Should I tell my boss I’m looking for a new job?

Dear J.T. & Dale: I have been working for my boss for two years, but now it’s time for me to find a new job. I feel so guilty, because my boss is going to be surprised and upset. There is nothing she can do to keep me, but how can I tell her I’m looking for a new job, so she isn’t blindsided? — Sydney

DALE: It does you credit that you care about your boss. And while your concern says a lot about you, it also says something important about your boss: The same traits that make your boss unaware or clingy (or whatever else it is that you fear in her reaction) make her someone you don’t want to count on to have the kind of smooth, professional transition you’re hoping for. In fact, the only boss you could count on to respond well would be a boss you’d never want to leave.

J.T.: Do not tell her you are looking. First of all, finding a new job could take you a while and the moment you tell her it’ll be hanging over her head, knowing that at any time you can walk in, and it could be your last day. That could make her want to resolve the issue, and she might even let you go. Additionally, as you go on interviews, you might just figure out that you don’t want to leave after all. I’ve seen this happen quite a bit.

DALE: It is also common for a boss — especially the sort who refers to employees as “family” — to take an employee’s leaving as a personal affront. When you announce that you don’t want to be part of the “family” anymore, it can turn ugly.

J.T.: So, go do some interviews and if you find a better opportunity, then let her know and try to give her more than two weeks’ notice. Also tell her that you are always available by phone over the first couple of months in the event they need your information or assistance. The solution is to let her know that while you’re moving on, you want to support her through the transition.

Dear J.T. & Dale: I am ready to move to a new state, but I would like to get a job there before I move. I don’t have enough money saved up to not be working. Any suggestions? — Thom

DALE: This has always been the classic standoff: you don’t want to move without a new job, and almost no one wants to hire someone who isn’t already local (unless you’re a hard-to-find specialist). However, here in the Yet Another New Economy, there’s an option: search for companies with remote employees. Then, once you relocate and settle in, you’ll be in a position to explore more local options.

J.T.: As for pursuing traditional employment in another city, it’s important to create something called an interview bucket list. This should be list of 20 or 30 companies in the area that hire for your skill set. Once your LinkedIn profile and résumé are updated, message the recruiters at these companies. Ask them to connect with you via LinkedIn and when they accept the connection, let them know that you’re moving to the area in the next six months and that you would love to know what it would take to earn an interview with them. The only way to get hired remotely is for you to initiate the contact and let them know you are moving there no matter what. Most companies aren’t going to pay your relocation expenses, and they want to know that you intend to move there at your own expense but that your goal is to get a job secured before you arrive. Also, if you know people in the area you are moving to, you should really try to leverage those connections as much as you can with these employers on your bucket list. Your network is your net worth, and the more referrals you can get, the better your chances!


Jeanine “J.T.” Tanner O’Donnell is a career coach and the founder of the leading career site Dale Dauten is founder of The Innovators’ Lab and author of a novel about H.R., “The Weary Optimist.” Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 628 Virginia Dr., Orlando, FL 32803. © 2021 by King Features Syndicate, Inc.


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