I believe in freelancing.

I believe in the future of freelancing.

As a way of working, remote freelancing just makes sense for a growing percentage of the workforce. By 2020, about half of all workers will, on some level, be freelancing or contracting out their work.

Half of all workers!

As we move in that direction toward a more self-directed economy, less dependent on companies to define our careers and establish security, what are the characteristics of successful free agents?

Some of the most talented, original creatives are freelancers. Working on their own schedules and delivering superior creative results for their clients. Because we come from diverse backgrounds and are free to take on projects that don’t railroad us into some simple box, I believe freelancers are better able to bring fresh ideas to a project.

There’s a definite independent streak among them. Many freelancers just sort of “fall into” freelancing, but some choose it purposefully. A common denominator, regardless of how they started, is their free spirit. They want to be their own boss, choose their own jobs, express their unique style, or enjoy a flexible work and lifestyle.

Most freelancers are good at what they do. They have to be, because their work must stand on its own merit. They own it, for better or worse.

Besides the incredible pool of talent among freelancers, is their incredible ability to get things done without being watched. Freelancing isn’t for everyone. It takes someone with an inner drive toward productivity. I used to call myself a “busy-body”, a slightly self deprecating way of saying I always had to be doing, producing, or at the very least, reading something. Now I know that self-starting engine is the reason freelancers like me survive.

They hustle. Freelancers are industrious, as a rule. Besides the obvious necessity to always find work, their hustle almost always comes from a deeper motive. Freelancers do what they do because they have other things to take care of: children, aging parents, animals, hobbies, or other social activities. Freelancers fit more things into 24 hours than most people.

In my mind, those are the defining characteristics of freelancers.

But what makes a freelancer tick? What keeps us going, besides the drive to keep the checks coming in. You gotta eat – but let’s face it, there are easier ways to feed yourself!

So where’s the icing? I think it’s in the ability to enjoy work that you freely choose. Being able to sit down, even when you don’t want to, and make something decent.

Some jobs are certainly better than others. Every creative has had the heady feeling of completing a job and knowing they crushed it. Nothing’s better than feeling proud of your work, if not the final result of the entire project. Those projects are the best!

But then there are those jobs that just get done.

There are a few distinct situations in my freelancing career when I wasn’t as proud of my work as other times. By my standards, the writing just wasn’t as good as it could have been. Although the client may have been happy, I didn’t love it; and while I had ideas about how to make it better, those ideas hinged on factors outside of my control.

When freelancing projects aren’t great…

The few problems I’ve encountered in delivering my best work for a freelancing gig fundamentally centered around the level of commitment involved from either or both parties.

I’ve thought about this a lot and I hope to explain where I see most freelancing gigs lose their luster, and how to fix that.

Stick with it, I promise this ends on a positive note!

Commitment to Communication

Communication is the key to happy working relationships. Client and freelancer need to connect regularly throughout the project, especially if there are many milestones involved, or work hinges on contributions from others. Sometimes touching bases is as easy as picking up the phone or visiting an online board to check or post updates, share work, or communicate changes. When either the client or creative is unresponsive for days, or fails to connect at the pre-designated time, it’s not only frustrating, but the work stops.

Missing deadlines is unacceptable for both the client and the freelancer. The number one way to prevent that is to keep communication channels clear.

Commitment to Sharing the Big Picture

In my 10 years of freelancing, my best work and the most successful projects were those in which I understood where my work would fit into the larger plan… of the company’s goals, the department’s goals, even the solo-entrepreneur’s goals. Unfortunately that’s not the norm.

When I first started freelancing, I had no clue how my work fit in with the overall plan. I took simple assignments: Write ten articles on [blank], or write a sales page for this or that product. While it’s nice to have work, these jobs were not the most fulfilling, nor did they produce my most inspired copywriting. Sorry, but there’s the truth for you.

It was only when I started taking on jobs that required more complex writing packages (online launches, email campaigns that led to a course offering or landing page, etc.) that I started thinking like a content marketer.

I began asking more questions upfront, almost to the point of coaching and strategizing with a client who had not hired me yet. Of course this added value to my services. Sometimes my voluntary assessment assistance resulted in the client taking what I had delivered on a silver platter, and going elsewhere for the copywriting.

In spite of that, I still believe that process if valuable, even though you have to be careful you’re not giving away the store or taking too much time doing it. I’m grateful to have unlimited creative, and original ideas, too, because even if a potential client doesn’t use my services, I know they could never extrapolate the same value from another writer.

As long as you keep the introductory calls short, then you won’t feel you’re being robbed of your expertise. Better ideas always flow from the initial ones, and I’ve learned the value of a good contract to ensure I have a deposit before I hand them over!

