While I was wedding planning, I found a great website: It offers sane wedding advice and a lot more besides. My favorite essays there deal with balanced relationships, thoughtful decision-making, women in the workplace, and entrepreneurship. Today there’s a discussion about roadblocks — the real barriers and self-imposed excuses that keep us from achieving what we really want in business and in life.

You all know about my goal to become a full-time freelancer. It’s been almost a year since I first posted about it. Today I have one regular client and a few Elance jobs under my belt, but other than the tax bills I just paid (OUCH) there’s not much evidence of progress. So what’s standing in my way? What are my roadblocks?

I’ll be honest: there’s a lot of fear. Fear of leaving my team in the lurch when I quit. Fear of failing to earn enough money. Fear of networking. Even fear of too much success — attracting so many clients that I get overwhelmed with work and can’t execute any of it well, ruining all my contacts and overworking myself into misery.

In the past, the best way for me to overcome roadblocks has been through research and preparation. Entering new situations unprepared makes me incredibly anxious. So I have learned to set myself up for success by picturing in detail how things will happen. If it’s a job interview, I can try on the outfit I’ll wear and drive to the location the weekend before, just to make sure I’m familiar with the place. If it’s my wedding, I can fill out the license application ahead of time so I don’t make a poorly considered choice on the spot (like my coworker who wasn’t prepared to decide her name change when she went to get her marriage license — she thought she had until the wedding date). If it’s woodworking, I can sign up for a workshop at Home Depot before using my new power tools at home.

The problem comes when research and preparation stop me from taking action at all. I’ve been reading articles and books on freelancing for several years now. I’ve created budgets in interactive Excel spreadsheets. I’ve done actual freelance assignments for actual clients. Still, I don’t feel prepared to take the leap.

Some practical roadblocks did clear last month when I married Dan. As his legal spouse, I’ll be able to go on his health insurance policy when I quit, at a much lower rate than private insurance. I also get the official commitment that he can support me financially if my income starts out slow. What’s his is mine, even more than it was before, and that’s really reassuring. Plus, my freelancing business and website carry my full name. I had worried about the problem of rebranding myself if I married and changed my name long after my business was established. Now, though, I can make that transition while the business is still in its baby stage. I’ve already bought the new URL and started working on a site migration plan.

My biggest remaining roadblock seems to be the false belief that I can and should be 100% prepared for everything. Of course nobody advises abandoning your day job without any safety net. But maybe I’ve done my due diligence. Maybe it’s time to gather my knowledge and climb over this roadblock with confidence, even though I can’t clearly see the other side.


Goal Progress: It Begins

Guess what?

I have clients. TWO clients. I bid on jobs on Elance, and they hired me. I’ve earned money (though not much yet). It’s in my bank account. And I got my first feedback:


Pinch me!

It’s been quite an experience so far. Two clients (including the one who skyped me) awarded Elance projects on the exact same day. I’m amazed that they took a chance on me, since I didn’t have any feedback yet.

The feedback above was for a really quick project I finished within two days. The client LOVED it. He didn’t ask for any revisions. It was a sample, a trial run for hiring out the rest of his website project, and I passed. He wants to give me more work!

The other project was more involved and I’m still working on it. Actually, it started out badly — the client didn’t like my first draft. He was polite but very disappointed because I didn’t achieve the tone he wanted. He sent some specific concerns and a sample of another passage he liked, and asked for a full rewrite or he’d have to cancel the job.

At first I was really upset but then I thought about it more. In my regular working life everything goes through tons of revisions before it’s published. Revisions are needed to hone in on the right tone and message. It’s rare for anything to go like the other job where it’s right on target with the first draft.

So I did a full rewrite and sent it to him with a cheerful explanation of multiple drafts being normal in copywriting, since I think he’s never worked with a writer before. I held my breath… and it worked! That next draft was much closer to what he wanted. He sent a few reasonable revisions, and is happy with the final result. We’re moving on to the remaining parts of his project with no more cancellation threats. I hope he ends up satisfied overall.

In other news, I met up with a friend who’s a graphic designer to discuss branding my business. We had bartered for some services and it’s her turn to help me out. I’d like a logo (probably just my name, but designed nicely, and maybe with some kind of mark or symbol) and business cards. Unfortunately, it turned out that my ideas aren’t organized enough yet to actually get her started. I’ll have to do some serious brainstorming to pin down my brand and requirements enough that I can send her some design specs. But at least we had fun catching up over dinner (at Punjabi Tandoor, thanks for the recommendation Karen)!

It’s hard to believe I’m actually gaining momentum. I have managed to get freelancing work done despite my day job, an obnoxious illness (started with a cough, moved to sinuses, approaching four weeks long now, doctor didn’t help), and my parents’ visit (which I’ll show you photos from soon, promise). Now I need to wrap up the second project and resume seeking out new clients. Don’t want progress to halt just when it’s begun.

