Why: a) Michelle Kaston could be you. b) Then again, she could be totally unlike you. c) Regardless, you both might be making decisions about some of the same things.

If you talk to Michelle Kaston, you might think she had it all planned. Skip the last year of high school. Get early acceptance to a prestigious college, learn to write code while the rest of the world is figuring out where the backslash is on their keyboards. Find a job, reinvent a company's key operating systems, earn a huge raise, go work for a big-name company and get another huge raise. Become an independent contractor and have a six-figure year in your first assignment for-oh, why not-the world's number one provider of on-line services, America Online (AOL). Then plot out your next big move: starting a Web-savvy company at the dawn of the Digital Age.

It doesn't always happen that way. The will to jump-from working for someone to being a contractor and working for no one or anyone-is often arrived at with much angst, even missteps. Thinking it through can lead to a yo-yo of risk assessments: on the upside, you would have more freedom and anything would be possible; on the downside, you'd have less security and anything could happen; on the upside, you might engage that fantasy of working in your pajamas; on the downside, there you'd be in your P.J.s, with no more guarantees of paid vacation, health benefits, or just a complimentary photocopy or bad cup of caffeine.

If you make the leap, will you end up taking a dive?

CP hears often from IT workers who struggle with the contractor within. Is that entrepreneurial spirit something to embrace or just string along? And if you leap, will you get hooked, longing for increasing professional liberty? How independent is independent enough? Is being your own president and CEO the ultimate in contractor status? Or does starting your own business sound better than it really is?

Researching Colleges and Dogs

Michelle Kaston has thought and talked and pro-and-conned her way through those critical questions, averting some potential torment by keeping an enthusiastic grip on the decision-making process itself. But it didn't all start out so systematically for the Washington, D.C.-based contractor.

Not that Michelle Kaston isn't a thinker and planner. She's had a research and selection process for everything from which college to attend to which dogs to own. But the first part of the story just happened to be real, unplanned life: She hated high school.

Social circles were tight where Kaston grew up in Decatur, Ga., and she found herself clique-less and restless in the 11th grade, amassing a 3.9-something GPA without really trying. She didn't know what would come next, but she knew it would be better than what she had at Decatur High.

"My father sat down with me, and we made a list of all the colleges that might be good choices for me," recounts Kaston in her fast-clip, I've-got-things-to-do way of talking. "Then we called all 18 of them, and six said they would consider me without a high school diploma or a G.E.D. Vanderbilt was the best out of those who accepted me-and there I was."

There she was in 1989, without so much as a G.E.D., transplanting herself from the periphery of Decatur High to the middle of everything. At Vanderbilt University in Nashville, Tenn., she had cool friends, an even cooler computer science and mathematics double major, went to a lot of parties, and in her sophomore year landed a work study job as a computer programmer. "They handed me this 800- or 900-page manual, and so I sat there with it in my lap and read it, cover to cover in a week. And then I just started doing it."

Teaching herself to write code, Kaston got to the point where she could do it in her sleep. "I would have these dreams about debugging C code," recalls Kaston. "I was so wrapped up in the systems and what made them work."

As graduation approached, Kaston started dreaming beyond code-to what would come next in her life. She exited Vanderbilt with not only a degree, but also a plan. "College was a lot of fun for me, but I knew it was time to get serious," says Kaston, who is now 26. "I decided that in five years, I wanted to have a house, a car I really liked, and be married." And she was well on her way-to at least two out of three.

After graduating in 1993, the five-foot-tall Kaston set out to conquer her first real job as a programmer for Memphis-based AutoZone, Inc., the largest retail auto parts chain in the country. She whizzed through her first assignment: creating and implementing an e-mail system for the company's 1,500 stores in 26 states (now it's 2,600 stores in 38 states). Then the bosses found something they thought would really keep her busy. They told her to design an electronic, secure, disaster-proof inventory system for the chain's $100 million worth of car parts in locations scattered across the country-in less than four months.

"I think they got a little nervous when I spent the first five weeks just basically talking to people," says Kaston. "But I knew I had to talk to the users and people taking inventory to understand what kind of system would work best for the company. And as I went along I would go back to people, ask them to try things out and tell me what worked for them and what didn't." That approach-along with a willingness to lose a little sleep-helped Kaston finish the project ahead of schedule, wowing the honchos so much that they made her a project manager, the youngest in the company's history.

