What stretch of your career was or is the hardest? (Class of 2026 through 2029?)

I have at least 9 maybe 10 years to go before I am FI, and I will re-evaluate my FIRE date as it gets closer. As for longing for ER, there are days off and on that I fixate on it as of recently, and earlier in my career those days came up in a more stressful way. The stressed out fixation came when I wasn't happy with my job/career and lasted longer pre-children. Now that my wife and I have 3 kids, the grind of that priority seems to push aside any stress that work causes. Basically, our lives are much more fulfilling and purposeful with children, but when it was just me, I fixated on ER a lot more.

Nowadays, since it's always been a "goal" of mine, and I am very much a person who strives to reach goals, its more just accomplishing my goal type of fixation. I used to take FIRE much more personal back in the day, but now that the gap is closing and the goal seems very much achievable, I don't worry so much about it. I do worry about age discrimination. I look around and see that there aren't a lot of older software engineers around me, and I am now getting on the older side of things. I worry that I could be aged out of my career that I genuinely don't mind as I am really good at it and it comes easy. I am wise enough to know I could always pivot and learn new skills and my network of professionals is very deep and vast so that gives me some peace.

It happened to my dad. He was pushed out of USWest/Quest in his early 50s as an engineer and he never really was able to land an engineering gig like he was used to. He drove semi for a while, getting his Class A through a company that paid for the training and hired him once it was complete. He took a pay cut. Then, he stumbled upon a job close to home where he was operating large printers...more of a mechanical engineering role if you will. He spent a lot of his days "keeping the machine running" and had the highest production rates of any operator since he was so good at fixing the machines as they broke. He really enjoyed that job and it carried him into retirement at 65. He would work the 2 to 10pm shift, some weekends, some night shifts and many holidays. He picked up a lot of OT pay during his last 10 yrs of work. That allowed him to FAT FIRE...although he retired at 65 so not exactly early. He never wanted to pay for privatized health care so he just kept working until he hit medicare age. He was happy, but I also feel like he didn't have a choice.

I want options. I want to have FU money if that happens to me in my 50s, which I am basically counting on. Sure I could go work at Home Depot, or drive the kiddies to school, but why if I don't have to.

I've heard so many stories of people retiring at 65 only to have their QOL seriously decline for one reason or another. I want to travel a bit, enjoy my health and be active in my early retirement. My ol man is 71 and still gets around, but a LOT slower then he used to. Seeing how much my folks slowed down in there 60s and now 70s is a real push for me to reach my FIRE goals. You only get one life. Why spend it working and then die a year after retirement.

My sister passed away at 47. She always had a goal to FIRE. We talked countless hours about our shared goal of FIRE. When she was on her death bed, all she cared about was spending as much time with her kids as she could. She completely stopped talking about money, and finance etc. It just wasn't important in her limited time left which I totally get. We can't pick our time...so make the most of it.
 
Last time in the corporate world.

The new department head was a...heavy social drinker.

He then made some poor decisions in his personal life, then got caught, which tipped the 'social drinking' into something much more serious.

Got tired of his erratic behavior and since mom was having serious medical issues chose to resign.

Poor guy died just a couple of years ago after suffering a minor fall & then bleeding out internally...IIRC, important clotting factors are made in the liver.
 
I think the toughest time for me was in the ~10 years away from FIRE timeframe.

At about that time, I switched companies and moved into a management role. I liked where I worked pretty well, but needed to make the switch to make more money to make FIRE a reality (I had worked at a small company for years and there was just no way for the owner to pay much more in salary).

After about 6 months in the new job I remember thinking, "I don't think I can do this for another 10 years." It was a soul crushing job. Luckily they laid me off after about 1.5 years (I'm exceptionally hesitant to change jobs proactively - always been a bit on the insecure side regarding my marketability). I quickly found a new job where I worked as an individual contributor, which I liked better.

Still, I found those last 7-8 years difficult. The work wasn't difficult, rather the waiting for the FIRE part of life to begin. Also, even though being an individual contributor was better than management, I was still burned out. I just wasn't all that interested in continuing to do the type of work I'd done my entire career, even though I was good at it. I thought a bit about changing fields and doing something more fresh and enjoyable, but being that close to FIRE it's tough to make a change, spend the money on the necessary education and certifications, start new at a lower level, and likely put the FIRE dream off further just so you can do something a bit more enjoyable (but still work) for a few more years.
 
disneysteve said:
I'm a physician. Without any doubt, the absolute hardest stretch of my career began when COVID arrived in 2020. I was working full time in urgent care so we were on the front line full force. Many days I was diagnosing 8 or 10 or more cases. And early on we didn't have adequate PPE, we didn't know everything about the virus that we know today, we didn't have good workflows in place to protect ourselves. Many of my coworkers came down with COVID though I thankfully managed not to. Never in my nearly 30 years of practice did I fear for my own well being every time I arrived at work. I also feared that I would carry the virus home and spread it to my family, especially my elderly mother.



