The Guilt of Early Retirement (And how to slap it in the face)

…..or rather, trying not to slap your past–self in the face.

Today I was having coffee with a friend who recently retired from The Job. He’s been enjoying it so far, but mentioned that occasionally he feels guilty about not working while there’s still obviously a need for cops, and wonders if he could have done more. This is from the guy who spent decades on SWAT, was shot on two different occasions, and saved many a life while spending most of his career on call and on late shift. The good things I did on the job pale in comparison to his accomplishments. In fact, most of the good shit I did was a direct result of the training he built. So to hear that he felt guilt in spite of all he’d accomplished was surprising.

But then, I’ve been there too. And it shouldn’t have surprised me; hell, I’d bet it’s pretty common.

There’s lots of jobs out there where you feel like you’re contributing to the greater good or whatever. Doctors, Dentists, Strippers, Firefighters…sure, all these make sense. But there’s plenty more professions out there that do the same thing-work to make the world better. Take my wife; she’s an engineer who builds and maintains manufacturing plants which produce live saving medication. Ok, so she’s not performing open heart surgery, but she is part of a bigger machine that is truly making a difference. We can split hairs about the relative impact of our work and all that, but many still have a job that exists because it does some sort of good. But what happens when we leave that job? We can feel a bit guilty. And I think that’s perfectly natural. Dealing with it is something we have to come to terms with, and I’ve stumbled upon a few ways to do so.

Don’t get cocky

Let’s go here first.

In the grand cosmic scheme of shit, none of us matter. Yup, we’ve all heard of that. But when we zoom in, we can see that what we do does matter to ourselves and those around us. Heard that before as well.

But in the mid-range, things can go back and forth as we change our perception. If we let hubris inflate our egos, we can start thinking our workplace depends on us, and without us everything would fall apart into some post apocalyptic zombie nightmare. This is generally a symptom of overwork, or worse a workaholic excuse.

This reminds me of years ago when I made this mistake: Back when I was a new detective assigned to an violent felon tracking unit, our city was plagued by a home invasion crew which started raping their victims. It’s one thing to rob somebody, but that level of shit pissed everyone off. Still pisses me off to think of.

Our unit worked 14-18 hour days with no time off for weeks tracking down these fuckers. A couple of weeks in, two good friends of mine were getting married, and I’d already RSVP’d and gotten the day off approved. My boss reminded me of my upcoming vacation time, and said it’d be fine if I took the day; the rest of my unit had plenty of help as they continued the manhunt. Did I take the day off? Nope. I wanted to be there when we got those fuckers, and I thought I’d miss out if I went to the wedding. I thought that maybe I’d see something that would make a difference in the case. I skipped the wedding, and spent another 14 hours checking houses and doing surveillance.

This was stupid, I let hubris get to me. In real life, there isn’t some hero detective that’s the only one who has the key to breaking the case. It’s always just slow, methodical work and lots of team efforts to make it all come together. My unit would have been fine without me, and my input didn’t make or break the case. Instead, I snubbed my friends because I thought I was special. We caught the guys, but not because of any great thing I did on my friends’ wedding day. I forgot that I was a small part of a larger system that can operate just fine without me.

If we’re not a completely self-absorbed narcissist, even a small amount of self awareness will help us eventually realize such self-centeredness is total bullshit. Even my knuckle dragging ass came to this realization, so it must be possible. I think this is an important part to get clear on if we feel guilty after leaving our profession which on some scale makes a difference. First, we must examine this guilt and see if hubris is a component. It’s ok if it is; we’re all human. Like them AA folks say, the first step is acknowledging a problem. Step two in this case is realizing we’re not the end all be all. Our former coworkers will get on just fine.

But hubris is usually only part of the story. We can end up like my friend who said “…look, I know I’m replaceable, and someone will come in and probably do my job better than me…but I still feel guilty getting to do what I want while I know there’s work to be done.”

Which leads to…

Don’t slap your past-self in the face.

If you can afford to retire, or even take an extended break from while you figure out what to do next, you have that capability because of your past-self. Are we getting into some woo-woo multiverse time travel bullshit? No…..? fuck it, let’s go there!

