I pride myself on being direct and being experienced enough as a freelancer to know
better. So why do I find it so difficult to bring up the dreaded topic of money and billing rates especially when I’ve already submitted a proposal to a client and go the extra step of doing initial exploratory work free-of-charge?

Me talk money one day

This particular instance which I’ve described above recently happened to me.

I felt even more worthless when I got off the phone with said client and realized I was so busy trying to sell myself that I’d forgotten to bring up my rates. In all honestly, my proposal outlined my hourly billing rates and he had skimmed it and given his initial “ok” but we’d never had a conversation specifically related to how much he was planning on paying me.

Ambiguity doesn’t sit well with me and in business, it’s the kiss of death. I realize that if I can’t have such a conversation with my potential client it might not bode well for our relationship longevity, but I opt not to think so deeply on this one. I don’t think it’s such a simple cause-and-effect.

I choose to think that much like I don’t like having to tell my boss I’m taking a vacation and might conveniently forget to mention it a few times before I eventually bring it up, this is another example of a conversation I’d rather not have because it makes me

uncomfortable and ok, if you want to get deep here, I fear (more than the rejection) that ugly word: Conflict.

I’m not throwing in the towel on this project or this client. Yesterday I had to send him a document I created and I used that as an opportunity to remind him of my rates. Sure, it’s a bit of a pansy move and it does little to further the line of DIRECT communication, but work with me here. It’s a start.

Worker Biatch is a wannabe Gen Xer (or “Millenial” as those labelists like to emphatically reduce her existence to) that has spent too much time in a cubicle. It’s a good thing she doesn’t go by labels or should might more accurately describe herself as a cusp middle child, stuck somewhere between the Xs and the Ys. Whatever the case may be, she’s accumulated some serious material over her years. She’s convinced this material hasn’t been too kind to her fragile psyche, but has made her a much wiser person overall and most likely funnier as a result.

In the past 48 hours, I’ve consumed roughly 12 hours of NFL. I’ve watched as more yards got run than plays got stopped, seen a team emerge from their imminent 0-2 status to clinch a game in the final 3 minutes, and another team rebound to new heights and a 2-0 lead with their back-up quarterback after their star QB had a season-ending accident last week.

We’re only a week into the NFL’s regular season and we’ve seen our share of daring athletic feats and bone-headed moves. (The Eagles’ receiver, DeSean Jackson, is a prime example of the lethal cocktail of talent and hubris.)

People ask me why I like football. I don’t entirely get the game to be honest. I do know that a team has 4 attempts to make a play and if they can’t, they need to rethink their immediate game plan. I know there’s a ton of strategy that goes into plays, that the quarterback may not be the coach but he has to a lot of quick-thinking and improvising on the field – often singlehandedly calling the play that can make or break a moment and determine a team’s success.

And that in the end, no single person on the team is any greater than any other, star QB or not, cause it takes all of the players working together (and parking their egos aside) to make it the post-season.

As it happens, football also happens to be a ripe metaphor for a freelancer due to many common, shared parallels:

• Be The Underdog: Peyton Manning & The Colts proved to us this week that sometimes smelling repeated defeat is all you need sometimes to catapult your motivational spirit to the next level. In my own experience, my confidence is never higher then when after I’ve failed at something big-time and can find within myself that driving force to start climbing back up the hill again.
• Let The Chips Falls Where They May: This one is hard, especially when you like to plan ahead, need to know how things will play out, and if you’re like me, even Wikipedia a movie while you’re watching it to see how it all unfolds. There’s a lot to be learned through process and results-oriented people need to remind themselves of this. Just like a football game has 4 quarters, life is also cyclical with its share of ups and downs and turning points. Learn to live with them and you’ll be much happier, or so people tell me!
• Embrace The Unknown: One of the reasons I dig football so much is cause there’s a lot of taking chances which sometimes results in zany, WTF-were-you-thinking moves, but I love it all the more when people get away with “the unthinkable,” debunk the system, and make up their own set of rules as they go along. Call it the rebel in me, or simply the idealist freelancer which hopes that risk-taking moves, such as working solo, will pay off one day.
• Make Time For Pep Talks With Yourself: In football, the coach takes “time outs” to amp up his players, get them focused, energized and feeling good.  In life, we need to make time for these moments too and just as often if not more often than just once a day.  On days I feel low I tend to build my confidence back up again talking it out with friends, family, or if all else fails a giant boost of caffeine! My sister swears by lists. Create a long list of things you like about yourself or your life. #1 on my list is the fact that I have the time in my day to write a meaningful post for my blog, make a mean pot of chicken soup on a seasonably Fall day, and feel a strong sense of accomplishment by 5 PM.

