Five Things I Miss About Work with ESI Money

The following post is by ESI from ESI Money, a blog about achieving financial independence through earning, saving, and investing (ESI). It’s written by an early 50s retiree who achieved financial independence, shares what’s worked for him, and details how others can implement those successes in their lives. Take it away ESI!

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 only 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. πŸ˜‰

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 $2 million on the table (not counting what I could have earned in my 60’s.)

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. πŸ™‚


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.

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. πŸ˜‰


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.


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. πŸ™‚

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.

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. πŸ™‚

Now’s your turn. Help me out a bit with my list. What do you like most about work?

Thanks ESI! To learn more about him get his free ebook Three Steps to Financial Independence.

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25 Responses to Five Things I Miss About Work with ESI Money

  1. The big one for me is visibility of impact. I can directly or indirectly trace my actions to large outcomes at work. I see my impact on a smaller scale as an individual but it is smaller.
    FullTimeFinance recently posted…Of Charm and PursuitMy Profile

  2. Always interesting to hear your perspective, ESI! While I’m in a little bit of a different boat than you (work is more like a bran muffin whereas not working is german chocolate cake), there are few things I would miss as well. And of those things I would miss, the money would be the only one that would be hard (impossible) to replace.
    The Green Swan recently posted…Opening a 529 Plan – Conclusions from Reader FeedbackMy Profile

  3. Bahaha, this is tough because so many people hate work. πŸ˜‰ I do like that my current job is more challenging. I hate travel, but it’s been good for me to stretch my boundaries. But I know if I retired early I’d explore all kinds of new shiz too. πŸ™‚
    Mrs. Picky Pincher recently posted…A Kickass Review On Infinity JarsMy Profile

  4. Oh I can tell you right away what I like about my work. I like to see people’s reaction when we ship something new, like to see this “Wow” effect on their faces. Yes, couple of time it was “meh” instead of wow, but usually it’s wow.

    Like the crazy rhythm and new technology, sometimes I hate it as well, but 99% of the time I like it. But as I said before, the most enjoyable part for me (beside my compensation) is to see customers satisfaction.
    Friendly Russian recently posted…How to budget the Russian wayMy Profile

  5. Team CF says:

    “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.” Ha, funny!
    I’m currently in the wrong business and not enjoying it as much as I used to enjoy work. Really trying hard to retire early.
    In previous jobs I was actually building things with a team, physical things with big equipment in foreign countries, like being a little boy in a sand box. Miss those days….. just is not possible with having a family.
    Team CF recently posted…May 2017 Savings RateMy Profile

  6. Joe says:

    It’s been 5 years since I quit working full-time and I don’t miss any of that. Life is so much better now so I rarely think about my working days. The last few years at work was really grueling for me, though. I just couldn’t wait to get out of there.

  7. ESI $, Your attitude towards work and things you miss are very similar to mine, the difference being I wrote about the things I expect I will miss when I retire early — I’ve got at least a year or two left.

    As news starts to spread that I may retire in my early forties, it’s hard for most people to comprehend. I’ll be leaving as much on the table as you did, and up to a decade earlier. Once you have Enough to make work optional, there’s got to be a compelling reason to keep working rather than doing all the other things you could be doing. I haven’t found one yet.


  8. Brian says:

    Interesting take. Still working, so hard to have the perspective. I think I’d miss the challenge, having new stuff to solve each week. I know I could find it personally, but not sure it would be the same.
    Brian recently posted…Redefining Debt DisciplineMy Profile

  9. Those are all great things to miss about work. Other than compensation though, they sound like things you can still experience post-retirement (albeit in a different way). Not in the immediate, daily-basis sort of way, but I’d be curious to know what fills those gaps now that you’re retired : )

    In my chosen field, I love seeing how our product affects people. Hearing testimonies of people who’ve changed their perspectives, or who’ve experienced a personal catharsis, is a huge part of what makes my job so rewarding.

  10. I FIREd about 5 years ago.

    About the only thing I missed when I quit working was the camaraderie of working on a close-knit team. I was a software engineer and it was fun helping other and being helped by others on the team.

