Should You Leave Your Cushy Job And How Long Should You Stay?

You may have experienced this pattern before. You start a brand new job and work extremely hard in the beginning to establish yourself and your reputation.


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At first, the nature of the work is extremely challenging. You are constantly learning and trying to keep up with your coworkers. You find yourself staying late at the office just to get by.

As time passes however, you become adept at your job. You find ways to do your work faster and more efficiently. You become proficient and an expert at what you do.

As more time passes, you feel comfortable and at ease with your job. You find yourself able to finish all of your work in an 8 hour day. You have more free time to spend at home. Things become cushy. Is it time to leave?

One Perspective

I was chatting with a close friend of mine over the weekend about complacency at the workplace. Turns out that he recently quit his job to join a company that builds completely different products than his last firm.

While the nature of his work will be fairly similar, the culture and pace of his new company will be a brand new experience. Inevitably, he will have to work longer hours as well.

So I asked him why he changed jobs. After all, he has a wife and child at home whom he loves spending time with. His former job was a 9-5 type job that lent him plenty of time at night to hang out with his family.

In addition, he never had to work weekends and the job itself was pretty low stress. Why did he give all of that up for a new job where he’ll have to work many more hours and re-establish himself?

Why did he sacrifice the additional family time for a new job that is more demanding?

My friend has a policy when it comes to work. He never stays at any company longer than 3-4 years and he’ll leave even earlier if he starts to feel complacent at any time.

He describes his job hopping behavior as an itch that develops when he starts any job that can only be scratched by switching companies.

In short, he always leaves his company if any of the following are true.

  • He’s not learning anymore
  • Company politics are getting in the way of work
  • He’s getting bored at work
  • He’s doesn’t feel like he needs to challenge himself anymore

His reasons seem fundamentally sound. Why stay at a job if you feel complacent? Why stay with your current employer unless it’s your dream job?

Another Perspective

While I agree with all of his reasons for switching companies, I can’t help but feel as though he’s missing out on a completely different opportunity. What opportunity am I referring to?

If your current job pays you enough to support your family and it also provides you with lots of free time, why not use that free time towards your financial independence? Why take on another job that will make you work longer hours for someone else?

At the end of the day, those additional hours of work at the new job are still going towards benefiting someone else. Those extra hours are not going to put more money in your bank account except for maybe a small raise.

Cushy = Opportunity

If you ever want to break out of the rat race and be your own boss, there’s no better time than when you have a cushy job. I’m not saying that you should slack off in any way.

You should still perform at your peak while you are on the job. But you should finish your work as quickly and as efficiently as possible so you can go home and work on your independence.

People always make the excuse that starting their own business is risky. But when you start a business on the side, you still have your entire salary from your paycheck and there is absolutely no risk whatsoever.

You will continue to be paid while devoting your extra time towards something more meaningful.

What Can I Possibly Accomplish On The Side?

You’ll be surprised at what you can accomplish with the time away from work. Hypothetically speaking, if you get off work at 6pm and eat dinner, that leaves about 3-4 hours a night that you can put towards your own business.

Couple that with the weekends and you can get a serious amount of work done.

If you want to think about it in a different way, you are devoting the extra hours you would have been working at your new job towards your own venture. All of your time goes directly to your own top line.

Should You Stay At Your Cushy Job?

The revised answer to this question should be a resounding yes, but only if you eventually want to be your own boss. Your cushy job presents a unique opportunity in which you can make a full salary while challenging yourself at the same time.

But heck, there’s nothing wrong with wanting to live the rest of your life working for someone else if that’s what you want to do. But wouldn’t it be nice to give yourself the ultimate challenge?

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About Steve Chou

Steve Chou is a highly recognized influencer in the ecommerce space and has taught thousands of students how to effectively sell physical products online over at

His blog,, has been featured in Forbes, Inc, The New York Times,  Entrepreneur and MSNBC.  

He's also a contributing author for BigCommerce, Klaviyo, ManyChat, Printful, Privy, CXL, Ecommerce Fuel, GlockApps, Privy, Social Media Examiner, Web Designer Depot, Sumo and other leading business publications.

In addition, he runs a popular ecommerce podcast, My Wife Quit Her Job, which is a top 25 marketing show on all of Apple Podcasts

To stay up to date with all of the latest ecommerce trends, Steve runs a 7 figure ecommerce store,, with his wife and puts on an annual ecommerce conference called The Sellers Summit.  

Steve carries both a bachelors and a masters degree in electrical engineering from Stanford University. Despite majoring in electrical engineering, he spent a good portion of his graduate education studying entrepreneurship and the mechanics of running small businesses. 

28 thoughts on “Should You Leave Your Cushy Job And How Long Should You Stay?”