Catching a fish is no easy feat.

While certain countries, such as Japan and Peru, show an increase in the # of female entrepreneurs, by in large, men are twice as likely to start their own businesses as women. More than that, there are very few dissimilitudes in the way both genders approach business to account for the disparity.

So what’s stopping us?

Well, for one, GEM’s study finds that women tend to be less optimistic about the risk of starting a new business or making a change. This causes women to be less confident about their ventures and as a result, the fear of failure kicks in and results in a flight response.

While fear of failure has often been attributed to killing a women’s drive, and I, for one, am no less of a chicken, in this regard, how do we go about dispelling that fear and ridding it from our consciousness?

Getting personal for a second, when I had a miscarriage earlier this year (from which I’m still reeling from a bit), my gut reaction was what an absolute failure I was. I had a similar reaction when I lost my job, a month after I had my miscarriage. It wasn’t quite as severe, but I the same feelings of shame surfaced again.

I was angry at myself for feeling like a loser, but came to realize, that falling short is perhaps a woman’s greatest insecurity. Just look at how we’re conditioned from our youth to find, not just any Alpha Male to mate with, but the one with the right genetic combination to satisfy the lofty expectations of our family and friends, and if we’re lucky to meet our own. We have to compete with how many other women? (aside from mom, sister and ex-girlfriends?)

So how do we empower women to feel confident and optimistic about change and risk without tapping into their deep-seated fears about their competencies? In short, how do we level the playing field?

The United Nations is working on an initiative called “gender mainstreaming” that is about identifying gaps and bridging understanding in developing countries. In Lativa, women-owned businesses favor hiring women and it’s proved to be an effective way of ushering a new generation of women into the workforce there. And in Finland, women-owned businesses show the most profitability so they are exploring ways to make executive roles more gender-neutral and merit-based. (as opposed to the ‘ol boys network)

With the word “Change” being tossed around like some cheap dime store whiskey lately in presidential campaigning, I’m hesitant to cheapen a sentiment here. Let’s just say the world won’t get better overnight, but progress can and should be made everyday.

Mary-Louise Parker looking sexy and smart

I’ve made no secret of my certain affection for a fictitious middle-aged widow who supports her extended family weekly on Showtime at 10 PM.

There’s something about the way Mary-Louise Parker saunters as she effectively multi-tasks – Running her underground business while trying to meet the needs of her brood, inevitably falling from grace episode after episode, only to stay afloat and do a public service (Juggling hats again!) by supplying every inch of the food train with much-needed “happy” relief in the form of marijuana.

I’m not advocating drug use here. I’m quite anti-pleasure derived from most substances. The exceptions being chocolate or ice cream. It’s just Nancy Botwin (or Mary-Louise Parker’s character on Weeds) is such a prime example of a social antipreneur.

She has her principles and stands by them – She won’t deal in elicit drugs like crack or cocaine, traded her SUV for a Prius in a way that even Al Gore might have to slap her on the rear for just out of sheer adulation, and she puts her family first before her work.

But Botwin isn’t just about the labels that go with her personal brand of soma. She’s an unsung feminist in the form of a single mother that’s had to act out of necessity to support her family. Sure, she might have chosen a less glamorous and perhaps more legal professions to dabble in, but having been a housewife for a number of years whose kids were accustomed to a certain middle-to-upper class lifestyle, mostly provided for by her dead husband, Parker’s character had to pick up the pieces.

