Dear J.T. & Dale: I work for a smaller company and have done so for 10 years. Last year, I got sick, and I had to be out of the office for six months. The owner (who’s my boss) was super understanding and kept my job available. Now that I’m back, there’s something about it that no longer sparks my joy. I want to leave, but I feel so guilty because my boss was so awesome about giving me the time off while I was on disability. How do I pursue this conversation so she isn’t so upset with me? — Deirdre
J.T.: You’ve been a longstanding, loyal employee. I’d sit down with her and explain how grateful you are and how lucky you feel to have been given the opportunity to take the time off you needed. I would then tell the boss that it’s incredibly hard for you to share, but you think it’s time to start a new chapter of your life. Together the two of you can talk about the best way for you to transition out so she can find the coverage that she needs.
DALE: Hold on. I wouldn’t be jumping into departure mode just yet. After all, a marvelous boss is not something to discard without being certain you have something better to go to. You want to be “pulled” not “pushed” — pulled into something new and exciting, not just pushed out of your current job by ennui. So, start your career and job research by trying to puzzle out what used to spark joy for you and where it went. Doing so, you’ll start to see what paths might be available to get it back. You probably don’t want to start over at rookie pay, so you’re going to want to evolve. That probably means jobs related to your current career or industry. After you’ve seen that future self, analyze whether that self couldn’t exist with your current employer. Maybe you can expand your role right where you are.
Dear J.T. & Dale: My cousin has applied to 200 jobs and not gotten a single response. He is a programmer, and he wants to get into the gaming industry, so he’s only applying for jobs there. He’s just graduated, no experience. He’s really frustrated. Advice? — Valerie
DALE: As soon as we hear someone is counting up their job applications, we know it’s a misguided search. The focus should be on meetings and contacts, not applications. This notion is foreign to many younger job searchers who’ve been raised in a world where everything is online — buy a car, find a date, order dinner. So, you’re going to have to break it to him that it’s now going to be about connecting with actual people.
J.T.: Moreover, the tech industry is getting hammered with layoffs right now. The gaming industry is extremely competitive. Lots of programmers would like to work in it, so there’s intense competition. If he’s really serious about getting into the field, he’s going to have to get a lot more targeted. Studies show that the majority of applications online never get seen. A lot of them are tossed out because they’re not an exact match. What he needs to do is start networking and meeting people who are working there. He has to build relationships and learn what it takes to get hired so they can hopefully help him out when a coveted position becomes available. It’s called proactive job search, and it’s the only way you really get hired for the jobs you want these days.
Experts always say it’s great to have questions prepared for a job interview, in fact the Washington Post notes that it can give you a competitive edge over other candidates but did you know that asking the wrong questions could ruin your chances of landing the gig?




