Three Tips For Leaving an Old Job and Beginning a New Future

By Robin Madell, San Francisco

Leaving a job by choice in the current economy is a difficult decision to make – particularly if you’ve already got a pretty plum position. But sometimes, it’s just time to move up. “I have many 3 A.M. moments,” admits Lisa Murray, who spent over seven years at international law firm Brown Rudnick LLP before opting to launch her own marketing firm. “Many friends and colleagues have said that my move was courageous, but I sometimes feel it was pure insanity.”

Sometimes others question the judgment of women who try something different. “I stepped off the corporate racetrack, closed the door to my big job as a vice president in financial services, and walked out the door,” says Marcia Mantell. “Everyone was shocked and wondered if I was crazy.”

Yet though it may seem counterintuitive and risky, many women who have spent much of their career as captains of industry in finance, law, technology, and other businesses find themselves doing just that. Women choose to leave for a variety of reasons, from office politics and inability to execute their ideas within the corporate structure, to poor work/family balance or the desire to just try something different.

Whatever reason drives their transition, it’s a decision that few take lightly. Parting willingly with a stable job and steady paycheck is a different experience than reacting to an unwanted layoff. It requires a leap of faith to be the driver of the choice to upend your career, family, and financial life in exchange for an unknown future.

Here are three things to keep in mind about how to land on your feet when you leave under your own steam.

1. Know When It’s Time to Go

There are times when it’s clearly time for a change. Perhaps you’ve realized that you’re not growing in a job despite your comfort in it, or a position may have become untenable due to factors beyond your control. What’s most difficult though is not just seeing the writing on the wall, but really reading it and making changes based on what it says. Many of the women we spoke with said that they reached a turning point in their career when they knew they needed to take action.

“I felt like I couldn’t contribute in my previous company,” says Erin Callaway, who forked off of her previous career path as a technical writer and now works as a director at social technology platform company Gloto Corp. “I worked hard and accomplished a great deal, but I was entrenched in bureaucracy and layers of management. There was no real path upwards for me.” Nancy Brook, who spent nine years as a VP of marketing at a major bank, sensed a similar roadblock. “I didn’t feel that I had a career path at the bank where I worked,” says Brook. “It seemed that as a middle manager, I was in a dead-end job.”

Political challenges were also behind Brook’s decision to leave her executive position. “For years, I had a boss who was domineering but who kept enticing me that someday I’d run the division,” Brook says. “Before she left, a man was hired to assume that job. In the end I really didn’t want my boss’s job. But it seemed to me that after years of my efforts to grow the business, the bank would have valued me enough to create a career path for me and try to keep me there.” Brook’s dissatisfaction led her to speak with a former vendor who was changing jobs, and ask him if he’d consider hiring her. Her strategy led to a position, and today she works in business development for a payments processing company.

The situation was different for Kimberlee Williams, a former executive at Merck whose roles included a senior director position in strategy/finance. Williams says that her family and friends were shocked when she told them she was leaving to launch a business, because they knew how much she loved the company. Yet despite this, she felt ready to move on. “I just had a sense for the last few years that maybe I was asking too much of any corporate environment,” says Williams. “I was looking for collaboration, autonomy, risk taking, and virtual work that would allow for a healthy lifestyle. What I was encountering in companies I was working for were the commute, bricks-and-mortar mentality, expectation to conform, rules of decorum, and always having to push for authority.”

Attorney Karen Eichman left an executive job of 25 years, most recently as General Counsel, to start her own law firm last year. A combination of professional, financial, and personal factors led to her departure. “When I was not getting sufficient work that satisfied me, coupled with earning ceilings and office politics, it became a ‘no brainer’ for me,” says Eichman. In Mantell’s case, reaching a critical juncture between work and motherhood caused her to pull the plug on her high-powered corporate career in finance to start her own business. “The demands on both job front and home front had reached such a breaking point that something had to give,” says Mantell. “It was time to deliver on my belief that my number-one priority was my girls.”

2. Consider Timing

When it comes to decisions about moving on from a job, you must consider not just whether to leave, but when. Rachel Stilwell, attorney at Gladstone Michel Weisberg Willner & Sloane, ALC, left a career of over a decade in the recording industry to go back to school to become a lawyer. Stilwell emphasizes that timing played an important role in her transition. “I am glad I made the switch when I did,” says Stilwell. “I loved my prior career for many years, but the problems caused by consolidation in the industry got even worse once I left.” She and others we spoke with advise the following in terms of transition timing:

• Keep a finger on the pulse of your industry. To make informed decisions about your career direction, you need to know what’s happening in your current industry. In Stillwell’s case, after experiencing a layoff and landing another job, she became aware that her industry was struggling, which influenced her decision to go to law school. “If the industry that you’re in is in a decline, leave before you have to, and invest the time necessary in your reinvention so that you can get the job you want rather than the job you have to take,” she says. “I left my old career in the nick of time.”

