The Worst Freelance Writing Career Roadblock

What’s on the iPod: Misfits and Lovers by The Wallflowers

Progress. That’s how last week ended. I’d made significant progress on a white paper project, and I hope to have it finished by Wednesday. Good thing — I have two more projects starting up, and a third that will show up right when I don’t have time. I got the nod for it three weeks ago, so I’m trying to get ahead of schedule just in case it’s a tight turnaround.

We spent Saturday in the city, where we walked a good bit (the pedometer app clocked 6 miles), ate, and did some shopping with my daughter. She took us to her office building, which is right behind Independence Hall. That’s our rest stop this coming weekend should the Pope’s visit become too much for our older visitors.

The whole process of coordinating a 45-minute train ride (which is now going to be about 20 minutes since they’re eliminating most of the stops on the line) has been one giant gray hair. First, we had to buy tickets at a certain time on a certain day online. Then the website crashed. That meant they had to rejig the website and process. The transit group implemented a lottery system. That worked. So I got the tickets and joy ensued. Only…

They’ve limited each train line to two stops. Now instead of having people well-disbursed around the area, they’re cramming them into two stations per.That’s so the police won’t have a tough time monitoring the stations, because their comfort is much more important than the comfort of the paying customers trying to get to the city….I get it, but wow. Makes terrible sense.

Then local authorities made getting to the station hundreds of times harder. They declared a state of emergency for that weekend. Fine, but in preparation and with the mindset of “making things easier” for everyone, they’re closing nearly every road getting to my station. That’s to “streamline” crowd, which is most of the 110,000 riders expected at that one station –five times the number of passengers at my station on an average weekday. Plus, they’ve restricted parking for miles, including the two really small lots at the station and the three bigger unused commercial building lots right next to the station. Because asking for cooperation (or allowing local businesses to charge for parking) is apparently a bad idea? So now five times the number of people will have to find some way to cram into the lot that holds about 200 cars…and with one taxi company in town and bus service shut down….

Their plan needs some work.

I’ve seen similar kinds of blocking coming from the freelance writer community — the “catch me if you can” approach to the career. It’s the flip side of the “I’ll take any work any time” attitude, which is equally damaging to a career (and earnings). It’s the “you have to convince me it’s worth it” approach, and it’s a major career stopper.

If you’ve ever said/done any of these things, you could be hurting your career.

The aloof “I don’t need the work” attitude. You might think your detached demeanor in a client conversation is sparking a client’s intrigue, but it could be your client is tired of ego-driven people (especially if they work in an ad agency or with creative people regularly). If the client thinks you don’t need the work, they’re going to go with the person who showed more of a collaborative attitude.

The over-sized ego. It’s great to have confidence in your skills. It’s lousy when that confidence comes off as boasting. No one enjoys listening to an elevator speech that is full of bragging, name-dropping, or “You won’t find a better writer” statements. Be confident, but don’t forget what really matters — your client’s needs.

The “get in line” approach. I’m busy. You’re busy. Sometimes we have to tell clients that right now, we’re not available. Typically, I like at least a week’s notice when possible. But if your regular approach is to put them off without trying to fit them in, you’re not creating the kind of “Gee, he’s sought after so he must be good!” response you think you are. If you push back every time on the clients who need you within a few days or a week or two, they may stop checking in because they’ve found someone who has a more flexible schedule.

The hard-assed caveats. You have a work process. Your client has a different one. It’s going to require give-and-take on both sides. So don’t go into your negotiations or initial conversation with guns blazing about what they must do and what the penalty will be if they don’t basically fall down and worship at your feet. It’s okay to set your boundaries — if there’s no feedback within a certain, reasonable period of time, you’ll assume the project passed muster and send the invoice. It’s not okay to unleash the fire-and-brimstone indignation on them. They don’t owe you their undivided attention or loyalty.

Writers, what career-killing roadblocks have you seen freelance professionals use?
Do you know anyone who’s lost a client prospect because of an attitude or action?
How do you walk the fine line between setting boundaries and pushing people away?

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  • Paula Hendrickson September 21, 2015 at 3:02 pm

    Despite the travel hassles, I'm glad you had a chance to scope out your rest spot ahead of time. It's going to be crazy in Philly, DC, and NYC when the Pope is around. I'm not even Catholic, but I'd love a chance to see him go by.

    The biggest problems I've seen — and heard about from my clients — come from writers who either don't follow through as promised or blow deadlines. The thing is, unless they're on a really tight schedule, most clients will extend a deadline by a couple days if you really need it. You just need to ask.

  • Lori Widmer September 21, 2015 at 5:39 pm

    That is definitely a problem, Paula. I wonder if these same writers were the ones who just didn't show up on test day figuring they'd already failed?

    Got one more ticket if you're interested — it's an easy Amtrak ride from your house to mine, and I have the room!

  • Cathy Miller September 21, 2015 at 5:51 pm

    Love the Pope but this reminds me of one of the top reasons I love freelancing – not dealing with traffic! 😉 As someone who worked in downtown LA (which I said I would NEVER do), I love my commute from my bedroom to my home office.

    Whether it is work or our personal lives, a major roadblock I see with so many people is the need for control. We put so many roadblocks in the way just so to control everything.

    I agree that doesn't mean you let clients walk all over you but ask yourself ~

    What is my ultimate goal? Is this going to get in the way of that?

  • Lori Widmer September 22, 2015 at 12:23 pm

    Control! Exactly, Cathy. I'd much rather let that be the client's problem and not my own. We writers should control the workflow process and the quality we put out. I like your litmus test — great questions.

    There have been projects that went much more their way than the way I'd wanted, but we have to be okay with that. It's their project –if the check clears, that is. 🙂

  • Paula September 22, 2015 at 4:02 pm

    I wish!

    I think it was the 70s last time there was passenger rail service in my city – or even in this part of the state. One theory is that city officials back then were afraid passenger rail service to Chicago meant lost revenue as people shopped and worked in Chicago. (Um, with Chicago's astronomical sales taxes, everyone I know in Chicago tries to make big purchases – even gas – outside the city limits!)

    The sad part is a year or two ago the state finally struck a deal to extend Amtrack out here, plans were set to repair existing tracks, and we would have twice daily train service beginning this fall, I think. But our new governor froze spending – despite the fact that the funds were already allocated and not part of his new lean and very mean budget.

    Sensing a theme here: politicians in my state tend to be stupid and shortsighted.