insurance job
Career Development

Career crossroads – my insurance job is boring

An insurance job is decent. It’s often low stress, steady and predictable. Sometimes, in rare spurts, it’s even interesting. However, most times, an insurance job is just plain boring. Hmm, maybe that just applies to most office jobs.

I, like many Americans, sit in a cubicle all day. It’s a spacious cubicle so I’m lucky in that regard. It even has high walls. There’s a computer there and a monitor too. I have a keyboard, a mouse and a comfortable chair. The company provided the keyboard but I bought the mouse myself, it’s an ergonomic one. I even have a view of a park since I have a window seat. Well, it’s half park and half the office building across the street. Still, it allows me to look out and see something other than my computer screen.

My office, one of many like it in my tall building, is a sea of these same exact cubicles. They all have the same exact set up and the same exact Cisco phone in all of them. Does Cisco have a monopoly on office phones? I see these damn things everywhere!

I have been here for ten years and I’m a bit bored and disillusioned. Can you tell?

The first few years were interesting. It was my first job out of college and I was learning a lot. The people were cool, the atmosphere was enjoyable, stress was low and my pay was rising.

2008 was my first year here which meant no raises as the economy was exploding. However, I was a high performer right off the bat and my company realized that.

I received 10-20% raises in the following years so I wasn’t complaining. I knew I was in a good spot as raises that big aren’t that common.

There was a reason for the raises, of course. My starting salary straight out of college was behind the market rate. The company didn’t want to lose me so they bumped me up rather quickly.

The money became decent and I was comfortable. Why would I leave? I got a promotion here and there, got a bit more responsibility but the job largely remained the same. I came in, did some data entry, talked on the phone a bit and went home.

As the years passed I got more and more efficient as did our internal programs. What took me thirty minutes before could suddenly be done in ten and then it became even faster.

That meant a few years in, I was starting to get bored. The work wasn’t stimulating and the amount of down time was insane. I couldn’t believe how a profitable company like ours could afford to pay people to just sit there. I’d literally surf the internet for seven hours and do one hour of work most days.

And I was a high performer!

I thought we were an anomaly but many former co-workers got other insurance jobs. The feedback from them is that it was even worse at other places. There was more down time, more soul numbing nothing.

They were just like us! They had a bunch of people moving one sheet of paper from the left to the right then back to the left again.


It’s clear why some people leave jobs after two years.

They get bored and/or the money isn’t there. If I was getting 2% raises every year then I’d have been out after two years.

However, my raises were solid and I wasn’t so sure the grass was greener on the other side. It was boring here but it was also boring there. At least here I was getting decent money.

Even a few years in, I was relatively content. The company was treating me right and I was still learning a bit.

The job wasn’t anything amazing but maybe that’s what jobs are for most people. The schedule was flexible, I didn’t have a ton of stress and I could go home and forget about work. Back then, that was what I wanted. I wasn’t looking for meaning in my job, I could probably find that elsewhere.

Perhaps this was where my financial independence journey started. I could see the writing on the wall. The job started good but stagnation was beginning to set in and I was only a few years into this gig. From what I heard from former co-workers, other gigs in this industry weren’t all that different.

I wanted to have options and saving more money would give me that.

Still, I was bored as hell and ten more years of pretending to be busy in a cubicle didn’t seem like an enticing prospect. I needed a change of pace. Data entry was boring and I wanted to try something new.

At that same time, maybe around 2 years ago, there was an opening for a team lead role in my department. It was the perfect time to try something new. I was stagnating and this would be different. It was still an insurance job in the same department in the same company but it would force me to get out of my comfort zone. Best of all, it would mean much less boring data entry.

My career as a repetitive task engineer was coming to an end.

The team lead role wasn’t one that naturally fit my personality type. You see, I’m introverted and this job required a lot more social interaction. However, I was far from a social pariah and thought I’d make it work. I’d have to deal with both internal and external parties more both in person and on the phone. However, I’d also get to try new things such as indirect management and training. Did I mention the potential to ditch the repetitive work?

The people who were hiring knew me, liked me and I got the job without any actual work on my part.