There’s this movie starring Bruce Willis, where he’s an old grizzled dude and he meets his younger self and they have to kill each other or something. Now imagine that this movie didn’t suck as much (to be fair I’ve never seen the real one, I’m just guessing it blows), but my version is really boring because it’s set in the real world thus lacking constant drama, shootouts, and unicorns. Here’s the plot of my imaginary Bruce Willis movie:

Young Bruce is your standard cop/assassin/stripper/whatever, because obviously he’s been typecast at this point in his acting career. But in this movie he sees the writing on the wall, and doesn’t want to turn into the old hard boiled version of himself that is so prevalent in his profession. He stumbles upon The Simple Path to Wealth, and sets about investing more than half his income for the next decade or so, all the while dreaming about the day when he won’t have to work anymore and he can finally dedicate more time to making cat themed pottery. Then one day as Young Bruce is halfway to his FI number, Old Bruce comes back in time and slaps Young Bruce in the face. Old Bruce yells “Fuck you past-me for working so hard so I could do what I want!! I realized I don’t want to make cat themed pottery all day, I just want to go back to my miserable job and hate my life!!!”. Then Old Bruce would get in his sweet retro pontiac firebird and peel out into the sunset whilst Journey plays. Roll credits, and we all go ask the theatre or Paramount+ for our money back because damn; we just wasted 2 hours of our lives watching that crap.

Not only would my imaginary Bruce Willis movie suck almost as much as the real version, it just wouldn’t make any damn sense. You’d be thinking, “Why doesn’t he just try something else besides making cat pots, or go find a job that’s similar but less demanding, maybe even try working on himself a bit to figure out why he feels the way he does??”. Duh.

The point of all this imaginary movie thought experiment is this: To get to some sort of FI, you worked hard in the past to get there. You probably spent a good amount of time back then dreaming of the day that you’d hit your number, and imagined all of the things you’d do with your free time. While the shock of leaving your job can be weird, and you may even feel guilty, if you let these feelings ruin your freedom, you are essentially slapping past-you in the face.

Personally, when I feel a little guilty for not working The Job anymore, I think about how I owe it to past-me to try and make the best out of my freedom that he worked so damned hard to scrape out for current-me. Like giving past-me a pat on the back instead of kicking him in the dick.

Of course this doesn’t completely get rid of our guilt for not working either. So finally we can also

Kick the can down the road

Or, in a positive reframe, we can work on figuring out what part of our old job we liked, and find something to do that has that component but less of what we didn’t like. Yeah, it’s still going back to work. But it’s way better than going back to our old full-time job. And for some reason I’m using the royal we-so let’s get less uppity: As described before, I went back to a part-time gig, and it’s been super helpful in helping me adjust to this post FI freedom which is both awesome and weird.

If I were sitting down for coffee with past-me it might go like this:

Past-JSD: “Wait, I spent all that time working so you could continue to work???”

Now-JSD: “Yeah man, but it’s part time, kinda fun, and I get to do it on my own terms. Still have lots of time to do whatever I want; mountain biking, writing, naps, etc,”

Past-JSD: “I don’t know dude, seems like all this work I’m doing right now is kind of a waste”

Now-JSD: “Yes and no-maybe you could have quit sooner if you knew for sure you’d be making money after leaving The Job. But I know you; you needed that money to feel like you had the freedom to do shit on your own terms. And it sure feels nice having it now, knowing I can leave this part time gig whenever I want.”

Past-JSD: “Still man, this seems weird”

Now-JSD: “Yeah, well, you don’t know me. We’ll continue to change, and what we want will change along with it. Also, due to our current understanding of physics this conversation is impossible, so I’m out of here. Deuces brah.🖖”

This all kind of relates to finding our purpose, and a whole other level of woo-woo shit. Feeling a little guilty about not working is ok. Maybe another part of that guilt is that when you were working you felt like you were fulfilling a purpose. Leaving work removes that fulfillment. If after some time you still miss that fulfillment, try to figure out why you felt that way and find another way to serve that purpose in a way that doesn’t run you ragged.

For me, I noticed I missed helping people. I was lucky that in my former job I rescued a few hostages, and also made other people’s lives better by subtracting those with bad intent from the general population for a while. I also got to help people by just being there on the worst day of their life, and try to be the kind of cop I’d want to interact with if my life had gone haywire.

After leaving work, I tried other ways to help people. I was a substitute teacher, I delivered people their lunch, and I even helped them file their taxes. These scratched that “helping people” itch to varying degrees, but it still felt like I was missing something.

As I dug deeper, I realized I missed helping people by protecting them. Apparently my love language is guns and threat mitigation. I tried training some soldiers, helping them build their skills so they could better protect themselves. I went back to executive protection. Both gigs pale in comparison to blowing up doors, throwing flashbangs, and rescuing hostages. But for right now, they fill that purpose void. They’re good enough while still letting me live a more enjoyable life.

Closing the Loop

Everyone is different. And I’m guessing everyone’s purpose, and what works for making them feel fulfilled will be different too. What’s making you guilty post work will be different then me. Though it will probably still be a mix of some of the above stuff. A little hubris, a little bit of forgetting what it took to get here, and some lost purpose. And likely at least one more factor I haven’t thought of yet.🙃 If you end up feeling guilty, hopefully you can use your hard won freedom to figure out the right mix of all of that which works for you. It’s some self-work that never ends. But it’s work worth doing. You owe it to yourself-past, present, and future.