Being Early Retired Won’t Magically Make You a Better Person

Being Early Retired Won’t Magically Make You a Better Person

(Or: Why I Sent Out My Wedding Thank You Notes 7 Months Late)

We all do it.

You’re sitting in traffic, or at your desk, or in bed trying to fall asleep, and you’re daydreaming about what life will be like once you finally have the time to do all those things you’ve been putting off because you’re just too “busy/tired/focused on getting that promotion right now.”

Once you’ve made the money you need to retire early you’ll finally be able to get organized, and be the person who remembers everyone’s birthday and sends them a nice card while also keeping a perfectly spotless house and starting that entrepreneurial passion project you’ve been thinking about and getting in shape and remembering to call your grandmother.

I know I certainly thought so.

Despite reading some very good articles by other early retirees about life “on the other side” I still swung into early retirement with a pretty rose-tinted view of just how much easier things would be when I didn’t have work filling up eight hours of my day.

early retirement piece of cake ocean
Early retirement is not…a piece of cake (sorry, sorry)

But as they say: no matter where you go, there you are.

Or in other words, I entered early retirement as the exact same person I had been the day before.

Even now, after over a year of being early retired, with every day fully open to me, with few obligations, and fewer needs, I’m not the super-organized, thoughtful, always-productive version of myself I envisioned when I daydreamed about life after leaving my job.

In fact, in a lot of ways, I’m much less productive and thoughtful, and I no longer have the excuse of “too fucking busy” to fall back on for my failings.

And that’s kind of a hard realization.

In fact, I think it made me a little bit depressed for a couple months.

So, in case it helps other people in similar situations, I thought I’d unpack a little of what I’ve learned about motivation and happiness, and how I’ve started to address my own deficiencies.

Why I Still Don’t Floss My Teeth

I don’t floss.

And it’s not just because the science is still out on the efficacy of flossing.

Even with all the time in the world, no set bedtime or wake-up hour, and a bountiful supply of the stuff (provided on every single office visit by, one can only surmise, dentists with more optimism than sense), I just can’t find it in me to take the extra 60 seconds to get my gums good and bloody every night.

I don’t take the time to keep the house spotlessly clean every day, either (or, let’s be honest, even every week).

I still take days or weeks to respond to emails or texts from friends and acquaintances.

And my wedding thank-you notes went out seven months late (I really do love our fluffy new towels though, thank you!).

So why don’t I do these things better, on time, and habitually now that I have all the free time I’ve always craved?

I’ve thought about this a lot, and have come up with a couple different reasons.

  1. I didn’t do any of these things well when I was working and, as the title of this article says, Being Early Retired Doesn’t Magically Make You a Better Person.
  2. I don’t want to do them, and that hasn’t changed just because my employment status has.

Let’s dive into each of these excuses.

1. Being Early Retired Doesn’t Magically Make You a Better Person

All the bad habits, corner-cutting life shortcuts, and coping mechanisms I’d developed over a lifetime of almost constant over-scheduling came right along with me when I transitioned into early retirement.

And guess what?

Being a better person is a deliberate process that takes time and conscious effort; it doesn’t happen magically just because you have more free time.

To get rid of those bad habits and all the other baggage takes work. 

It’s not an “on/off” switch; it’s closer to an old-time submarine hatch (you know, with that wheel thing that always seems to get stuck in action movies: you gotta push on it hard to get it to move and open before the rushing water reaches you).

And because I wasn’t actively working on improving myself, surprise surprise, I didn’t improve.

2. I Don’t Wanna

When I was working I always thought the reason that I didn’t get all those “extra” things done—like thank-you notes and house cleaning and returning emails—was that I was just too tired from having done all my “real” work at my day job.

I thought I arrived home burned-out from meetings and answering emails and writing blog posts and that I just didn’t have any reserve left to do any additional “work” that day.

Until I early-retired.

Because even after sleeping-in until 11, eating a leisurely breakfast with tea, and maybe reading the paper or a novel for a few hours, I still didn’t want to do any of that stuff.

Steven Pressfield, author of the novels The Legend of Bagger Vance and (the far more badass) Gates of Fire, has a term for this that, in his short book The War of Art, he names Resistance (capital “R”).

He defines it thusly:

“Resistance cannot be seen, touched, heard, or smelled. But it can be felt. We experience it as an energy field radiating from a work-in-potential. It’s a repelling force. It’s negative. Its aim is to shove us away, distract us, prevent us from doing our work.”