    To be honest, I don’t even miss that anymore. The freedom of retirement is too awesome!
    Mr. Freaky Frugal recently posted…Adventures in negotiating rentMy Profile

  11. Great post ESI, I like the positive spin about work and talking about how it’s not the arch-enemy. I think a lot of life is like that, for example, I actually liked parts of high school, but I don’t want to go back. I miss a lot of aspects of college, but there were plenty of challenges I’m happy to be past (especially the long hours of studying and being broke). Work seems to be similar, where it’s a chapter of life with good aspects and bad aspects. Retirement will be better, and we won’t want to go back to work, but there’s still some parts we’ll miss.

  12. I love your comments about experiential learning and about the challenges. We think alike! One thing I will miss about work (education) is what influence you can have on students. I just got a FB message from a former high school student who graduated in 1996. Twenty years later he contacted me to tell me what a huge influence I was in his life – and that he is in his second career now and he’s teaching. He loves it and feels like he is making a huge difference in this students’ lives (very low socio-economic school). I’m early retiring soon – only 12 more work days! But I will miss the kids and my peers.
    Vicki@MakeSmarterDecisions recently posted…Ignoring Frugality To Maintain Our SanityMy Profile

  13. wendy says:

    Cool write up, thanks for sharing that!

    I’m still working, in my mid-40’s with 5 or so years to go to FIRE (misspent youth). The thing I think I will miss the most is structure in my day… I currently have a fairly fast paced engineering job that pays well, with a great boss and team, in a location I enjoy… but my work is fairly transactional and I’m at the point where I don’t learn much on the job, so I get my enjoyment out of helping/mentoring folks on my cross functional teams.
    It gives structure and meaning to my day, along with some volunteer ESL tutoring I do.

    A lot of the bloggers I read in the FIRE universe seem to be couples, many with kids, so there’s a built in mandatory ‘To do list’ or structure with that. I am single/no kids/renter and my biggest worry is that I’ll have too much time on my hands… I love to travel, have crafts, and hobbies, etc., but I’m a fairly ruthlessly organized geek so I’m pretty efficient with my time… It may sound weird, but I worry about having too much time – paralysis of choice. I’m not even gone yet, but my panic/worry is all about the lack of schedule….
    These next five years I’m evaluating where I’m going to move to and how to ensure that I have enough schedule in my life to not freak out πŸ™‚

  14. It’s a shame more companies don’t offer flexible schedules/earning arrangements so that you’d be able to take a bit more of the good without the bad. I know I would happily take a 20% paycut for the privilege of only working 4 days a week, and once I hit FI I’d even stay on 3 days a week just for the fun of it!

  15. I may miss the compensation…maybe.

    I do have friends at work, but I often wonder if we would be friends if I didn’t have the job. So many of our personal relationships are sort of arbitrary like this.

    As far as learning, challenge and influence I see these as either ego driven or accomplished better in other ways. I’m not fully retired though so I can’t know what I will miss about work if anything. I can say that working part-time I do not miss the work on the days I have off πŸ™‚

  16. Honest reflections about work, ESI. I can relate to many of what you wrote. This is why I often say FI is mandatory, RE is optional. Work gives meaning to many, and it can play a role in serving our ‘self-actualization’ need. Sure, there are some toxic work environments where it makes sense to leave early but that’s not the case everywhere and for everyone.
    Ten Factorial Rocks recently posted…Stress-test Your Financial IndependenceMy Profile

  17. Ed69 says:

    Hi Esi Money,

    I happened upon your blog a few months ago. I had read through some of it but haven’t digested all of it yet. I appreciate you sharing your story on your blog and with this post.

    I have to admit that whatever had originally drawn me to your blog (maybe another guest post or an interesting comment in another thread) I got the impression that you were stuck in the OMY (One More Year) time loop, even though you had enough to retire. It reminded me of a comic that gets posted all the time on the Early Retirement Forums:

    It shows a business man rushing by the cemetery looking at his watch thinking “time is money” and in the cemetery there is a headstone that has inscribed ‘time is greater than money’

    I’m glad to see that you FIRE’d before one of your plans I had seen that was a year or two out. I am currently trying to plan out a more concrete exit from FT+ work with DW in the next 5 years. It may even include going down to PT.

    Thanks again for your experiences and I am off to digest more of your blog.

  18. Suresh Patel says:

    There are very few people who miss their workplace after their retirement and I think one among them thanks for sharing your thoughts. Great work!!!

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