The revolution has begun, and if you haven’t noticed, you’re missing out on an enormous opportunity.

Freelancing has always been a common “hobby” for creative professionals like designers and writers, but in the last decade or so, creative pros have started leaving the 9-5 life in droves.

Now, this post isn’t meant to lure you to the “dark side” of freelancing, but to explain why it’s become the fastest growing professional group of our time.

But if you’ve even thought about taking the leap, now may be the best time in history to do so.

Why has freelancing become so popular

Surprise! The answer is: tech.

Every aspect of workplace logistics now has an app that lets you join and chime in from anywhere.

And if you can work from a laptop anywhere in the world, why bother spending time at a desk?

And again, thanks to technology, much of the work traditionally done by creative professionals (like web design), can be done more quickly.

I know that personally, before Webflow, it would take me weeks (or months) to complete a website project. After Webflow, that same project sometimes take hours.

This gives freelancers an all-new ability to take on more than one project at a time. Leading many creative professionals wondering: Why work for one person/company/project, when I can now work on many at the same time?

These shifts in tech have led to a similar shift in attitude. Years ago, the idea of leaving a stable job to pursue your “craft” was *cough* stupid. Freelancing was something you did at night before bed, like a hobby or after-school project — not a career.

Yet more and more people are taking the leap into the unknown. Leaving their nine-to-five cubical cells for the freedom of becoming a digital nomad.

And freelancers aren’t the only ones who find the freelancing life seductive. Companies are following suit.

Companies are driving the shift to freelancing

In an interview by PBS, author Richard Greenwald stated that companies as large and prestigious as NASA and IBM have been turning to freelancers at an accelerated rate. And they aren’t alone, with the likes of Pinterest, OpenTable, Panasonic, Unilever, NBC, and many (many) more right beside them.

But why?

I’ve found that there are 3 core reasons why freelancers make sense for business:

1. Cost / affordability

Although many freelancers charge a premium rate, the vast majority undercharge for their work (stop it!). These low rates make it extremely attractive for companies to hire freelance workers.

2. Flexibility

Many freelancers enjoy their flexible lifestyle, and companies are no different. The cost of hiring a full-time employee stretches beyond salary and insurance, including time and commitment in training, culture, etc. With contract workers, companies can cut these costs and gain the flexibility to hire/fire at any time.

3. Speed

Having both freelanced and hired contractors for a company, I can say that freelancers work faster. Maybe it’s the freelancer’s sense of urgency about completing the project and moving on. Maybe it’s the fact that the business can skip traditional onboarding/training. Maybe it’s that freelancers can skip meetings and internal politicking. But whatever the cause, freelance projects often move much faster than in-house jobs.

All of which means that freelancers can now blend their flexible lifestyle with the opportunity to work with some of the largest and most respected companies in the world.

It’s not all roses

I’ve spent plenty of time on both sides of the fence, being a full-time freelancer and a full-time desk jockey. Both have their pros and cons, but here are a few things you should know before jumping in to the freelance world.

Taxes suck

They suck no matter what, but they suck harder for contract workers. As a self-employed contractor, you’re not only responsible for paying your own income taxes, but also self-employment taxes.

To make it more complicated, you must also be prepared to track all money going in and out of your business to prove it. You can’t count on HR to handle your monies. You are HR.


This problem is typically a symptom of early-day freelancing, but you will overcome it. Not necessarily because you’ll always have work lined up (although you might), but because you’ll start to charge enough to keep you floating (happily) between projects.

Still, it’s a bit harder to manage ongoing expenses like rent, utilities, food, etc. without a consistent paycheck. This is why I recommend starting your freelance career as a side project. When you aren’t worried about basic living expenses, you’ll be more likely to take on better projects (as opposed to whoever’s willing to give you money).

It’s lonely…

Most freelancers who’ve been doing it awhile will agree: Freelancing can be lonely.

At first it’s nice not having to leave your house or see another human being for days at a time, but eventually, you begin to miss the team environment of your office.

I learned that the best way to combat this was to simply put yourself in additional social situations. Instead of meeting clients over the phone, offer to meet in person or at least over video chat. Instead of working from home every day, head down to your favorite coffee shop, or better yet, a local coworking space.

Is it worth it?

Yes. There’s nothing more empowering than knowing that every dollar you make is an exact reflection of the work you put in. If you work a few extra hours over the weekend, that’s more money going into your bank account — you can’t say that for your typical salaried job.

Plus, many of the pitfalls of freelancing can be resolved by simple preparation and planning. Yes, there will be hurdles, but when aren’t there?

Ready to take the leap? Sweet. Let's do this.

Start with the First Chapter
Why you should consider freelancing