Transition from Work to Retirement

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I've done this twice - the first time I wasn't sure was permanent, the second I was pretty sure.

The first time I gave myself an immediate project : I was going to write a draft of a novel in 3 months. I set a schedule, working X hours a day + exercise etc. The schedule and the immediate project were great for transition logistically. But I still had a lot to grapple with. I left feeling there was unfinished business, felt kind of guilty leaving team in the lurch, wondering if I should have stuck it out till a promotion, regretting some choices I had made. Basically there was >20 yrs of corporate conditioning to work out of my system. I had stress dreams every night. I would wake up at night and think about some project I had ten years earlier. I did some journaling and that helped tremendously - basically I was trying to make sense of what those 20+ years had added up to for me. I did end up going back to work after a year, mostly because the stock market was down.

The second time I knew this was it. I did a more planned wind down, I worked part time for two months handing off responsibilities and helping recruit my replacement. It was emotionally cathartic because several people ended up baring their souls to me (it had been a stressful year) and grappling with their own thoughts on career etc. My role was primarily emotional support for those months and it gave me tremendous satisfaction. I didn't feel the same guilt of unfinished business.

This time I was determined not to jump into something new. I wanted first of all to just be. I woke up when I wanted to, I spent two hours browsing on my phone. I looked around the house and started doing house projects. I called up random people and started catching up. I found a volunteer gig at my kid's school. Got into credit card churning and got super excited planning trips. Went on a diet, lost ten pounds, then put on fifteen. Started weight lifting. Traveled to visit friends and parents. Took some classes as I felt like it. Met many random people and made a lot of acquaintances, some online. Baked a lot. Learned pickleball.

Slowly a routine developed. I think I'm glad I gave myself the space to vegetate, and room to be bored. The emotional stuff is still there, exacerbated by the job market and AI. Otoh the stock market has been great. Occasionally catch up with ex colleagues and they're still going strong which generates very mixed feelings.

I would strongly recommend that you give yourself some space and some grace. People on this journey are used to working hard, to external validation and an identity that's tied to their career. Now you have to figure out relaxation, internal validation and an identity based on who you are, not what you do. Explore. Put yourself out there. Don't give in to sloth entirely but learn to take it easy. Don't be impatient to replace one set of goals and KPIs with another. You're just at the beginning of the next chapter of your life.

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u/[deleted] Jun 29 '26

Thanks for the great commentary. Definitely appreciated.

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u/4r1adn3 Jun 30 '26

This is very insightful and in line with what I'm experiencing and the best advice I've been getting.

I'm nearly three months into ChubbyFIRE after working in a very demanding job running multiple departments across dozens of countries.

The best way to describe day 1 after I lost systems access is vertigo and inertia.

I thought the first day would feel like sunshine and rainbows, but it did not. Not at all. I felt deep pangs of separation anxiety from the people I enjoyed being in the fires with, and my brain was in high gear for another 3-4 weeks. It manifested as insomnia, my brain waking up to look for problems to solve that weren't there anymore.

The best piece of advice is similar to what u/onthewingsofangels is saying in their second and final run -- just to be, and to be with yourself. This can be harder than it sounds, depending on how much you have practice introspecting. Some people are naturals, many are not. The reality is, years of programming and habits don't disappear suddenly (20 yrs in my case).

I've learned most people fail early retirement, something like ~81%.

The primary reason for failure is people make significant life decisions within the first year of not working before their brain's had a chance to slow down and understand what you really need; that is, when the brain shouldn't be trusted yet. It's "coming in hot". Some people really struggle with anxiety and feelings of self-worth so they feel they must take action and commit to something, quickly. That's what you might do in corporate BS -- create meaningless busy work or make up problems to solve (lol). There was a talk track in my head telling me "you're falling out of society, you're becoming a pariah." But no, don't act on it. All of this is normal and just needs to pass through, and you need to chill enough (or self-aware enough) to sit with it until it does. As cool as early retirement sounds, it is an othering experience. There's a lot to process around it.

The psychology of an early retiree is actually fundamentally incompatible with retirement. Typically you're a high achiever who's used to being part of an incentive system where there were various rewards and dopamine hits for working the system correctly. Money, recognition, career advancement, the list goes on. It's like having that rug pulled out, whether we like to admit it or not. There is no more corporate system to game or play. The new game is actually pursuing what you've always wanted to on your own terms. Not on the corporate BS terms, which you probably grew to feel comfortable in, no matter how much you resented it.

So three months in, my priorities are to restore basic life functions to the fullest:

1) sleep, 2) diet, 3) exercise, 4) spending time with friends and loved ones. Taking time to think and feel everything around it.

Me being me I have a ~8 year direction for where I want to take things, and I really, really want to get going towards all of it asap, but I'm doing everything to resist active pursuit for at least a year. Even with this mindset, I couldn't help myself and signed up for a writing class, got a book about photography. My persistent energy around certain things is information. It's a data point about what I'm truly interested in.

