5 Things I Miss About My Day Job

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Even though I love self-employment and don't want to go back to working the 9 to 5, there are things I miss about my old day job.

I don’t know what it is about us as humans, but we tend to think that the grass is always greener on the other side. It’s inevitable in my opinion. Things may be going great for us, or they could be going terrible. We see something else and we are tempted to think that it will be better than what we have. Of course, it might be the case that it actually is better but often times it’s not. It largely depends on the given situation I guess. Take working from home as an example. Before I started my own business, I always thought working from home would be a breeze and that there couldn’t possibly be anything I’d miss about working in an office.

Now that I work from home, I realize there are a few things I miss about my day job. I wrote a post a few months ago about things I don’t miss about working in an office and thought it would be a good exercise to go through what I do miss. I do that as it might be easy to see working for yourself as a life of luxury filled with puppies and lollipops, but it’s not.

Things I Miss About My Day Job


While there are some things I don’t miss about my former 9-5 gig, like my self-grooming neighbor or fabric prison, there are some things I do miss about my day job. Such as:

The camaraderie: This is likely the thing I miss most about my former day job. While the meetings might have sucked, being able to collaborate with others on a project was enjoyable, generally speaking. I’m an individual who likes to take the big picture and help determine what’s needed to hit that end goal. My day job provided a way to scratch that itch at times. This is not to say that I don’t have that now that I work for myself, but I’ve found there is just something about physically working together on a project that helps take it to the next level.

Social interaction: I’m an introvert by nature. I’m not the life of the party that my lovely wife is and tend to prefer opportunities to connect with others in smaller settings. Now that I work from home the large majority of my social interaction is either digital or with the little Frugal Rules.’ I love my kids, I really do, but there’s not much in terms mental stimulation. Call me crazy, but discussions about Frozen do little to sharpen my mental acumen. 😉 Since I’m an introvert, this forces me to step out to further develop relationships. I think you could argue that that’s a good thing and I’d tend to agree. However, my day job provided a way to get that social interaction.

The paycheck: Ok, I know this is the obvious one. Who doesn’t miss a paycheck? It goes beyond that though. Getting a regular paycheck for a known amount meant I had a network to save for retirementprovide for health insurance, etc. That is simply not the case when being self-employed. Saving for retirement while being self-employed can be a challenge at best, and don’t get me started on the health insurance – as I’ve discussed it at detail before. The paycheck provided a felt sense of security. However, I’ve come to see that felt sense of security as a mirage in many cases. I’d much rather depend on my wife and myself to provide the income as opposed to a firm.

Feeling like a productive member of society: This sort of goes back to the social interaction aspect, but I miss that feeling you get of going to the office. There is just something about going in, putting in your time, physically working with others and getting your work done. That is not something I have now that I don’t have the stereotypical day job. However, like the felt sense of security with the paycheck I believe much of this is misplaced at times. When I look at my production level now against what I was able to accomplish in my former day job, I’m much more productive today. I also enjoy my work now more, so there’s something to be said for that. 🙂

Definition: The last thing I miss about my day job is the time aspect. I was somewhat privileged in that I didn’t have to bring much physical work home. The mental work is a different story. That meant I could typically leave around 5:00 and be done for the day. I loved this as it provided instant structure. The structure my day job provided is much more difficult to re-create now that I work for myself. That’s not to say that it’s not possible to have some sort of balance, just that it requires work, discipline and assessing priorities to reach any level of supposed balance. As I get older though, I’ve learned that we all make choices and that balance largely is comprised of that.

While I don't regret taking the plunge to work for myself, here are 5 things I miss about my day job.

I don’t know if there is anything else I miss about my day job, but these are the main things that come to mind. Going back to the grass being greener at the beginning, I always dreamed about working for myself in running a business. I never thought it was possible and believed that those who had it were better off. Being at this for over two years now I see that it is indeed possible. You just have to want it and put in the work to get there. I don’t know that those who are self-employed are better off, but I do know that I’m much happier and thus much better for it.


Do you work for yourself? What do you miss, if anything, about your day job? If you work in a traditional office setting, what is your favorite aspect of it – minus the paycheck?



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John is the founder of Frugal Rules, a dad, husband and veteran of the financial services industry whose writing has been featured in Forbes, CNBC, Yahoo Finance and more.

Passionate about helping people learn from his mistakes, John shares financial tools and tips to help you enjoy the freedom that comes from living frugally. One of his favorite tools is Personal Capital , which he used to plan for retirement and keep track of his finances in less than 15 minutes each month.

Another one of John's passions is helping people save $80 per month by axing their expensive cable subscriptions and replacing them with more affordable ones, like Hulu with Live TV.


  • MMD says:

    I can totally see how working at home would eventually have you craving for just about any adult conversation you can find.

