I'm Retiring on Friday. What's My Plan?

Time flies.  Two years ago I wrote a post called Operation Endgame where I vented about my work situation and casually mentioned that financially speaking, I didn't need to work any longer.  I outlined a couple of options, one of which was continuing to work until I was 50 just to be sure that leaving work was what I really wanted.

If there is one thing that we can say for sure, leaving work at the age of 50 is something that I want even more now than I wanted it two years ago.  

My last day of work is this Friday, October 31st, so let's talk about the game plan.  Why am I leaving work?  What will I do for money?  What will I do with my time?  What will happen when I walk through that open door on my jail cell?

Why I'm Leaving Work

Simply put, I have gone from loving my job to hating it over the past few years.  In the past when I've hated my job, the solution has been to get another job, but that hasn't been working for me.

Lots of people can shrug off a bad day at the office, but I can't, especially when pretty much every work day is a bad day.  When work isn't going well, it tanks the rest of my life.  I have been incredibly unhappy for the past few years.

With that said, I am glad that I took the two year cooling off period, because I needed a hot minute to think through how money would work and how I was going to spend my time.

Money!

Background
I might come back and write more about money later, but right now let's do the Cliff notes version.  I am a life long saver and investor.  The investment method that I use is The Extreme Boredom Method where I've been slowly dumping tiny amounts of cash into mutual funds/ETFs for the past 30 years.  As all of the disclosures say, past performance is not indicative of future results, but I have observed that since 2009 my portfolio has doubled every six years [I lost the hard drive where I stored my pre-2009 Big Money Spreadsheet so that's why 2009 is the starting point for my numbers].  In addition I have a HYSA with a WOC.

[HYSA = high yield savings account.  WOC = wad o'cash.  The amount is a few years of living expenses, which is a combination emergency savings fund and security blanket]

Want more specifics so that you too can get in on the goods?  Like I said I might write more later, but the full story is "I had no idea what I was doing so I kept doing it and things worked out" so my specifics might not be helpful.  Let me hook you up with a few folks who can give you the information in a better format and/or are qualified to give it.

The Simple Path to Wealth by JL Collins (confession: I have not actually read this.  I've heard JL on one billion podcasts and sampled his blog here and there.  But he is hella cool dude, and his advice is simple/easy to follow)

A Purple Life blog (a case study of someone who follows JL Collins and retired at the age of 30 with $500,000 in 2020.  She has not worked since and her net worth in late 2025 is just under $1 million)

The Money Guy show (it's on Youtube and it's a podcast.  If you would prefer to get the info in book form, that would be Millionaire Mission by Brian Preston)

The ChooseFI podcast

The Plan

I've been tracking my spending for a few years now, so I have a good understanding of how much I spend and the cost of things that I want to do.  I will withdraw 1/12 of my planned annual spending amount from my brokerage account each month, so that I have a steady "paycheck" coming in.  Any unplanned expenses will be funded by WOC.  If I ever get to the point where money looks dicey then I will get a jobby job, with the understanding that it might take time to get back into the workforce and it will most likely be for less than I currently make.

Long term, if I've done the numbers right, my brokerage account/WOC should tide me over until I reach 59 1/2 years of age and can access my retirement accounts.  At that point I will make the judgement call on when to start taking money out of retirement.  62-70 year old me will figure out when it makes sense to start social security.

Family wise, I was the breadwinner for family health insurance for many years, and now Hubs is taking over that role.  If he were to lose his job, or you know, want to join me in early retirement, we'll figure out ACA.  Kid wise, we saved more than the boys will ever need for college in a 529 account, and the boys are well on the path to adulthood so we should be set there.

I plan to live entirely off of my money's money and will not pursue other money making activities, at least not right now.  Yes I could get a part time job and yes I could pursue a side hustle, but it doesn't sound like fun.  

Time!

Now we're getting into it.  Once I stop working, how will I fill my days?  Will I spend the rest of my life lazying around the house and watching TV?