  1. Carla | Green and Chic says:

    I can relate to your friend. I have never stayed at a job/company longer than two years in the eleven or so years I’ve been in the job market. By the end of year one, I am bored out of my head. I try to stick it out for another year or so then I have to go.

    The problem is this “time away from work” to work on your business is that it doesn’t leave a lot of time for family or for yourself. Its great if you’re young, healthy and don’t have other responsibilities though. I tried it and it was a killer. If you can swing it, part-time work while working on a business is more ideal.

    1. Steve says:

      It’s definitely a sacrifice, but only a short term sacrifice until your business is up and running. The main thing that you need to ask yourself though is why should you work all of the extra hours at a new more demanding job when you could be spending that time directly improving your own situation.

  2. Jeremy Day says:

    Hi Steve,

    I love the point this article makes. I am in this position right now. Im actually in my dream job right now, but I am getting bored. People are either envious or hate me when I tell them about my job… how fun it is… how much time off I get… the only downside is how much I get paid.

    I figure I need to leave that job so I can use my MBA to go make possibly double my current income and bankroll a bit of cash to start a business.

    Your idea makes sense and I think I may try it once I get cushy in my new job. However, you can’t underestimate how powerful our personalities are. Some people just need to keep trying new challenges. Some serial entreprenuers make it work, but they do it with angel funding, and they go big.

    Someone building a business on the side is probably planning on keeping the business. What happens in 5 years when that person gets “cushy” in their new business they started? They can’t exactly just go start another one can they? They need to build plans for someone else to take over management, and the business make not produce enough profit to do that.

    In any case, I love the idea, and I was basically just taking it a step or two further. Would love your thoughts.


    1. Steve says:

      The beauty of getting cushy in your own business is that you can sell it off at any time and start all over again. Alternatively, you can just hire some good managers and set it on auto-pilot. The end goal at least for me is to put down some automated processes in place so that I can quit my job and pursue whatever I want to do.

  3. Evan says:

    Another challenge would be to get closer to your friends and family. (Why not? Scary? Then you have a new kind of challenge).

    PS boredom is usually clash of two competing desires – it is different to just being tired.

    1. Steve says:

      My wife and I run our business and this blog so that we can become closer to our friends and family. My wife quit her job to spend more time with our daughter. Currently, I’m working on some side projects as well which will hopefully allow me to quit mine.

  4. Keri says:

    I think the friend has the right perspective. Even if one of the benefits of your cushy job is that you only work 40 hours per week, it’s still 40 hours per week for most of your life. Yes, that could give you an extra 3-4 hours a day during the week, and all of your weekends to pursue your other interests, but the bulk of your life is spent on the job. Why waste that time being bored or allowing your mental capacities to shrink? Why spend it in a den of political intrigue, stressed out from the invisible enemies? Why not find a job that makes you excited to get out of bed in the morning instead?

    Life’s short, and you spend a great deal of it at the office, however you define office. Enjoy that as much as you can.

    1. Steve says:

      What you say is completely true if you choose to remain working for the rest of your life. Starting and growing a side business will hopefully allow you to generate additional income so that you can go full time on your own. My wife has a pretty great setup right now. She runs our linens business for several hours each day and then plays with our daughter the rest of the time. Our business brings in much more money that she would’ve made at her day job.

  5. Stephen - Rat Race Trap says:

    Steve, fantastic article! I think you hit the nail on the head with this:

    “You’ll be surprised at what you can accomplish with the time away from work. Hypothetically speaking, if you get off work at 6pm and eat dinner, that leaves about 3-4 hours a night that you can put towards your own business. Couple that with the weekends and you can get a serious amount of work done.

    You can use the job to support you while you figure out a way to become independent. The perfect setup 🙂

    1. Steve says:

      Thanks. It is the perfect setup. It just takes discipline.

      @Ching Ya
      Thanks! It sounds like your goals are aligned with ours. Hopefully you’ll have your blog running full steam by the time the little ones arrive (if they haven’t already)

      Cool. Is your side hustle or do you have other side businesses as well? I’d love to check them out.

      Thanks! Your comments are always appreciated

      Oops, I guess I took your comment out of context. My buddy is just one of those people who loves new challenges and he always works really hard at whatever he does. I’ve been trying to convince him to channel that energy into his own venture but thus far have been unsuccessful.

  6. Ching Ya says:

    This article pretty much summed up our plans for future. Couldn’t agree more. I had the exact feeling with the daytime job, feeling complacent and obviously had reached the point where I felt ‘lack of input’ and mechanical. To use the extra time and energy from work to try out something new, that’s how I got into the blogging area, and hopefully to work towards the home-based idea, where I get to spend time with my family while earning a living. That’s the ultimate goal basically.