And, as I’ve learned, just because you have more time, doesn’t mean you have less Resistance.

My own mental resistance (sorry, Resistance), it turned out, was to the kind of work, not the quantity of it.

But, Being Early Retired Does Give You Time to Work on Being Better

The silver lining here, of course, and the reason you’re reading a 2,000 word blog post on the subject, is early retirement allows you the time to think about and work on yourself deliberately.

In fact, you might say it forces you to think about and work on yourself deliberately, because you can no longer excuse your behaviour as, “Oh I’m just so busy right now!”

I’ve learned a lot about myself, whether I wanted to or not, and that’s certainly a good thing in the long run, but it’s not an easy thing.

And the good news is, with some of these hard lessons I’ve been forced to learn I’m coming out of the downcycle I was in (even as the CCP Flu is doing the opposite to just about everyone else in the world…) and, with the excitement of finally starting work on a core passion project, have learned and written more in the last three weeks than I did in the previous three months.

I’ve also been getting better sleep, maintaining a healthy workout routine, and generally feeling more content and productive than when I was flitting around across ten different projects and ideas. And all these little changes and habits tend to compound (as I talked about in my Purpose post) and so their positive results are more than just a sum of their parts.

But to pay-it-forward a bit, here are some applicable things I’ve done to address me being a total piece of shit for several months.

Some Tools and Mental Models I’ve Used to Stop Being a (Total) Piece of Shit

1. Working on a single, unified passion project.

Having lots of different hobbies and projects is fun, for a while, but it grows tiresome after you realize you’re not making deep progress on any single one of them. Focusing on one project at a time helps you to not spread your effort too thin, “like butter that has been scraped over too much bread.”

2. Having an accountabilibuddy.

One of those hard things I’ve learned about myself is that, despite wanting to be the type of person who can just start a project and be self-motivated enough to make it wildly successful all on my own, I’m actually the kind of person who works better with someone else to bounce ideas off of, talk through plans with, and hold each other accountable to shared goals. Once I let go of my ego enough to realize this, things started flowing a lot faster and I was finally able to start the passion project I’d been wanting to start for a year-and-a-half but had been putting off for bullshit reasons.

3. Upgrading my to-do system.

This could be a whole post in itself (and maybe it will be), but my previous system for “getting things done” was, charitably, a mess. Three different to-do lists plus a grocery list on the notes app on my phone, another as an unsent email draft in my online email client, and another as a .txt file on my desktop. No method for prioritizing what to do, and no habit for deciding what to work on the next day.

Now, I’m as much a sucker for productivity porn as the next unemployed tech worker, but “GTD methods” and “Elon Musk’s top productivity tips” blog posts are usually just so much wantrepreneur wank, and never stick. So when I read about the “Rule of 3,” despite my in-built skepticism, I liked the simplicity of the idea.

It’s basically just; write down three things you need to do for the month, three for the week, and three for the day (and then update in the evenings for the next day). Just three. 

As someone who used to write 15-item to-do lists every day, get through four of them, and then feel shitty for the rest of the evening, three is a nice change. It also forces me to choose only the most important to-dos each day/week/month.

With this new to-do method, I also upgraded and rationalized all my various to-lists into a single location: the free Todoist app (picked out of the many others I tested because it auto-syncs between desktop and mobile versions, and I like the ability to see previously checked-off items).

4. Consciously tackling bad habits.

I’ve found, for me, removing bad habits is more effective than adding good habits. For example, not looking at screens between dinner and bedtime helps me sleep sooner, and better (he says, writing this sentence at 11pm on his computer—hey, I’m a work in progress).

5. The “Enthusiasm Slingshot.”

I think this idea is somewhat original to me since I haven’t seen it laid out in this exact form before, but it’s probably not. Anyway, this is a small “hack” that helps me get excited to sit down and work on an important project. 

Basically, using the research/theory of “mood momentum” and applying it to the feeling of a caffeine high (sorry, this likely won’t work if you’re the type of addict that has numbed your dopamine receptors by drinking 12 cups of coffee a day), I try to do the following:

I combine the “soaring feeling” you get from caffeine (I usually drink some strong green tea or matcha) with, at the same time, reading something interesting or positive in my field of work. As soon as I feel the caffeine high peak I try to then immediately get started on my work.

I’m convinced this mental association between the positive feeling of the caffeine high and the news and information about my field gets me excited to “do something productive” and make a contribution to the space, and so it’s easier to overcome my Resistance and sit down to get started.