The answer is: if I want to, then yes.  But I don't want to.  Here are my goals for the next few years:

• Travel!  I like to go places and see things.  I also like my family and my dog, so there is a balance of being away and being at home.  My trips will be a mix of local tourism, short trips, and some longer-but-not-too-long things.  My general rule is that two weeks is too long to be away from home.  As of right now I have one trip planned for early November, and then I will likely stay mostly home as the weather gets colder, and then I'll plan where I want to go in 2026.
• Time at home!  Here is what I think my typical weekday will look like:
• Get up when the Hubs gets up, hang out with him and the dog until he goes to work (no change from my current routine).
• Work out for as long as I want 
• Learn stuff!  Currently my morning routine is to work out and then go to my office.  My retirement routine will be the same, but instead of logging into work I will be logging into my brain.  Potential areas of study are:
• Continuing education for my CPA license, which is a low cost/low time commitment activity.  Even though I am not planning to work ever again, it's just smart to keep that active.  A CPA license is a very hard thing to get and a very easy thing to maintain.
• Math!  I am notoriously bad at math, which is not just my opinion.  I scored in the 20th percentile on the GRE and GMAT.  As I've said repeatedly, you do not need to be good at math to be an accountant.  What got my wheels turning on this is the Chelsea Callahan YouTube channel.  She is a content creator who recently started working on a computer science degree and took a remedial math class over the summer.  If I poked around in this area, what would happen?
• Languages.  I do not think I will ever reach fluency in another language, but I enjoy playing with words.
• Photography and photo editing.  I have a couple of photoshop self study books that I did a long time ago and I have always wanted to repeat the classes but I just never found the time.  I've got time now!
• Hmmm, would I ever want to get into video and video editing?  The implication is that I would do something on YouTube or social media with this.
• A topic for late January/early February me to figure out is if I want to renew my CPP certification (payroll thing).  Reasons not to are that it is time consuming, expensive, and God willing I will never use it.  Reasons to do it are to be obnoxious and prove that I still got it.  For this reason, I will probably do it.  I can either take the test in the spring or fall, but if I do it in the spring I'll be studying in bad weather instead of good weather, and if I fail then I can still retake it in the fall (although surely if I failed I would take my lumps and give up because I can't imagine going through the test twice in one year).
• Eat lunch and walk the dawg.  No change from my current routine except that the walks can be longer if we want.
• The first priority for the afternoons will be doing stuff around the house and adulting/life admin activities. I might just be able to carve out some leisure time as well.
• No changes to the nighttime routine: cook dinner, hang out with Hubs and walk the dawg, chillax in front of the TV, go to bed.
• Other things to do
• Social stuff!  Between being an introvert and being stressed out of my mind for the past few years, my local friend group is pretty thin.  Even I am not an introvert to the point that I want to spend all day everyday at home not talking to anyone.  
• Have I mentioned that I like hiking?  Have I also mentioned that there are a few local hiking groups in my area that meet on weekdays?
• Check out my local ChooseFI group (aka hang out with like minded money nerds).
• Continue to pursue other areas of interest that are also social (ex: book club).
• Volunteer.  This is more of a next year thing, but there are some things that I want to get involved in for a variety of reasons.  Areas of interest are animal shelters and local historic and nature sites.  The reason that I'm not going gung ho and getting involved in these things now is that I need a period of chill/no obligation time to decompress.  The last thing that I need is to jump from 40 hours of paid work to 40 hours of unpaid work.
• Family.  My parents are in their early 80s and in disgustingly good health.  At some point that will change, though hopefully not for many years to come.
• Part time/contract work.  I will not seek it out, but I have a habit of getting talked into things.  I can see the appeal of working in the winter and then taking the rest of the year off. Well, right now this has zero appeal but in a few years I might be interested.

What If

What if I am making a terrible mistake?  What if I don't like not working? What if the stock market crashes?  What if the world comes to an end?

• What if I don't like not working is the easiest problem to solve.  I can always go back to work!
• Duh I am aware of things like age discrimination and that it's hard to get a job.  I would have to do more than want it, I would have to work at it and I might have to settle for (gasp!) making five figures instead of six figures and going to a physical work site like a plebe.
• Dear God, I cannot imagine going back to work as a corporate accountant/payroll guru but it's an option.
• Since I don't need a high income, I'm free to pursue something lower paying but more rewarding.  Possibilities are a pet sitting side hustle or working for a kennel (experience to be gained by volunteering for a shelter).  On the hooman side, I can see training for a skilled healthcare job like a nursing assistant or phlebotomist and working at that for a few years, after which I imagine that I would hit another patch of burnout so I would do another retirement to recover.
• Um the stock market is always crashing.  What goes down has consistently gone back up for the entire history of the market.  I only need to sell off a small portion of my portfolio each month.  If something heinous is going on when it's time to sell, I can always take the money out of my WOC and make up for it when the market goes back up.
• What if the world comes to an end?  Well then I'm screwed along with everyone else and having a job will not save me.  I don't want to make light of today's troubles, but there is always bad stuff going on.  The worst outcome would be to take the path of guaranteed unhappiness and stay at work.

Alrighty friends, that's what I have to say about that.  Now for the hardest part: getting through the final five days/40 hours of work.  See you on the other side!