Understanding more about the client’s unique value, key performance or success indicators, his audience, and his company’s culture all result in better creative content.

Yet too often, creatives are assigned projects with merely a sketchy discussion about the target audience, the company’s culture, or the image the brand wants to project.

When freelancers are told these things, many times it’s different from one creative to another. It may even differ from what the marketing department and C-suite understand them to be! To make matters worse, it’s usually one person’s job to hire the freelancer. In this case, where just two people are communicating, it’s like playing telephone, and the final result is never ideal.

In the case of a solo-preneur or a new company, it’s likely they simply don’t know yet, but in an established business, these things should be clear. I say “should be”, but in so many cases, it’s not clear at all.

You have to ask, and then they have to do that work. At least that’s how I do it. If the client can’t fill out a simple brand assessment, then they might not be ready to spend money on marketing their products or services. I’d rather know that at the beginning of our relationship and not sometime in the middle of a project.

My goal is to bridge that communication gap before I undertake any project. The most important factor in the success of a creative project, especially one that involves creative freelancers — graphic designers, web developers, copywriters, photographers, etc. – is communication about how their portion of creative work fits into the content marketing campaign or project.

It doesn’t take very long to have that discussion – usually less than an hour — and if it’s not possible for the client to answer these questions, then we’re probably not a good fit to work together.

[Spoiler alert: Can you see where I’m heading with this? I want to raise the bar on the whole freelancing industry, at least my little corner of it!]

Commitment to — and Mutual Understanding of — of Goals

Just a short cautionary tale: I once worked on an ambitious and really juicy content marketing project with one large company for months. The work I produced and the short-term results we accomplished were awesome. and I was amazed at what one other guy at the company (a WordPress developer) and I had created entirely on our own.

The weird thing about that project should have triggered suspicion. For an entire year, I communicated with only one or two people from the company — and this was a mid-sized company!

Let’s just say I wasn’t really surprised when the project suddenly dried up. I wasn’t unhappy about that, necessarily, because the workload was all-consuming; I was beginning to feel like an employee to this one manager; and I getting the sense that I was losing my grip on my own marketing efforts. My phone wasn’t ringing anymore. And that’s a bad, bad thing for a freelancer!

On one hand, I was paid well. No complaints there. On the other hand, I felt kind of slutty when it ended, if that can even be “a thing” in the world of freelance copywriting. I admit it; I invested energy and emotion into this job without knowing where it was headed. I thought I was working on something big, when really it was just a little pet project one guy dreamed up.

I’ll never forget our last conversation when he said, “I proved to myself that I can build this thing quickly if I need to.” (The funny thing is that if I had known that was his goal, I would have invested exactly the same enthusiasm, and energy. It just would have been nice to have known that all along.)

These things happen. It’s the world of freelancing, after all. I never thought to ask any difficult questions or include a retainer fee in my contract. Again, I blame myself for learning what countless freelancers learned before me the hard way. Now that I know, I’m sharing it with you, fellow freelancer.

Besides pulling the rug out from a freelancer, which is bad karma (we all know that), it doesn’t seem like a company averse to sharing it’s real agenda is using its resources very well. There are many good and understandable reasons, however. The project is “only” temporary, or they don’t have a budget to hire a designated employee for the job, or they are testing a project and don’t want to divert their full-time, invested team members from their core workload.

The moral of this little story? Don’t overcommit to someone who is not committed to you.

But you will, of course. We all do it once or twice. Learn from it, then move on.

And another thing… Yes, you are being “used”. It’s the nature of temporary work, and even part of the verbiage in the freelancing world. (“I use this copywriter” or “I use a VA who knows the Adobe suite.”) But it doesn’t have to feel that way.

Telling the truth goes a long way.

Commitment to Teamwork

If my work falls flat, doesn’t “connect”, or fails to get the intended results, it could very well be that I can’t write.

OK, I can write a little bit; I just can’t write well enough to call myself a copywriter.

These kinds of negative thoughts plague all but the most Dunning-Kruger-affected creatives. You know that syndrome where the person is so incompetent, he doesn’t even know he lacks skill, and he can’t recognize genuine skill in others? Well, if you’ve ever felt like someone was going to find out that you suck, you probably don’t have that syndrome. You’re probably just human.

Or you could be working on a project where teamwork and feedback are not valued.

Freelancers often find themselves working on projects where many creatives are working toward the same ultimate goal, say a product launch, a list-building campaign, or a crowd funded project.

