Should I Quit My Job and Go Freelance? 5 Challenges Freelancers Face

Should I Quit My Job and Go Freelance? 5 Challenges Freelancers Face

Quitting your job to head into the freelance marketplace can feel a little daunting — even if you’ve been freelancing on the side for a while. Before handing in your notice, consider some of the challenges freelancers face after they quit their job. While we always encourage women to seek alternative job opportunities, we also believe in walking boldly into new chapters of your life with eyes wide open.

1. Getting Paid 

One of the most harrowing factors of freelancing can be getting paid — whether it’s on-time or at all. Many freelancers spend an inordinate amount of time and money trying to get what’s owed to them. Invoicing, sending late notices and hiring collections firms all cut into your bottom line. Prepare for the worst by following these tips.

Have a Contract

Before you begin work, get everything in writing. Include your exact fee and due dates. If your clients don’t pay, remind them of your contract. It’s also important to have everything in writing should you need to take them to collections or bring a lawyer in for backup.

Ask for a Deposit

Losing half your fee is slightly more palatable than losing all of it. Ask for a deposit upfront before starting any work. You might even want to consider asking for small milestone payments before beginning work on a project to ensure you have the payment before wasting any time after you quit your job.

Go Through a Third-Party Platform

One of the most hassle-free ways to deal with clients is by placing your money into escrow or in the hands of a third-party platform. That way, you can simply refer to an impartial bystander to assuage all disagreements and ensure everyone gets paid on-time.


2. Feeling Motivated to Work

We love non-traditional work schedules. Some of us were just born to burn the midnight oil, toiling away on contracts and marketing decks until the wee hours of the morning. Others simply need routine and schedule. Ask yourself if you’re comfortable answering only to yourself. Can you monitor your own productivity? Are you able to stick to a set schedule? Do your order and discipline originate from outside sources? Try working from home for a few days to determine if working solo will be a challenge or a setback.

3. Living With Uncertainty

The freelance lifestyle often means living with uncertainty. Sometimes there’s plenty of money coming in and you’ll need to beat back clients with a stick they’re so plentiful. Other times, you’re going to find yourself giving your bank account some serious side-eye and wondering if you’ll ever be able to afford anything but happy hour ever again. Freelancing comes with some serious freedom. But it also comes with a ton of uncertainty. The most successful freelancers are the ones who can plan for the future while understanding that everything is temporary.

female entrepreneurs working

4. Benefits and Insurance

One of the most underrated reasons to stay at your day job is the benefits. Many freelancers don’t get sick days, personal days or vacation days. And health insurance? It’s harder to come by for someone not chained to a larger corporation (though not impossible as many weekend warriors would have you believe). 

5. Fighting for Fair Pay

We believe one of the biggest skills you’ll master as a freelancer is understanding your worth. Freelancers deal with getting low-balled almost every day. Many companies simply believe that your rates are a jumping-off point to start negotiations. Before you can convince someone else of your worth, you’re going to need to convince yourself first.

Should I Quit My Job and Go Freelance? The Bottom Line

The short answer? Yes. 

We believe that if you’re asking these questions, it means you’re probably going to make the leap at some point. But we also believe in the importance of preparation. Before changing gears in your career, take a few weeks to find out what your biggest challenges will be as a freelancer so you can come up with a strategy to deal with them — or avoid them altogether. 

Leave a Response

More like this