Five Things I Miss About Work

Did anyone see this a while ago?

It’s an article about Sam at Financial Samurai.

He’s been retired for seven years (he retired at 34) and is supposedly looking to re-enter the workforce.

Here’s what I see as the key parts of the post:

Due to his child’s education, a slumping economy, the cost of living in San Francisco and a general ennui with the retirement lifestyle, Dogen, which is his writing alias, says he’s planning to look for his first full-time job since stepping away over seven years ago.

It’s not uncommon for those that have retired to circle back to the career, once they get a glimpse of what retirement looks like. Estimates find that more than one-in-ten return to the workforce. But when it comes to extreme early retirees within the financial independence, retire early (FIRE) crowd, the notion of returning to the day job can come with a whole lot of guilt and sense of failure.

Despite earning about $250,000 a year in passive income streams, he estimates he’s about $93,000 a year short of living comfortably in San Francisco, particularly if his family has another child.

When talking with Dogen, though, there’s a sense that he might not actually want to remain retired, which has fueled his focus on his fears of what costs could lay ahead for him.

“Once you see a hundred European churches, they all seem the same,” he said. “[I’ve] done everything I’ve wanted to do.”

I have a TON of comments on this:

  • Financial Samurai is one of my favorite financial blogs. Since he comes up with the most unique spins and topic ideas, I just can’t resist reading it! He also has a contrarian viewpoint to much of what’s written about money, and I appreciate that as it challenges my thinking.
  • That said, Sam is a master of publicity and he usually accomplishes it with some sort of outlandish claim that gets people all riled up. For example, he’s written about how it’s hard to get by on a $500k annual income. You might imagine the backlash he got for that, but it received widespread coverage and I’m sure his site benefitted greatly. He’s also written about selling his site which got his readers in an uproar. Now he’s “thinking about” going back to work. I think this is another in the line of his great controversial marketing campaigns.
  • In other words, I think Sam manufactures over-the-top claims for the attention. Maybe he’s sincere and maybe he’s not, but if I was a betting man, I’d say he’s not really looking at going back to work and especially not full-time. I’m writing this post at the start of December and it will publish almost two months from when I write it, so we’ll see. Will he have a full-time job by the time it posts? I doubt it.
  • LOL! He’s $93k “short” on annual expenses. But he doesn’t want to decrease his lifestyle. And he doesn’t want to move. Doesn’t this seem far-fetched to anyone else?
  • “Once you see a hundred European churches, they all seem the same.” This is a quote made for publicity (I know, I used to write them). Does anyone think he’s really seen 100 European churches? I don’t. But the quote is compelling and attracts attention, the whole purpose of it and the article.
  • “[I’ve] done everything I’ve wanted to do.” Really? Everything? I highly doubt that, especially for someone of Sam’s intelligence and curiosity. I think I could live several lifetimes and not do all I wanted to do. That’s because new things keep popping up. Have I mentioned pickleball in this post yet? 😉

Maybe I’m wrong. I’m sure Sam will comment on this post and set me straight — he’s a master of making the absurd seem reasonable. But I wasn’t born yesterday and despite what he might say to the contrary, I’m not buying it.

Now if he gets a full-time job and works at it for a few years, maybe I’d buy it. But otherwise color me skeptical.

Nevertheless, I still love him. As a marketing guy, I have to admire his creativity in getting coverage. 😉

Failing at Retirement

All the above said, obviously some people do fail at retiring.

In fact, this was the premise of the first retirement seminar we went to. Their thoughts were that “more people than you might guess” failed at retirement because they didn’t have a plan for retirement going into it. Of course they didn’t have exact numbers, so how did they know it was more than what I would guess?

The article above refers to this AARP post on why people work after retirement. Some of their key thoughts and my comments on them:

“When I got [to retirement] it was like, ‘What am I going to do with all this time?’ “ says Saegesser, 66. “It snuck up on me.”

