Pros & cons of freelancing: You’re your own boss

Now that freelancing is exploding in the US workforce, everyone has an opinion about it. 

Is it the best, most freeing career path ever or a hell of insecurity and stress? Is it a giant engine of creative empowerment or the downfall of civilized society?

Does it require pants or not? 

Of course the answer depends on who you ask. And here are kernels of truth in most of the opinions you hear. 

To lay out some of the tensions and contradictions within this conversation, I am launching a regular “pros and cons” series that will explore the joys and challenges of a career in full-time freelancing.

A lot of these pros and cons are actually the same thing, such as “pants optional,” that will strike some as freedom and empowerment and others as a slippery slope into laziness and ruin.

So here is installment number 1 of “Pros & Cons of Freelancing”

Pro: You’re your own boss 

As a freelancer, you won’t have anyone telling you what to do. Well, your clients will, of course (if you’re lucky), but you’ll have no supervisor telling you how to manage your work, drum up new work, administer your logistics, or resolve problems. 

For some of us, this is one of the best things about freelancing – a big checkmark in the “pro” column. 

While all the bosses I’ve had in full-time jobs have been just fine (and some of them downright enjoyable), I simply do not like the feeling of someone looking over my shoulder and telling me when to come and go and how to do my work. 

The ability to decide all that for myself is a freedom that I find very empowering and motivating. The flexibility has allowed for many options I wouldn’t have if I were tied to desk in an office job.  

Con: You’re your own boss 

Of course there’s another side to this coin — it’s all on you. There will be no one to tell you how to do things, solve problems, improve your skills, or hone your strategy. 

Sure, you can find online courses, communities, and gurus to advise you, but even deciding who to listen to and trust is a decision you’ll have to make all on your own. 

Another thing you need to do on your own as a freelancer is manage your time. If you’re lucky you’ll be juggling a variety of projects for several clients, each with its own dictates, tasks, and deadlines.

It will be on you to figure out how to get everything done to the right standard at the right time. For those who aren’t organized or who are prone to procrastination, this can be a major challenge and a profound stressor. 

So, being your own boss can be overwhelming and stressful. But it can also be empowering and stress-reducing. 

How it feels to you will depend a lot on your own personality, motivations, and background. But even if it feels like a “con” at first, you can learn to embrace it by developing the skills and approaches that will make bossing yourself around feel more like a joy than a chore. 

Now I’ve got to go – I hear myself calling myself to a meeting.

3 thoughts on “Pros & cons of freelancing: You’re your own boss”

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