    It’s funny you mention being a productive member of society. I completely see where you’re coming from on that, but at the same time aren’t you contributing just as much to the economy and taxes as the next working Joe?

    • Yep, that is definitely a challenge I deal with especially since I’m more introverted by nature.

      Ha ha, I think we’re putting more in taxes now – even more so now that we don’t have an employer putting in their part of the taxes. πŸ˜‰

  • I left my workplace in September and have so far being working for myself from home for 3 months.

    The pros DEFINITELY outweigh the cons at the moment.

    Are there things I miss? So far, not really…

    I read often before I made the jump that people found solitude when working as a problem. This absolutely is not an issue for me. While I’m working, I want to work. I find that “office banter” is pretty distracting to get the job done.

    However, I’m a social being, so I knew I would miss out on seeing people. Therefore, to make sure I don’t succumb to loneliness at home, I make at least 3 appointments a week to meet up with people for a coffee, have them round for lunch if they work nearby, etc etc.

    Regarding the downside of regular income, it was good to have a paycheck that I could “count on” each month, but the frustration of earning a lot more for the company than I was for myself was one of the primary factors I left in the first place.

    • Overall, I agree Graham – the pros definitely outweigh the cons. I also found office banter to be distracting and thus really a big part of the reason why I can get so much more done now in a day.

      That’s awesome you set to have 3 meetings a week – I need to do that myself.

  • I hear you on this list John! As I was reviewing my numbers the other day and planning for the next few months, I thought that it would be nice to create a budget with known numbers rather than unknown numbers. Yes, my unknowns can be larger than my knowns, but there is something very reassuring about making the same thing every month.

    • Oh, I can definitely relate to that Shannon. The OCD leanings in me crave for those “known” numbers, but you just have to do what you can. But, that aside, I’ll take the unknown in a heartbeat vs. working for someone.

  • I’ve worked for myself, as well as now working for a company. The best thing about corporate life (other than the steady paycheck!) is the freedom to focus on my “one thing” rather than needing to be a generalist.

    When I was on my own, I needed to be a lawyer, accountant, project manager, salesperson, QA, DevOps, Support, and many other roles. At my current job I can just do my area of expertise and let others do the things I don’t do as well. It’s fun to focus.

    But it’s also an interesting challenge to be a generalist.

  • I too am an introvert and not having very much social interaction is tough. I will go out to lunch sometimes, even by myself, just to be out and about. I also reach out to old colleagues to have lunch sometimes too.

  • I miss the camaraderie too. I went to lunch with a few of the people I hung out with at my old job recently and it reminded me of how much I missed that part.

  • I miss the daily rhythm of always knowing where you’d be and what you’d be doing at a given time or situation. Working from home is much less structured and distractions come all the time. It’s much tougher to stay focused on the task. And I’m surprised how much I’ve missed the social interaction as well. I’ve found myself going to work at places such as the library or Starbucks just to be around people.

    • Part of me really misses that structure as well Brian. I think it’s somewhat natural to crave that as humans. I’ve not done much of that, though I should as I find myself where it has been a week since I last left the house.

  • I would say the thing I miss most is the paycheck. I could skip the rest of it forever. πŸ™‚

  • Kathy says:

    Interestingly the thing I miss most is exactly what I was looking forward to when I was planning retirement. I miss getting dressed in work clothes. When I was working, I looked forward to just wearing jeans or shorts during the day. Now, I still have the desire for nice clothing, just don’t have anywhere to wear it.

  • 1MansMoney says:

    I left my company of 13 years in September in order to spend time with my newborn daughter and 3-year-old son as well as to pursue a new career. Feeling like a productive member of society is one of the things I struggle with. I love being my kids more but it’s a little awkward when people ask, “what do you do?”

  • Kassandra says:

    I also miss a lot of what you listed. Fortunately I get to visit on-site one of my clients every few months and consequently catch up with my former colleagues. I am an introvert as well so although I thrive in many ways working for myself at home, it was easy to get my fix of social interaction when I worked at corporate.

  • This post reaffirms my desire to get a traditional job outside my house. I had really considered putting more concentration into developing my freelance work. I’ve slowly discovered that I really do find satisfaction in getting out and interacting with others in a professional setting. I think you hit the nail on the head with your point about feeling like a productive member of society. Working from home may be the dream for some, but I don’t think it’s for me at this point in my life. That doesn’t mean I won’t hate the frigid commute this winter or workplace politics, but in the end it’s whatever makes you feel most fulfilled.

    • I completely agree that it really comes down to how you feel most fulfilled Natalie. I’ll be the first to say that working for yourself isn’t for everyone. The good thing is realizing that before you get too far in.

  • I’ve been with my company for 20 years, I do enjoy the social interaction with my co-workers, the water cooler talk. The brain storming and fixing of problems, the team work. I could certainly do without the micromanagement.