This person clearly didn’t have a plan for retirement. Not having a plan for a major life event is a recipe for disaster. No wonder he went back to work. But is he one of ten or one of a million? Articles like this dig to get one example of someone who did something, then craft their entire story around that idea. It’s not Fake News, but more Manufactured News that’s magnified beyond recognition.

Saegesser represents a trend of older people who are either retired or nearing retirement but continue to work regularly. Some need the income they make from working postretirement jobs to cover their bills; others use the money to pay for leisure activities such as traveling or hobbies. For some older retirees, however, a big part of the appeal is the personal fulfillment they find through employment.

An AARP survey of 3,900 people 45 and older found that even those who were retired (13 percent) said they were either still working or looking for work.

Haha! It’s a “trend”. Really? Where are the numbers to back that up? Surely they have stats from years ago to show that it’s now a much bigger thing, right?

And while the group who “failed at retirement” (as defined by going back to work) is at most 13%, that’s not a big number. It’s certainly not “much more than I would have expected.” When articles like this (or the seminar I went to) talk about failing at retirement, they make it seem like it’s a third of the population or more. But of course they can’t say that because it’s 13% at most, so they have to try and blow it up with clever writing and statements.

But it’s not really 13% either — at least it’s not 13% who fail at retirement because they are bored, miss work, etc. Of the 13% noted above, they don’t share the breakdown of how many now work because of financial challenges and how many did for “I failed at free time” reasons. My guess is that the former greatly outweighs the latter (just look at the sad state of wealth in America and you’ll probably come to the same conclusion). So the numbers of people failing at retirement because they simply don’t know what to do are probably at 5% or less.

That said, I know some people do fail at it, so it’s an issue. I just don’t think it’s as big of a problem as the media paints it to be (they thrive on sensationalism anyway). I think they are trying to make a story where one does not exist.

That’s not to say there are some benefits to working. Or that people don’t miss work.

Some time ago I wrote a guest post for 1500 Days titled Five Things I Miss About Work. I’m running that post here (with just a few slight changes) along with some updated comments since that was over two years ago.

Here we go…


Let’s start out with the obvious: I LOVE early retirement!!!

I retired a year ago and haven’t looked back. My life is full of both expected and unexpected joys.

My biggest mistake was that I waited too long after reaching financial independence to retire.

That said, there are some things I miss about working. I had a 28-year career in business and much of it was rewarding — I certainly didn’t spend almost three decades hating every minute of my existence. I liked my career for the most part (I just like not working better). It’s similar to the fact that I like peanut butter cookies, but I like chocolate chip cookies better. 😉

Today I’ll share the five things I miss most about work. I hope this will encourage those of you still working that employment isn’t a complete disaster.


I have to put compensation at the top because it’s what I miss the most.

High salaries, bonuses, benefits galore, special perks, and on and on. What’s not to love?

Over 28 years I averaged 8% annual pay increases and built my income to a high level. In addition, I was about to hit my highest-earning decade (my 50’s) when I quit early, leaving somewhere around $3 million on the table.

I’m not sorry I quit, but it’s kinda a big amount, especially when it’s typed out right in front of my face.

So yep, it’s the money I miss most. The MBA in me just can’t help but list this #1.

[Update: This is still the thing I miss most about work — the nice, fat paycheck. But it’s still better to be retired and not have it. Hahaha!]


Of course I miss the people too — specifically some close friendships I formed.

There’s something about going through the battle of business challenges that forges close relationships. Even the often mind-numbing day-to-day routine and collective groaning at stupid things like company bureaucracy develops the bonds of brotherhood.

And, of course, there’s the camaraderie of working on a team to hit a goal that simply makes you like the people on the team.

For me, I had a special affection for my subordinates. Many were young and wide-eyed. I saw it as my responsibility to help grow and nurture them so they were successful in their careers. When they got promoted I was as proud as if my own kids were recognized.

All of these factors worked to develop some great friendships.

And yes, I realize that if this post was “The Five Things I Don’t Miss About Work” that “people” would be listed there as well because people can be pains.

Sure, there are always jerks, but mostly it was good and I miss the friendships.

