Or, The First Six Months of Freelancing

It’s been six months since I started Second and Park. I have been fortunate in almost all respects: a full load of clients from the beginning, a supportive group of former colleagues and professionals cheering me on, and a very patient husband / business partner who’s willing to talk me down from scary freelancer ledges.

But despite all the kind people and good luck, I’d be lying if I said it was skittles and scones every single day. On bad days, this work can make you feel tired, confused, and annoyed. On really bad days, it can lead to escapist fantasies about joining the circus.

Still, I’m convinced it’s possible to make freelancing (or small agency-ing) an energizing and creative experience far beyond the 3-month honeymoon. You just have to know what the problems are, which ones are your fault, and which ones you can fix.

In the spirit of optimism and flexible circus performer strength, I’d like to define the problem (in this post) and offer a few inchoate solutions I’ve found (in a later post).

So first, the problem.

The Problem With Freelancing

The biggest problem with freelancing is, ironically, that you have clients. Clients give us life and money, but I’ll bet that not learning how to handle clients is why 90% of unhappy freelancers are unhappy.

If you’re like me, you probably started this biz with a sweet, subconscious chip on your shoulder, thinking to yourself, “I am a fair and balanced communicator with wolf-like business acumen and an advanced ability to distinguish good prospects from bad ones.” I hate to say it, but you thought wrong.

No amount of studying, working out, or late-night practice (you plucky go-getter, you) can prepare you for your first piece of client hate mail. Or the first time someone doesn’t pay you, treats you like a ‘dumb woman’ or ‘lazy web person’, or thinks that if he just emails you enough, you’ll work for free.

It would be tempting to beat our chests, rip out our hair, and create secret drinking societies where we sit around and talk about how mean and dumb and quaint our clueless clients are.

But of course, this would be the wrong answer. The right answer is to learn about clients—what they want, how to talk to them, and what to expect.

Learning About Clients

Successfully handling clients is about more than “Building Great Client Relationships!”. It’s about learning to build and navigate actual relationships with warm-blooded, mercurial people who, no matter how professional, have moods and unstated expectations and a completely different way of looking at the world than you do.

When you and your client have professional, thoughtful, flexible expectations that you communicate to one another and gracefully agree on, the results are magical. You feel good because your client trusts you. Your client feels good because he/she trusts you. Before you know it, you’re baking your client a layer cake, and doing a little extra work just because. This high-quality relationship is sustainable and energizing—it’s the kind you should aim for.

But in many cases, your client (or you) do not exude this measured positivity. You’re suspicious of one other, in a hurry, and determined not to get burned. Therefore, the bar for freelancer happiness is set depressingly low.

Freelancing is the wild west of business, and it’s just you, that one psych class you took, and your current maturity level versus the wild unknown mess of the self-interested masses. You have to be strong and confident—not to mention organized, decently nice, and good at your job—to make this work sustainable.

Your New, Super Extreme Independence

The way one handles independence and personal agency is, paradoxically, what makes or breaks the freelancer experience. To succeed, you must embrace it, come up with a plan, and sit calmly poised in anticipation of the inevitable fire. Then, you have to be strong, calm, and patient enough to steer things back in the right direction when they veer off.

And so in a way, the problem with freelancing is not clients—it’s us. Only we can determine who we should work with and how to adjust to new situations as they hop in our laps. Only we can engage our inner armchair psychologist. Only we can decide if we’ll be happy doing the work. Like it or not, the ball is so squarely in our court, we’re tripping over it.

In my next post, I’ll stop talking about problems and get down to some “we can do it-style” solutions.