Being Early Retired Is Still Great

Reading all the above you could be forgiven for thinking this whole early retirement thing is more trouble than it’s worth.

Like Cypher in The Matrix, you may want to throw your hands up and concede that “ignorance is bliss” and that all this messy self-discovery stuff is less fun than distracting yourself all day with work and some juicy steak.

And in the short-run, having to confront your own failings is definitely not fun, but I’m pretty sure it’s better in the long-run to understand who you really are. And I still eat plenty of juicy steak in the meantime.

hanger steak keto paleo
Sure seems real to me.

I still certainly stand behind the sentiment I expressed at the end of my last post that: 

When I’m asked if I ever want to go back to a full-time job, my answer always has been, and continues to be, a very quick, “No.”

And now you’ll have to excuse me: I’ve got some long overdue Christmas thank-you notes to write (sorry Aunt Jennifer!).

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9 thoughts on “Being Early Retired Won’t Magically Make You a Better Person

  1. JP, as for your rule of threes, a couple of questions:

    1) Do you allow yourself any “nothing” days where you don’t get anything accomplished, or is that too disrupting? Or can you kind of make it work with clever choice of to-do items? I’m thinking of, say, a day where you are traveling/on vacation: do you just make up items like “get to destination” and “see the Mona Lisa” as to-do items? IOW: are these items always “work” or can they just be fun goals?

    2) Do you pay any attention to the weekly cadence, e.g. treat weekends differently than weekdays?

    3) Are the monthly and weekly goals “meta goals” such that the weekly and daily goals (respectively) are in the service of those monthly goals, or are they just “less urgent” things like “I will send out thankyou notes by the end of the month?”

    Anyway, appreciate the observations! And don’t be too hard on yourself, there is no cosmic score-keeper tracking “how well does JP live his life” and as long as you are doing exactly what you want to do, I don’t see how that can be something you feel guilty about…

    1. Andy, to answer:

      1) I do find if I take a day off in the middle of the work week it’s disrupting and hard to get back into the groove of being productive (kind of like how “task-switching” on a more micro level is also disruptive to productivity) however, related to 2) I do take weekends off generally, especially since that’s when most social events happen. Though I will try and shoehorn in work on side projects that are not my main focus on those days (with varying levels of success).

      3) Generally, yes, daily goals serve weekly goals serve monthly goals (e.g. if the monthly is “write 4 blog posts” the weekly would be “write 1 blog post” and a daily might be “write introduction to blog post”) but I do treat the daily goals as allowing a little more variability within those. For instance, a monthly goal will never include “schedule my eye doctor appointment” but that may be a daily goal, and while most weekly goals roll up to monthly goals, I may have a single weekly goal that doesn’t (for instance, “clear out my email” or similar).

      And thanks! Though for me the difficulty is doing exactly what I want to do in the long-term, because often “short-term me” has different ideas…

      1. BTW, I have effectively retired as of this week… I still have a couple of weeks of vacation that I am playing out, but I’m no longer doing any work and will not be doing any. I can tell you, though, it has not been a smooth transition, not yet, anyway: too many external things getting in the way in general and playing with my mind in particular… The COVID thing most notably, not only did it all the sudden change what “normal” was so that, just when I had the time and freedom to go and “do things”, all the “things” were closed off; it also played havoc with my nest-egg and for a while it looked like I would have to delay retirement (fortunately, stocks returned to close enough to normal that it’s back on). In addition, I had a couple of personal tragedies with a good friend and my sister in law passing (both younger than I am), and I’ve had some medical problems that culminated in a night in the ER/ICU (mostly ok now, but still do not have a complete diagnosis). So I haven’t really had a chance to “get in a groove” yet. That said, I think it’s starting to head in that direction as covid restrictions loosen up and there are more things to do etc… Hey maybe it’s time to start my own “retirement blog”! 😉

        1. Congrats!! I was actually thinking of you when some of the market craziness hit. Glad you’re going through with it even in these non-normal times! (I’m still up from when I left work in 2018, despite being down about 3% for this year).

          And make sure to take care of yourself. You have the time now to focus on health and it’s a pretty rewarding area to learn about (as I’m finding for my side project).

          But definitely DO start a blog, I’d love to read it 🙂

  2. Dearest Son,
    –I enjoyed reading your interesting post.
    –Only floss the teeth you want to keep.
    –I still think you should get a job.


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