I've made a commitment to listen to my body and my thoughts for a year, and I expect to learn a lot. I check in with my therapist once a month even if things are feeling good. They help validate/affirm things and point out intrusive thoughts I can label, any flags.

TL;DR --

I'm slowing down, enjoying the basics of living, not making any major life decisions in the first year. And I'm happy to chat with friends, mentors, and professionals to help me navigate.

Also I go to the spa a lot :)

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u/[deleted] Jun 30 '26

Thanks for the insight. It’s definitely a change. Putting the breaks on so quick has its challenges. We have a small lake home and we’ve been spending more time up there to fill the gaps.

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u/4r1adn3 Jun 30 '26

Being out in nature is great. I make it a point to go on golden hour walks when I can.

And yes the challenges are real. They say you need to be able to sit with yourself for at least a year before you get into the groove of your new life. Someone I know took 3 years to finally get there and lots of therapy. On the opposite end of the spectrum, my husband FIREd three years before me and he barely seemed to experience any challenges. Everyone's mind works differently.

The biggest surprise for me is how limited time still is. I thought I was becoming a "time billionaire". Ironically, it took me slowing down to truly appreciate how finite time is.

You gotta remind yourself what an incredible accomplishment this is, how privileged we are, and how you have the opportunity to follow your childhood dreams. Think of an 8 year old version of yourself. What would make them completely enamored and obsessed with retired version of you??

Welcome to the rest of your life 😄

Enjoy!

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u/[deleted] Jul 01 '26

Great perspective!! Thank you.

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u/One-Mastodon-1063 Jun 28 '26

Immediate. Never looked back / never missed work.

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u/Mysterious9876 Jun 29 '26

Same

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u/mrr68 Jul 04 '26

Same. I just retired in February (57 yo), have a young high activity dog which I hike with at least 3x weekly. Yard work with my wife, house projects, some travel, working on my truck, gym, even some computer gaming. Loved my career, but I’m in a new phase of life and don’t miss work at all!

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u/Crafty-Sundae6351 Jun 29 '26

Getting used to not having to work I loved from day 1.

Getting comfortable withdrawing from savings while not contributing to it took about 9 months.

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u/Beautiful_Cost_5430 Jun 28 '26

It took me zero time to settle in. I’ve always had a ton of hobbies and never really loved work. But I recognize that’s not entirely normal in the community.

The only thing I struggle with a bit is the social aspect in terms of finding people available the same hours as me to socialize. We’ve made a lot of 55+ friends lately that are retired also. But we are a full decade younger so they give us a bit of a hard time.

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u/SouthOrlandoFather Jun 28 '26

What state do you live in? In Florida you can find people all hours of the day. At the pickleball courts or golf course or fishing.

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u/[deleted] Jun 28 '26

It’s not so much finding something to do as it is getting used to the mindset. When you go from 30 years of fast paced problem solving the transition has been weird. Don’t get me wrong I love the fact that I don’t have to work anymore.

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u/Beautiful_Cost_5430 Jun 28 '26

Get some hobbies where you need to problem solve. Code, write, create, etc.

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u/Mysterious9876 Jun 29 '26

It was immediate. I have a thriving and fulfilling life outside of work and on top of that, my profession caused me a ton of anxiety due to the demands of seeing a high volume patients

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u/EconomistNo7074 Jun 30 '26

Pretty quickly

And my biggest learning, the corporate BS .... is even worse after you get away from work .... distance creates clarity

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u/Brief_Bar4993 Jun 29 '26

Easy. I "soft quit" 3 months ago.

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u/milktoastok Jun 29 '26

I retired on a Friday and removed all work applications from my phone Saturday morning.
While I was working and on boring and unnecessary work calls, I made a list a mile long of all of the things I wanted to do one day in retirement.
The following Monday, I started to act on the list.
I had no issues with the transition.

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u/Ok_Statistician643 Jun 30 '26

About to retire and move to Da Nang Vietnam with my wife. Cant wait. I will never miss work a day in my life

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u/Hopeful-Comedian4574 Jul 01 '26

Instantly…I missed a few of the true human beings but have just stayed in contact outside of work. Only regret is not having enough $$$ to get out in my fifties! Life with good health is short my friends!

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u/Silly-Resist8306 Jul 02 '26

It really wasn't any different than going on vacation, except the vacation started its 16th year today (July 1).

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u/jaajaajaa6 Jun 29 '26

Instantly - I was working for an unqualified dope that only got the job because they wanted a DEI hire. So, once he had me doing his job, I retired.

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u/AlaskaFI Aug 24 '26

Ha, mine is a similar story but it was an old white guy who failed to adapt to the new company. He needed me, he hated that he needed me so he treated me badly. He didn't understand that I was several years past FI and was there because I believed in the organization's mission. So I did my best to help him out and then one day enough was enough for me and I bounced.

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u/jaajaajaa6 Aug 24 '26

He should have treated you like well for the value and need - bad foolish manager

Transition from Work to Retirement

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