When several people are all working separately on the same thing, and they can contact each other throughout the project, the creative experience is more enjoyable and successful. When the team members at least meet each other on a short teleconference, it makes a huge difference in the excitement generated for the project.

In fact, my best work has been when I was made part of a remote creative freelance team, and we were all pulling together, even for just a few weeks. Getting feedback and upvotes on your deliverables is not only sweet, but the knowledge that your work contributes to a seamless whole can be what keeps you energized, motivated, and organized.

Working with a team is fun, too! Let’s not forget that.

Unfortunately, what happens sometimes is that the organizer of the project is so motivated to protect her baby that she goes around getting too much help, gathering too many outside opinions.

This isn’t teamwork; it just makes everyone crazy. Too many opinions, if you take them to heart, can make you feel like your work is under par, to say the least.

There’s nothing worse than pouring your heart into a project only to hear that the “other copywriter” (or sister or best friend) has other ideas.

One time I was even blindsided and pulled in on a call with another writer and we were asked to write copy for a flyer – together! I can imagine an equivalent scenario in a graphic designer’s world. He chooses a shade of green and someone reaches over and slides in just a touch more blue. “There, that’s better,” the other designer would say as the first designer fumes, and turns an alarming shade of green.

[Newsflash: it only takes one writer to write a sentence. A good editor is valuable, but the writer and editor should never sit side by side with a red pen in front of the same text.]

I’m sure every creative has had a similar dismal experience. I’m not talking about contributing to a project in cooperation with other creatives. I’m talking about someone deleting a word you just wrote as you share a Google doc and squashing an idea you’re trying to birth.

Creating by committee is an impossible way to work; yet some people (usually women) think it’s a good idea. It’s not, and never will be. Don’t let someone talk you into it. It wastes time, and kills creativity. You have to trust the creative to go off alone, and do the work.

Good teamwork means that if the freelancer is hired to make a contribution to a project, then it’s only fair that she be entrusted to do her job with professionalism and competence, without others stepping on her toes.

I feel strongly that the flip side to committing to the idea of teamwork is equally important, and that’s committing to your team members.

Sometimes clients don’t bother to get all their freelancers on the same project together because it’s a temporary work situation, and it adds yet another step in what’s designed to be an expedited process.

The solution is to allow team members to make contact and introduce each other with respect and enthusiasm for the project. It’s a small step, yet it has exponential rewards. I’ve seen it work myself, when the organizer has clarity about the project, and can relay the vision coherently.

Team meetings and brainstorming, even among strangers, can be very effective and inspirational. In fact, some of the best ideas come about when team members don’t know each other very well. Thumbs up to the client who encourages teamwork among freelancers working on the same project!

And when it comes time to do the actual work, let the designer, writer, coder, or photographer go off on his own and create!

When freelancing doesn’t work, on some level it’s a commitment issue.

I’m going out on a limb to say this, and I’m sure some folks will disagree, but when there’s a commitment gap on the part of the hiring party, then sometimes there’s commitment gap on the part of the freelancer, too.

Companies and clients that want freelancing creatives to give 100% to their projects need a better solution. They need to hire freelancers with the confidence that they care about their project; that those freelancers think about the company’s problems as deeply as if they were their own.

Most freelancers genuinely care about their clients’ work, even though it may be a temporary or smallish job. You’re probably committed to results for a few obvious reasons. If a client meets their marketing goals due to our efforts, you feel good about how you spend your days of solitude; on top of that, you’ll have created a piece you can be proud to add to your portfolio.

It’s a win-win when freelancers commit to meaningful working relationships with their clients, and others on their team.

In turn, freelancers need to feel like they have genuine freedom to deliver their best creative work, and that it makes a difference.

I’m building something that’s going to change the way (at least a few) freelancers work, and allow clients and freelancers to commit… To go all in on projects they love and want to be memorable, amazing, lucrative, forceful, and fun.

It’s an agency where freelancers work together in teams to deliver the best content for their clients. It’s called Content Boomer, an agency made up of content-creating freelancers who “get” content and know that in order to create amazing content, you have to tear down the silos among creators and even the people who hire them.

Most creative folks will freely admit that they work best alone, when the spirit hits them, and OMG, not in a could-killing cubicle! (Can I get an “Amen!”?) We also enjoy the freelancing lifestyle so we can tend to kids, aging parents, hobbies, travel, etc. Maybe you’re the type of freelancer who doesn’t want to work full time, or for certain industries. That’s cool.

I freelanced for years because I have kids who need me at random hours, and because I’d turn into an ugly, mean momma if I didn’t get in a workout at the gym after dropping them at school. Did that make me any less capable of delivering kick-butt copywriting? Nope. It just meant I had to work on my terms, which meant 5:00 am mornings, sketchy availability between 9 am and noon, and lots of weekends. I was happy because my hours were my choice.

