Abandon Your Cushy Job To Expand Earning Potential

cushy jobHave you ever declined a work opportunity because you didn’t want the hassle of learning something new? Maybe it was a chance to enhance your skills or get promoted, but it required leaving your cushy job.

You declined because the job would have taken more effort and initiative on your part. Or it might have cut into your lunch breaks on Facebook or Pinterest. Or limited time normally spent with the kids at home or watching sports.

Some people never get new opportunities because their manager or co-workers know they’re not interested (evidenced by their work ethic). Still more pass because they’re perfectly content in their current cushy job.

The Sneaky Mid-Career Morass

Many mid-career workers want to ride their current gig into retirement. Ambition and motivation are gone.

I know plenty of people who are good at what they do and enjoy their work but aren’t striving for anything more. To each his or her own.

But what if a new project or job came along that could lead to higher income? Would you leave your cushy job to take on a new challenge for the chance of greater success and a higher salary?

Younger readers are probably thinking, hell yes I would. Youthful ambition is admirable.

But I have some depressing news for the twenty-somethings reading this.

Aspiration fades.

Stinkin Chart 1Think of a forty-something with a few kids, mortgage, and a couple of car payments, who is comfortable in a mid-level corporate job or local government position. It’s been 15 years. Retirement is in sight.

They’re reliant on this job (see above), and judge the path of their career on job security rather than success milestones. Each night they pray for no layoffs or changes to the status quo.

Is it worth leaving their comfort zone to try something new for a chance at extra pay?

Why Stay with A Cushy Job?

Reasons to stay at or leave a cushy job depend on the mentality of the worker.

Sometimes I see people on CNBC who appear to be in their 60’s and recently started a new investment firm. Some people love to work. Others love personal development and will never stop learning or being a “productive citizen”.

But we’re not all wired that way. In fact, most of us aren’t.

Reasons are plenty why someone would avoid career development and higher pay by parking their butt in a dead-end but comfortable job.

A worker may like their job and not want to leave it. Coworkers may be friends and fear of letting the team down can play a role.

Maybe the commute is great and the work/life balance makes the job hard to give up.


Job security can play a big part of comfort in a job. When a company is growing, there’s relief in knowing that more money is available to pay a salary. Government workers often accept lower pay for job security. With that comes lower expectations for performance. So why leave a secure job for another that would require harder work?

An IT term I hear a lot is domain knowledge. That’s when someone knows a certain part of an organization very well and serves as a subject matter expert. Being an expert in something has value, even if it’s a small part of a complicated organization. Why give that up? People look to them for help and the position is a bit more secure because of it.

In a cushy job, a manager may have put systems in place so that the organization runs smoothly without much effort. An old Steve Case adage says a good manager should wake up with nothing to do. If that manager went to a new organization, new processes would need to be in place. That would be a ton of work.

Another reason could be because a worker is overpaid. Peeking into the marketplace for a new job would be a rude awakening. Why get paid less when length of service has entitled someone to an over-sized salary and benefits package?

With so many reasons to stay, why leave a cushy job at all?

Reasons to Leave a Cushy Job (and Why I Left Mine)

Comfortable jobs usually come with an income ceiling. Only so much money is available for raises and promotions. Once a worker hits a certain level, raises flatten.

So a primary reason to leave a cushy job is to expand earning potential. This can be done in a variety of ways.

Living in a small town or city with high unemployment can be a damper on salaries. Move somewhere with a more robust employment market and you’ll find higher paying jobs.

Another way is to leverage a skill set in a different industry. For example, if someone has expertise in building computer systems for grocery stores, they can probably find a higher paying job working on banking systems. A move would involve new coworkers and domain knowledge, but banks have deeper pockets than grocery stores and that would be reflected in salaries. The skill set used would be the same.

Once someone has mastered a skill in an organization, they may have run out of new things to learn. In order to keep growing a career, they may need to look elsewhere.

Curiosity and self-improvement are other reasons to leave. If you’re barely using your brain for eight hours a day, is that making you a smarter and more productive person?

For the past five years, I became comfortable in an increasingly easy and low-profile position. I was a subject matter expert, but the position didn’t require a lot of brain power anymore. My intellectual capacity as an IT consultant was not being fully utilized. For a while I was OK with that. I channeled excess cognitive capacity toward personal finance and writing.

Until recently. My mindset changed.

Instead of continuing down easy street, I decided to abandon my cushy position for something more challenging. It’s a risky move that I’m still adjusting to, but so far it seems like the right decision.

One week I was on cruise control, just like I have been for the last seven years. The next week, suddenly I’m busting my ass on a new project with a tough manager and demanding client. No salary increase (yet).

So why leave a cushy job for a harder one that pays the same?

