How I'm Managing Anxiety As An Overplanner Who Wants To Enjoy The Moment, The Process And Semi-Retirement

Plus, within this context, how I think my semi-retired life might play out in Spain

In this final installment on semi-retirement (not forever, just for a moment), I address something that dogs me.

Find the first three installments here, here and here.

The idea that when you’re well-prepared, it can be difficult to enjoy the moment and the process and let life happen. For me, it’s an incredibly hard balance to strike and maintain.

I live with an underlying anxiety about all aspects of the plan—how I’m executing it today, how I need to execute it going forward and how it will take shape (if it goes right and when/if/where it goes wrong) along the way. So—over the last few days—I acknowledged this anxiety and considered ways I can address it. Particularly in relation to the plan.

In today’s installment, I discuss how I hope to strike a balance between preparation and anxiety related to preparation.

The plan being all of the moving/visa/work/financial-related preparations as we get set to leave for Spain on the second day of January 2025 and everything that will/needs to happen once and long after we arrive.

While I don’t think you can go into this type of endeavor without a plan—or, at least, I’d advise against it—obsessively devising, altering, executing and anticipating within the plan runs counter to my conception of semi-retirement. To the level of semi-retirement I ultimately want to end up at.

This makes the question—What will semi-retirement look like in Spain(?)—tough to answer.

But here’s how I’m approaching it and handling the anxiety that can come alongside having a plan.

The reason why my obsessiveness over the plan runs counter to my conception of semi-retirement is because—in addition to wanting to work less now so I can work less longer—a big reason why I like being semi-retired is to have more time to do things other than work.

If I’m spending a meaningful amount of time dealing with the plan, going over it repeatedly and trying to find holes in the plan to fix, this isn’t time well spent. Of course, you have to do some of this stuff some of the time, but you can’t do all of this stuff all of the time. As much as I do enjoy planning, strategizing and problem solving, there comes a point when it’s pointless, if not overly stressful.

In recent days and weeks, I have felt that stress and anxiety more than usual.

Most of us probably should accept the reality that we exist amid a baseline level of anxiety that—ideally—we prefer not to have. If you don’t acknowledge and understand your baseline, it can be more challenging to rein things in when you breach your anxiety threshold. This isn’t fun and it’s certainly not healthy, physically or mentally.

Just as one example—

When we arrive in Spain, one of the first things I have to do after receiving visa approval (also a potential source of distraction and anxiety) is register as autónomo (self-employed) and with Social Security. Once I do this, I have to get on top of managing taxes and my Social Security payments.

I plan to manage and file taxes myself. Haré mis impuestos yo solo. It’s not an easy process, but one I’m convinced I can handle. Over the last few months, I have gotten a pretty good handle on the many moving parts and components of self-employed tax management in Spain. I have a general and good idea of what to expect. I have a picture in my mind of how and when it will all play out. I can see myself actually doing it.

All good things.

However, there’s a lot I can’t do right now.

Because I don’t have the credentials at the moment (they’ll come with visa approval), I can’t get a Spanish (resident) bank account or, more importantly, access the government platforms where you actually deal with Social Security and file quarterly and annual taxes.

I’m not going to start paying for tax management software until the time comes. Same applies to if I end up deciding to have someone help me.

There’s also no reason to obsess over and get certainty—which, often, isn’t possible at this point—on every little thing that comes up related to taxes. I understand the general framework and what to expect. I need to leave it there—for the most part—for now.

Especially because when I search for answers I find them fast. This is one thing I’m realizing that helps me control the obsessiveness and anxiety.

I find a resolution for most unanswered or unclear questions or concerns within 30 minutes or way less, even if one query leads to another, which is often the case. By the end of the 30 minutes, I have a better-than-decent idea on how I will likely proceed. So, why should I bother doing these types of things today when I can do them when they matter, which will include not only resolving, but immediately executing on my new information?

Same goes for renting an apartment to thinking about the visa requirements after approval and, if necessary, when the time comes to renew.

Curiosity—and accumulating knowledge and resources—are great until they kill the cat.

I’m better off dealing with the matters at hand, which, interestingly, give me much less anxiety.

On Monday, we’re going Downtown to get our marriage license apostilled. I haven’t thought twice about the process in weeks, if not months. I know what I need to do and we’re about to do it.

While work—specifically maintaining my present output and income going forward commensurate with working less than 30 hours a week—triggers some anxiety, it’s typically not over the baseline. I don’t give too much thought—(only a little)—to things changing or going awry down the line.

Why? Because I am in the middle of these things and I have—or feel like I have—immediate control over them.

More than anything, anxiety is about control.

The tax stuff is—at the moment—out of my control, in that I can’t do much with the information I have other than absorb and find more of it. This is how I attempt to secure some control over the uncertainty. The uncertainty being the inability to go beyond the planning stages and execute now, which I won’t be able to assume comfortable and meaningful control over until I start actively working on the project.

I’m doing it now. I can control it. My anxiety is in check.

I can’t do it now. I can’t control it. My anxiety crosses my threshold.

Pretty simple. The first step is realizing this shit. The second is dealing with it appropriately and productively.

So, to the question, What will semi-retirement look like in Spain?

I don’t want to think about that much. Because it’s mainly out of my reasonable control.

Instead, I am fine maintaining my current level of semi-retirement (illustrated at the links at the beginning of today’s installment) for the foreseeable future. To set (yet another) plan, especially one that’s too rigid, would go against much of what I just wrote.

So I have made a bit of a turn in this regard.

I still have a general sense of my final semi-retirement level—

• Working less than 20 hours a week, ideally on this newsletter primarily and on articles (or other work) here and there for other sources as I see fit.

Realized after—

• We buy and pay off (or just about) an apartment in Spain.

If I obsess over long-term semi-retirement today, I run the risk of obsessing over the components of the plan that must happen first, such as my workload/schedule and the apartment purchase.

I want to enjoy these things when and as they come. Just as I want to enjoy the iteration of the semi-retired life I’m currently living as I focus on what I can control when I can control it.

Handling life the way I handle my (bad) pool game. One shot at a time.