Freelancing exposed: the pros and cons of self-employment

It’s been almost two years since I left my desk job to focus on freelancing and being self-employed full-time. There have been some cons but mostly a lot of pros. It is crazy how fast the time has gone. It’s also been one year since I went back to work for my former employer, but as a freelancer not as a full-time employee.

I’m winding down my partnership with them soon – probably mid-next month or by year-end at the latest – which is partly due to changes on their side and also due to some lifestyle changes I have in the works for next year.

Thinking back on my experiences so far and also looking forward is a fun exercise for me. I recently had a blast writing about the great, so-so and downright crappy aspects of being a manager, so now here’s a similar analysis on the pros and cons of freelancing.

Freelancing exposed: PROS! 🙂

1. Whatever, whenever: One of the my favorite perks of being a freelancer is the flexibility to set my own hours. Of course some projects can require on-site work at specific times, but as a freelancer you have full control over what hours you choose to accept, negotiate or deny. You decide when you want to work – it’s awesome! When I can work remotely, I prefer to work first thing in the mornings and leave the afternoons and evenings for things like administrative tasks, errands and personal time.

2. King of your castle: One of my favorite aspects of being a manager was the autonomy. For the most part I had a say in who I hired, who I worked with, and what I chose to delegate and to whom. Plus I got to make a lot of decisions on my own. Freelancing is great because it provides a lot of autonomy as well and often without the crappy parts of managing other people. Working as a freelancer also comes with the huge benefit of being able to control your workload. If you want more work you can hustle to find it and if your plate is getting too full you can simply say “no thanks.”

3. Here, there, anywhere: There’s a decent amount of freelancing work that can be done remotely, which I love for the convenience and flexibility. Some companies actually prefer freelancers to work remotely because they simply don’t have enough office space. Just be prepared that some companies are still old school and require freelancers to be on site, but you don’t have to work for them if you don’t want to. Having the power to find assignments that let you work anywhere you want is priceless.

4. Hello excitement: We’ve all been stuck in a rut before and had to do the same things at work day after day after day. Man, that can get incredibly boring! The great thing about freelancing and taking on various independent contracting gigs is that you can mix things up to your heart’s content. Get excited! Having control over which projects you take on keeps things fresh and engaging.

5. Goodbye FOMO: Things can be pretty tough when you first start out as a freelancer, but once you get enough experience your lifestyle is bound to get a boost. I’ve had significantly less stress and seen my health improve since I left my full-time job. I’ve also been able to travel as much as I please. I’m also so much happier all around and get so much more fulfillment out of my work. A lot of this is thanks to the many years I worked in corporate, which enabled me to save a lot of money and take risks. I don’t recommend freelancing full-time if you are not financially stable.

6. Write-offs, yes please: I love saving taxes! And one way I do that is staying on top of tax rules and asking my accountant a ton of questions each year. As a freelancer you get to deduct a lot of expenses on your taxes that employees can’t. Examples of business expenses that self-employed folks can deduct from their income include office supplies, equipment, software, subscriptions, conferences, and travel expenses.

Freelancing exposed: Cons 🙁

1. Hello weaknesses. Has your boss ever said you need to improve your communication skills or decision making skills? If you’ve ignored constructive criticism over the years, you will get a slap in the face as a freelancer. Being self-employed exposes your weaknesses so don’t expect to survive if you are a procrastinator. If you want to thrive as a freelancer, be prepared to sharpen your skills, pitch your strengths and eliminate your weaknesses.

2. Here today, gone tomorrow: If you’re uncomfortable with uncertainty and not having a regular paycheck, stick with your day job. Freelancing can be extremely unpredictable. When things get rough, independent contractors are usually the first to go and don’t expect to get fair warning. Read your contracts carefully too – just because you get a contract doesn’t mean you’ll get regular work. I signed a contract with one company that lured me in with a target of 12 assignments over the course of three months but I only got one assignment before the company shut down.

3. PAY ME ALREADY!: A major pain of being a freelancer is having to create and track all of your invoices. SO many companies are horrible at paying their bills. I’ve had to chase down invoices countless times because people forget to pay me for the work I’ve done. Seriously?! If you don’t stay organized and keep track of what you’re due, it’s almost guaranteed you will wind up working for free and that should piss you off. Never assume you will get paid automatically; always be on alert to re-send invoices and follow up until you get that hard earned money in your hand.

4. One of these things is not like the others: Working for a company as a freelancer can make you feel like an outsider. Some companies and their employees are snooty, cheap and/or security freaks and may say things like, “you can’t have a company t-shirt because they’re for employees only,” or “freelancers aren’t able to attend our team lunches,” or “contractors can’t be issued laptops or keycards” and plenty of other stuff like that. Some employees also discriminate against freelancers even if they’re working just as hard, if not harder, than the employees themselves which sucks. It’s not a good feeling.

5. What benefits?: You’ll miss employee benefits when they’re gone. If you want to be self-employed, you need to be prepared to get your own insurance (accident, health, dental, vision, life, etc.) and retirement plans (SEP IRA, solo 401(k), etc.). Find a good agent to help you sort through all the options and find plans that work best for your needs. Don’t overlook the importance of insurance and retirement planning. Also be prepared for work to pile up if you’re sick or take vacation unless you have a dedicated backup.

6. Multiple bosses are harder than one: As the CEO of yourself, you get to choose your clients and assignments. But, depending on the type of work that you do, your clients might act more like a bunch of disorganized, indecisive, clueless bosses. For me, my clients are essentially my bosses as long as they’re paying me. I typically just do what they want, even if I disagree, because it usually isn’t worth arguing. I’ve also had to report to multiple people at the same client before, which can get frustrating. Do your best to be as clear as possible in your communication and practice patience. If things get too out of hand, don’t be afraid to end a client relationship and move on to a better one.

Further Reading:

Here are some additional freelancing articles on Untemplater you should check out.

Seven Unexpected Aspects of Freelancing

Personal Finance Goals For Freelancers

Pros and Cons of being an Independent Contractor

Top 20 Wish List For Entrepreneurs And Freelancers

Recommendations

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Untemplaters, have you ever been a part-time or full-time freelancer? What were/are your most memorable pros and cons of freelancing? Do you dream of becoming self-employed?