Posts filed under 'Toolbox'

Five types of freelancer in seriously high demand

Being your own boss means different things to different people.

For me, it means kissing those dreaded dry cleaning bills goodbye and working in my sweatpants. For Harris, a Web programmer I met at a friend’s wedding, it means never having to set the alarm clock again. For my friend Tammy, a marketing maven and mother of two, it means losing the commute and saving a bundle in day care.

Contrary to popular belief, achieving this kind of career autonomy without winding up on food stamps is entirely possible. And it doesn’t even require a four-year college degree or a significant financial investment.

Even better, there’s a rich market of customers just waiting to be tapped.

The U.S. Bureau of Labor Statistics reports that more than 12 million people work for themselves. And I can tell you from years of experience in the freelance trenches that many of us self-employed slobs need help with everything from setting up a blog to tracking our business expenses to keeping up with our blasted e-mail in-boxes.

In honor of Independence Day, I’ve outlined five low-cost freelance businesses that you can start from the comforts of your home and market to other independent professionals — plus, the skills, training and overhead they require. See if one lights a firecracker under you.

You can read the rest of the article here, at

3 comments July 4th, 2008

Q&A: How’d you score THAT gig?

gig_big.jpgIf you or someone you know is graduating this year or thinking about changing careers, check out Alexandra Levit‘s brand-spanking-new book, How’d You Score That Gig? A Guide to the Coolest Jobs — and How to Get Them. Reading this book is like going on 60 informational interviews for some of the most coveted careers out there — boutique owner, inventor, video game designer, archaelogist, landscape architect, futurist, classic-car restorer, and on and on and on. Happily for us, Alexandra answered a few of my questions about writing this book and some of its most important take-aways.

Q. What prompted you to write this book?

A. The idea originated as a result of several conversations I overheard at friends’ dinner parties. It seemed that someone at every event always had a job that totally intrigued the rest of the group. People were completely captivated by this individual, and were always curious to know how s/he scored the gig, and what exactly it entailed.

Q. In doing your research for all these careers, what did you unearth that surprised you most?

A. First of all, because I tend to caution people against going to graduate school to prepare for a career they have no experience in and don’t know if they even like, I was encouraged to discover that so many of the dream jobs didn’t require a master’s degree for entry into the field.

Second, it was interesting to find that so many of the jobs I was profiling attracted similar types of people. For example, documentary photographers, travel journalists, news correspondents, and oceanographers are all rather spontaneous and thrive on new and varied experiences. This led me to develop my seven “passion profiles” — adventurer, creator, data-head, entrepreneur, investigator, networker, and nurturer — and place my 60 cool jobs into the appropriate categories. Readers can take a quiz at the beginning of the book to see what passion profile and corresponding jobs best suit them.

Q. Was there one refrain you kept hearing over and over in the interviews you did with these dream careerists?

A. It’s not about talent, it’s about persistence. Most of these careers are tough to penetrate, but not impossible. If you take the right steps and push hard enough, for long enough, you will eventually break through the wall.

Q. Were there any dream careers you once mythologized that now have you thinking, “Ugh, I could never ever do that!”? Any that you’d initially looked down on that now have you raising an eyebrow?

A. I used to think that it would be amazing to own my own business, but after speaking with dozens of entrepreneurs, I’ve realized that it’s incredibly hard work. You have to sacrifice your personal life for a long time to get things off the ground, and frankly, I don’t know if I have what it takes. I didn’t exactly look down on any of the top careers per se, but I was pretty surprised when school teacher ranked so highly in the survey. I wouldn’t have personally considered this a dream job, but the teachers I interviewed were some of the happiest, most satisfied people in the entire book.

Q. What are the top three things a newbie with no experience in their dream field can do to break in (aside from applying to grad school)?

A. This tends to vary by field, and How’d You Score That Gig? provides specific guidance on how to break into different ones, but here is some general advice:

  1. Join an appropriate professional organization and attend events regularly.
  2. Seek out volunteer opportunities.
  3. Research individuals doing your dream job, and set up informational interviews with them.

Q. Give us your best informational interviewing tips.

A. Use the Net, your contacts, and your college’s career center to set up informational interviews with people already working in your career of choice so that you can learn more about what the job actually encompasses. In these meetings, which will usually take place via the phone, don’t be afraid to ask specific questions about training requirements, responsibilities, salary, work environment, and opportunities for advancement. As long as you are polite, no one will fault you for wanting the real scoop, and if a job is not as glamorous as it sounds, you want to know that before investing your time and energy.

