Dear Reverend,
I’ve been in the same job for 11 years. It’s not difficult for me and has the benefit of being remote. I make my own schedule, get things done in my own way, and I’m used to having lots of autonomy. On the other hand, my salary hasn’t budged significantly, and I haven’t had a promotion in six or seven years. A couple of times a year I go through a spree of applying for jobs, but I haven’t had any luck. Should I just be happy with what I have and stop trying to get ahead? I feel a bit undervalued, but the ease of the job keeps me there. I’m not struggling much financially, but I’m not saving much either. What should I do?
Old Pro (woman, 43)
Dear Old Pro,
The fact that you’ve stayed at the job for so long tells me that you already know you have it pretty good. However, feeling undervalued is at odds with overall job satisfaction.
It sounds like it’s time to ask for a raise. Get your ducks in a row and go through whatever official channels your company has to request a salary increase. The worst thing that can happen is that they’ll say no, so you’ve got nothing to lose.
Going on a job-search spree every once in a while isn’t the best way to find a new position. You need to be persistent. Be sure your résumé is always up-to-date and ready to go, then incorporate checking listings into your daily routine. Take five minutes to peruse the postings during your morning coffee or lunch break. Don’t be too serious, or it could get discouraging. Just keep it a casual browse. You never know what gem might pop up.
In the meantime, why not take advantage of your flexible schedule and explore side gigs that could bring in extra cash? Sell stuff you don’t use anymore online. Pick up some freelance work or a very part-time shift at your favorite shop or restaurant. Walk some dogs. Who knows? You may stumble across a new career when you aren’t looking for it.
Good luck and God bless,
The Reverend
This article appears in May 13 • 2026.
