re: Has anyone left a “cushy” job and regretted it?

I just faced this decision. I have a king Cush job but felt that my variable comp took an unnecessary dip last year. Another company came after me hard but in the end I decided to stay because to the total comp was going to even put in year 3 and my current deferred comp cannot be matched.

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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.

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I made this exact decision about three months ago. I thought the grass would be greener on the other side and I'm starting to totally regret it. I was very comfortable in my prior role and I knew and could very easily manage the expectations. The position I'm in now, the company is growing so fast no one knows the expectations and there aren't any processes or training in place for new employees coming in. You are thrown in the fire from the get go and expected to perform. Every damn day I feel stressed.

If I were you I would evaluate how much stress your new job would add into your life. That's something I really didn't consider when I made my decision and now I've learned that's worth a lot more than I realized.

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Just love the job security. And I'm not willing to risk it for a "challenge."
Find that outside of work via hobbies.

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get side gigs, side businesses ,etc.

Id wait until after this recession to move. Milk the easy job for the next year or so

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I am torn between keeping the stability of a low stress/low expectation position versus getting into something more fast-paced and fulfilling.

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If you are going to continue to work for someone else, stick with the easy job. These fast paced jobs you speak of in my experience are not any more fulfilling.

And yea I have left a somewhat cushy job. Big company that I was on an upper management track for. I wouldn’t say I regret it but I’m not in a better position now than I would have been if I just stuck around. But if I was still there, the money would be to good to walk away from and would have wound up “stuck” which is what I was afraid of

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Possibly, but I’d like to think not. I read a lot of leadership books and listen to podcasts on work life. I have even tried to suggest potential new initiatives to improve work flow and motivate employees. We are a company of less than 50 folks.

The company founder/owner has another 8-10 years (maybe a bit less) before retiring which will be the first real shake-up for the company.

Another reason for posting the OP is because I have also considered leaving to gain some new skills and management experience with the intention of possibly coming back later when this group of old hats decide to l start retiring. Just not sure how favorably my leaving and then trying to come back would be looked at.

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It sounds like you are itching to try new things now. If you wait 8-10 years, you will either get really frustrated or the itch will subside. Plus you may be surprised how you slow down and settle in over 8-10 years--some of that is good and some of it is bad. (This is less likely if you are currently 25, but more likely if you are currently 35.)

Also, you might consider that jobs that are "cushy," stable, and predictable are actually sort of rare these days, and maybe it wouldn't be that great to shake it up for those who like having that sort of a job. There are lots of other places you can get metrics, stress, fast-paced, and "fulfilling," if that's what you want.

Yes. I left a low stress low expectation job where my coworkers and boss loved me for a break and a challenge. Wanted to, as you say, 'learn more skills' and be more 'fulfilled.'

and ended up working with a bunch of catty bitches, boss only showed up to bitch and micromanage everyone and then vanished, and an administration was always on my arse, nitpicking every piece of documentation I did. And finally, I worked my arse off, physically and mentally, and was always exhausted when I came home.


In the end I went back to the low stress/low expectation job who gave me a pay bump. It worked out, I got a dose of reality and that the grass isn't always greener.

Eventually I left that job when I got my advanced degree, which I probably couldn't have had the time to get with the tougher job.

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What are these well paying, cushy jobs you guys speak of?

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My job pays me very well and I have enough free time on my hands during the week to do pretty much all I want to around the house without saving it all for the weekend.

For example, I prepared a memo, did a little research and met with one client today. That took maybe 2.5-3 hours. I also brought my kid to camp, went out to lunch, stopped at the grocery store, did some yard work, and met with some guys doing some work at the house.