Goal Progress: Skyping a Client

Freelancing progress has been slow since I last reported to you, so I’ll distract you with my lovely iPhone photos (downtown waterfront, Padres fireworks, Mission Bay):


BUT! This morning a potential Elance client emailed me to request a Skype call! The project is right up my alley — rewriting a photographer’s website. His time zone is 8 hours ahead of mine, so to work around my day job I have to call him at 6:30am. And because it’s a video call, I have to get up super early to look presentable. Ugh. But it’ll be worth it if I’m hired.

Tonight I’ll review my portfolio and prepare answers to expected questions. I wonder whether I’ll have difficulty understanding an accented voice over a digital connection. Oh and I hope this cold/cough I’ve had all weekend subsides by then. Otherwise, I’m comfortable with Skype after using it recently for fun (hi Em & Lindsey!) and for a full-time job interview a few years ago.

Here are my main tips for a business call or interview on Skype:

  • Camera angle: Set the webcam at or slightly above eye level for a flattering angle. For me, this means propping my Macbook on a shoebox on the dining table. I like to sit so the camera can see from above my head to below my shoulders. If you sit any closer, it looks too intimate (or like a myspace photo).
  • Lighting: Webcams need lots of light to record well. Position the light so it’s shining on your face, not behind you. I plan to face a big window for flattering daylight. If it’s night, use bright lamps at eye level — overhead lights cause harsh shadows.
  • Clothing: Avoid red (shows up like a glowing blob) and thin stripes (they “vibrate” onscreen). Choose a higher neckline so that your shirt doesn’t disappear below the screen. Comfy pants are tempting, but you should wear nice pants in case you have to stand up to grab notes or coffee.
  • Speaking: Talk slower to compensate for lag and poor audio quality. Don’t speak over the other person as you would in a normal conversation, because overlapping voices tend to cause the audio stream to blank out.
  • Sound: Close windows and doors and ask family/roommates to stay quiet while you’re on the call. Consider using a microphone headset if your built-in mic isn’t that great. Mine is decent close up, but gets worse when you sit farther away.
  • Eye contact: Your caller’s face onscreen is lower than the webcam, so when you look at their eyes it seems like you’re looking down. The best advice I’ve read is to alternate views: look directly at the webcam while you talk, and look at their face while they talk.
  • Notes: You can’t check info on your computer without looking weird. So print any reference materials ahead of time, and keep a notebook and pen in reach.

That list got longer than I expected… but I hope these tips help you someday. And I hope they help me tomorrow — wish me luck!

Goal Progress

On Sunday I got a haircut. Even though this style is my favorite ever — it looks nice air-dried wavy or blow-dried smooth — I had put it off for seven months because, well honestly? I dread making small talk.

But during the 45 minutes in the chair, I had a really fascinating conversation with my hairdresser. She and her new husband are working toward self employment because they want the freedom to set their own schedules, live wherever they like, and build a flexible lifestyle before having kids. I told her about my recent thoughts on the same kind of thing. We talked about how it’s so easy to get complacent in jobs like ours — decent jobs that pay well enough, but don’t allow the lifestyle we truly want. We agreed on what it means to live a good, self-directed life. I left with bouncy hair and bouncy ideas, too.


Then today I read a beautiful post about the art of being a goal-getter. The author, who’s only a few years older than me, talks about how she’s managed to build a rewarding career that led to freelancing and self-employment. And there are illustrations, too! So go take a look if you need some uplifting stories.

This inspired me to share what I’ve been working on since I wrote about my career goals. I plan to start by freelancing a few hours a week, on top of my day job, until I get a good sense of whether full-time self employment is truly right for me. So here’s what I’ve done the past two weeks:

  • Updated my professional website. I’ve had it for years, but really only used it while hunting for full-time jobs. Now I’ve added different pages and rewritten the text to make it clear I’m a freelancer (with a day job). I’m slowly adding more portfolio samples. And I want to blog there with a content marketing focus.
  • Created a new resume. The last revision was a year ago, when I was gearing up for my job hunt. This new version presents me as a freelancer and includes details about my current full-time job.
  • Filled out an Elance profile. Elance is an online staffing marketplace that matches freelancers with clients around the world. Unfortunately, it’s filled with a lot of low-quality, low-pay assignments like “write thirty 500-word articles per month for $1 each.” But there are also some high-quality jobs mixed in.
  • Applied to three Elance jobs. For instance, there’s a wedding photographer who wants to rewrite his website, and a small business owner who needs product descriptions. Each job has a few dozen bidders, so my chances are slim. But I’ve got to start somewhere! My main client from the past has switched jobs, and doesn’t need writing services right now.

Now that it’s all written down, I’ve done more than I thought. Maybe if I document my progress regularly, no matter how small, I’ll be able to look back someday and see how it all added up to something big.

Seeking balance

Did you miss me? I haven’t been posting regularly the past few weeks because I’ve been slowly writing down thoughts that turned into a kind of manifesto. If you’re interested in my navel-gazing, in which I ponder a possible solution to the past six years of angst, do please read on. I don’t expect this to apply to anyone other than myself. But if you’re facing similar challenges, maybe reading my thoughts might help you begin to organize your own. So, here it goes: an essay on the meaning of life. Continue reading