Q: I've invested 16 years working for the same company, and I am now asking myself why. My job is secure and so is the company. When I think about staying, I feel the knots in my gut clenching tighter. When I think about leaving, I feel a mixture of excitement for the adventure and fear over the potential loss of security the change represents. While staying offers a hint of job security, it continues to bind or limit my creativity.

Ever since I was a child, I loved to write. I rediscovered this passion when I attended and finished college later in life; I'm in my late 40s. I also discovered a passion for travel and photography, and my dream job is to be a travel writer. I framed some of my photos and had small art shows at restaurants. I've begun a travel blog, which combines two of my passions. This was my way of testing the waters; I now feel inspired, passionate and happy when I share these moments with whoever reads my posts.

How do I prepare for making the transition from a life of drudgery to one of passion. I don't know where to start.

A: An in-house corporate lawyer described going to work everyday as "looking into a tunnel that has no end," so you are not alone in your dislike of drudgery. Make three lists — positives, negatives and tolerable — tasks in your current job. This will help you see all perspectives since you seem to be focused on the negatives. Now create the same type of list for writing, photography and travel. You may want to interview people in these fields so you include the realistic tasks and activities for each, such as sitting before a computer with nothing entertaining, clever or even interesting to say; reviewing photos and discovering they seem average or commonplace to what's in the market; and dealing with the inconveniences and serious problems in planning your trips, making reservations, buying nonrefundable tickets for those plans and dealing with any problems that befall all travelers at times.

Now you must review your financial situation. Have you saved enough to live without a regular income for six months to a year? If you have, consider how that situation will affect your self-esteem and general well-being as you continue to live without income for an extended period. There is a difference in stress levels between people who live off the interest from millions invested in fairly secure choices compared to those who feel the pressure mounting as they use the finite amount of funds saved. None of these considerations will be easy or pleasant, but all are necessary before deciding.

Also consider how you will do living daily with the excitement of traveling, writing and recording your travels with photos mixed with the potential realities of each activity. This planning period is not intended to kill your dreams for a potentially rewarding lifestyle change, only to temper them with what you will have to face after leaving your secure job. Remember, after you live the dream, you will have to sell the results of it when you return.

Before finalizing your plan, ask your boss and HR if you can return to your job if this adventure turns out to be less exciting and prosperous than you planned. Some companies may welcome you, while others may thank you for leaving so they will not have the dirty job of including you in a future layoff. If the company will not hire you again, research your field to find the ones that will if you decide independence is not for you.

Email your questions to workplace expert Lindsey Novak at [email protected] and follow her on Twitter @TheLindseyNovak. To find out more about Lindsey Novak and to read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate Website at www.creators.com.