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Benefits and Risks of Freelancing After 50


To date, I have talked about why you should consider freelancing, how to get started, and how to choose which freelancing path to take. But I would be remiss if I didn’t address the benefits and risks of freelancing.

Consider it a “cutting off at the pass” (to use western movie parlance) moment. I don’t want you to head down the trail without understanding what you’re getting yourself into, both from a benefit and risk perspective.

Freelancing Benefits

With that said, what benefits does freelancing offer? I can speak to the issue from my experience and that of other freelancers.

One… freedom… to be your own boss, work when and where you want… and with whom you want. (Apologies for all the ellipses… stream of consciousness kind of day.) For many, freedom suffices as the sole reason to become a freelancer. Flexibility is a closely-related benefit. Independence is another.

Two… money. Financial opportunity is a double-edged sword. (I’ll talk about the risk aspect in a moment.) I’m earning a better living now than when I was an employee. And while finding new clients isn’t a cakewalk, once you reach a base sufficient to pay your bills, anything else is “icing on the cake.”

Freelancing Risks

The biggest risk is money — both how much you make and, to reflect on a statement my wife made in her podcast interview, when you make it.

Regarding how much, the biggest mistake freelancers make is not charging enough. Unless you are an absolute fledgling with limited experience, take the time to assess your value honestly. Don’t sell yourself short. You are worth more than you think.

Regarding the “when” you make it — you won’t survive without a steady inflow. That’s where contracts can help.

Clearly state your terms in the contract and invoices. Most clients pay promptly, but there may be the odd one or two whom you will have to “dun.” Don’t hang an albatross around your neck, either. If you get a client who is consistently reluctant to pay, cut them off. There is plenty of fish in the sea. (Did I mention that I am the king of cliches?)

Speaking of the sea, don’t be surprised if your income ebbs and flows. At times, you’ll have more work than you can handle, and, at others, not nearly enough. The tide comes in and goes out — it’s the same with freelancing.

Set aside funds during the good times to cover the lean. If the thought of scarcity is frightening, the freelance lifestyle may not be for you.

Taxes are another risk. (I should say paying taxes.) I’ll admit I’m not as adept at making the quarterly payments as I should be. In which case, do as I say, not as I do. If you’re making a good living, you can get in tax trouble by not staying paid up — the taxman cometh. You are self-employed, a small business owner. Think like one.

Lack of benefits is the last risk I’ll mention. Healthcare is expensive. If you’re over 65, like me, you have Medicare. If not, finding an affordable healthcare provider can be tricky. There are also retirement benefits to consider — you’re on your own there, too.

A biblical passage (Luke 14:28–30) asks a salient question, “Suppose one of you wants to build a tower. Won’t you first sit down and estimate the cost to see if you have enough money to complete it?”

Before you start building your freelance career, count the cost. Weigh the risks and rewards, pros and cons, in the balance. Then, if you’re still willing to walk the path that leads to freedom, take a deep breath, swallow hard, and step out. I’m here to help.

This story is reprinted from my bi-weekly newsletter, Freelancing After 50. Feel free to subscribe. You can cancel at any time.


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