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Pamela Skillings is the founder of Skillful Communications, a career and communications consulting firm in New York. Previously, Pamela spent more than twelve years as a marketing executive for companies including MasterCard International, Morgan Stanley, and Citigroup. She recently published a book called Escape from Corporate America: A Practical Guide to Creating the Career of Your Dreams

  1. Question: How do I know if I should get out of the company I work for?

    Answer: I talked to one corporate escapee who made her decision after a senior manager threw a Lucite paperweight at her head. That’s a pretty good sign. But for most of us, the decision isn’t quite as clear cut. No job is great all the time. You have to diagnose what it is that’s making you unhappy. Are you just having a horrible week? Is there something you can do to make your current job more satisfying? If not, you owe it to yourself to get out. If you’re not sure whether you should stay or go, check out my interactive Are You a Corporate Casualty? quiz.

  2. Question: Why don’t people who are unhappy leave to find something better?

    Answer: A lot of people stay stuck in corporate jobs that don’t inspire them because they’re afraid they can’t make “enough” money doing what they love. Others don’t believe that it’s actually possible to love your work, so they try to make the best of a bad situation. Then there are those who are spinning their wheels waiting for epiphanies about their true callings before they make a move.

    I can relate to all of these feelings. I worked in Corporate America for more than twelve years. It was fun at first and I learned a lot, but I eventually reached a point where I wasn’t feeling challenged or engaged anymore. For years, I tried to suck it up and make it work. But eventually I learned that my energy would be better spent on figuring out a career path that would make me happier.

  3. Question: Can bad jobs be saved or fixed?

    Answer: Yes, sometimes. It’s worth trying if you mostly like your work and your company and can clearly identify the problems that need to be addressed. You should also be aware that sometimes it’s not the job, it’s you. There’s something to be said for being able to recognize when a position or a company is just not the right fit for you.

  4. Question: Is there more danger in sticking too long with a job or leaving too soon?

    Answer: No one should quit abruptly without a good career transition plan. However, there are also dangers in staying too long in a job you hate. The longer you stay stuck in a rut, the harder it is to get out.

  5. Question: Then what are the components of a good escape plan?

    Answer: The first step is to take a good hard look at what’s missing in your current career and figure out where you want to escape TO when you escape from Corporate America.

    Then you must identify the best route to your dream job. That might mean getting some additional training, updating your resume, or starting your business from your kitchen table in your spare time. The important thing is to take some action and start building momentum. And you can do all of this before you quit your current job.

    A solid financial escape plan is also essential. Money concerns stand in the way of a lot of potential corporate escapees, but it doesn’t have to be that way. Even if you think you can’t afford to make a career change right now, do the math and you might find that your dream career is possible after all. You might have to make some temporary budget cuts or wait until you’ve accumulated enough in your Escape Fund to finance your transition, but you will likely discover that there is a way to make the numbers work if you’re willing to make some compromises.

  6. Question: How can I get a job that doesn’t suck?

    Answer: There are a lot of great companies out there, both big ones and small ones. The key is to figure out what’s really important to you at this stage in your life and what you need to thrive. For two years in a row, Google has been ranked as the #1 Best Company to Work For by Fortune. It’s a great company, but it’s not the right fit for everybody. If you’re not comfortable working in a very fast-paced environment, a dream job at Google might feel like a nightmare. And even at a great company, you have to be careful when choosing your specific job role to make sure it fits with your talents and preferences.

    Once you define your priorities, you have to do your homework and identify which companies are right for you. Reading the rankings of best companies is a good start, but you shouldn’t stop there. Reach out to your network and see who can provide the real inside scoop on the companies you’re considering. It’s important to work for a company that you respect. However, when it comes to job satisfaction, it’s even more important to make sure that your day-to-day duties and work environment are engaging.

  7. Question: How can I tell if a job is going to be good (or bad) for me during the interview process?

    Answer: Be observant, ask questions, and don’t take anything at face value. Of course the recruiter and human resources representative will tell you that the job is your dream come true. That’s what they get paid for. Often, they’re not trying to trick you; they just don’t truly understand what the job is like from the inside.

    Be diplomatic when you probe for details and save the hardest questions until you’ve got an offer on the table. If things look promising, ask if you can meet with some of your potential peers and team members. This accomplishes two goals: 1) You can get a sense of how crazy your future coworkers are; and 2) You can get a better idea of what it’s really like to work in the department from a non-boss point of view.

    Always remember to keep your eyes open for clues and listen to your instincts. I know what it’s like to end up in a job that’s a terrible fit despite the best of intentions. Looking back now, I realize that it happened because I ignored red flags that I didn’t want to see.

  8. Question: What are the downsides of working for a startup or small company?

    Answer: Working for a startup or small company can be incredibly exciting and rewarding. At the same time, it’s even more important to do your due diligence when considering a job offer at a smaller firm, especially if you’re making a move from a larger corporation. Small firms tend to be more vulnerable to market forces, so you want to make sure you know what you’re getting into and believe in the company’s potential. You should also be prepared to make do with less infrastructure and fewer resources. Even senior managers tend to pitch in where needed and wear multiple hats at smaller companies. And make sure you do your homework on your CEO. The leader sets the tone for a small company and often determines success or failure.

  9. Question: Is it true that if you “do what you love, the money will come”?

    Answer: Yes and no. Job satisfaction is a wonderful thing, but it doesn’t magically pay your bills. However, people are more successful and often make more money in the long term in work that they love. One of the key reasons is that you work a whole lot harder when you’re passionate about what you’re doing.

  10. Question: What does it take to work solo?

    Answer: Entrepreneurial attitude is key. The most successful solopreneurs understand that they are running businesses, not just hopping from freelance gig to freelance gig. You also have to be versatile and willing to step outside your comfort zone to handle sales, client management, invoicing, marketing, and other duties that may not be your greatest strengths. You may be able to eventually outsource some of these tasks, but you will still have to understand enough to manage the work effectively. The abilities to prioritize work and manage yourself are also essential. You won’t have an annoying boss to complain about, but you also won’t have anybody else to blame if you screw up.

    On that note, I guess I better get back to work now or my inner boss will get after me.

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