Q. How do you account for a complete career 180 in a resume and cover letter, say if you’re applying for an internship or entry-level gig in a field you have zero experience in? What do you say (especially if you’re in your mid-thirties and above)?

A. Instead of writing a resume that lists your previous and unrelated jobs, which might have your potential new employer questioning the relevance, create a functional one that’s organized by transferable skills that would be applicable in your new career, such as client relations, project management, and budgeting. This will turn their attention to what you know already as opposed to what you might be missing because you haven’t worked in the field before.

Q. So many people choose miserable complacency in a career they loathe because they’re worried about the financial ramifications of starting at the bottom again. Or they’re scared of change. What advice can you give to light a fire under their butts?

A. First, ease into a new career one foot at a time. Perhaps this means earning a paycheck at your current job while doing a part-time internship in your new field or taking an adult education class or workshop on the weekend. The only way to find out if you’re passionate about something is to try it, and to do so risk-free will make it less daunting.

Also, remember that any progress is good progress. As you say, even confident people stay in unsatisfying jobs because they feel safe, and because they’re afraid of making a bad decision. But in the quest to uncover a source of meaningful work, your worst enemy is inertia.

Q. Were there any careers you’d initially planned to put in the book that landed on the cutting room floor? Why?

A. There was only one — astronaut. This career made the Top 50, but I couldn’t include it because NASA refused to grant me an interview. I pursued their PR department for weeks to no avail. I feel they missed a terrific opportunity to promote their field to the public.

4 comments April 16th, 2008

The way freelance writers never were

Exhibit A: I’m sure you’ve by now seen the sensationalist New York Times piece that might as well have been called, “Blogging Killz!” While it’s tragic that three prominent bloggers have had heart attacks recently (two of them fatal), this article was a huuuuge stretch. It did remind me, however, that no career is worth compromising your health (as I write this at 5 am, said the insomniac).

Moral of the story: The webconomy didn’t invent workaholism, crappy pay practices, and on-the-job stress. Workaholics, companies with crappy pay practices, and stress bunnies did.

Exhibit B: It’s worth reading Freelance Fizzle! The Decline and Fall of the Writer in the New York Observer, which pines for a freewheeling freelance past (complete with expense accounts!) that died decades ago — and probably only existed for a handful of A-list writers anyway.

The Reader’s Digest version: Once upon a time, magazine writers in Manhattan supposedly had it made. Today they have dwindling markets/readership/budgets to content with, not to mention — cue scary music — the web. Believe me, it saddens me greatly that print pubs are in peril. (Just this week, one of my beloved print clients had massive layoffs.) But I can whine about it, or I can wake up and smell the new economy.

Moral of the story: Freelance publishing rates haven’t gone up in decades. And unfortunately print as we know it is rapidly becoming yesterday’s news. Writers who want to eat need to have at least a couple toes in the digital pool (and depending on how much money they need to make, perhaps a couple more in the copywriting world).

Exhibit C: Procrastinating writers, take heart! Now you can strip away all toolbars, inboxes, and web connections and focus on the blank page at hand. Two distraction-busting word-processing programs (Mac version here; PC here) try to recreate the supposed glory days of writing by typewriter or clunky 80s computer, only with today’s processing speed.

On the one hand, I’m sorely tempted to check out this cool-sounding app. On the other, I did a fine job of procrastinating in the 80s and 90s, first with a typewriter, then with a Mac SE.

I applaud entrepreneurial software devs who sell their creations one download at a time, so I’ll skip the snide moral of the story here. And if anyone’s tried an app like this, I’d love to know what you think.

2 comments April 10th, 2008

Fun with freelance links

Still chugging away on writing my new book. Meantime, some links you might like:

Inkthinker skewers 7 heinous freelance writing practices. Kudos to Kristen King for reminding us why acting like a selfish, immature, vindictive freelancer is unbecoming. Best blog post I’ve read in ages.

Getcher top 100 freelancer blogs here. The listmaker (Bootstrapper) does it again. Everything from The Golden Pencil to DIY Photography to The Anti 9-to-5 Guide. (Aw, thanks, Bootstrapper.)

The readers speak: Your on-spec design contest sucks. Sounds like this guy was trying to be helpful to newbie designers, but he should know better than to announce an on-spec design contest to a community of professional freelancers (given that he writes about freelancing). I’m glad he pulled the plug when the peanut gallery threw tomatoes.

Red Herring deflates Personally I wish freelance “marketplaces” like Helium‘s would shrivel up and die. Once those new freelancers using the site get tired of competing against each other, on spec, for $.10/word gigs, they’ll still have to learn how to go out and look for decent-paying work.