The whole COVID ordeal (which certainly hasn't ended) definitely accelerated me easing into retirement. I dropped to part time last November and then to per diem this past August so I only work 8 hours/week now. If not for COVID, I'm not sure I would have been so quick to cut back.
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You and every other front line health care worker are true heros and it is sad that you are not being recognized for your heroism. I'm a math guy, not involved in health care. But when I started monitoring the covid numbers in early 2020 (January-ish), I knew it would be big.

I watched as people in italy, spain, and portugal thanked health care workers every night by singing to them on their balconys during lockdowns. The US Navy deployed mercy ships. In my state they had to store bodies in refrigerated shipping containers. You folks were fighting a war as deadly as any involving bullets except that you did not even know when you were under fire.

But then we politicized it. Both sides did it so that is not a political statement nor do I want to start a debate. My only point is that we had a very serious public health crisis for once in a century and people like you put your own lives on the line to help the US and the world. People who did this during wartime get honored with presidential/congressional medals.

But I doubt you got anything beyond pressure to stay on when you could have easily retired.

I personally salute you as a hero as much as anyone who served in the military in combat defending out country!

I know my personal salute means very little to you nor should it. But I hope people on both sides of the politics can eventually accept that, regardless of their beliefs, someone who goes to work into what they know to be a life threatening situation everyday just to help others is a true hero.

I am fairly healthy and was never that worried about dying of covid. But I did take my public health responsibility seriously and kept a log of all of my trips away from my house for over a year, and limited them to about once every 2 weeks to shop. That was not out of fear. It was to respect others who might be more vulnerable than me.
 
SecondAttempt said:
You and every other front line health care worker are true heros and it is sad that you are not being recognized for your heroism. I'm a math guy, not involved in health care. But when I started monitoring the covid numbers in early 2020 (January-ish), I knew it would be big.

I watched as people in italy, spain, and portugal thanked health care workers every night by singing to them on their balconys during lockdowns. The US Navy deployed mercy ships. In my state they had to store bodies in refrigerated shipping containers. You folks were fighting a war as deadly as any involving bullets except that you did not even know when you were under fire.

But then we politicized it. Both sides did it so that is not a political statement nor do I want to start a debate. My only point is that we had a very serious public health crisis for once in a century and people like you put your own lives on the line to help the US and the world. People who did this during wartime get honored with presidential/congressional medals.

But I doubt you got anything beyond pressure to stay on when you could have easily retired.

I personally salute you as a hero as much as anyone who served in the military in combat defending out country!

I know my personal salute means very little to you nor should it. But I hope people on both sides of the politics can eventually accept that, regardless of their beliefs, someone who goes to work into what they know to be a life threatening situation everyday just to help others is a true hero.

I am fairly healthy and was never that worried about dying of covid. But I did take my public health responsibility seriously and kept a log of all of my trips away from my house for over a year, and limited them to about once every 2 weeks to shop. That was not out of fear. It was to respect others who might be more vulnerable than me.
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I wholeheartedly agree with this, and again, continue to appreciate all of your responses!

I think that they are valuable not only in helping me think through more of my original concern, but hopefully to others. I believe that others who come to this forum can learn quite a bit from your experiences, for those who have dealt with various forms of adversity at work and outside of work as many of you have mentioned.

So thank you, thank you, thank you! :)
 
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The first five years of my career were the hardest. Right out of school, I was immature, combative and it took me awhile to get my feet under me. I'm now amazed I didn't get fired, but stayed with the same company my entire career.

Having started out as a test technician I found my calling in sales and public speaking, climbed a long ladder and retired 34 years later as SVP and Director with 1800 reporting to me.

The last 30 years were a breeze and the perks were rock star level.
 
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Marko, your second sentence is pretty descriptive of our oldest son who has a mechanical engineering degree. I wonder if you wouldn’t mind elaborating on how you were able to change those behaviors.
 
fisherman said:
Marko, your second sentence is pretty descriptive of our oldest son who has a mechanical engineering degree. I wonder if you wouldn’t mind elaborating on how you were able to change those behaviors.
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Unfortunately, my path is not one easily replicated. It went something like this:
Mid 1970s, we were a much smaller company at the time, about 150 employees. I was in a very small, highly dysfunctional technical service department made up of 100% Prima Donnas. I was 26 at the time.

Over a period of about six weeks, our boss was fired for repeatedly showing up falling down drunk at 8AM, a coworker died, two others quit and another was away in a long term equipment installation in Turkey.

I ended up alone and the only one who "knew what was going on". I ended up temporarily reporting directly to the president, which resulted in my having a great deal of autonomy and responsibility without any downside from failure; very high visibility. I just saw it as my big opportunity.

