As many of you know, after 15 years of the indie company and freelance lifestyle, I recently took a full-time gig with Classroom Inc. as the Vice President of Product Development. It’s been a fabulous experience for me, but getting here was a process that took many months, a lot of soul searching, and some serious back and forth with friends and colleagues about whether or not I was the “full time” type. After all, I’d been working from home for the vast majority of my career, doing things more or less on my own time and schedule, spared the crush of rush hour subways and the 9 to 5 grind.

Because the games and television industries present many divergent opportunities for both full time and gig-based work, I find that these days that I’ve been talking to a lot of colleagues about the pros and cons of “going staff.” So now that I’ve been three months into the office-going lifestyle, I’m here to tell the tale from the other side, and offer a little advice for those who may be considering settling down with one special company after a few years of sowing their wild oats.

Here are some signs you may be ready to take the plunge.

1.  The Risk is Getting to You

This may be the number one reason people leave freelancing or small start-ups for staff work, and it makes sense. It’s exhausting when you’re constantly worrying about drumming up new business and chasing down invoices. Without a fixed office space, you can waste a lot of time wandering around looking for a quiet place to make a phone call or write that next draft of your script. And, frankly, it’s hard to be your best creative self if you’re not sleeping because you’re worried about paying the rent.

If the work is extremely rewarding or you’re confident that your entrepreneurial abilities offer you better prospects than a fixed salary, the freedom of freelance may well outweigh in-house perks like health insurance and pre-tax MetroCards. But that warm fuzzy feeling of a direct-deposited paycheck is what drives many people to give up some freedom in exchange for more security.

2. You Miss Humans

Depending on where and how you’re freelancing, you may find yourself looking up at the end of day spent alone and wondering, “Have I actually talked to anyone today?” For me, this was a major downside of working from home. Sure, it was convenient, the commute couldn’t be beat, and I’ll admit that it was much easier to carve out creative time to get things like writing done without the interruptions of tons of meetings and colleague drop-bys. But as the mother of two young children, I spend plenty of time at home by myself or with two little people who don’t really want to talk to me about the finer points of game design. Though I’ve been blessed to have wonderful colleagues throughout my working life who made even Skype instant messaging feel like great companionship, there’s nothing like an informal chat while the coffee is brewing or swinging out to an impromptu lunch with some co-workers to make you feel like a real live human being.

3. You Need Help With Your Work/Life Balance

Ok, I know this one seems counter-intuitive. Freelancing and working from home are supposed to be ideal for those seeking a work/life balance, and I certainly know many work-at-homers who have great systems in place for getting their work done and shutting their machines down at the end of the day. I also know plenty of people who bring their work home with them from the office on a regular basis. But in my case, I found that the longer I freelanced, the more work began to creep into times that it probably shouldn’t have. Because there was always an urge to clock hours on projects or pursue new leads (see item #1 about trying to keep one’s head above water), days off seemed like wasted opportunities. Freelancing can also make your schedule unpredictable — projects come in when they come in, and they need your attention whether it’s convenient or not.

When I asked a friend who was quitting a staff job a few months ago what she was most looking forward to leaving behind about office life, she said, “I hate the feeling that someone is always looking over my shoulder counting how many vacation days I’ve taken.” My mental response was, “I haven’t taken a vacation in three years.” It was at this point that I realized I probably needed someone else to tell me to take a vacation and how many days it should be.

4. You Feel Like You’re Missing Out on the Big Picture

In most of my years of freelancing and working for small companies, my primary work was as a writer or consultant. There were huge creative upsides to these roles and I wouldn’t trade those work experiences for anything — I am keenly aware of just how fortunate I’ve been to spent the majority of my career doing things like thinking of funny names for baby sloths or brainstorming the best way to make Cookie Monster wield a mallet at a strongman’s booth. However, when I handed my work into the client, the publisher, or the network at the end of a production cycle and they were free to use it (or not) as they wished. I worked on tons of projects that had an enormous amount of potential that were scuttled for practical or logistical reasons that had nothing to do with my creative contribution or that of my collaborators. Pretty much all of the freelancers or consultants that I know have had this experience multiple times.

One of the big upsides of being in house at a larger organization is that you are part of projects for their full lifecycle and can really play a role not just in shaping the creative vision, but in strategizing how they’ll get made and what resources will be needed to achieve your goals. Budget meetings and vendor contract negotiations may never be my favorite things, but they also make me actively responsible for the practical considerations related to my creative work. And when it comes to doing things like instituting company policies such as starting a new tradition of game play days at the office, I know that I am setting things up for the long term, not just the duration of whatever project I’m working on.

5. The Opportunity Presents Itself

No matter how much you might be ready to say goodbye to the freelance life, finding a staff job that’s a good fit can be tough. We work in a competitive, creative industry, and there aren’t hundreds of great jobs just waiting for you to fill them. Especially if you’ve been working for a while, finding a sufficiently interesting and well-paying job can be a waiting game. This means being open to interviews and talking to headhunters even if you’re not actively looking — there’s no reason not to have a conversation and get your name out there a bit more, even if you’re happy in your current situation. But when it’s taking awhile to find the right position, freelancing can be a great way to keep bringing home a paycheck and remain visible in the industry while you’re waiting for that perfect fit to come along.

6. It Feels Right

This was the biggest reason that I jumped on board at Classroom Inc. I already knew several of my new colleagues, including the president of the company, and had great previous experience working with them. The hours are reasonable, the people are friendly, and they weren’t locking me into a six-year contract. As far as the work itself, I love the mission of the company, I knew I would be taking on a lot of responsibility, and I felt confident that I would learn different and important things for my career while doing the job. Critically, the company has also been very supportive to me maintaining my independent identity in the industry, encouraging me to continue with this blog, collaborating with Carla, and writing and speaking elsewhere. I wouldn’t have known all of this without going through several rounds of interviews and having frank conversations with the people hiring me about our expectations, but having vetted all of those things made me confident that I was making the right decision.

So, those are some of the headlines from the past few months of my staff life. It’s important to note that this is just my experience. I’ve certainly seen friends in recent months leave their full-time jobs to strike out on their own equally happily. I have plenty of successful colleagues who are more than willing to trade the financial risks of freelancing for the creative freedom to work for themselves or with a small, tight group of start-up co-workers. And I have every confidence that many of these freelancers will realize the potential of their great ideas, which may prove to be the building blocks for larger, more stable companies in the future. It’s important to remember nothing is forever and no decisions are etched in stone — we see seemingly “stable” companies lose funding overnight and two-person bootstrappers rocket to fame and fortune every day.

My advice is to try to understand your own working personality, where you are in your career, and what kind of job is likely to work best for you, and be open to the possibilities that may be lurking around that office door.

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Photo ©Phil Whitehouse