Should I focus on trying to retire?

Two years ago I realised for the first time that I end up making the “right” moves in life, but often I make those changes later than the average of my peers.

Owning a house, investing money, getting married, having kids… It's not that I fail at those projects, or shun those life decisions: it's just that sometimes I get to those places a few years later than would be desirable — judging with the benefit (and the bias) of hindsight.

That was stating the obvious, I guess. Of course you want to start earning money earlier rather than later. Of course you want to travel soon, so that you'll have more time to visit more places in your life. You'll probably end up marrying and having kids (like most people do), so why postpone it unnecessarily? And yet, for me, strangely, that was a novel realisation.

Armed with that silly “insight”, in 2023 I noted that

“now that I've spotted a trend in my life trajectory, it should be ‘easy’ for me to course-correct. […] That means making an effort to identify the next life goals, and acting quicker to get there. And so I have been wondering:
What are people my age starting to do now?
What will they be doing in a few years' time?”

Well, in the last year or so I have had a few surprising conversations with at least four friends (who are more or less my age and lead similar lives), all pointing in the same direction: their desire to retire asap from “work” — and in some cases, even their ongoing efforts to do just that.

When that idea had popped up in only one or two casual chats, I didn't give it much import. After all, there are always some people who find their work extra tiring, or feel stuck in a career that bores them to the bone. Those people may long for early retirement, or at least a sinecure (here in Spain, that means joining the civil service or getting stable employment at a very large company).

But this “I hope to retire in a few years' time” thing kept surfacing with more friends I met. What was going on?

To be fair, I kind of saw this one coming two years ago, too:

“Some people my age who can afford it […] even retire from work altogether. What's not to like about that? Of course I'd want that, too.”

Would I, though?

I am still confused about how to frame this, and so I keep on contradicting myself in conversations (and in posts). What does “retiring” mean?

If “retiring” means “getting the same money you earn now but with no obligation to work at all”, then everybody (including me) would like that, right? After all, if one really likes their job, or derives a lot of meaning from it, or is the kind of person who needs a job (any job) to rescue them from boredom or from the presence of a family they don't like or from the angst of existence… well, one can always insist on going to work “for free”.

If, on the other hand, “retiring” means “landing a job so comfy and so secure that in practice one works very little and can stop worrying about money and about old age altogether”, then I'm not so sure. Barring aristocracy, diplomacy, high-end PR, the world of celebrities, etc, it is rare for a job to be both very comfy and very secure. Also, the logic of the market tells us that such positions, to the extent they exist at all, have to score abysmally low in some other important dimension (occupational hazards, social stigma, poor salary, negative externalities, soul-crushing nature) or else they would be The Job That Absolutely Everybody Seeks. Many of the typical public service jobs that seem so coveted in Spain are unappealing to me — even if they often mean working 35 hours/week with no overtime, a predictable stream of easy tasks, no stress, generous time off, and employment virtually guaranteed for life. Still, I have to admit that getting such a position may be objectively a good move, if you can live only for the excitement derived from areas of life other than work and you are able to put up with the tedium of bureaucracy and stagnation until (actual) retirement.

Finally, “retirement” to other people means “not being on a payroll, not ‘having a boss’”. Those people mostly are (or are trying to become) freelancers, contractors, self-employed, artisans, artists, entrepreneurs, “content creators”, “influencers”, etc. If they say they are “retired”, I think they are deluding themselves: they are working, only not regular jobs. So for the purpose of the discussion, I will exclude this definition.

Thinking of meaning #1 (ie, proper retirement), this is what I was thinking two years ago:

“The question here, I guess, is whether it's important enough to put the effort and make the sacrifices necessary to get there some day. Retiring early is very tough.”

So, is it worth it?

To try to understand this better, I thought about these four friends of mine. This is roughly who they are (they are all male, Spaniards, married or in stable relationships):

• A bit younger than me, one kid, inheritance, sources of passive income, recently joined an IBEX35-listed company.
• A bit younger than me, two kids, engineer, employed, sources of passive income.
• My age, two kids, side gig, more than a decade working at an IBEX35-listed company.
• A bit older than me, two kids, two decades or more working at an IBEX35-listed company.

Now, how do they plan to “retire”?

• One of my friends invested quite successfully years ago and now hopes to grow his portfolio enough to actually stop working altogether and live off of it (meaning #1, proper retirement).
• Two other friends have their eyes set on the very generous early retirement programmes offered by their private employers (meaning #1, proper retirement). They can't retire just yet, but it seems they could in the not-so-distant future (a decade or more before the standard retirement age of 67). And I think one of these two earns nearly as much from a side gig which occupies little of his time as he gets from his full-time employment.
• The last one doesn't expect to actually retire any time soon, but looks at his current employer as the last career stop for him — for the job security, the work-life balance and the ease of mind (meaning #2, the sinecure). This one is also building significant wealth and alternate sources of income, so I see him easily pivoting from #2 to #1 in the future.

Here comes yet another very silly insight of mine: by looking at their individual situations so dispassionately and trying to describe them in writing as I did here, I noticed common patterns that should have been obvious to me from my conversations with them. (Yes, really.)

• Three of them work for one of the thirty-five largest corporations in Spain (and two of them have been there for many years).
• Three of them are benefiting from sheer luck (family inheritances, questionable investments that worked great in the end) or from an extra shot of industriousness (working harder than average, finding side gigs, being restless in their careers) — or from both at the same time.
• Three of them are the analytical type (number-oriented).
• Two of them have been watering additional sources of income for years.
• I know them well enough to say that at least two of them are for sure more intelligent than me. Probably the other two are more intelligent than me, too; I honestly don't know. I'd say I'm in the same ballpark of IQ as the other two. (I'm trying to be objective here, but at the same time I don't want to conclude that they are all significantly smarter than me, because that would absolve me of due introspection and of the responsibility to conduct myself better than I do!)

So what are the conclusions of all this?

Conclusion number one: I guess I am late. Again.

I don't feel like retiring. But then, I didn't feel like settling down or buying an apartment — until I did. Judging by my peers, I guess I'll be dying to retire in a few years' time, just like them.

Conclusion number two: strangely (I guess) I don't have any desire to work for a megacorp today. I like my messy career of scrubby start-ups, beautiful non-profits that don't pay much, small companies building a cool product, and so on. I have switched jobs because I liked the tech, because it allowed me to move abroad (or to return home), because it let me work from home with no schedule, because it paid well, or because the organisation was (really) making the world a better place. And yet this has happened to me before: the likes of Inditex, Santander, Repsol, etc. aren't especially attractive to me today, but perhaps they will be in 2030 or 2035. Shall I orient myself towards that goal already, just in case?

Number three: ditto about a sinecure. I do not want an “easy and secure job” today. Even at a sinecure one needs to spend hours with a computer, answer to a boss, (probably) commute to an office, ask for days off, justify absences and, well, work. But, will I want an easy job between now and (actual) retirement? Shall I pursue that?

Number four: I should probably be more determined at work, more focused on long-term career growth. Perhaps I should dedicate more time to position myself as one of those serious and reliable old-time corporate employees, instead of looking for synonyms of “determined” late at night for a post no-one will read. Perhaps I should get industry certifications or other titles and work to be promoted within the same org, instead of studying philosophy or literature for fun and letting myself get captivated by cool tech or cool start-ups. I like my job and I am reasonably good at it, but I like so many other things that in certain areas my CV does not shine as it should.

Number five: I ought to find additional sources of stable income. I already invest what little money I have sensibly enough, but I should work on passive income and/or side gigs too. Having that in the future will come handy, no matter how or when I retire.

If ever.

(What do you think?)