It came with a decent raise too. I checked on Glassdoor and basically figured out I was overpaid

Now I found myself at the top of the market in terms of my salary. I started at the bottom and now I was at the top! I liked the extra money but the move wasn’t just about the raise. It was about something that wouldn’t bore me to death.

Since my salary was high, that likely meant 2% bumps from now on and that is what happened. It wasn’t unexpected but after years of 10% raises, it was a bit of a morale killer.

It’s funny how that works, even if i’m overpaid and I know I don’t do a ton of work, I’ll be disappointed in my yearly increases.

Part of it is just being used to certain numbers and setting unrealistic expectations based on that.

Since I started, my annual salary has gone up 9.4% annually. That’s amazing considering it includes no raise in my first year and 2% raises in the last two years. I know I’m lucky in that regard. It’s also one of the reasons I stayed with the company. They treated me well.

I often thought about jumping to another job in the industry but there was a level of comfort here.

The truth is that Insurance jobs don’t seem to differ all that much from one another. Whether it’s health insurance, car insurance, life insurance, it’s all pretty similar.

If you’re in the sales areas, you go out there and meet customers. In other areas, you come into the office and key in data using Microsoft Office programs. Of course, there are technical jobs and product jobs that may entice some but a lot of it is based around repetitive tasks.

I work in the underwriting department of a brokerage firm.

The basic idea is that I try to figure out what the rates should be for our customers and help negotiate them down with the insurance carriers. As an individual contributor, I was the person doing all the calculations in our models. That meant data entry, reporting running and more data entry. Beyond that, I was involved in discussions with our client team and the insurance carrier. We talked about why our calculations were right and why theirs were wrong and settled in the middle.

If you’re not familiar with the insurance industry. We are basically the middle man between the client and the insurance company.

I often ask myself if my job needs to exist and if I bring any value? I don’t know, the clients pay us so maybe. Then again, people pay the financial industry a lot to bring little to no value so who knows with these service industries.

In either case, my role gave me some insight into the insurance industry as I worked with many of the main insurance companies.

They’re all pretty much the same to me. The people I deal with seem to do the same thing in the same way. Some clearly have better technology, products and reporting and some are stuck in the past. I feel bad for those that have to work with antiquated and slow systems. In an odd turn, also feel bad for those whose systems are excellent.

I know how they feel. Our systems are excellent! I know saying I feel bad for those people may seem weird but let me tell you why. It’s because insurance jobs are boring!

I know this first hand. I’ve talked to many people in the industry who feel the same way.

However, now that I was no longer an individual contributor, I was hoping it’d be different.

New Role

In my new role, I don’t have any direct reports but I don’t do nearly as much data entry.

It’s this weird middle role between actual management and what I had before. My roles are simple. I train our team, manage the book of business and provide reporting to my manager. That manager, the director is responsible for the markets we work with and also has direct reports under him.

He’s responsible for the actual performance for our book of business, I’m just the guy that makes him look good by making sure things run smoothly, the team is trained and everything is accurate. I work with actuaries, clients and other internal teams to make sure things are humming along.

It’s a good gig. The stress is low since my manager is the one who stresses for both of us. The good thing is that I actually have a say in how things are run. That’s different than when I was an individual contributor and having autonomy is really nice.

I loved the job for the first few years. I learned new things again, got to improve my interpersonal skills and felt good about training up a high performing team.

The problem is that the work is getting boring again. I’ve done a great job training our team and have become more efficient at what I do.

That’s why I say I feel bad for people that work at a company where systems and processes are excellent. I’ve had a big part in making our team more self-sufficient and giving them their own autonomy. I’m proud of that but I’m back to a similar spot I was two years ago.

There are days when I come in to work at 8:30 and literally do nothing until I leave around 4:30. I may answer an email or give some guidance to my team, but other than that, I’m sitting on Reddit or playing on my phone. I’ve heard things about government jobs being inefficient but can it be worse than this?

These people are paying me how much to do this?

Part of the problem is that insurance is rather seasonal when it comes to workload. Yes, we have busy times where I do a lot of work but beyond those few months, I’d say I do a good two hours of work a day at maximum. That’s probably stretching it too.