A brilliant 28 year old female executive took it upon herself to become my mentor and advocate (you can read between the lines), and a few older managers would take me aside when I strayed too far from the center line.

After a year or so of essentially running the department, I was wandering around the facility one night, found out where they hid the corporate ladder, grabbed a rung and started climbing. And the rest, as they say is history.

Fact, I never really thought about my 'turning point' until I started answering in this post. But there it is.
 
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Hardest part were the last two years of a thirty two year run in petro-chemcial operations management. Just got bored, sick and tired of the never ending soup du jour programs and political BS squabbling and back stabbing. Throw into the equation the company being bought and sold and new overlords coming in every few years didn't help either.
 
This was in the early 80's. I was a staff accountant at a family owned company. Elderly Mom and Pop, two sons and a daughter all involved and trying to control. Oldest son fired his siblings and took all control from Mom and Pop. Then he was murdered, leaving a young wife and 3 kids.

The company was in turmoil and the employees all worked to keep things going. Then the remaining brother came back and took over control, fired all the bosses and installed his own team. In the accounting department we just kept doing our thing. The sales were high, there was growth and expansion, plenty of profit and plenty of cash. But we knew the families involved in this tragedy and it got emotional at times.

In the meantime, the police were tracking down the killer and found that there were TWO plots to have him killed and both of them led back to his brother! So the brother who was now running the company, our boss, was arrested and kept in jail with an outrageous bail amount.

Scary, sad, tragic all around and there were times when we didn't know who was running things. Tough times but the staff really pulled together to keep the company going. I never thought about quitting as DH was in graduate school and I was supporting us. Also, i liked the job and I felt bonded to the team.

The killer brother pled not guilty, later changing to guilty by reason of insanity. He was found guilty and sentenced to 15 years to life and later died in prison in his 50's.
 
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I've been at my current company for ~25 years and have worn several hats since I've been here. I would say my first 2 years in my professional career were challenging to get myself established. However, I will say the next few will probably be more challenging. I would prefer to get back into operation engineering, but I may have to leave my company to do that. My current role is in continuous improvement, and it has its good and bad days, lol.

I always envisioned I would retire at this company (early of course). It's truly a good place to work, but my drive at my current role is not what it used to be. I think as I get closer to FI, my appetite for BS gets less and less. It might be the same no matter where I go, though!
 
Right now is the hardest for me. We have elder care issues in two cities and I need 4 to 5 years of work to get where we need/want to be financially. This means my wife and I are often not in the same city. Maybe it is the family issues that impact my motivation at work or maybe it is knowing I’m entering the last few years. I don’t know what it is but many days I openly wonder if I can juggle everything for 5 years.

If the health issues get too much worse I may not be able to stick with work as long as my projections assume. We would make do even with what we have today, but I have not worked all these years to have a retirement where I have to be overly frugal. We’d prefer to have a chubby fire where we can just do what we want within reason.

I wonder if being focused on our FIRE number is a big part of my problem and if I should just leave my ETF’s and mutual funds on auto pilot and just ignore how they are doing for the next six months and see if that helps my attitude?
 
The most challenging stretch of my career happened later as I started losing mobility walking long distances. I worked as a Registered Respiratory Therapist for forty years in a large Atlanta/Sandy Springs hospital and I loved it. I was assigned all areas of the hospital (Ex. floors, AICU, ER, NICU, and Deliveries). But I slowly lost the ability to rush to emergencies with my much younger colleagues. I was embarrassed and tried to hide my physical and emotional pain by denying anything wrong when asked by my fellow colleagues. I finally was relegated to the NICU taking care of neonates on ventilators that were grouped together in the same pod area. I could help and instruct my less experienced colleagues to learn the ropes. I really missed helping my very small babies and their parents. But a few years later, my manager had an emergency with staffing another department called the Sleep Disorders Center that needed help teaching new patients how to use their new C.P.A.P. machines and fit them with the appropriate mask. And instead of working 12-hour night shifts, I switched to 8-hour day shifts. I no longer had the stress of worrying about rushing to emergencies. And for four years I enjoyed the relaxing atmosphere. I finally retired when I was 68 years old. Although I enjoyed my work But I got bored of performing the same tasks compared to my previous work every day. I went from always having new experiences and sudden emergencies at any given moment to do the exact same tasks every day. My latter-day mobility issues were the most challenging stretch of my career. Now, I am retired, living alone with no family and using an electric wheelchair.
 
marko said:
Unfortunately, my path is not one easily replicated. It went something like this:
Mid 1970s, we were a much smaller company at the time, about 150 employees. I was in a very small, highly dysfunctional technical service department made up of 100% Prima Donnas. I was 26 at the time.

Over a period of about six weeks, our boss was fired for repeatedly showing up falling down drunk at 8AM, a coworker died, two others quit and another was away in a long term equipment installation in Turkey.