[Update: I don’t really miss the people from work that much anymore. The ones I care to stay in touch with I do. I have also developed new friendships built around my new lifestyle (pickleball mention #2!), and that gives me more than enough social interaction.]

Experiential Learning

There’s something in me that’s always been a learner.

I love to read, listen to podcasts, take in audio books — basically any form of learning is good for me.

While working, you experience a whole different type of learning and resulting growth that can’t be obtained out of a book. It’s a practical growth that’s learned by doing and experiencing and not hearing or reading.

It’s often coming up against something that you have no idea how to solve. Then working both individually and with others to create new solutions. It’s awesome to learn this way and, of course, so rewarding when you do it and have success.

I am getting some of that with the projects I’m working on, but it’s not at the “professional” level so it’s just not the same.

Of course the stress is not the same either, so maybe it’s a wash. 😉

[Update: This is one reason I enjoy writing at ESI Money — there’s always something to learn.]


You may have guessed that I’m sort of a goal-oriented person.

That’s one of the things I like about business — there are goals. Everyone knows what they are and is working together to accomplish them.

They are not vague. In fact, they are often spelled out clearly in black and white documents called “budgets”, “plans”, or “forecasts.”

It’s the challenge of working to hit these goals that makes me love business so much. I compare it to playing a game. And in the game of business you “win” by beating your goals.

Once a month you get a progress report (monthly financial reports) which tells how you are doing and provides instant feedback.

When things were great and you were winning, those were some of the highest highs. Of course if the news is bad, that can be a bummer. But it can also motivate you to take action and become better (which involves both a challenge and learning).

Yes, I miss the challenge and the game of business. Monopoly is great, but it just can’t compare.

[Update: Another reason for ESI Money. It’s a challenge to come up with new stuff four times a week, keep the site growing, etc.]


I was going to say “power” but I didn’t want to come across as a jerk.

Then again, I just said “power.”

Especially at the highest levels of a company (I worked my way up to be president of a $100 million company) the influence/power can be intoxicating.

People do what you say. Whatever you say. Of course you seek feedback and input to get to the best decision, but you make the final decision. And what you say goes.

I must admit, that’s a lot of fun.

Of course it’s hard to switch off when you leave each day and wonder why everyone at home isn’t bowing down to you like they do at work. 🙂

Even more, the influence I had in many positions helped me do a lot of good. Because I was at high levels in business, I knew others who were as well. I often recruited these people to work with me on non-profit committees. I also asked them for donations to help those less fortunate. So the influence was great in these areas as well.

Now if I’m lucky I might be able to influence the waitress at Cracker Barrel to give me some extra maple syrup. It’s just not the same.

[Update: I am less and less concerned with influence as time goes by. Maybe it’s an ego thing and as I’ve separated myself from my career, my ego has waned too. I’m not sure, but I’ve certainly entered the “I don’t care what anyone thinks of me” stage of life. You have to if you want to get away with wearing athletic clothing to almost every event like I do. LOL!]

Miss but Don’t Miss

So work isn’t the all-hated entity that many make it out to be. It’s not our arch-enemy: the Joker to our Batman, the Lex Luthor to our Superman, the Patriots to our Broncos. (Sorry, couldn’t help that last one.) There are some really positive and redeeming features about work. Of course, maybe it’s just easier for me to say that since I’m not working.

But I don’t think so. There are many good things about work and I do miss them. The five above are starters but I’m sure there are more I haven’t considered.

Of course I don’t miss them so much that I ever want to go back. 🙂

[Update: Nothing has changed here. In reality, I miss work less every day. And I’m thankful for owning my time. I’m writing this on December 2, the Monday after the Thanksgiving weekend. As I was walking this morning I noticed the hustle and bustle of cars scrambling off going back to work. I recalled the dread I used to have heading back to work after a nice vacation and I was even more thankful that I am retired.]

Now’s your turn. Help me out a bit with my list. What do you like most about work? What do you think you’ll miss when you retire or, if you are already retired, what do you miss most?


Originally posted at

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