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stressed freelancer

The allure of freelancing is ever so tantalizing: independence, control, flexible hours, and the freedom to create whatever kind of business you want, with a pot of gold waiting at the end of the rainbow. But a freelance career isn’t for everybody, and the sad truth is most freelancers struggle to cobble out a living, work under constant pressure, and put in far more hours than they ever imagined.

If this makes you more intent on being a freelancer rather than less, then congratulations. You’ve exhibited the first sign that you’re cut out to be a freelancer: relentless determination.

1. Can You Do Whatever It Takes?

It’s easy to say you have relentless determination, but another thing altogether to demonstrate it. Here’s a little story. When I was starting my career, I worked under a man who became one of the most successful entrepreneurs in the packaging industry. One day we were trying to move a very large band saw into the warehouse. After half an hour of trying to muscle it through a doorway, he completely lost his cool and grabbed the saw by the blade to pull it through the door. He cut his hand to the bone and ended up spending a couple of days in the hospital, but mission accomplished.

Now, I’m not saying a person has to go to this extent to be a successful freelancer. But right then and there, I knew definitively that this guy was not going to let anything get in his way. He applied that same ferocity, intensity, and single-mindedness to every business challenge that came his way. So the question is this: How far are you willing to go? Remember, when you’re freelancing, there’s no net, no backup, no bailout. If you like to play it safe, freelancing is a tough row to hoe.

2. Can You Always Be Closing?

In his famous Glengarry Glen Ross speech, Alec Baldwin presses his salesmen to always be closing, always be selling. It’s another over-the-top example, but the point is crucial. If you’re uncomfortable selling, you’re in for a rude awakening because clients have to be sold. No matter how nice you are, how competent you are, how brilliant you are, nobody is going to hand you business. You don’t charm your way to success; you sell your way to success.

This is why social media sites are a deadly trap for would-be freelancers. They encourage a mindset that says, if I just put out enough great content (whatever that means), if I just connect with enough people on LinkedIn, if I just accumulate enough Twitter followers, I’ll magically develop a client base.


Social media sites are useful adjuncts to a sales and marketing plan, provided you knock on a lot of doors, shake a lot of hands, kiss a lot of babies, and ask for orders. Otherwise, you’re just wasting your time.

3. Can You Put In the Hours?

Let’s suppose you have relentless determination and you love to sell. Is success around the corner? No, because there’s one more obstacle staring you in the face — a 60-hour work week. Remember, you don’t have a team behind you to balance the books, prepare taxes, design business cards, print business cards, set up phone lines, update computer programs, make copies, expedite rush orders, pay suppliers, and the 1001 other things that every business needs to handle.

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About Brad Shorr

Brad Shorr is Director of B2B Marketing for Straight North, an Internet marketing agency in the Chicago area. With in-house, freelance and agency experience, he writes frequently about content marketing, SEO, social media and small business strategy.

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  • somparkash

    A highly encouraging, exciting and informative article. Perhaps, pragmatic, progressive and practical persuasiveness could be suitably incorporated to make it more effective.