But nearly four years had passed and her greatest challenges at AutoZone, it seemed, had already come and gone. Kaston was restless. She considered other job opportunities, and one offer from Washington, D.C.-based AT&T Solutions looked particularly attractive. "Senior associate" didn't sound like much, but it paid 50 percent more than what she had been making in Memphis, and it came with the promise of Web training. "I took that job because I really wanted to learn Web development," explains Kaston. "It was worth it to me to step down from a management position if I could do that." She knew the cost of living in D.C. would soak up some of that pay hike, but even so, it was a good move. Or not.

"They ended up putting me back into what I had been doing the past four years-writing batch programs and C code," says Kaston. After a few months at AT&T, she saw that the Web development part of her job wasn't happening. "The Web training kept getting pushed aside because they didn't want to lose out on any of my productivity. I was working 60 to 70 hours a week and not getting to do what I wanted to do. I realized then that you really have to look out for yourself. No one's going to keep checking back with you to see if you're happy and challenged by your work-that's something I have to take care of myself."

Job Fairs and Handshakes

And so she did. By June 1998 Kaston was scouring a job fair, shaking hands with people from agencies, and distributing resumes. By July she had decided to leave AT&T. "I know a lot of people working for big companies, but based on my experience with AT&T, I didn't think that was for me. I wanted to have more control over my quality of work life."

This big decision required little methodology. She was going to make it on her own. The only question was whether to work through an agency or start a company. The process gave pause for deja vu: a call to Dad, a list, more careful thinking.

"My dad's an entrepreneur, so he understands some of the considerations involved in a choice like this," says Kaston, now a long way from her serendipitous days of a code manual and career falling into her lap. "I made a list of the pros and cons on the issues most important to me." For example: "I knew it would be tough to qualify for a house if I wasn't at least connected with an agency. I didn't think the mortgage company would go for it if I told them I just left my job and started my own business. Plus I still wanted my dream car. So I set a goal of working with an agency for now, getting the things I wanted in place and some money in the bank, then going completely independent in a year."

Stepping Out

She chose the Vienna, Va.-based Mindbank Consulting-one of those agencies she saw at the job fair-in part because it presented her with several options, one of which was doing Web development work for AOL. She also liked the idea of being able to take charge of a project without getting caught up in company bureaucracy or office politics. "Some companies put contractors in management positions, and I didn't want to be in a situation where employees would resent taking leadership from a contractor," says Kaston. "I also didn't want to take something that might end after just a month or two. I like being able to take on an assignment, figure out my own approach, and stay with it," she adds. "With AOL, the project was long-term enough to offer some stability, and it was going to be the hands-on Web development I've been wanting to do."

And she's been doing it. Kaston is happy, and so is AOL.

"Michelle has adapted very well to our work environment-and quickly," says Michael Brown, Kaston's supervisor at AOL in Dulles, Va. "She's able to work independently, but she also has a lot of experience working with people and the user community. That combination is really important," he adds.

"If I wanted to, I could probably go on for a while contracting-working hours that aren't too bad, doing Web development, making good money," muses Kaston. Indeed, contracting these days is more than a job bridge for IT professionals and their clients. "We don't just bring in contractors for coding anymore," says AOL's Brown. "They take on a variety of tasks and responsibilities. For all intents and purposes, if you walked in here, you wouldn't necessarily know they were contractors unless you checked the paperwork."

But for Kaston, The Plan beckons.

Stepping Up

In June, she got her dream car, a Volvo S70 T5 (the "T" is for turbo). In September, she bought her house-on a 9 1/2 acre lot near the Appalachian Trail just west of D.C. And she's got the canine search down to a short list-two large dogs, each a different breed. Maybe the marriage thing is malleable, but the impending launch of Kaston Technologies is not. She's already claimed the address: www.kastontech.com. Her firm will do Web development and network administration for start-up companies, a target market she discerns is flush with ambition and fresh bank funding. The plan is to stay small-herself and perhaps two other people (a networks person and an accountant-type; she'll do the design). It's not just about ambition, says Kaston, it's about who she is and how she works: "I've got the mindset to do this, and I have the temperament. I love this work but I also can't stand to sit still-so doing it in my own setting with my own clients is what I want. I can stay busy with different aspects of the business-keep the clients happy, but be autonomous, too.

"I want to have my corporate paperwork finished by the end of [1998]. By January [1999], I'll have my business plan together. Then I'd like to start taking on a project or two on the side," she says with the confidence that's a by-product of hard-earned success. "By August, if not before, I'll be ready to go out on my own."

Or more than ready. That's the plan. CP will keep an eye on Michelle Kaston-and we'll keep you posted.

S.C. Biemesderfer is a frequent contributor to CP. Her profile of Jerry Weinberg appeared in the September/October 1998 issue.
Contract Professional/CPUniverse, Dec. 21, 2000.