Heroines of Personal Finance and Entrepreneurship #5: Michelle Goodman

Ramit Sethi

Interview contributed by Cody McKibben

Michelle Goodman is a bold Seattle freelance writer who’s been working for herself for 15 years, contributing to Salon, Bust, Bitch, Bark, the Seattle Times, and the San Francisco Bay Guardian. Now she’s compiled the book she wished she’d found when she first started out on her own — The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube — to help wage slaves transition to flexible, alternative work, and help “cubicle expats,” as she calls them, avoid the mistakes she made early on in her self-employment. Today she talks with us about the book and about women in the workplace.

You just wrote a book called The Anti 9-to-5 Guide. What’s it all about?

The Anti 9-to-5 Guide is about working outside the typical mind-numbing 9-to-5 office grind. In the first part of the book, I tell people how to figure out what they want to do instead, research a new career path or business idea, network like crazy, and infiltrate an industry they have no experience in. In the second part, I tell people how to find and negotiate flextime and telecommuting work, start your own business, work from home without losing your mind, survive as a temp, move from corporate to nonprofit work, and work overseas, outdoors, or in a male-dominated trade. I wanted to cover as many nontraditional career paths for women as I could, from freelance writing to firefighting to flying to Japan to teach English for a couple of years.

Your book is geared specifically toward women. You say it “shows women weary of the corporate hamster wheel a better way to make a buck.” Why just women? Are there issues specific to women that made you write about them?

The easy answer is that my publisher, Seal Press, only does books for women. That’s their niche. I had been writing articles on the topic for indie women’s publications like Bust and Bitch, as well as a special women’s section for the Seattle Times, so Seal Press seemed like a natural fit.

That said, I wanted to do a career book aimed at women because we do have unique challenges in the workforce that men don’t necessarily have to deal with: the wage gap, the glass ceiling, the mommy track and mommy wage gap. Given all that, I don’t think it’s a coincidence that women start businesses at twice the rate of men. And study after study shows women more likely than men to want, ask for, and take flexible work options (alternate schedules and telecommuting), probably because we’re still the primary caregivers for kids and elderly relatives in society. I will say that 95% of the book’s contents apply to men, though, and I’ve heard from many men who’ve enjoyed and gotten a lot out of the advice in the book.

What about young women? How does age factor into the equation?

Twenty-something and thirty-something women have far more of an entrepreneurial spirit than their parents ever did, partly because it’s such an at-will employment workforce these days, and partly because we saw Boomer women (often, our moms) working their asses off trying to prove they could have it all and burning out. After witnessing Enron after Enron go down in flames, and friend after friend get laid off, the message is now loud and clear: It doesn’t matter how dedicated an employee you are — companies are only out for themselves. So why work your butt to the bone like your mom did when you know you stand a decent chance of not getting a company healthcare or retirement plan and of winding up on unemployment any given month of the year?

Instead, younger women are all about quality of life. A job is a job — it’s not a way of life. I wrote the book for women who are starting to suspect this, or have already come to realize this. I wanted to tell them all I could about all the alternative ways of working I’ve tried over the years, from stringing together a handful of part-time gigs, to temping, to working a flex schedule or telecommuting for a corporation, to working for myself.

The younger you are, and the less encumbered you are by kids, partner, and mortgage, the easier it is to try some of the less conventional ways of working — especially working overseas and starting your own business. You’re not tied down by location quite so much, and you’re able to take more financial risks without worrying if you’ll be able to clothe and feed your kids six months down the line.

I know you’ve spent a lot of time interviewing women freelancers and what you call “mompreneurs.” What insights have they taught you, and what differences exist for women in these different settings?

The other self-employed women I talked to — freelancers and business owners alike — confirmed that many of my experiences and philosophies about working for myself are pretty universal. A big overriding theme in all the interviews was, No matter how shitty a week I’m having (perhaps a cash-cow customer cancelled a big order, or all your computers up and died), I’d still rather be working for myself than back working for the man — even if it means sometimes working longer days or dealing with headaches I used to be able to make accounts payable, the resident geek, or customer service handle.