Freelance Switch launches a Client Analyser tool. Is your client bleeding you dry? Now you have a digital algorithm to help you make the call. You have to enter eight clients into the tool for it to work.

Want to know what editors want? Check out Editors Unleashed: Magazine editors growl about their writer peeves, a much-needed e-book from The Renegade Writer. Short, sweet, and endlessly informative.

Seattleites, want to know how to sell your writing without checking your soul at the door? Check out this one-day marketing workshop in April taught by my buddy Diane Mapes. (For full class description, click here. Then scroll down for description or search on “Mapes.”)

Are you Not An Employee? You might like this fun new freelance site/swag seller/blog. I’ll be curious to see where it goes.

2 comments March 13th, 2008

Happy international women’s day

In honor of March 8, I thought I’d list eight of my favorite women’s media outlets in autobiographical order (that is, my autobio):

  1. Ms. — Used to steal my mom’s issues when I was a kid. Thank god for Gloria Steinem.
  2. BUST – Still have the “Sex” issue with John Spencer of JSBX on the cover. (Mmmm.) Still devour every issue.
  3. Bitch — Cannot read an issue without having a debate with someone about something I read in it, even if it’s just an internal, telepathic debate with one of the mag’s writers. In other words, the mag makes me think. Which is a good thing.
  4. Seal Press — What can I say? I heart my publisher’s MO. Always have, always will.
  5. Broadsheet on — Brilliant, insightful, hilarious writers. Always classy, already a classic. I pretty much bow at their feet.
  6. Women’s eNews — Most underrated women’s media outlet. Remember back when web stories were 100% reported? That parallel universe still exists on Women’s eNews. This site’s top-notch.
  7. Feministing — Because in-your-face is good.
  8. Jezebel — Because snark is even better.

How about you? Got any faves to share?

1 comment March 8th, 2008

Freelance tax FAQ #117

I subscribe to a lot of self-employment and freelance writing discussion lists. Not surprisingly, this month everyone’s been buzzing about how to file their freelance taxes. Here are a few recurring questions I’ve seen.

(Note: These answers are geared toward sole proprietors like me, not LLCs or corporations, which are subject to different tax laws, about which I know diddly. Double note: I’m a freelance writer, not a financial professional. If you want solid tax advice you can bank on, you’d best check with your friendly neighborhood accountant. Okay, now that we’ve got the requisite ass-covering out of the way, let’s talk taxes…)

Q. Help! I earned more than $600 in 2007 from a client, but they didn’t send me a 1099 form. Do I still have to pay taxes on that money? Do I need that form?

A. You do still have to pay taxes on that money. But no, you don’t need the form to do so. Also, in case you were wondering, if your client tries to claim the money they paid you as a business expense, they could get into trouble with the IRS for not sending you a 1099 form. But that’s their problem, not yours.

Q. Help! I billed Client XYZ for $3,000 in December of 2007 but wasn’t paid for it until January of 2008. Do I have to pay taxes on this money with my 2007 fed tax return or should I pay those taxes with my 2008 estimated tax payments?

A. Since the client paid you this amount in 2008, you will owe taxes on it for 2008, not 2007. You go by the year paid, not invoiced. If the client tries to put this amount on your 2007 1099 form, you need to talk to their accounting department about correcting this mistake. Otherwise, you’ll be paying taxes on money you technically didn’t earn in 2007.

Q. Help! I just measured my home office and it’s 20 percent bigger than I’ve been reporting to the IRS for the past three years. Can I tell them my office is actually bigger? Will this trigger an audit?

A. Congrats! You get a bigger write-off. It’s perfectly reasonable that your home office size would increase as your freelance business blossoms, so just tell the IRS that your office space has grown. (Actually tell your accountant, and s/he will know how to indicate this on your fed tax return.)

This minor change in office size alone should not trigger an audit, unless of course you’re unfortunate enough to be randomly selected for an audit (like jury duty, only more painful). As I understand it, if the IRS intentionally audits you, it’s because you have some serious red flags on your tax return — for example, an inordinate amount of expenses claimed. Your accountant is there to ensure this doesn’t happen. Yet another reason you should not solely rely on random internet advice when doing your taxes.

Final notes: There is a limit to what percent of your home you can write off as office space. Because I’m too lazy to Google it, you’ll have to ask your accountant about this. Also, the IRS wants your home office space to be solely dedicated to your business, so be careful that you don’t blur lines here.

You can find more of my freelance tax FAQs here and here. And you can find an accountant by asking your freelance friends who they use.

