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Has anyone left a “cushy” job and regretted it?
Posted on 8/3/22 at 8:05 am
Posted on 8/3/22 at 8:05 am
Currently working for company and have what most would consider a “cushy” job. Mediocrity is the expectation, there are no set KPIs or goals for any groups, and everyone shows up at 9:00 and leaves at 5:00. Pay is good to very good depending on the position. Options to move up are limited with company men often getting put into leadership roles, keeping the status quo and retiring after 20 years.
I am torn between keeping the stability of a low stress/low expectation position versus getting into something more fast-paced and fulfilling.
Has anyone left a “cushy” job for something more fast-paced and regretted it? Still have many years left to work and looking to gain skills and be more fulfilled.
Going to the MT instead of the OT on this to maybe get some thoughtful responses.
I am torn between keeping the stability of a low stress/low expectation position versus getting into something more fast-paced and fulfilling.
Has anyone left a “cushy” job for something more fast-paced and regretted it? Still have many years left to work and looking to gain skills and be more fulfilled.
Going to the MT instead of the OT on this to maybe get some thoughtful responses.
Posted on 8/3/22 at 8:12 am to TigerVizz87
I've done the opposite and have never questioned the decision.
With that said, I am grateful to have spent some 20 years in that high stressed environment - a lot of life lessons realized and likely needed improvements in self happened.
But then again, am not one to view much of life through a lens of regret.
With that said, I am grateful to have spent some 20 years in that high stressed environment - a lot of life lessons realized and likely needed improvements in self happened.
But then again, am not one to view much of life through a lens of regret.
Posted on 8/3/22 at 8:24 am to wfallstiger
Would keeping the job and finding the challenges and fulfillment in your personal life/and time be workable?
Posted on 8/3/22 at 8:28 am to TigerVizz87
Left a job recently that was considered a retirement job to get back in the rat race with a better company.
I was bored to death and needed a challenge.
I kept my same salary but added a bonus incentive plus better benefits. The target 12% bonus will help keep my fire every year.
I was bored to death and needed a challenge.
I kept my same salary but added a bonus incentive plus better benefits. The target 12% bonus will help keep my fire every year.
Posted on 8/3/22 at 8:33 am to TigerVizz87
quote:
Has anyone left a “cushy” job for something more fast-paced and regretted it?
No. I left a big company cush job in January for a startup. Big bump in pay, high risk, high reward, fast pace. Been a fun year so far.
Posted on 8/3/22 at 9:13 am to TigerVizz87
quote:
Has anyone left a “cushy” job for something more fast-paced and regretted it?
Yes
Posted on 8/3/22 at 9:21 am to DiamondDog
quote:
I was bored to death and needed a challenge.
That’s where I am currently at. Trying to decide if it’s worth hanging in here for another 8-10 years until the old hats roll out and take it from there.
Posted on 8/3/22 at 9:41 am to TigerVizz87
Yep, left cushy job at the peak of my career after 25 years to run my own business. Toughest two years of regret before I was able make it work. All is well that ends well.
Posted on 8/3/22 at 9:42 am to TigerVizz87
I have a cushy job right now and they're going to have to fire me because I'm not fricking leaving.


Posted on 8/3/22 at 9:53 am to TigerVizz87
The second firm I worked for... I had it made. I was good at what I was doing... everyone liked me... I was getting nice bonuses and promotions... I had a clear path to partner.
But I thought the work I was doing was too simple. I wanted to work on more complex clients and more complex situations.
So I listened to a recruiter and left. The pay increase was like 5K which my current firm immediately offered to match. But I had decided I wanted more of a challenge.
The new firm was an absolute disaster and by the time I realized that... my old firm had filled my position. I left the new firm after one tax season and bounced around trying to find a new fit.
I'm in a great spot now... but I had about a 4 year run where I really hated what I was doing, and strongly regretted leaving.
Even now... looking back... I wish I would have stayed.
But I thought the work I was doing was too simple. I wanted to work on more complex clients and more complex situations.
So I listened to a recruiter and left. The pay increase was like 5K which my current firm immediately offered to match. But I had decided I wanted more of a challenge.