    Thanks, Steve. Your blog has been an inspirational read. Glad to find it.

    social media/blogging

  7. PT Money says:

    I couln’t agree more. I have a cush job and thank God everyday for it. It allows me time to spend with my family and to build up my side income. I wouldn’t have it any other way.

  8. Jeremy Day says:

    @ Steve

    – I wish you the best of luck! I am always inspired by your story!


  9. Evan says:

    I was thinking of your friend rather than you when I wrote my previous comment. From your earlier posts I know that spending more time with your family was part of the motivation for starting your business (though there is no way of you knowing that I read them I guess).

  10. Marc and Angel Hack Life says:

    Interesting perspective. I kinda expected you to go the other way with this. But I agree with your conclusion.


    1. Steve says:

      @marc and angel
      hehe. Just trying to be unpredictable:)

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  12. Evelyn Guzman says:

    Those are all good arguments as to whether to quit the cushy job or not but I agree with you when you said, why change job for longer hours when you can use the extra hours developing your business? It will be a challenge I know but it will be worth it in the long run.

    Evelyn Guzman (If you want to visit, just click but if it doesn’t work, copy and paste it onto your browser.)

  13. mitzi says:

    I think it depends also on where you are in your expected working life…
    I can retire anytime now – but choose to work for the free company paid
    health insurance. So I work the 30 hrs/wk required for that, and have a
    nice cushy job. I say cushy, because the demands are low, and the free time
    is high. Plus I can take off if needed to babysit grandkids, catch a school bus,
    or bring a grandkid to work with me if needed. And I can do my ebay sales from
    work, or read, do bookwork, etc….. a lot of personal stuff can get done at work.

    So for me, it is well worth it to keep the cushy job as it fits my needs for extra
    personal time, flexible hours, and free health insurance.

  14. Dana says:

    Loved this article! I also have a pretty cushy job and I have been in a major hurry to quit so I could build my own business. However, I realized a few months ago just how good I do have it. So if I have to wait another year or two to be able to leave, then that’s another year or two that I have to grow my emergency fund.

  15. Deneil Merritt says:

    Great article, I find trying to build a business online and stay motivated to do is the ultimate challenge. I love it.

  16. Charles - Big Idea Blogger says:

    Great article!

    It’s the mindset behind. Using Robert Kiyosaki’s Cashflow Quadrant, your friend is the classic E who wants to find his success in working for others. I have friends like that too. My thoughts are exactly like yours.

    It’s hard to change their minds, but my friends seem happy doing it. For me, as long as they are happy, I’m happy for them.

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  18. Ragnar says:

    Really insightful, this will hopefully help me power through my first job while I get my own business started. I might try to find a job that has fewer hours, or more flexibility, like letting me leave work when I’m finished. But with the little experience I have, perhaps I should be happy just having one at the moment.

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  20. Rudiger says:

    I think I can speak to both sides of this argument, based on my own experience. I had a pretty “cushy” job for 5 years between 2005 and 2010. It did not pay all that well, but it paid enough. It helped that I lived in a low cost of living area of the country. The work was low stress and I could get it done in a few hours each day, leaving several hours of relaxing downtime. The perks were outstanding too. I was on the road most of the time, which meant no boring cubicle life, safe distance from office politics, and amazing earnings of air-miles, hotel points and other rewards programs. I was flying first class, staying in resort hotels, and my meals were all on the company dime for those 5 years. For some silly reason, I started to feel unchallenged. Bored. Although the money was ok, I began to desire a higher salary as part of climbing the salary ladder so I could command more money in future salary negotiations. So I left this cushy job for what was a notable bump in pay at a company that was, as it turned out, stressful, toxic, disorganized and cubicle based. I absolutely hated it, and it did not end well. I quit when my blood pressure reached dangerous levels. Now I am in a job that pays even more, and has a low-moderate stress level. The people are nice, the work fills 7 hours of an 8 hour day and I have no REAL complaints. But I still regret not being at that old cushy job now. That toxic job before this taught me a very important lesson: It is better to be bored and unchallenged than to be overwhelmed, over-worked and and highly stressed. A cushy job, or at least one you are comfortable in, is a rare prize. If you have one, keep it. The grass is NOT always greener.

  21. Kylie says:

    oh man. i was hoping to find people encouraging me to heck it and just move on to a big new world. i have a cushy job too. i only work less than 1 hour a day on average and i’m paid 70k a year. i just have to pretend to be busy everyday sitting in my cubicle, and see the same faces that i’m sick of seeing, talk about the same issues over and over. Tell me; is it worth it to quit and find my passion/being self-employed?

    1. Kylie says:

      *pretend to be busy for 8 hours a day

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