4 comments February 27th, 2008

How to beat the web into submission

connect-cover-small.jpgIf you’ve visited this blog before, you know I have a love-hate relationship with the web. In the interest of attempting to overcome some of my Luddite fears, I recently put these web productivity questions to Anne Zelenka, web technologist, former editor of Web Worker Daily, and author of Connect! A Guide to a New Way of Working.

Q. Some days, I feel like email is the bane of my existence, tempting me away from deadlines and productivity. How do you recommend self-employed types stay on top of email without letting it rule their life?

A. There are numerous schemes for managing your inbox, but what’s worked best for me is a post-email era approach. I don’t get all my information through email. For example, I use Twitter to stay in touch with my online professional network, instant messaging for quick discussions with colleagues or clients, bookmarks to share things I find interesting, and blogging to think out loud with feedback. That lightens the load on my email inbox and it makes me feel more hooked in throughout my workday. Email on its own can feel a bit disconnected, I’ve found.

Q. At the expense of sounding like I’m writing a white paper for one of my software clients, I have to ask: What are three things even a Luddite like me can do to use the web more effectively and boost productivity?

A. You’re a great example of the most effective way to use the web to succeed in your work life: get yourself a professional presence online with a blog or other website. Don’t focus on making advertising dollars from it — use it to make connections and promote your work. Most of all, be authentic online so that when opportunities come to you because of your online profile they will be opportunities you’re really excited about pursuing.

Q. What are some of your favorite online tools for freelancers?

A. The tool I rely on most for managing my work life is Google Docs. I use spreadsheets to track income and expenses and documents to plan projects and collaboratively edit papers. Gmail, Adium (an instant messaging aggregator), and Twitter keep me hooked in with my professional network — and I couldn’t succeed without that.

Q. You have an entire chapter on online money management, including tips for freelancers. Can you share one or two of those web banking tips for freelancers?

A. If you’d like a good and secure way to manage your various financial accounts, check out Wesabe. It offers a downloadable tool into which you input your login and password information, then you can regularly update your transaction information and see where you’re spending your money and what your balances are. It includes a social network where you can swap tips and share financial goals — so it’s like the Web 2.0 version of Quicken.

If you have a lot of clients and need to manage a bunch of invoices, check out FreshBooks. That site makes it really easy to create and send invoices then track payments.

Q. Despite the fact that this will be outdated next month, what are your favorite social networks for freelancers who want to mingle and market online? Or do you think social networks are one big fat timesuck?

A. Three sites I like for freelancers and in particular freelance writers are Freelance Switch, Freelance Writing Jobs, and mediabistro. These aren’t specifically social networking sites, but Freelance Switch and mediabistro include forums and Freelance Writing Jobs gets good discussions going in the comments.

I tend to network with other web technology geeks, since that’s my main area of expertise. For that, I like Twitter and also networking via blogging. I’ve tried Facebook and it hasn’t been all that useful to me professionally.

Q. As a freelance writer, when I’m in the thick of trying to bang out a draft, email and an open browser is the kiss of death. Do you work on deadline with your inbox and browser open? Just wondering.

A. When I was working on the book, I regularly closed my browser, including my inbox (I use Gmail), and set my instant messaging status to “writing.” I write blog posts on deadline with my browser open because I need it to do research and I’ve trained myself to work while I’m connected. This kind of group-oriented productivity is something you can learn to do, and it’s a mode that we see teenagers of today often using. They stay in constant contact with their friends and use multiple electronic tools, switching back and forth as necessary.

Q. You mention a preference for pen and paper when it comes to writing to-do lists. Why is this? Any other parts of the workday we should be reserving for paper?

A. I personally love the physical experience of writing and rewriting my to-do list, then crossing off items when I’ve finished a task. I also like to be able to take my to-do list away from the computer to work on it, where I feel like I gain some perspective on my priorities. Paper is generally useful for you want to slow yourself down and take a broader perspective. If I want to really think about something — a blog post I’ve written in draft, a project plan, a list of goals — I do it on paper.

Q. In the book, you talk about this brave new way of working called “bursty work.” Can you explain what that is and why we should be doing it?

A. I came up with the idea of bursty work when I realized that many career achievements arrive in discontinuous leaps rather than through step-by-step action.

I observed that many people working online had different habits than [those in] the typical 9-to-5 gig. Instead of working standard hours, they would work when they felt like it, according to their energy, sometimes in bursts. Instead of shutting themselves off from other people in order to get solo work done, they would stay connected via instant messaging or social networking or other electronic tools and get information and inspiration from colleagues and associates throughout the work day. Instead of building things totally from scratch (or just on top of what their coworkers built), they would use what they found online — whether open source software or research that someone had already done or photos that someone else took — to get where they needed to in leaps and bounds rather than step by step.

