r/earlyretirement

Having worked hard my entire life I neglected having any kind of hobbies or interests. I worked and that was my entire personality. I worked hard so I could retire comfortably and now that I've done it I feel lost.

I feel like I need to redefine myself but don't know how. I'm the first to retire in my limited friend group and my wife is still working for another 2 years.

For people in a similar situation, How did you transition and reinvent yourself?

You guys! I did it! I feel incredible! Last day was my last day. Turned in the phone and laptop. Had a very long, detailed meeting with HR yesterday where they seemed VERY concerned about confidentiality and me going to a competitor.

Hmmmm. I don’t think anyone at the gym, on the beach, nor in my family care about any corporate info and most importantly- nor do I! I kept reassuring them and highlighted the travel I have planned, my volunteering, the extensive activities I’ve organized ( book club, hiking, camping group etc). I was confused why they are so worried I could go to a competitor. I. Do. Not. Want. To. Work. Anymore. They might as well have been warning me ( with slightly threatening overtones)?not to punch myself in the face. Ya. Uhm. Okay. No problem. We are on the same page here. The HR guy seemed nice- just very concerned and intent on going through my employee agreement.

Now, I’m off to go celebrate with my family at a nice lunch!

I feel amazing! If you guys have any thoughts, words of wisdom, please send them my way!

☀️☀️☀️☀️☀️☀️☀️☀️❤️❤️❤️❤️❤️💗💗💗💗💕💕💕💕💕💕💕💕

My spouse and I both retired at 50. Throughout our marriage, I've been the primary breadwinner, but I've also been the one who managed our finances, tracked spending, planned for retirement, and generally knew what things cost.

Now that we're retired, I'm realizing my spouse doesn't seem nearly as aware of the cost of everyday purchases, travel, or how our spending affects the long-term plan. It's not that they're irresponsible—they just never had to think about it the way I did.

I'm curious whether anyone else has experienced this. It doesn't have to be a husband/wife thing—I'd love to hear from men or women whose partner isn't as engaged with the financial side of retirement.

How have you handled it? Did your partner become more involved over time? Did you change how you talked about money or set spending guidelines?

I retired early at the end of June 2025 from teaching at 52, before I was of official retirement age. I was vested, but didn't have 30 years in to get my full benefits. I currently have insurance through our state exchange for myself and my 2 daughters, costing us $1400 a month.

I got a letter from my previous employer, stating that they reviewed my records and I am eligible to join their health insurance, costing $550. The criteria for eligibility were vague - worked 30+ hours a week or be rehired with 26 weeks. I was rehired in that time frame, but as a sub. I worked probably 20 days last year. Subs do not qualify for health insurance.

I called and went in and was told I got the letter because I am eligible to join their plan. I questioned them, but they just keep saying I am eligible. The letter says I would have insurance through Dec 2026 and could fill out the paperwork to continue for the next year (if I still meet the eligibility requirements).

Is it worth it to save $850 a month for the next six months, knowing that I might have to go back on the exchange at that time? Could they at some point say that I wasn't eligible and I needed to pay the full price?

Retired earlier this year after 30+ years in the corporate world.

I started working with a holistic wealth manager (financial planning, tax management, estate planning). He is a fiduciary who has been in the business for decades and was recommended by two colleagues that work with him. I really like him. I enjoy our conversations. He seems trustworthy. His firm gets strong marks in various reviews. But I am still so nervous about moving all of my money into his firm's care.

For decades, I had been managing my money myself -- and by managing I mean having CDs, and high-yield savings accounts, and getting into mutual funds and then just letting them sit. And I had them at different places (Fidelity, Schwab, Vanguard), thinking about this as one component of diversification. And I've watched them grow to be upwards of $4M in total. Which is a LOT of money.

Now, he wants me to put all of the money into Schwab, into different accounts, that will be invested in different custom portfolios with different risk/return dimensions -- that will align to "now", "soon" and "later" buckets.

It all makes sense intellectually -- but I find myself so anxious and nervous to actually pull the trigger on all of this. His recommendations look like they would definitely out-perform what I am doing now. But (and I know this is silly) what if something happens to Schwab? And what about embezzlement?

Has anyone else experienced this feeling? Did you get over it? Do you regret anything?

I am thinking of rolling my 401K which has a mix of mostly Roth and the company match in pre-tax into my existing Rollover IRA and Roth IRA. It seems like it will be simpler to manage and I will be able to see exactly how much Roth I have (today I have to do some math). I know there are some protections with the 401k from creditors that might not exist in the IRAs (I’m in NJ).

The 401k is at Fidelity with all my other accounts and has decent investment options and fees.

I just wanted to get other peoples thoughts whether to roll over or not. I am not sure I am thinking of everything.

Was reading this amazing article on X just now about a Southwest pilot retiring and doing his final flight with his daughter.

However sweet this is, I'm like 65?! Ok, maybe just maybe he truly loved his job. Flying. But it's a corporate airline so it can't be that perfect stay forever job. He seemingly retired in the military so can't be struggling. He's also making tenured pilot money.

Why didn't he just retire early and maybe just do part time instructor work?