  Murray experienced something similar when deciding to make her career change. After spending several years at one firm, changes in the legal industry, such as budget cuts and administrative restructuring, led her to feel constricted in her role. But because she was aware of it, she was able to make a timely change to take on a different role in the industry. “In 2008, when the economic crisis was in full force, law firms began to rethink their overhead, infrastructure, and business development efforts,” says Murray. “This resulted in many changes to the way law firms operate, and I began to feel that my role was minimized. Once the value was gone, I knew I had to move on.”

• Keep an eye on the clock. There’s more to career transition than work concerns— family life is often interlinked. If you’re orchestrating a major change such as going back to school and planning to start a new career—and a family—thereafter, Stilwell recommends factoring in timing for having children. “Consider freezing your eggs,” she says. “I got lucky and had a beautiful daughter at age 42, without IVF. But developing a new career and fighting infertility at the same time is challenging and stressful.”
• Take your time. Callaway adds that you might not find what you’re looking for right away, so you should give yourself the time you need to conduct a thorough search. “If you’re unhappy in your job and you feel like it’s not what you should be doing or you aren’t contributing as much as you’d like, start looking around,” says Callaway. “I jumped around to a few different jobs before landing, which is perfectly acceptable.”

  If your transition is to self-employment, Stephanie Sanoja, who previously held a position as director of marketing for a tech company, emphasizes this can take time as well. “Give yourself a couple of months to get out of your corporate habit,” she says. “Think it through. You may have to get bored before you are able to work without dictated deadlines.” Williams makes the point that your support system also needs to understand that Rome wasn’t built in a day. “You need to manage expectations with family and friends,” she says. “I have many milestones, big and small, but they seem to focus only on the big ones (for example, how many clients do you have?) when I am still at the point of building a foundation (for example, getting my website online).”

3. Learn to Earn

After nearly two decades in the technology industry, including seven years at Intel Corporation, Sierra Modro switched career paths to become an entrepreneur. Modro notes that one of her main challenges has been learning to operate financially without a corporate buffer. “After a successful 18-year career in high tech, I no longer have a paycheck,” she says. “I’m building my own business from scratch, so I feel challenged every day by the knowledge that the money won’t just show up every two weeks like it used to.”

Sanoja found herself preoccupied with financial concerns when she prepared to make her career gear-shift. Though she had some funds set aside for her business, she recognized that unlike an earlier business she had when she was single, she was now putting her entire family’s future at risk. “When everything took much longer than I anticipated, and funds depleted much faster as a result, I panicked,” Sanoja admits. “I wondered, should I cut my losses and go find another job in this recession mess?”

Mantell also found her primary challenge was money-related when she voluntarily left her executive role at Fidelity Investments after 13 years of juggling corporate life and motherhood. “Financially, it was a really big deal for us as I was the larger earner,” says Mantell. “How can you just leave a big bonus on the table? How can you really walk away from a paycheck when you need to feed your family?” Now that Mantell is self-employed, finishing up a project can be nerve-wracking because she is not always sure what will come up next. She recommends the following strategies to other voluntary career changers:

• Bank your bonus money. If you’re planning to make a career transition, you’ll need financial reserves to help bridge the gap between your current job and your next one. Open a separate account to save bonus money or other funds that you can put aside toward your goals.
• Have a cushion. It’s not enough to save just one bonus—try to have at least a two-year minimum financial cushion before you quit your current job to prepare for a future opportunity.
• Protect your cash flow. If your transition is to self-employment, never let one client take up more than 50 percent of your billable hours. “I try to always have two to four clients in the hopper at the same time,” says Mantell. “It makes for some long nights and many weekends, but it also helps with the revenue stream.”
• Figure out your pricing model. Those who are making the switch to running their own business must determine how much to charge for services and whether to offer discounting. “You need revenue but without pricing yourself out of the market,” says Mantell.

No Excuses

While the current economy adds a layer of complexity, the women we spoke with were happy with their choice to make a jump. Most emphasized that while it’s important to know what you’re getting into and to be financially prepared, you should not let the economic slump keep you from doing what you want to do.

“It’s tougher now because of the economy but if you have the determination and a dream, I say follow it—but with eyes wide open,” says J. Kristi Feathers, who managed the collection division of a $20 million credit union for a decade before leaving to start her own personal financial education website. Eichman advises her peers in the legal industry to stay focused on solutions rather than problems when it comes to career transitioning in a down economy. “People need legal services now more than ever,” says Eichman. “Don’t let the recession be an excuse.”