The Truth About Freelancing:  Rolling the Dice and Resiliency

October 15, 2018

We've all heard about the appeal of the freelance life. These little nuggets of hope and promise are what got many of us into this thing called freelancing in the first place.

But what you don't see publicized so much is the uncertainty that accompanies each and every “advantage” of being a freelancer.

Now before you start thinking I'm just being “Debbie Downer” here, let me remind you that you came here for the truth!

You do want to know the real truth about being a freelancer, don't you?

Of course you do.

The Truth About The Risks

Here's the truth for most freelancers:

Every day you wake up and roll the dice.

I hope you have a good poker face because being a freelancer is a lot like being a gambler. Instead of betting money on roulette or craps, the freelancer bets their peace of mind on being able to keep at it for one more day.

Like many freelancers, you might not have insurance. (You know, that sweet little perk you had when you worked a regular job.)

So today, you roll the dice hoping no one gets sick.

You probably don't have life or medical insurance because you can't afford it. But deep down, you know you can’t afford the risk.

The freelance life can be stressful enough, so you don’t need the added pressure of waiting for a catastrophe to derail everything you’re trying to accomplish.

Traditional insurance is often out of reach because it is notoriously expensive, so you’re going to have to find a plan with a very high deductible or find another way. There are some viable alternatives to traditional insurance coverage. But you’re going to have to do some research and find the best solution for your circumstances. Whatever you do, just don’t keep putting it off.

Today you roll the dice and hope there won’t be any surprises when tax time rolls around.

When you’re on the road to the freelance life, you want to hang on to every dollar you get because there’s no guarantee when you’ll see the next one.

But unlike those “regular” jobs, there’s no one up in the company office taking out income taxes, social security and all those other things that happen to a “normal” paycheck.

It’s up to you to put away some of that hard-earned cash yourself.

And unless you’re a freelance fitness trainer or success coach, you’re going to need some help with the discipline aspect.

The best solution is going to be using an application or some software that automatically takes out your taxes and other deductions before you get paid. If you’re anything like me, this “out of sight, out of mind” trick works pretty well.

Because you are self-employed, you are responsible for other taxes too. But the hard part probably isn’t going to be figuring out how much taxes you’re going to owe; it’s going to be putting that money aside, before you get your greedy little hands on it!

You’re already rolling the dice in so many areas, the last thing you want to do is roll that dice with the IRS!

Do yourself a favor. Find a program to handle your “payroll” so you don’t panic in April.

(Rattle, rattle, rattle...or whatever sound dice make!)

The Truth About Staying the Course

You already know that the path to freelancing success is littered with obstacles, what-ifs, and risk.

So how do you navigate such a rocky road?

You keep moving, keep going forward. You'll get there eventually, but there's no guarantee of what “there” will be when you arrive!

A better question may be, how do you keep going when there aren't clear directions, and your “transportation” isn't the most reliable?

Resiliency is the key to staying the course.

Don't worry about being on the right road either. Because in freelancing, there is no “right road.” There is only the path you are taking on your journey. This path will have its share of wrong turns and dead-ends, but you have to keep going anyway.

Doubt, financial strain and risk are natural elements of becoming a freelancer. Know this going in and expect it. Better yet, prepare yourself for the inevitability of the unexpected. Be flexible.

The Stoics have a saying: Premeditatio malorum (premeditation of evils). This sage advice tells us to prepare ourselves for the unexpected. We know it's coming, so why not go ahead and anticipate it instead of being taken off guard?

Being as ready as you can be when the unexpected happens makes resiliency a whole lot easier.

And no, I'm not talking about any ability to see into the future or to try and account for every possible outcome. I'm talking about keeping a frame of mind where every hurdle doesn't come as such a surprise.

When you accept that you will face adversity, as opposed to ignoring the inevitable, you steady yourself for the unexpected because you are prepared. So in some ways, the unexpected loses its power to throw you off course and makes it easier to “spring back into shape.”

If you want to be a freelancer, then you are going to have to keep rolling the dice. Sometimes you'll win, and sometimes you'll lose, but you have to keep betting on yourself.

Be flexible, be ready for the unexpected and develop the habit of being resilient. I hope this is what you expected! Stay tuned for more about the truth of freelancing.