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In my post on remote contract work, I wrote about how piecing together part-time remote contracts allows me to travel and live a generally flexible life. A lot of strangers have gotten in contact with me, and I’ve noticed a general feeling of starry-eyed disbelief that such a picturesque lifestyle is possible. I’m happy that people are so moved by the idea of an alternative lifestyle, but I also feel conflicted, because the grass always seems greener yet it’s not all sunshine and roses on this side of life. So in the spirit of full disclosure, I feel it necessary to expand on the pros and the cons of life as a remote freelancer.
The Pros
Location flexibility ✅ With remote contract work, you can work from anywhere where you have reliable internet.
Time flexibility ✅ With many contracts, you set your own hours, so as long as you get your work done, you can work whenever you’d like.
Variation in work ✅ If you take on a variety of smaller contracts, you can piece together a variety of work that you find interesting, fulfilling, and challenging.
Being your own boss ✅ Freelancers are usually treated kind of like hitmen (or hitwomen). You’re hired to do a job and left to do that job. This means that you usually don’t have a boss breathing down your back or micromanaging your work.
No workplace drama ✅ If you’re like me, you get a little tired of workplace politics and drama. As a freelancer, you’re usually detached from all this nonsense.
The Cons
Gross vs. disposable income ❌ This is probably the biggest bummer. When you first start freelancing, you’ll be amazed at the amount of money that gets deposited into your bank account for every paycheck. (Not to be coy… 100% of the money gets desposited!!) The issue is, you have to remember to set aside money for, at the minimum, quarterly estimated taxes, healthcare, and retirement. When all is said and done, a large proportion of your paycheck gets eaten up. It’s complicated and disheartening to say the least. Check out this guide if you’re confused about your finances as a freelancer.
Open-ended schedule ❌ Time flexibility is listed as a pro, but along with that comes open-endedness, which means that it’s hard for you to say whether or not you’ll be working on any given day in the future. You’ll probably know your schedule a week or a month out, but scheduling a vacation in a few months might be tricky… who knows what contracts you’ll be working on then or what their time requirements will be.
Detachment from workplace ❌ While you get to avoid much workplace drama as a freelancer, you usually miss out on the chance to develop deeper professional relationships. You’re not exactly seen as a co-worker by most members of the team you’re freelancing for, so you’ll often feel like an outsider.
Breadth vs. depth ❌ Often times as a freelancer, you’re hired to do a task or set of tasks that the team doesn’t have the bandwidth or skills for. This task-based work means that you usually get to do a wide range of work, but you don’t get to dive deep or develop a complex, long term project on your own.
General instability ❌ Instability and flexibility have a lot in common, but there are definite downsides to having a flexible work life. Your employment depends on a lot of things like available budget and workload—it’s not uncommon for your contract to end for reasons other than your work quality or merit. There is always a chance that, next month, your income could be chopped in half. If you’re prone to anxiety, this can surely become a problem.
Day-dreaming is easy, but the hard truth is that basically every lifestyle poses some challenges. Hopefully you can choose a lifestyle that matches your priorities and lets you focus on the things that are most important to you in life. For people considering quitting their full-time job for freelance work, I’d urge you to consider these pros and cons before taking the leap.
P.S. Check out this guide for a rundown on freelancer finances… another consideration to make before (and after) you start freelancing.