The Good, the Bad, and Not-So-Ugly Of Freelance Life

It’s not all tea and roses, but it’s still pretty sweet.

I was not suited for office life.

Oh, sure, I managed all right. I did my work, and I did it well. I got through the days with a combination of coping mechanisms and minor rebellions, but when your own boss suggests that you might be happier working from home and you end up quitting that same day… well…

The writing was on the wall for a while. It didn’t take much of a push to shift from working a “traditional” job to self-employment. I was fortunate in that I was able to hit the ground running. I had already taken on some part-time freelance work at night. When I informed that client I had a lot more time available, they happily filled it up and gave me a couple of leads that paid out.

Not everyone is so lucky, so I do acknowledge and appreciate my early advantage.

This was all over 20 years ago.

Since then, there have been some ups and downs. Some booms and busts. There have been times when I’ve considered returning to more traditional work.

But I’ve managed to survive and even, most of the time, thrive. And I’m a bit of a freelance booster. That is to say, I support freelancing as a viable lifestyle and encourage others to try it.

But I’d be dishonest if I were to ignore the less-pleasant sides.

Here’s a rundown of some of the good, the bad, and the hey-this-is-still-pretty-good things about going freelance.

The Good: Working from home is just the best

Comfort and convenience.

I can wear whatever I want, for one thing. No suits with jackets. No ties.

I live in jeans and t-shirts. I keep a couple of sets of “nice clothes” on hand for the occasional meeting, but most of my clients are located several states away.

I know many people think we work in our pyjamas, robe, and slippers. Some maybe do. I prefer to dress as if I’m going to have to go out at some point. I feel more professional in real clothes and real shoes. I’ve tried the slippers and bathrobe thing but always found my productivity dipped.

The point is that I can dress as I please. My workspace is suited for me and my wants and needs. It’s not a sterile office. You won’t find any fluorescent lights here!

As for convenience, I no longer drive or take a bus to get to and from a job I didn’t want to be at. That saves money, maintenance, and gas. And it saves a lot of time. That’s nearly two hours saved in my day.

My schedule is more flexible, as well. I can more easily schedule things like doctor appointments or service calls. I can actually get to a post office during opening hours without sacrificing my lunch break.

So there is a lot to be said for the comfort and convenience factor of freelance. It takes a lot of unnecessary stress out of the day.

The Bad: No such thing as a real day off

My wife works a more traditional job. That means she gets holidays, days off, and scheduled vacations.

I don’t.

And have sometimes clashed because it’s hard for others to understand that just because they have a day off, it doesn’t mean you do.

Deadlines are deadlines. And as a freelancer, you’re responsible for making sure work is coming in and going out regularly. This means that a day off work is a day in which you’re not generating any income.

I’ve managed to arrange my work so I can take weekends off without much of a problem. I still sneak in some work now and then, but I try to keep my weekends open more. More extended vacations are challenging. Why would I want to spend a week in the hills of Pennsylvania where there’s no cell or WiFi connection when I could be working instead?

It’s actually good to get away now and then, but many freelancers are going to find their early years just consumed with staying busy.

The Not-So-Ugly: The potential for a good living is within your power

The money’s not bad. It’s not great, but it’s not bad.

Beginning freelancers will have the hardest time getting paid a living wage, so the conventional wisdom advises building up a bit of savings before striking out on your own.

But that said, once you’ve had some experience, built a portfolio, and nurtured some contacts, your only real earning limitation is you.

Yes, competition from overseas freelancers who have lower costs of living can be frustrating at first, but if pick and choose your clients carefully, and keep your eyes open for opportunity, you’ll be fine no matter where you live.

The Good: You can spend more time with family and friends

Working a day job in which I left first thing in the morning and often didn’t get back until sunset was a drag. When you add to that the general exhaustion for the day and the commute, it didn’t lead to a lot of time with friends and loved ones.

Being a father now, I can’t imagine how much I’d have missed had I been pulling the ol’ nine-to-five.

Enjoying a flexible schedule means I can be there for my kid’s medical appointments, playgroups, story-times, and so forth. With a more flexible schedule, I can plan meals more effectively and basically cover all those little niggling things about life that get more challenging when you’re stuck in an office building most of the day.

I can go out with friends on some nights and not feel tired all the time!

How many adults can say that?

The Bad: The paperwork kind of sucks

One thing I will give the day job is that they took care of all the paperwork. I had to file my taxes once a year, and they were pretty easy.

Now I have to file quarterly. I need to keep track of my own expenses, keep and scan receipts, do my own billing, chase down my own invoices, handle my own promotions, see to my own health care, etc.

This is time that could be better spent working on something or being with my family. But if I don’t keep on top of it, it’s surprising how quickly a small mess becomes a big one.

The Not-So-Ugly: After a while, you can pick and choose the work you want to do

At first, I pretty much took any job that came along. I couldn’t afford to be picky. After a while, however, I was able to pick more jobs that interested me personally. There are still times when business is slow when I might take on something just to make sure I have the holiday bills covered, but as I’ve established myself and my history more, I can turn down jobs that I feel don’t suit me.

You can’t do that at a traditional job.

A few other points to ponder

Whether you call it self-employment or freelancing, it’s a career path to consider. One article isn’t going to cover everything about freelance life as thoroughly as one would like. There are issues such as job security, distractions, health, home office space, networking, and so forth. There are even cybersecurity issues particular to self-employment to consider.

Long story short, self-employment may not be for everyone, but I’ve never seriously regretted my decision to go freelance. Despite the ups and downs, I believe it’s the perfect lifestyle for me.

It might be for you as well.

If so, good luck, and I’ll see you in the job forums.

Cheers!

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