So she went with a job that could make her a ton of bank, lend itself to the hours she could afford while raising two sons, and allow her to use her feminine wiles to get her out of potentially hairy situations, if needed.

And from what I hear a little flirting in the workplace has never hurt productivity.

But there’s more to being a successful entrepreneur and owning your own company than just being a MILF. Parker’s mentors in the biz have paved the way for her to learn and grow (no pun intended). She spent much of the 1st and 2nd seasons honing her craft and business sense from a family-run pot business that took her in and showed her the ropes.

Through trial and error and some tough love, Parker’s character emerged as a shining heroine and somewhat to root for in all her flawed splendor.

She’s had her share of failures including a bake shop (a front for money laundering) that burned down (strike 1), then taking a front-and-center role in burning down her entire community and house (strike 2), and somewhere in the middle getting her DEA ex killed (not really a strike 3).

Through it all Botwin has reinvented herself and managed to adapt to the changes in her business, meandering in and out of leadership roles ranging from entrepreneur to intrapreneur, all the while seeking independence and authority in a industry plagued by certain dudes at the top of the ladder. She’s also managed to stay super cool and nice, but firm and assertive when the situation warrants it.

In just this week’s episode Parker decided it was high time for her to get a cut of the action and start selling again to her patrons. She didn’t want to be the middleman/woman. When she didn’t get the go-ahead from her direct superior, she went to the top and wasn’t afraid to take a couple of bruises to get what she wanted or temporarily damage her friendship with her boss.

“It’s just business,” Botwin told him.

Spoken like a true lady. And a businesswoman.

I’ve been living la freelancing vida loca lately and enjoying the grind quite a bit. Between web copywriting gigs and generating entrepreneurship content, I’ve kept myself busy enough to feel productively sane.

I’ve also benefited from a bit of “trialing.” It’s a term endeared to consultants and employers who’ve taken on enough stringers in their lifetime to know that there’s such a thing as over-promising on a relationship that might not work out.

The same concept applies to us lowly stringers on the opposite end coming from a place where I’ve signed on to work for/with someone only to realize a few weeks into it, that it just wasn’t meant to be.

I liken trialing to boot camp for contractors. It’s like getting a scholarship to go to school and having your education paid for by a benefactor. In this case, it happens to be a potential employer and the trade-off is a week or two of intensely hard work and crunch time which either leads to landing the gig or getting your stomach punched in – figuratively.

So having been put through some trialing recently with some new clients I engaged through virtually networking my little tush off, I’ve come to realize the benefits of trialing far outweigh the cons.

• Commitment-free means fewer facial lines: Being a successful freelancer demands you try your hand at many different jobs before you can pick the ones that are right for you. This also translates to having the time available to do this which means before you commit, do yourself a favor and walk the walk. You’ll be less stressed out for it!
• Choosy freelancers choose the best gigs: Don’t be afraid to turn down something you don’t really want to do. If you can swing it financially and have enough on the backburner (even if it’s on a low flame), then respectfully decline the project, but don’t burn the contact. Your contact will respect that you were self-aware enough of your enthusiasm (or lack thereof) to let this project go, not to mention considerate enough to be upfront with them.
• Juggle freely but don’t lose focus: Be mindful of learning curves while trialing. Most of the time what on average might take you half the time once you’ve mastered the rhythm of a particular project and aren’t reinventing the wheel each time, will take you double or 3X the time in the beginning. Be patient with yourself and factor in the excess time when taking on a lot of trial gigs at once.
• Flat rates work best: I remember feeling so guilty when I charged a client an hourly rate for my first assignment and it took me twice the time it should have. I felt pressured to get it done faster so as not to charge too high while trying to put my best foot forward and make a good impression so I could land more work. Recently, when a new client approached me and suggested a flat rate for copy for the first two sites she commissioned me to work on, I was able to to take my precious time and make sure that I got the copy down pat before sending it off to the “printer.”