So you’re thinking of quitting the office job, huh? Leaving the ol’ 9-5? Kissing that cubicle goodbye? It’s a good decision, trust me. Well, it was a good decision for me, and that usually means it’s a universally accepted truth.

Okay, maybe not, but whether or not you should take the leap into the great unknown, you’re obviously thinking about it (that’s why you clicked the headline, right?). There’s a lot to consider in a decision like this. One of the most important considerations is, of course, what will you do when you make that terrifying leap? Where will you go? How will you pay rent?

You’re clearly not going back to an office job; that would just be more of the same. Which leaves you with three options:

1) Freelance work

2) Starting your own business

3) Finding that magical unicorn of a job which provides great pay and total security as well as the complete, utter freedom (I’m holding out for traveling waterslide-tester).

I’m going to assume you haven’t found #3, because if you have, you’ve also stopped reading this and gone to lock that down immediately.

Which leaves us with the first two options: Freelance work, or starting a business?

Now, a lot of people are going to read that and yell at me through their computer screens, Excuse me! Freelance work IS a business! Okay, okay, yes, I know, technically, you are correct. Both, to be clear, do require immense amounts of independence, focus, and hard work. However, as someone who has lived in both worlds, I would argue that the kind of hard work is often of a very different flavor. They will certainly overlap, but understanding these differences could give you key insights into which route is best for you. Which will fit most snugly in your life, with your personality? Which will give you freedom and joy, and which will make you feel just as trapped as your current cramped cubicle?

Here, for your consideration, are a few important questions designed to help you figure out just that.

  1. Are you an Introvert, or an Extrovert? Personally, I’m an introvert, so my freelance lifestyle is perfect. I absolutely love time alone; a great work day for me is staying by myself, in my room (or maybe a coffee shop), literally writing alone all day. If I don’t see another human being for six or eight hours, that does not bother me in the slightest. On the other hand, I’ve heard some of my extrovert friends say things like, “My roommate was gone all week, and no one came over! I had the place to myself for days — it was horrible!” Now, that sounds like my dream vacation — but my life is clearly their nightmare. Entrepreneurs, however, are notoriously extroverted, and there’s a reason for that. When you’re building a business, you have to meet people, you have to chat people up, you have to actually hire and work with other people. It’s all about building relationships, making connections, building a team. Of course, that’s certainly possible to do as an introvert, it will just require a lot more intentional self-care. Which lifestyle sounds energizing to you?
  2. Do you like a little structure in your life, or need total freedom? When you’re first starting out, the freelance lifestyle and the entrepreneur lifestyle have about the same amount of structure: it’s just you disciplining yourself to get things done. You may or may not have an official workspace, you don’t have a schedule that other folks are monitoring, and you’re making all the decisions for yourself. The difference comes further down the line as the entrepreneur builds out structure — that’s their ultimate goal. They want to build a functioning business, which might eventually have an office, or brick-and-mortar storefront. They want business hours. Freelancers, however, are not looking for that. The only structure they will ever have is the deadlines they negotiate themselves, their own arbitrary self-regulation, and the tax laws in their state. Some people thrive in that setting, but it might not be what you’re looking for. It will depend, in a way, on why you want to leave your current job: what’s pushing you out the door? Is it the type of work you’re doing, or the setting you’re doing it in? If you like having an office but hate your boss, it might not be the structure you’re trying to get away from — just someone else’s structure imposed on you.
  3. What’s your vision for the future? When you think about working on your own, what do you picture? What’s your dream for five or ten years from now? Freelancers and entrepreneurs both have goals, dreams, and markers for growth — they just look really different. Do you picture your product on display in hundreds of storefronts? Would you ever want to go public? That kind of scale can only happen with a team, most likely in a business. When it’s just you, on your own, you can only scale up so far. That’s not necessarily a bad thing, but if a key aspect of the work you want to do involves that kind of massive growth, you might consider the entrepreneurial route. If your goal is simply to support yourself or your family with your work, to be free to do the work you want to do, regardless of scale — well, you may be happier as a freelancer.

Ultimately, the biggest factor in the route you choose will be the type of work you want to do. Some work can only be done in a business setting; if you want to open a bakery, you’ve already made your decision to own a business. Likewise, if you want to be a writer, your lifestyle will probably be more in the freelance realm.

Then again, you’d be surprised how often some creative thinking can shift those perspectives. If you want to run a bakery but found, with these questions, that you’d prefer the freelance lifestyle, an online baked goods mail-order shop might be where you really succeed. A writer can write alone as a freelancer, or she can start a literary journal with a team of friends. If you know what your passion is, you’re already ahead of the game, but finding a lifestyle that gives you joy is the next step towards truly, and sustainably, thriving.

Like what you’re reading? Access HER magazine’s monthly publication in iTunes or Google Play – it’s where we feature powerhouse women you can learn from and share exclusive content you won’t find here.


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