Five Secrets to Freelancing (Un)Success
20
May
This week we’re looking at the Secrets of (Un)Success. When launching, maintaining or building a freelance career, we’re inundated with blog posts and books about methods for success. But just as important to think about? Ways you can kill your career and livelihood.

We’ve chosen a pretty unique path. By forging our own way, scrounging our own work and assuming complete responsibility for every dollar that comes in, we’ve chosen a career with kickass perks and pain-in-the-ass side effects. The biggest way that we can wound a fledgling or thriving career such as ours, then, is to think of it just like any other career.
Forgetting the uniqueness of freelancing means it becomes just another daily activity and job. A drudgery. A thing to get through before a night of TV love/Family quality time/Guitar Hero debauchery/Happy Hours. It can lead to burnout, to laziness, to apathy, and finally, to failure, however you define it.
And so, here are some of those ways freelancers achieve (un)success, consciously or unconsciously putting a career out of its misery. Before it gets miserable.
- Maintaining a consistent schedule. Oh sure, we’re told that if we want to maintain any semblance of productivity, and make the money to keep our ass in those pajamas we wear each day, we need to emulate the corporate world as much as possible. Regular 9 to 5 hours, nice clothes, even (for the truly ambitious) an outside office.
To me, this kills the whole point of freelancing. Yes, we need to show our clients that we are professional. Yes, we need to be smart, proactive, and comprehensive in our business dealings. But we also have to take advantage of the flexibility our career affords. If you want to sleep in occasionally, take a long, luxurious lunch, exercise mid-day, run errands, schedule dentist appointments, take the day off, take the week off, take the month off, then you can do it. If we deny ourselves the ability to do this that our career inherently offers, then we might as well just be another corporate drone.
- Specializing. Freelancers are told that a niche is the way to go, and it makes sense. By honing in on one or a few key areas that you can write/design/photograph/code well, you can sell your services relatively easily to the groups that need that specialized writing/designing/photographing/coding. You can establish yourself as an expert, and charge fees that indicate it. You can obtain that ideal which many freelancers lust after with undisguised abandon: a full pipeline.
But here’s the danger: boredom. One of the things I enjoy most about freelancing is the variety of work. While I definitely have a majority of clients from the medical arena, the topics within it are endless. Plus I still produce work in the general B2B and consumer realm. Every day, every week, is different. If it weren’t, it would be like the jobs I left behind.
- Joining. To combat the loneliness and isolation many freelancers are warned about (and some experience), a natural piece of advice is to join organizations. There’s plenty to choose from, depending on the area of freelancing and the region. Since most assume that the main drawback of freelancing is the lack of guaranteed social contact, this makes sense.
But I object. First, there’s the mistake of joining too many organizations in attempts to build up a new social network. Chances are, some of these groups you devote money and time to are a waste of both. Then the meetings become just like corporate meetings of yore: a time suck, a colossal bore, an exercise in mediocrity and pointlessness. Plus? Loneliness is not a given with freelancing. In fact, freelancing could be the ultimate escape for us introverts who disdained office conversation as a dreaded necessity. No point in joining a bunch of groups to ward off what will probably not be experienced anyway. Instead, freelancers should choose carefully the groups they decide to join, and choose them for the enrichment they promise rather than as a salve for potential undesired solitude.
- Sharing. I know. For many of us who toiled for years in jobs where they felt like Pink Floyd’s bricks, the idea that we found our calling, that we’re finally excited by and proud of what we do, makes us want to sing it to the heavens. What that usually entails is telling all of our friends and family who will listen how freaking’ awesome our life is. We may even be inclined to brag a bit, especially to the doubters, about the banner month we had, or how we make more now than ever before, or how we have a cover story in this month’s Blah-de-Blah Blah.
Most advice on secrets of success will have you think that this well-intentioned boasting is ok, and could even be the key to a random new client met through some social get-together. Sure. Could happen. What’s more likely if the sharing continues is people who think your life is perfect, and are flummoxed when the bipolar nature of freelance work rears its ugly head. Or they simply get annoyed and bored. Either way, not a good result.
- Listening. Everyone’s got a secret to success. Everyone wants to tell you all about it. And while some of this is useful, there comes a point when you have to stop listening to others, and make your own way.
The point is simple. A rigid freelance career, one that forgets the coolness inherent in freelancing and the joy with which we embarked upon it, means a return to job hell. That’s (un)success. That’s the denouement to avoid.
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1. Lisa | May 21st, 2008 at 8:43 am
I especially like the last part - listening. Thank you so much for this excellent post!
2. Amy | May 21st, 2008 at 11:18 am
@Lisa - thanks! And stay tuned for the rest of this week’s theme as well…
3. Johnny M | May 21st, 2008 at 8:20 pm
That bit about the social network (organizations) was purrrdy helpful. Since that’s what I’m thinking about right now, any bit of organized thought on it will help.
One of The Floyd’s best albums in my opinion, by the way.
4. Amy | May 21st, 2008 at 9:26 pm
@Johnny - Don’t take my opinion totally to heart, as I fully admit I’m an mostly an introvert. I do know that other writers, especially freelancers like myself who work alone, do get lonely. But I think a lot of us don’t
5. Rebecca Leigh | May 23rd, 2008 at 7:31 am
The whole (un)success theme this week is awesome - kinda turns your head inside out.
I particularly liked how the main point here (for me anyway) was how turning your freelance dream into a J-O-B slog was a guarantee for unsuccess. If we wanted a fixed schedule, narrow scope of work and lots of boring networking we could have stayed in the cubicle - so true.
6. Amy | May 23rd, 2008 at 8:39 am
@Rebecca - glad you liked it, and glad I turned your head inside out. That’s my goal at QRW :)And i completely agree on your takeaway point. If we allow our freelancing to turn into just another job, we let the terrorists win. (What? Oh, wrong argument) By forgetting about the coolness of our job, we set it up for failure in the form of drudgery.
BTW, wonderful site. As a gal with chronic stomach problems myself, it’s lovely to see others facing it head on. I would also recommend another site to check out if you haven’t already - chronicbabe.com. Run by a friend of mine, and a truly great resource for babes with chronic illness.