How is this possible, you ask? Have I found the holy grail of jobs for the lazy person? Am I just awesome and efficient? Do I have some sort of unique job or is this common in the insurance world?

I firmly believe it’s the latter. I believe many insurance jobs have become this way in recent years. The trend to improve systems and hire younger, more efficient people is showing in my job and many like it.

When I started this job ten years ago, I was the only person under 30 on my team. Our systems sucked and everything was manual. Now, at 34, there are only two people older than me on my team and everyone else is below 30. Our systems are great, our team is larger and each person has less work on their plate than I did when I started in 2008.

There are companies that are behind but many are like this and others are following suit.

It all comes down to the Pareto principle(80/20 rule).

You know, the idea that 80% of the results come from 20% of the effort. I came to realize that early on in my career and I think many young people these days do too.

In reality, these large insurance companies don’t really expect a ton out of you. You can be a high performer with relatively little effort once you figure out how to efficiently do things. The funny thing is that many service jobs are based around inaccuracy. Pricing insurance is a guessing game as is investment advice as are many other service jobs.

Sure, there are guidelines and reasonable results but it’s not like engineering where you have to build a bridge or being a doctor where you have to save lives or being a coder where you produce software. In my job being close enough is the best you can hope for.

In reality, right now, with the systems we have. It’s more like the 95/5 rule. I can get 95% of the results with 5% of the effort. I could try harder but what difference would it make? The incremental gain in performance is not worth it. I’m already at the top of the pay chart so I’d still get a 2% raise.

That’s the reality in office jobs right now. If you get a 2% raise, why bother going overboard if a tiny amount of effort will yield the same results.

Maybe I’m being pessimistic but that’s been my experience so far. High performance works to get your salary up initially. On top of that, in certain industries, you are very much rewarded for the quality and intensity of work you put in but that’s not every industry.

In some industries and insurance seems like it’s one of them, 5% of the effort is enough to get by once your salary is near the top.

Part of me says that my job now is great.

I have low stress and have trained a team that does awesome work. There are days where I feel crummy and I don’t feel like doing any work and I have that flexibility. I know there are jobs out there where people make a quarter of the money and work ten times harder than I do. I am grateful and thankful for what I have. My life is great even if my job bores me. I worked hard early on and have this opportunity to be lazy now if I want to take it. There’s a part of me that says, stop being dumb, stop whining and just enjoy what you have.

However, there’s another part of me that disagrees. It’s a part that wants something more. I go into the office at 8:30 and do nothing.

That may sound great and it is at first but after a few years, it’s draining. It sounds stupid but I’d MUCH rather have something to do than be bored all day. There’s only so many articles a person can read on Reddit especially since work blocks 90% of the interesting websites.

The truth is that It’d be nice to actually feel like what I’m doing has an impact. I felt that way in my first few years when I was learning and growing. That feeling disappeared but returned in my new role when I was learning again, forcing myself to build new skills and mentoring and helping other people grow.

I don’t feel that way now.

The Crossroads

An insurance job is boring and I’m exhibit A.

I guess the crux of the question is whether a boring job is a blessing or a curse? I know many will read this and say I’m crazy for complaining about what I have and I agree with those people. However, there are others that will probably shake their head in agreement. It’s no fun to be bored at work all day. It may not seem like it but it’s tiring and it’s demoralizing. It’s very easy for that boredom and lack of motivation to transfer into your regular life.

I’m not sure if I have the answer to that question. Is it a blessing or a curse? At times it feels like both. All I know is that I’m ten years into my career and I’m at a crossroads. The way I see it is that I have two options.

The first option is to keep my head down and continue doing what I’m doing for another decade, keep earning, keep saving and retire early. I’m lucky to have that option and I’m glad I started saving early on knowing that my job probably wasn’t going to be answer to whatever question I was going to have later on in life.

Some people love their job but for me, it’s just a way to earn money right now. It’s possible that it always will be and I’m not sure if that will ever change. However, I’d much prefer it to be like it was when I first got hired or when I first got my new role. I’d prefer to be interesting and help me grow in one way or another.