  • Jenna says:

    I love interacting with others, so the lack of conversation does get to me a bit. I enjoy the ability to build a business though!

  • Joe says:

    I only miss the paycheck, but not really that much. Life is so much better now. I don’t really miss anything else. Oh yeah, the free gym and coffee. That was nice.

  • I currently work my corporate job from home. The office, and clients, are ~250 miles away, so I really don’t have much option to get out and about with it. I communicate with co-workers by phone and email. I do miss the change of scenery. Being a homebody outside of work, and now spending all day here too, can get a bit monotonous at times. Despite those drawbacks, I wouldn’t change it right now… I’ve been able to return to work earlier while keeping my infant home longer. And I have a bit of a chance to do the housework during the day instead of saving it all for evenings and weekends. With two small children, that’s a huge bonus. To me, it’s a small sacrifice to reap the benefits. Likely not a permanent situation, but definitely appreciated now.

  • Chris has worked from home for many years (not self-employed though) and I know one of the things he misses the most is having the camaraderie of co-workers. Granted, co-workers can be difficult, but it is also nice to feel surrounded by others who can help versus isolated. He is on the phone so much so that helps out a lot. I think the fellowship aspect is what I would miss the most too. I have staff to manage and see clients every day so there are days when I wish for a little solitude. Like you said – the grass is always greener on the other side. πŸ™‚

    • It’s funny how much of that camaraderie aspect is a balance. I thought I’d not miss it at all and there are days I really do. But, that also comes with the office politics which I’m glad to leave behind. πŸ™‚

  • This is a tough one to answer, mainly because you added “besides your paycheck” to the question πŸ˜‰ Honestly the financial benefits are by far the biggest “win” of having a traditional office job. You really can’t beat the benefits and you have to make up for the lack of benefits when you work for yourself. It’s a big reason I have started to see myself working an office job for much longer than I did a few years ago.

    • You are definitely on to something there about needing to make up for your own benefits DC. That said, I think the income is somewhat tied to what you’re doing. We’re making quite a bit more than we ever did in the corporate world and thus makes it worth it. But, if that were not true then I don’t know I’d be as quick to say that.

  • Kim says:

    I’ve never had a real corporate type job, but on the days I do work, I think I do enjoy the feeling of self worth that comes with it and I feel most confident in my work clothes. I know that’s stupid but I just don’t feel the same in a sweatshirt and yoga pants.

  • This brings to mind the age old debate with my wife of how I’m so lucky to go to work and be around people! This is completely unappealing to me, but from her perspective (spending most of her time at home and being way more outgoing than I am), I am living the dream.

  • J. Money says:

    Amen brotha. Self-employment ain’t for the faint of heart! I’m really just missing working on something that someone ELSE is in charge of, haha… Tired of making all the company’s decisions πŸ˜‰

    • That it definitely is not sir! I want to give up some of those decisions as well on certain days…but then I remember my OCD tendencies are not always the most willing to hand them over. πŸ˜‰

  • I agree there are definitely plusses and minuses about both. I miss a steady, nice paycheck, health insurance, paid vacations, and a 401k. The people not so much. πŸ™‚ OK maybe a little, but I get a lot of social interaction at my gym and playing beach volleyball.

  • The social interaction that comes with entrepreneurship is amazing! I feel like I’m always being asked to do projects with other entrepreneurs and invited to things, and I’ve not even left my day job (yet) – this is just from business on the side. But, I see that you aren’t near adult humans for 8 hours a day like in an office.

  • It’s really nice to read this from someone with the perspective of both working for yourself and for a company. Sometimes I get down about my job, but you’re right… a steady paycheck and health insurance are amazing benefits I don’t have to worry about right now. Thanks for the perspective!

    • Not a problem Melissa, glad to offer it. πŸ™‚ They are good benefits to have and the key really comes down to finding what works best for you and your situation in life.

  • Creativeme says:

    I agree 100%
    I’d like to add paid vacation and sick days to your list… Leaving for a vacation and time off for the flu are financially treacherous and can threaten client loyalty.
    I’ve been freelance for 13 years now, and having someone to bounce ideas off of (and small talk with) is my single biggest loss. I took a 1 day per week casual job just to fill that void for a while, but my “real” job got too busy so I had to let it go.

  • catherine says:

    Most of these are exactly why I couldn’t stay home to work. I love interacting with the people I do on a daily basis and I like the schedule of leaving home and coming back. I’d lose my mind staying here all day I think πŸ™‚ I would however like to eventually work professionally 2-3 days per week (likely will be physically forced to unfortunately) and work on ramping up my freelance work, something I’m really trying to do now by looking for more writing gigs but couldn’t rely on it until debt paid off.

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