The reason the web promotes a bursty style of work is because of the network of people and ideas it makes available to us. Instead of just having ourselves and our office coworkers available to us, we have a whole wide world of resources just a hyperlink away. This means you can navigate shortcuts instead of always working step by step.

In practice, bursty work often builds on busy work — there will always be projects where you have to spend lots of dedicated, focused time working step by step towards a goal. Building a network of professional connections, for example, takes effort over time. But once you’ve done a lot of the busy work, bursts of innovation or achievement may happen almost as though by magic. It’s not magic, though; it’s navigating a network.

You can read more about busy vs. bursty in the Web Worker Daily article I wrote on the topic.

Want more web tips? Visit Web Worker Daily and get your copy of Connect! A Guide to a New Way of Working. 

1 comment February 25th, 2008

Open thread: Professional memberships and other resources for freelancers

In light of my most recent post, I thought it would be fun if people chimed in with the professional organizations, services, and resources they’ve found helpful in their freelance career, regardless of the industry they work in. I’ll go first.


Articles, classes, and parties:


My don’t-bother list:

Okay, now it’s your turn…

3 comments February 12th, 2008

Ask the cubicle expat(s): Should I sign up with

MB asks: I was wondering if you’ve had much luck with I’m trying to save money, so I don’t want to join unless I think I will make money from it. What do you think?

I answer: MB, here are three things you probably did not know about

  1. Back in the late nineties dotcom startup heyday (the first time around), was cool. I’m not saying Guru isn’t cool now, but back then it had personality, spunk, sass. It had articles, freelancer haiku*, and a bit more of a community feel. It had Free Agent Nation author Dan Pink as a columnist.
  2. I wrote several articles for in its first year or two, and was paid handsomely, before the dotcom bubble burst and the site went on hiatus, then was sold, then re-emerged as the you know now.
  3. While I loved writing those articles, I also had the worst editorial experience of my life on one such piece, where my editor introduced not only a rash of typos and inaccuracies into my story, but an embarrassing bit of outright plagiarism. It landed me some angry mail from readers. (Lessons learned: (a) Always ask to see the final article before it runs, especially when you’re not familiar with an editor or publication. (b) You can recover from even the most shameful of freelance experience.)

Of course that doesn’t really answer your question. Truth is, I have never used in its new incarnation, a freelance job bidding site. In fact, I have never used a job bidding site. Here’s why. Short answer is, I’d try getting work on your own first through your personal and professional face-to-face and online networks. Or go through a creative agency that doesn’t charge you a subscription (or make you bid) to get the work.

I just spent a few minutes on today’s Interesting business model. I’d be curious to hear if anyone reading this has had any luck with it (particularly the Basic membership, which appears to have no monthly subscription rate but allows them to skim 10 percent off your project payments). If you do go this route, be sure to pad your fees by 10 percent so you make up the difference.

Also interesting are the invoicing and arbitration services (which I presume cost extra; seasoned users, feel free to correct me if I’m wrong). Cool that they offer these services, especially arbitration, which goes after clients who refuse to pay up and gets you your money. But ick to having to route your pay through this site. I’d rather deal directly with a brick-and-mortar creative agency I can call up. Sometimes it’s not the easiest getting customer support from a “faceless” online service provider (paging Amazon).

In sum, I supposed if you’re starved for work, others say they’ve had good experiences with the site, and you can get a good rate for your projects, could be worth a trial run. But I’d put it in the “last ditch effort before I ask for my day job back” category.

*If I find the freelancer haiku of mine ran (with commuting monkey illustration!), I’ll scan it and post it here.

3 comments February 10th, 2008

Greatest hits: Freelance tax tips

It’s the most wonderful time of the year (that is, if you’re a CPA). That’s right, folks, tax season is upon us. And not surprisingly, I’ve had a couple requests recently for a round-up of this site’s past posts on paying your freelance taxes.

Before we get to the round-up, I’d like to take this opportunity to remind you that I’m a freelance writer, not a financial professional. Tax laws change every year, and no one knows their nuances better than your friendly tax professional. So although you can get some initial pointers from a freelance blog, I wouldn’t substitute them for the almighty input of someone who’s trained to fill out tax returns. Capiche?

OK, back to our regularly scheduled programming…

Additional resources:

6 comments January 24th, 2008

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Hi, my name's Michelle Goodman and I've been freelancing since 1992. I'm author of My So-Called Freelance Life and The Anti 9-to-5 Guide. Read my full bio here.

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