The Workologist | A smart manager ought to prefer satisfied and engaged employees; a worker who is grudgingly marking time is probably not great for the enterprise.

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Q: After graduating from college, I landed a position with a large company in a small Midwestern city. I stayed for more than 2 years of heavy travel and intense hours. I needed a change. But I also needed to stay in the area while my significant other finished grad school. Job options here were limited, and a noncompete agreement meant I couldn’t work in my field for a year after leaving. Luckily, a significantly older friend helped me get a job with his software company.

One of the verbal conditions was that I would stay for at least two years, but I dislike working for this company. I think my performance meets expectations, but the job is a bad fit. Plus: That noncompete agreement from my previous firm will soon expire, and I think I could double my compensation elsewhere. How can I preserve the friendship while leaving before the two-year mark?

A: It sounds like you’ve made up your mind about moving on, and your reasons for doing so seem solid. You should probably have a direct discussion with your friend to explain your decision to leave his company — although there are some points here I’d emphasize more than others.

If the job really is a bad fit, and you’re not as happy with it as you assumed you’d be, that’s reasonable. A smart manager ought to prefer satisfied and engaged employees; a worker who is grudgingly marking time is probably not great for the enterprise. Besides, if it had turned out that you were really lousy at your job, I’m pretty sure your failure to live up to expectations would have overridden that “verbal condition” by now.

On the other hand, I’d skip any details about how much more money you could make elsewhere. Perhaps, in addition to maintaining a personal relationship, you’re concerned about being pegged professionally as a flighty, flaky youngster. Surely you are no such thing, but that you’re coming to this decision just as your noncompete expires might well seem suspect. So you should probably de-emphasize that, too.

Instead, express sincere gratitude, and at least offer longer-than-usual notice (although be prepared for that offer to be declined). Underscore that you took the job in good faith, and put time and sincere effort into making it work, but you believe it’s better for both parties if you move along. And frankly, it probably is. While his first reaction may be annoyance or worse, your goal should be to convince him that ultimately the company will be better off with someone more genuinely enthusiastic.

When loyalty delays a career change

Q: I have a two-part question, related to a major career shift. Specifically, I want to leave the publishing business to pursue a manual trade. It’s something I’ve wanted to do for a long time, but I’ve been scared because of cultural pressure to stick with a more staid, office-based career. And I still wonder: Is this a crazy change to make?

But here’s the twist that makes things even more complicated. Just as I’ve been planning to leave my job and start attending an appropriate trade school, my boss has been dealt a serious family emergency and everyone on staff has had to step up to support him and our business. It’s unclear when he’ll be back full time. He has been a tremendous boss and a great mentor, and I feel I owe him a ton for the opportunity and skills he’s passed on to me. Do I put off my pursuit of this transition out of a sense of obligation to the company that I hope to leave?

A: To answer the first part of your question: No, it’s not crazy to make a big change if it means pursuing a career that excites you more than what you’re doing. Cultural or peer pressure to play it safe should not deter you. Think about what you might regret more: taking a chance to chase this dream, even if it doesn’t work out exactly as you imagine, or looking back years from now and wishing you’d made the leap when you had the opportunity.

It’s often the case that the longer you wait, the harder it becomes to make that leap. This is partly because it always seems like change will be easier at some unspecified point in the future than it is today. And it’s partly because life will always come up with some new twist to make that feeling more acute. So don’t let this sense of “obligation” become a rationale for ducking a scary decision.

Still, it’s understandable that you don’t want to feel like you’re abandoning someone you feel indebted to — and you certainly don’t want to be burdened with the lingering sense that you were a heel.

So at the very least, come up with a firm backup timetable: Decide exactly when you will make this move if you don’t do it now and commit yourself to doing it then, no matter what. Depending on your relationship with your boss, you might try to have an honest conversation with him about it, in effect asking for his advice. Be frank about your desire to honor your relationship with him in the short term, but be just as frank about your need to honor your own sense of what’s best for you in the long run.

Whether you have that conversation or not, the important thing is to make sure that, whatever you decide, you don’t allow your real goals to become derailed.

Submit questions to Rob Walker at