The mompreneurs who run businesses out of their homes taught me that my multitasking challenges are nothing compared to trying to juggle five client deadlines with five hungry kids. Suddenly, having to schedule a daily walk or two with my dog, evening plans with friends, and half a dozen editors pinging me for information on any given day seems like a cakewalk.

The biggest differences you see with employees vs. entrepreneurs (including freelancers) is that unless they have flextime or telecommuting privileges, employees who are moms feel very under the gun to get everything done. It’s hard to get all those mom duties squared away before and after hours — even if you have a domestic partner to help.

One benefit that employees have over entrepreneurs/freelancers, though, is that because they’re not working for their own company, they have an easier time compartmentalizing work. Unless you’re in one of those industries where you’re married to the job (law, medicine, software development), when you clock out, it’s totally Miller time. Your evenings are yours and yours alone, so you put up your feet and relax. Whereas the freelancer or indie business owner feels more like a student during finals — the work is never done, and if you’re not good at compartmentalizing, you might feel like there’s always something hanging over your head.

Ramit writes about personal finances for young people, but only about 20% of his readers are women. Why do you think this is? What can he do to improve the balance of his readers?

I think this is sad. But I know that women are still less likely than men to get a grip on their money as soon as they could. Many of us dread negotiations — as if asking for what we’re worth will sound boastful or make you unlikeable — so we don’t always make as much money as we should or could. We’re also taught that talking about money is uncouth, which is a twisted way of thinking that does not help at all when it comes to negotiating salary, getting a grip on your checkbook, or learning what it means to invest. I’m talking in generalizations here, but women are nurturing to a fault; we’re likely to put everyone else — friends, family, kids, boss — before ourselves. And that factors into not getting our money — essentially our livelihood and security — straight from an early age.

This isn’t going to be a very popular thing for a feminist to say, but there are still an awful lot of Gen-X women out there who think that their financial life will begin when they shack up or get married and have someone to pool their resources with (someone hopefully more financially savvy than them). But that’s a pretty big unknown. You may not get married. Or you may get married much later in life. Or you may marry and then lose your spouse one way or another and still have to fend for yourself. Or you may marry someone who’s a total financial mess. For the record, I’m 39 and have never been married. And yeah, I didn’t get my shit together financially till I was in my thirties. I have my divorced mom — who didn’t learn her way around investments until becoming single in her forties — to thank for forcing me to get my financial life together.

I’d like to see some female guest bloggers write articles for women about retirement (women are more likely to be impoverished in their golden years than men), homeownership (single women are the largest segment of the population buying homes), saving and investing, merging our finances with those of a domestic partner, paying down consumer debt (women have a lot of shopping-related debt!), and so on. I suspect that female “experts” will be able to nail the female psychology — and the “Girlfriend, let me tell you how it really is” tone a bit more.

Thanks Michelle! Head over to to follow Michelle’s great blog, where she shares research and profiles of women who are doing it! And you can buy The Anti 9-to-5 Guide: Practical Career Advice for Women that Think Outside the Cube at Powell’s Books or at

Cody McKibben is a blogger, web designer, and career instigator in Sacramento, California. He blogs about leadership and innovation at

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  2. April D

    Hmm…seems like her book was written for me. I’ll have to check it out.

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  4. Telemill

    Good girl! We need more books like this on the shelves. I’ll make sure to read this one.

  5. Terry

    I read Michelle’s book and recommend it highly. As a female entrepreneur who writes dating advice with a feminist slant, I definitely agree with her when she says a bad week working for myself always beats any week working for the man.

    Thanks for this post. I’ll be back!

  6. Abby

    I read Michelle’s article on phobias. It’s more than just “confronting your fear.” I have a phobia of throwing up. At one point, it took over my life. I hardly ate anything because I was afraid of vomiting. I saw a shrink. He tried hypnotizing me. It didn’t work. I refuse to exposure therapy. Whenever I am nauseated, I take all kinds of medicine to keep the vomit down. I shake, have major panic attacks, and get to the point where I think I won’t survive. It’s awful. I am also afraid of other people throwing up. So, Michelle’s article addressed the issue, but it’s not such a simple fix. I am seeking other ways to get over my fear. So far, I haven’t found any.