Billings works perfectly for me because it creates and organizes time slips efficiently, has professional-looking and intuitive invoicing, and tracks all my accounts in a way that makes sense.

Communicate clearly

Sometimes this feels like over-communicating, but it’s better to be a little tedious than to be misunderstood. Especially when a deadline is at stake. A few tips to get you started:

  • • CC whenever it might be necessary to keep people in the loop (and don’t worry about clogging their inboxes — that’s their issue).
  • • Send “heads up” and “FYI” messages if you know something is coming up that might affect your client’s schedule — especially if you’re asking for something.
  • • Explain your actions (“I tracked my changes so you can distinguish between the first and second round of revisions”).
  • • Repeat details from past correspondence to give context.

Don’t assume everyone else is organized just because you are. Make it easy for your clients to figure out what’s going on without referencing past messages or files.

I recently got props from a client because I asked him to confirm his receipt of a very important email, since my phone’s email app wasn’t showing it in my sent folder. It had sent (whew), but that simple follow-through was followed up with an “I really, really appreciate the way you take care of business.” Now, I might just have a very affirming client… but either way, being conscientious never hurts.

Be resourceful

Sometimes your client is your best resource. Other times, it’s Google. Learn to distinguish between the questions you need to ask and those you can find the answers to. And give yourself plenty of time, in case your research doesn’t pan out — if you are going to ask questions, it’s better to do it early on in the process so you don’t look like you procrastinated.

Find out who your resources are at the beginning of a project, and ask if it’s OK to contact them directly. It will be a lot less likely that your emails and phone calls will get lost in someone else’s shuffle. Basically, don’t be presumptuous, but do take charge and solve problems.

Have questions or anything to add to this list? Let me know!



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  • MyMoneyDesign

    Congratulations on your two year anniversary. My older sister is a free-lancer as well and we talk about this kind of stuff a lot. Being ready to go and having a solution I think would be a big help in that line of work.

    • Brynna Lynea

      Thank you! It’s been an interesting ride. I love talking to other freelancers about their strategies. (And I only wish I was this organized in every other area of life….) :)

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