Another thing that always stumped me when looking for jobs, was that little line, “agency work required”, which I didn’t have. I had lots of experience working on remote creative freelance teams when it was possible, and even organizing projects and ensuring everyone’s contribution dribbled in on deadline; but “agency work” was the mysterious gap in my resume that prevented me from applying for and doing many jobs that seemed interesting.

These days, I’m almost sure that’s the hiring company’s loss, but I doubt I’ll ever really know. It doesn’t matter anyway, because I’m building a new kind of agency — the freelancer’s way.

Content Boomer is a digital marketing agency that appeals to both our clients, baby boomer entrepreneurs, and our freelancers.

By sharing a client’s “big picture” – and a cohesive marketing strategy — with our freelancers, we believe everyone’s able to contribute their best work.
By organizing projects using online scheduling, and work-sharing software, we keep everyone in the loop.
By providing a platform where freelancers can draw together and share ideas about the same project, we raise the bar on the freelancing industry and deliver the finest “freelanced” creative product.

We handle the project and ask both the client and our freelancing team to check in periodically, usually Thursday afternoons.

There are tons of benefits to a remote, digital agency for both clients and freelancers.

For clients…

Because the client gets the best freelancers working together on their project, they can expect off-the charts quality work.
Because the work is organized by an agency experienced in delivering digital content on deadline, the project stays on schedule and on budget.
Because the work is done remotely, clients get unsurpassed creativity from a diverse team focused on their project.
Because we’re flexible, it doesn’t matter if the client’s project is temporary, a short, intense campaign, or even a smallish part of some larger scope. The client can relax and depend on our agency to pull it together.

For freelancers…

Because we’re working with higher-level clients, freelancers enjoy working on juicier, more involved projects, which means more interesting, challenging, and satisfying jobs,
Because the agency manages the project, freelancers can focus on creating and hitting their deadlines.
Because we often work in teams, freelancers will enjoy the refreshing and social experience of creative contribution. (You get to see your work in a larger scope and even, hopefully, the good results of the project.)
Because we believe in remote, creative freelancing as a core value, freelancers maintain your independence, working exactly the way you like to work.
Because the agency attracts and works directly with clients, freelancers can worry less about negotiating fees, contracts, and collecting payments. When the agency gets paid, you get paid.

I’m beginning to put a team together. Here’s the deal. This is new, so I’m not exactly sure how everything will roll out, but I’m committed to you, the freelancer; the client the agency serves; and the success of the agency. That’s what I can promise right now.

I’m not asking for a forever commitment, just a few freelancers who love what they do — and the freedom to do it well from a remote setting, as part of a working team.

I can’t guarantee that freelancers will have 40 hours of work each week. Most client projects are on a per-project basis, and I’ll be searching for the best freelancer for the immediate job to work with me on those projects. This could look like 5 hours a week for six weeks; it could also look like ten solid 8-hour days… or four 12-hour days. It will depend on you and what we, as a team, need to accomplish.

Consider this a manifesto, of sorts.

All of the above, plus this…

Content Boomer is an agency made up of freelancers and contractors who are committed to their highest level of creativity, expertise, and professionalism… and to a remote, freelancing lifestyle.

I’m committed to bringing freelancers cool projects they may not otherwise “qualify” for, because it doesn’t matter to me whether you’ve worked in an agency.

I care about each and every one of you, and I respect your decision to work from home, or on the road, or wherever you want to work; for whatever your reasons you chose this way of life.

I value your experience and talent.

And hey, it’s really fun to work together with a team on something big, so I’ll be looking for projects that have some sticking power so we can be proud of the combined contributions we make. (Lasting value is missing link in a freelancer’s ‘job satisfaction, I believe.)

Finally, there’s a chance the freelancing team would get together on a retreat occasionally… involving Texas BBQ, perchance?

I reserve the right to edit this manifesto if the need arises, but you get the gist.

Would you like to join us? I’m working on a forum where freelancers can

Meet and share what works and what doesn’t work.
Share how they set up their offices and schedules.
Recommend tools and SaaS that make freelancing easier.
Access and participate in recorded interviews by and for freelancers and other remote content creators.

I’d also like to hear what you have to say about this, whether you think it will fly, and if not, why not. I’m excited to meet you if you want to be part of this hardworking, virtual, remote creative freelance team of A-List creatives at the top of their game.

Please add your comments below, and if you’re interested in learning more, I invite you to take this short survey to share more about yourself. I’d love to take this convo further…

Thanks!