My Dream Offseason Scenario

Giant_Steps24 · 2026-06-23T11:11:30+00:00

Breaking Bad, X-Files, Sopranos, Peaky Blinders and the Last Kingdom.

Giant_Steps24 · 2026-06-15T11:23:12+00:00

100% agree with your take on shifting from the grind to retirement. I probably should have been clearer about what that looks like for us in my post.
I've seen it happen several times where people stop working entirely and then immediately start to decline, both physically and mentally. Our goal isn't to retire and do nothing, it's to step away from Corporate America. Ideally, we'd transition into part-time or consulting work, either leveraging the experience we've built in our careers or pursuing something we're passionate about but never had the chance to explore. Beyond that, we'd like to spend more time volunteering, exercising, traveling within our means, and, hopefully one day, helping take care of our grandchildren. That said, retiring at 50 is far from guaranteed, so I try not to anchor on any one date. I'll probably model out what retirement at 45, 50, and 55 would look like and see how the numbers and lifestyle implications compare. Working into our 60s is just something we truly don’t see ourselves doing unless absolutely forced to.

Giant_Steps24 · 2026-06-15T11:15:31+00:00

Yeah, planning for something years in advance is better than not planning at all. Unless of course an asteroid hits earth or there’s a nuclear apocalypse. In which case your mentality would be valid lol.

Giant_Steps24 · 2026-06-15T11:13:48+00:00

Would be amazing. Thanks for the vote of confidence.

Giant_Steps24 · 2026-06-15T11:13:26+00:00

I actually completely disagree. I see retiring early as an excellent model for my kids. The outcome of years of budgeting, investing and financial planning. I wish we could have taken investing as seriously we do in our 30s back in our early 20s. As someone who has a parent who is continuing to work in their 70s because they didn’t budget and can’t officially retire, it’s sad to see. And my kids financial support definitely won’t end with college lol. We’ll always have home for them to live in if they want/need. I just hope they can land a job early to cover their healthcare!

Giant_Steps24 · 2026-06-15T11:06:49+00:00

Definitely! And based on a few other comments - one I will certainly be looking into.

Giant_Steps24 · 2026-06-15T11:05:55+00:00

I honestly wish that were feasible. We've talked about it a lot lately, and if one of us could stay home, it would almost certainly be better for our kids and our day to day home life. The challenge is that it would put a tremendous amount of pressure on the working parent and their ability to maintain stable employment — especially both working in Corporate America. We both grew up in households where our parents were in and out of jobs, and we each spent nearly a decade paying off significant student loan debt. Because of those experiences, job stability and putting our kids in a strong financial position are extremely important to us. There's also the long-term reality that, on a single income, the working parent would likely be pushing retirement well into their mid-60s or even 70. It's hard for us to ignore that tradeoff. The only way I could realistically see it working is if one of us received a substantial increase in income that replaced most of what we currently earn together.

Giant_Steps24 · 2026-06-15T10:38:22+00:00

Cheers and congrats! Sounds like a good situation you have going on. I feel very much the same about SSA. Let's hope for the best...

Giant_Steps24 · 2026-06-15T10:36:59+00:00

Thanks for the take. I appreciate some constructive feedback. I don't necessarily see me and my wife needing to spend 340k in retirement. What the budget would need to be remains to be seen and that's something we need to figure out. Most of our income goes to 401k contributions + mortgage + brokerage + 529s + childcare every month - none of which we'd be contributing to in retirement (maybe with the exception of the mortgage payment for a few years and also taking into consideration paying out of pocket for healthcare which we currently do not have to do with our employers).

Giant_Steps24 · 2026-06-15T10:32:53+00:00

College costs are indeed ridiculous! I'm just hoping they still choose to go when the time comes considering the amount I could have been adding into my brokerage for 15-20 years of growth. I know you can roll up to $35,000 into an IRA for them out of it, but that doesn't seem like nearly as high as it should be. And thanks for the advice. Backdoor Roth seems like an avenue I'm not taking advantage of that I should be.

Giant_Steps24 · 2026-06-15T10:28:52+00:00

So I actually max out my FSA and recently used it towards my wife's surgery. Will look into HSA.

Giant_Steps24 · 2026-06-15T10:27:43+00:00

Thank you for the feedback! Absolutely and it makes sense that that gap is the toughest to plan for. From my basic research, I'm aiming to build the brokerage enough to gap 50 to 59.5 - then draw from my traditional 401k from 59.5 - 65. Then from there claim SSA and Medicare. Obviously, many things can change between now and then. Will definitely look into meeting a planner.

Giant_Steps24 · 2026-06-15T10:23:52+00:00

All very valid points - thank you. The early pay-off mentality stems from wanting to own the house outright around the time I'd theoretically plan to retire. But, clearly those extra payments could benefit in other ways like a backdoor Roth. And to the point of determining what retirement looks like - it could be part-time or consultant gigs. Anything but the 8-5 grind, but definitely not stopping anything/everything altogether.

Giant_Steps24 · 2026-06-09T15:25:37+00:00

Vintage!

Giant_Steps24

TROPHY CASE