I ended up alone and the only one who "knew what was going on". I ended up temporarily reporting directly to the president, which resulted in my having a great deal of autonomy and responsibility without any downside from failure; very high visibility. I just saw it as my big opportunity.

A brilliant 28 year old female executive took it upon herself to become my mentor and advocate (you can read between the lines), and a few older managers would take me aside when I strayed too far from the center line.

After a year or so of essentially running the department, I was wandering around the facility one night, found out where they hid the corporate ladder, grabbed a rung and started climbing. And the rest, as they say is history.

Fact, I never really thought about my 'turning point' until I started answering in this post. But there it is.
Click to expand...



Thank you. Very interesting story.
 
fisherman said:
Thank you. Very interesting story.
Click to expand...

Maybe this might help your son.

Among the many things my 26 year old self learned from my ummm.... "mentor" was:

Calm down; this isn’t high school, its a business; it's about making money.
Be aware of political predators but not everyone is a competitor, form alliances.
Only fight the battles you think you can win.
Fairness has nothing to do with anything.
Never take a job for what it will give you; take a job for it will give you in the next job.

Wishing him well.
 
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OP chiming back in:

Something that I think may be an interesting experiment would be, at least on a weekly basis if not daily, to assign each workday a score (i.e. 1 is awful; 5 is average; 10 is wonderful), and chart out how the weeks and months are going.

Maybe there could also be a brief work happiness diary that notes what is making us happy and what is making us miserable. Over time, it would be good to chart out the longer-term trend. We could see if March was a 6.7, but what happened in September that made it a 3.7, and then a 3.9 in October, and lower than 5 for the next 6 months.

So then the question would become what happened that would move it significantly one way or another? Is there a way to get things back on track to a more fulfilling time during the remaining working time. And does this speed up or slow down the retirement plan? I think it would be interesting and so I may try that.

I continue to be appreciative every single comment and how supportive they are by sharing experiences that can help not only my situation, but be helpful to others.
 
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My last few years working as a retail pharmacist were easily the most difficult of my career. Thankfully I escaped that awful working environment and I can honestly say that I will leave the profession of pharmacy or retire before going back. Left retail pharmacy in early 2018 before COVID. Can’t imagine how terrible things are now and I don’t intend to find out!
 
I am a little different as I enjoyed my career. The most difficult stretch was actually mid-career, after I had been with Megacorp 11 years. I started on the technical side and by that point had risen to a level of management where one had to be very good at playing Megacorp politics, and over the next 3 years I found out I was not. Many times I saw politics acting against the best interests of our clients and our corporation.

I also was becoming more and more removed from the technical side (Megacorp did not have a good long term career path for technical workers at the time, one reason I moved into management) having to deal with more administrative/personal issues. I began to realize that the technical/project type of work I truly enjoyed, interacting regularly with clients to understand their needs and provide solutions.

Couple that with a family move that took us several hours away from established friends and family, and there was a lot stress on both DW and I, to the point where we sought marriage counseling to deal with our relationship, and the temptations the stress was leading us to.

After those several leaves I decided the stress to my family and to me was not worth it, and I debated leaving Megacorp at that time. I even went to my manager (who in my view was part of my problem) and said this was not the right job for me. But I had a peace after that meeting, feeling regardless of what happened it was worth it.

Lo and behold, a new initiative came out that just "clicked' with me, as it involved both technical and project/management skills; I ended up writing a 3 page reply to an email requesting my input, next thing I knew I was called up to corporate to explain and defend my reply. That resulted in me being put in charge of that project, which while challenging was something I thoroughly enjoyed. During my years on that Megacorp realized they were losing a lot of technical talent because of a lack of long term career and began establishing one. When the project was completed (and very profitable), I fell into that career path, which made the last 24 years of my Megacorp career thoroughly enjoyable.
 
I ER'd in 2011 at the age of 55. I had a 30 year career as an engineer in a Department of Energy National laboratory. I had a great job and looking back I concluded that I only had 3 bad years out of 30. The first time I was transferred to a group that I decided, after about a year, that I didn't really have much of a future there. Management knew I was unhappy and transferred me to another group. The second full year of hell was when I got caught in the middle of some office politics between my boss and other project managers. They were both pulling at me and I had to make a difficult choice. I choose right and the next dozen years were some of the best of my career. In the end though, thanks to technology changes, my group and our department started to suffer some extreme downsizing. I wasn't necessarily in danger myself but the job became sufficiently unpleasant that I was motivated to look at our retirement benefits program. That was the Eureka! moment and I was gone 6 month later.
 
The first million net worth was the most difficult. Then it was the recession.

After the first million, I learned to let things go and focused more on living quality. Haven't mastered it yet but it helped with anxiety.
 
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