That brings me to the other option, the other path on this crossroads. One of the directors in our company recently quit and there’s an opening for a job one level above me. The job that my manager currently does for another team. It’d come with direct reports, more responsibility and potentially more stress, some travel too. It might also come with some actual work, some growth and learning potential.

It’d be a whole new team to train and whole new external teams to work with.

My insurance job is boring. The question is do I want to continue to be bored or do I want to do something else with my career? I’m not sure of the answer right now.

However, I think I at least want to try the latter. I’m not sure if it’s the best choice for me but it seems like I need a change again.

I updated my Linkedin page and I applied for the job. I’m not sure I’ll get it since there are other more experienced people in my department. However, even if I don’t, it’ll be good experience as I haven’t interviewed in ten years and maybe it’s time to finally look outside the company as well.

Another ten years in my current role doesn’t sound too great but it’s not the worst thing in the world either. I’m lucky to have what I have and do what I do. I have plenty of free time to pursue other things and maybe that’s what I need to focus on these days.

It’s quite possible that even if I get this job or another new job, I’ll just be in this same spot in two years.

However, maybe that’s OK and maybe I finally understand why young people these days are so eager to job hop. It’s not just salary but the search for something interesting. There are plenty of jobs out there like mine and if you’re not getting a 10% increase every year then why stick around?

Now that my raises are 2% again, I can potentially be just like everyone else who job hops to get a better salary. Only, I’m not really chasing salary, I’m just chasing something that will make me less bored. I don’t know if I can find it but it’s worth giving it a try.

The potential truth is that an insurance job may always bore me. I may get two years of being interested and then fall into the same old routine.

If that’s the case then it’s a good thing I’ve been saving money all along. It’s possible I just stay at my job and work on side projects like this one more. I don’t know what the right answer is right now but I’m willing to pursue some different paths to see how they feel.

At that the end of the day, that’s why many of us are doing what we’re doing when it comes to saving. It’s good to have options which is what financial Independence is all job



  • Diana

    I also work in the insurance industry — and agree it’s incredibly boring! It’s funny how you get out of college, need to find a job, and think “oh I’ll just start working in insurance, until I figure out what I really want to do…” And then years down the road, find you’re still working in insurance. But I’ve got about a decade on you — 20 years in the industry, and have never done anything else. And no, I don’t find it terribly interesting — and I also haven’t remained in the same position the entire time. Since starting out at entry level, I think I’ve moved on to different positions every 4 years or so. Then I get bored, and antsy, and look for a way out. And while the role I’m in right now doesn’t have a lot of automation or downtime, it doesn’t induce any excitement either. On the one hand, I have job security because our process is so manual (reviewing legislative changes and state regulations). But on the other hand … holy snoozefest! But all in all, I’m allowed a lot of flexibility, can work when I want & where I want, and don’t have any direct reports (thank God…)
    Just wanted to let you know I hear where you’re coming from and have felt the same way. Best of luck on your career journey, and hope you find something that gives you the best of both worlds!

  • Dave

    I can relate to your boredom. It comes with most office jobs. Not having direct reports is a gift. I currently only have one. At my last job, I was responsible for many people. Like you, I get above average raises and have autonomy. I have been in the workforce for over 20 years and Have learned a job is not the place to find my identity or happiness. On a good day it is a place to be productive and to be of service. On a bad day, it is a paycheck until I retire.

  • Money Beagle

    I’ve been at my current job for twelve years now. It’s definitely not as exciting as I once found it. For me, I haven’t looked seriously at leaving. I have a fantastic work-life balance, including tons of paid vacation, and with two kids growing up and getting the opportunity to spend more time with them, that’s a fair trade off for me.

    I’m also at the point where I’m getting the 2-3% annual raises. The excitement definitely isn’t there but one thing I do is consider that those raises are more from a dollars perspective than I was getting with 7-9% raises earlier on in my career.

    • TimeintheMarket

      Sounds like we’re in a similar spot.

      It’s an interesting area to be in as moving up can mean giving up the work-life balance. I’m still waffling on what I want to do as I do like the freedom my current job gives me.

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