I’ve never worked at a job I liked, and DH has been so over his very stressful job for years now. Two years ago, we sold the house we raised kiddo in and bought a new, solar-powered home in a very low cost-of-living area about an hour from our old neighborhood in a beautiful part of the AZ valley. We are mortgage free, tuition free, debt free, and made our retirement number a while ago. At our annual checkup in October, our broker asked us what is keeping us at our desks as our original plan was to step off at the end of this year, but we’ve moved that up to April ’17 when DH turns 60. We have been solidly working this retirement plan for 20 years (14 years with this broker)–mapped out the timeline, put in the milestones, did the work, and crossed the finish line. You’d think we’d be jumping up and down. DH is, I’m not.
I absolutely hate my job, hate working-always have, have never defined myself by my work, and don’t plan to work another day in my life after I step off. So what’s the problem? I’m not mentally ready in a way I never anticipated. I’m struggling with accepting that I’m moving into “that” phase of life. You know, the phase where you are “retired,” the phase where AARP describes you, the phase where you are admitting that you are in your third quarter, the phase where no matter how you occupy yourself (and I have zero concerns about occupying myself), you’ve joined the ranks of a club that doesn’t seem quite as attractive close up as it did at a distance. I know I need to get over this and just be OK with the fact that I AM an aging Boomer. Nothing to be done about that. Continuing to work won’t change that. I haven’t been a kid for a long, long time, but there is a subtle mental shift in how I perceive myself now that I am able to join those ranks. I feel like I’m sitting at the top of a very tall slide that I was so excited about during the climb but, now that I’m sitting here, I don’t want to go down. I do, but I don’t. Don’t push me.
Then, in addition to my ridiculous inability to come to terms with my age, I’m also struggling with voluntarily turning off the cash flow. We allowed our son to attend a pricey boarding school as a full-pay student, and those four years were very lean for us as we’ve reached our retirement goals very methodically and by being very frugal over a very long period of time. Those tuition payments weren’t easy for us. Now he’s at a service academy, so we do not have a college obligation and, for the first time in our lives, our income is all ours with very few expenses. So, I’m thinking perhaps we should just enjoy this situation and suck up the jobs for a while longer. DH is NOT on the same page there and is absolutely going to retire at the end of April. Me working while he doesn’t isn’t a good scenario because he wants us to go out and play. He has been on the road for the past 17 years, and he’s looking forward to us both being free and unencumbered to reconnect and just enjoy.
I know no one is crying for me; this is not a bad place to be. It was the “are you ready” part of this thread title that attracted me because I thought all I needed to be was financially ready. That has turned out not to be the case. I guess I need to get that book.

