Your career – when to stay, when to move and when to go out on your own

Dear Joan:

I am at a crossroads. I’m 32 years old this year. I have an MBA. I have been with my company for the past 7 years. I started mid-level upon graduation from school and have quickly moved among the ranks, to a senior level position, within the department. I love my job. I love my coworkers. I work hard, but my work comes easy. I do not feel challenged. Some days the comfort and ease of the work is a blessing; other days it is maddening. I fear I have no room to grow.


However, I feel if I leave I will never find the comfort, joy and ease of work I currently possess. Am I blessed or dooming my career?


I have been soul searching and am at crossroads. What is someone in my position to do? Seek an alternative company with whom I feel there is growth potential, yet risk my title, environment, comfort, and seniority level? Continue with my current position and satisfy my desire for growth and challenge outside the workplace?


I have thought about starting my own company. I feel if I did this part-time, it would fit well with my current unchallenging position, yet would be half-done. Or, should I stick with my position, as is?


I feel like I am young and naïve. I don’t know what else is out there, yet I don’t want to leave where I am now. Any thoughts or suggestions?



To people reading this, who don’t have a job, or hate the jobs they have, your predicament may seem trivial. They might think, “Geez buddy! I’d sure like your nice boring job!” Yet, if you are unchallenged and feel underutilized, your dissatisfaction is very real and unsettling.


I’ve been in your situation in the past and found myself asking the same questions. While I can’t tell you which direction to choose, I will suggest some strategies and questions to pursue that may help you make a decision.


First, have a discussion with your manager and other senior people who can influence your career direction. Tell your manager that you are looking for more challenge. Explain that you love your job and the people you work with but you find that you want more challenge.


They will ask you what you are interested in, so be ready. Think of the gaps you have on your resume. Are there any new products or processes that you would love to work on? Is there a new area of the business that you would like to learn about? What skills do you want to learn or hone?


You may get lucky. If the organization wants to keep you (and it sounds like they do), it will be in everyone’s vested interest to keep you challenged. Don’t expect immediate action, but if they really want to keep you—and there is a business opportunity that matches the challenge you want—you have every reason to stay. The worst scenario would be to say nothing and then announce you are leaving for a new job, only to have your manager say, “If only we had known, we could have given you X opportunity.”


On the other hand, there may not be much to challenge you there. If nothing results from your discussion with your boss, start looking at other options. If you are already bored at 32 years old, how will you be feeling at 35—or 40?


I find that giving myself a six-month deadline really helps me make a big decision like this. Pick a date six months from now and make an appointment with yourself to review what you have learned.


For instance, over the next six months, why not give yourself permission to explore? That may mean going on interviews at other companies. That may mean contacting those headhunters who have been calling you, and tell them about your ideal next job. Tell them you don’t want a call back unless they have a job that fits your specifications (why field offers if they don’t significantly improve your situation?).


Explore starting your own business, rather than just dreaming about it.  Do some informational interviewing with entrepreneurs in fields in which you’re interested. Ask them questions about how long it took them to get established, how much money they invested, how many hours they work, what skills/abilities help them succeed, and the valuable lessons they’ve learned.


Pick up a few books at the bookstore about starting your own business and see if it interests you. Take a hard look at your lifestyle and finances and go talk to your banker for some advice. Being your own boss sounds glamorous and lucrative but it isn’t for everyone. Before you jump ship, test the depth of the water.


During your six months of exploration, fight the urge to make a final decision. This will free you up to pursue many areas of interest and it will take the pressure off. At the end of the six months, I suspect a clearer picture will emerge. You will be much wiser about outside opportunities and you will have more information to work with. Unless you take this exploratory step you will have a difficult time moving out of the indecision zone.


And in the end, if you do leave, what do you really risk? You are young, smart and well educated. This isn’t a life or death decision. If you do make a move and it isn’t right for you, so what? You’ll just start looking for something else that is better. When you’re 80 years old and looking back on your career, what do you want to say about it?

Joan Lloyd is a Milwaukee based executive coach and organizational & leadership development strategist. She is known for her ability to help leaders and their teams achieve measurable, lasting improvements. Joan Lloyd & Associates, specializes in leadership development, organizational change and teambuilding, providing: executive coaching, CEO coaching & leader team coaching, 360-degree feedback processes, retreat facilitation and presentation skill coaching and small group labs. Contact Joan Lloyd & Associates at (414) 573-1616,, or 
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