Searching for a New Career Direction?

Every week I meet with a number of new clients expressing interest in exploring new career options. What surprises me is how frequently I encounter a “stuckness” on their part that stems from one (or more often all) of the very same causes – a feeling that the task is too overwhelming, too time-consuming, too confusing, or too unlikely to succeed.

There are two analogies I use in my work with these clients that seem to resonate with them and propel them into action. I will lay them out here:

1) Moving

Imagine that you’ve lived in the same house, in the same neighborhood, for ten years. There’s nothing horribly wrong with where you live, it’s just that you feel it’s time for a change and that you know deep down there’s a residence and a neighborhood that will be better suited to you and your family, and that you’ll enjoy more. That’s all you know at this stage: you’re not sure whether you’d prefer a condo, a townhouse, or a traditional house – each has its advantages. You’re not sure how you’d be able to afford a new place to live. Would you rather live downtown, in the suburbs, or in the country? Etc. Contemplating all of these unknowns could lead you to throw up your hands and say “it’s easier just to stay where I am.”

2) Vacationing

Imagine that after almost three years of working very, very hard at your job, with no time off other than a few four day weekends, you decide to take two weeks off and enjoy a real vacation with your spouse. Grandma and Grandpa have even offered to stay with the kids. But where should you go? The beach or the mountains? Visit museums or vineyards? Europe or a national park tour? Plane, train, car, or boat? It seems like the options are infinite.

How would you approach answering each of these two challenges? You could take a test with a series of predetermined questions that might point you in the right direction – questions (in the case of housing) such as: “Check the three of these six words that most appeal to you: cozy, open, charming, contemporary, exciting, homey” or “Rank these six attributes in order of importance: lots of closet space, a place to garden, a large kitchen, a space to entertain graciously, guest rooms, a fireplace. Or in the case of vacationing: rank these six in order of importance: lots of activities, beautiful scenery, places of historical interest, good nightlife, fresh air and sunshine, immersion in a different culture. How helpful to you do you think a series of questions like this be?

Answering these questions would certainly enable you to narrow the field, but to make the best decision you’d have to look at some specifics: photos and specs of houses for sale, guide books,, or asking friends about possible vacation destinations. The key is to EXPLORE, and put your mind into a place of NOT KNOWING, where there are all kinds of possibilities. As you begin to investigate those possibilities (for example by talking to friends about what they think you’d be good at, or by undertaking the kinds of exercises laid out in a book like “Pathfinder” by Nicholas Lore, or “Renaissance Soul” by Margaret Lobenstine, or by going onto and reading about what other people like and dislike about their jobs), you’ll gain greater clarity. Perhaps by eliminating certain fields or positions, or perhaps by recognizing that there’s a genuinely deep-seated interest that has lain dormant.

As I’m working with clients in the “career option exploration” phase, I rely a lot on questioning them from a number of different angles: “What were your favorite classes in high school or college?”; “What did you hear growing up in your family about the importance of money?”;”What aspect of your current job / past jobs do you most like / hate?”; “When you retire, what accomplishments would you want the toastmaster at your retirement party to enumerate?”, “When do you feel like you’re ‘in the flow’?”, etc. As I listen to answers, I draw attention to unnoticed contradictions or synergies in the responses, or to shifts in body language or tone of voice that lead to realizations (e.g. “I guess I actually don’t mind certain aspects of being a lawyer, it’s just that I feel stuck”). Almost invariably a realization leads to a slight “course correction” (or perhaps a large one). Let’s go back to the househunting analogy. Maybe you’ve lived in an apartment and have decided that you want to buy a house, but discover that the expenses involved in buying any decent home on top of the purchase price (taxes, insurance, and repairs, for example) are too large for your current budget. You might begin looking at condos, or decide to postpone a purchase until you’d saved more money. The vacationing analogy? You want to vacation in Europe, but you can’t use your frequent flier mileage as all the available seats are gone. You can postpone, or explore and realize that Quebec City, Canada or San Juan, Puerto Rico offer most of what you were looking for (different culture and cuisine, places of historical interest) but are accessible now.

Quite simply, career exploration, like househunting or choosing a vacation destination, is a process. One step will either lead naturally to another or, if you hit a dead end, you can back up and take another step in a different direction. But you need to be willing to put one foot in front of the other to begin the process, and keep moving forward. I’d be happy to help.