So You Think You Can Freelance? Part I: Mindset

Photo courtesy of slworking2, Flickr Creative Commons
Photo courtesy of slworking2, Flickr Creative Commons

Have elaborate fantasies of spending your days in pajamas, checking Facebook, sipping lattes in coffee shops … and maybe jumping into the occasional Slayer match on your lunch break?

Sure. It’s a little of that sometimes.

But I can tell you from five years of experience, you better be able to hang with the following tough guys, or as the saying goes: Don’t quit your day job.

So you think you can freelance? Meet your new work force.


  • You do not know what your next job will be. That can be exciting.
  • You don’t know how to plan your time for gigs that may or may not pan out. That can be aggravating.
  • You don’t know when you’ll have your next paycheck. That can be terrifying.


If you want to attract clients, be referred, and have clients come back, you’re going to need talent. Period. Unless you’re already independently wealthy, but even then, I’d suspect the negative feedback would be a major ego punching bag over time. Which brings me to …

Self Doubt

We all have a little of it, and if you don’t, that’s a red flag. Self doubt, as annoying as it is, keeps us striving to do better.

And you need to constantly make yourself do better in freelancing. There are no TPS reports to file or self assessment forms due at the end of the year. You are your own boss—and you need to be a hard ass.

On the flip side, you need to know self doubt’s limits, too. Start by having a realistic understanding of your talent and how much that talent is worth. Then if someone tries to give you a raw deal, be willing to walk away, even if that leaves your calendar wide open. Doubt yourself, and it will show. Clients will treat you accordingly, word will spread, and the rest is downhill.

Penny Pinching

Here are just a few of the tips I employ. I’m sure you could brainstorm many more.

  • Work from home whenever possible. Save on coffee, snacks, and lunches.
  • When you do need a change of scenery, keep your cafe receipts for taxes (a percentage of food and drink can be deducted if you’re self employed).
  • Research what purchases can count as deductibles. Keep careful records.
  • Find a smart, affordable accountant who can help maximize your money.
  • Take the bus to your client meetings instead of paying for gas and parking.
  • Turn that trip into an article.

In Glengarry Glen Ross, Alec Baldwin’s mantra was ABC: Always Be Closing. In freelancing, it’s ABS: Always Be Saving.

You don’t know when your next job will come or how much you’ll get paid (if you get paid … because sometimes you don’t). You need to make financial contingencies so any little bump in the road doesn’t send you careening back to that cushy full-time job you didn’t want in the first place.

Rampant Organization

You need to maintain up-to-date contact info for the clients you have, as well as the ones you want to have … and the people who can influence those people.

You’ll also need pristine accounting skills. Only you know what you’ve been paid (or haven’t), when, and how. Come tax time, that info will be crucial along with your expenses and receipts.

When a past client contacts you, you’d better be able to pull up what you did for them, how much you charged, and any pertinent info about working with them.

Contracts will be an everyday part of your life now—and the way you ensure you get paid. Search online for templates, ask fellow freelancers to forward you examples (with the client name and rate omitted, of course), and file all of your past contracts for easy reference.

You’ll also need to organize your day into paid work and “unpaid work.” What’s unpaid work? Balancing your books, reaching out to prospective clients, creating business cards, updating your website, posting industry-related info to LinkedIn, and the list goes on and on and on. You’ll see …

Scared Yet?

You should be. If you’re not at least a little scared of freelancing, you’re not being realistic. That said, if you know the risks and think you can handle it, it can be the best job ever, working for the best boss ever: YOURSELF.

Part 2: Ground Work
Part 3: Money
Part 4: Q&A

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17 thoughts on “So You Think You Can Freelance? Part I: Mindset

  1. I worked freelance for about 8 years (in my 20s) as an actor, writer and general theater roustabout (electrician, box office manager, assistant stage manager, etc.). It nearly did me in. It didn’t help that discipline is not my strong suit. But the penury, the other full-time job of just finding jobs, the taxes, the clients who had the net-whenever-we-get-around-to-it pay schedule… I had to stop. I’ve done a few freelance gigs out of necessity in my 30s and 40s but it is a hard row to hoe. I tip my hat to anybody who can make it work. As for me, I hope to never see another 1099 again.

    1. The non-work work is like another job. It’s certainly not for everyone, and that’s why I wrote this, to clear up some misconceptions. I’ve heard people muse, “Cool. I could work from home and watch the kids at the same time.” So not true! All that said, I personally love freelancing. It’s my perfect balance of creativity, freedom, organization, and project diversity.

      1. I know you have the skills for it and I know you went into it with your eyes wide open. I’m glad you are thriving at it. Me, I was not cut out for it. At all.

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