The new firm was an absolute disaster and by the time I realized that... my old firm had filled my position. I left the new firm after one tax season and bounced around trying to find a new fit.
I'm in a great spot now... but I had about a 4 year run where I really hated what I was doing, and strongly regretted leaving.
Even now... looking back... I wish I would have stayed.
Posted on 8/3/22 at 10:02 am to TigerVizz87
Currently in the same situation as you. Not a lot of room for advancement and bored shitless. Pay is decent.
Posted on 8/3/22 at 10:12 am to TigerVizz87
quote:
That’s where I am currently at. Trying to decide if it’s worth hanging in here for another 8-10 years until the old hats roll out and take it from there.
I'm 36/37. If I was making this move, it had to happen now. I still have a good 25+ years until I retire. I wanted to know what it was like to be rewarded for good work...something I never had besides a marginal raise.
It blows my mind that most people see some sort of bonus. I have never experienced that. Ever.
Now I think about how I could see 12-15% extra every year plus a raise? Plus remote? Come on.
I've worked in some crappy situations and environments before. Whatever this is can't be no worse then what I have experienced.
My advice, is know your limits. If you're lucky to have the job you have, stay. If you're actually good and a grinder, go elsewhere.
Don't ever try and change somewhere that doesn't actually want it. Been fired for that before. If they don't want change now, chances are they don't want change in 10 years.
This post was edited on 8/3/22 at 10:16 am
Posted on 8/3/22 at 10:17 am to Wraytex
I would think a lot depends on the out of work social structure you have to rely upon and their respective levels of tolerance - I am a lot nicer now, LOL. There were many moments when one could describe me as an absentee landlord, the office my mistress and my wife had second chair. Fortunately, they loved and supported me through all the ups, downs and yes; growth
Hope I came close to answering
Hope I came close to answering
This post was edited on 8/3/22 at 10:20 am
Posted on 8/3/22 at 10:29 am to TigerVizz87
If you don't at least try it, you won't ever know. Yeah, I tried this same thing and it did not work out for me, but at least I know what my limits are and I don't have to ask myself "what if."
If it sucks you can find something else.
If it sucks you can find something else.
Posted on 8/3/22 at 10:43 am to TigerVizz87
Don't live to work, work to live.
Posted on 8/3/22 at 10:59 am to Costanza
quote:
Don't live to work, work to live.
This is the right outlook. I'm just not wired to operate in this manner. I love to work and have no interest in ever retiring. It's deranged. Ultimately once I really understood this about myself is when I ventured out and started my own thing.
Posted on 8/3/22 at 12:00 pm to WhoGeaux
Depends on your risk profile too. In my 20-30’s I would have left said cushy job to pursue something more of a challenge or opened my own firm/business. Now at almost 50 with a wife that doesn’t work and 2 kids in private school, a mortgage, two car notes etc my risk tolerance is almost zero as theres just no room for error. So I sit in my cushy boring job and make a very nice living.
But to your point, I have zero fire in what I’m doing. I’ve moved up as high as I want to and I’m just going through the motions until retirement. Still blasting out my goals, but nothing excites me anymore about it all.
But to your point, I have zero fire in what I’m doing. I’ve moved up as high as I want to and I’m just going through the motions until retirement. Still blasting out my goals, but nothing excites me anymore about it all.
Posted on 8/3/22 at 12:58 pm to TigerVizz87
Same as some others, I wanted new challenges and opportunities from about 25 to 40. By 40, I had a wife and 3 young kids I wanted to spend my time with, and had come to terms with where I was professionally. I switched to a cushy, low stress job with adequate pay; and have spent the last nine years trying to hold off people trying to get me to work harder than I want. By those terms, I've been pretty successful.
Posted on 8/3/22 at 2:57 pm to TigerVizz87
I left what most people would consider a dream job because of how “cool” it is. (Low 6 figure job in professional sports) for a cushy job. Still have responsibilities, but when I’m off, I can turn my phone off and not have to worry about anything. Best career decision I’ve made.
Posted on 8/3/22 at 5:11 pm to TigerVizz87
(no message)
This post was edited on 10/26/22 at 9:25 am
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