The answer is earning potential. If I work harder on this more important, higher profile project, I can potentially earn a lot more money while working the same 40-hour week. It’s not easy anymore, but I believe I’ll be a better professional for it.

Maximize The First Stream First

I’m a proponent of building multiple streams of income, especially investment related streams that are more passive like dividends and peer lending.

However, if you’re working a full-time job, the most efficient way to increase your overall income is to increase your wages.

Building a large salaried income, spending below your means, and investing the surplus is one tried and true path to wealth. If you’re already working 40 hours a week somewhere, why not get paid more to do it?

For those that are pre-FI and still need/want a job, focusing on increasing income per hour should be your primary goal. Other streams come next.

One of my favorite blog posts to write was called This Job Post Is Not Safe For Work (nsfw). I wrote this:

Everything I do at work is for one purpose… to make as much money for my family as possible. Satisfaction doesn’t come from collaborating on successful projects with a team, learning new skills, exceeding the customer’s expectations or impressing my manager… At this point and for the past decade, I’ve determined that my current job is the path of least resistance to financial independence.

Much of this statement remains true. As I analyze my earnings options, my current employer is still the best place for me to be. However, through my employer, I proactively found another position working with a smarter group of people that should lead to a higher salary and better job satisfaction.

Headaches will increase. Stress may creep in. Hours will likely increase (as will paid overtime).

And time with my family may decrease in the short- term.

I don’t take that lightly. Time with my family is my number one priority. But this new project shouldn’t cut into family time over the long-term. Only upfront.

The significance of the new project is that the probable salary increase for working on this new endeavor could help accelerate my retirement date. I’m making some sacrifices today that should pay off tomorrow.

How do I know I can make more money on this new project? The billable rates are higher. So when my annual review comes around, my knowledge of the rates gives me leverage while negotiating my raise.

On top of that, the client I’m working with is more professional and has a higher standard of work. I’m confident I can harness my prior experience to provide a better service to the customer for their money. The project I joined is uniquely positioned for growth.

If I am not retired yet and still working 40 hours a week for someone else, I owe it to myself and family to earn as much as possible in those hours.

I believe I’ve found a new path of least resistance to financial independence.

Leave a Cushy Job to Start a Business

The freedom attained through entrepreneurship is a powerful lure. Leaving a cushy job to start a business is the ultimate risk.

Young people lack the confidence, but are in the right part of their lives to take big risks.

Mid-career workers have the experience and confidence, but lack the drive and risk tolerance. And they don’t want to put their family’s comfort and well-being on the line when there are no guarantees.

Freedom through entrepreneurship can be interpreted a few ways. Not working for the man is a liberating thought, but many of us pursuing financial independence don’t want to own businesses. We don’t want to work at all!

But I’ve seen it over and over again, once someone hits financial independence, the tendency is to continue working, but now on their own terms. Starting a business becomes a lower hurdle because the consequence of failure is not catastrophic.

I admire anyone who puts it all on the line for a business idea. But that kind of risk taking isn’t for everyone.

Enter the side hustle. With a side hustle, both young and old can start a business while still maintaining a steady income. Plenty of online entrepreneurs started their businesses by wading in first. The internet not only opened up many opportunities to start online businesses, it became a forum to learn about and teach almost anything.

Starting a blog was my way of wading into online entrepreneurship without knowing what the hell I was doing. It’s a low-risk endeavor that you can start for a very small investment. This blog is a small little side gig. However, through the blog I’ve learned what is really possible. Sure blogging can be a career, but making money online can be much more than a blog. A blog is simply the entry point. Starting one can increase your earning potential without abandoning a cushy job first.

One Last Personal Discovery

When I wrote the NSFW post, I did believe money was my only motivation for working. Since then, I’ve discovered another.

The last few months on my old project felt rather mundane, much more so than the seven previous years. Part of it was lack of challenge, and part of it was me beginning to see the light in other areas of my life.

As I’ve built this blog and learned about running a small business online, I’ve turned to books, podcasts and other writers and entrepreneurs for inspiration.

One consistent self-improvement technique is to surround yourself with other successful people. They say you are just like the ten people you spend the most time around.

My wife is brilliant and keeps me sharp (although she says her brain is going to mush dealing with kids all day). And my kids are incredibly entertaining and a joy to be around. They challenge my nerve, not my intellect.

The second biggest chunk of my time is spent around my coworkers. The old team was a bunch of great people. But they were all in that mid-career morass, always gossiping about how secure their jobs were.

No one talked about starting a business or going after a promotion. Career discussions revolved around being underpaid and the allowed frequency of telecommuting. My former coworkers were all very content simply having a steady job.

I realized through my own pursuit of self-improvement, that I wanted to be surrounded by more ambitious people who would challenge me to reach for higher performance as a professional.

Being around smarter people will require me to up my game, something that hasn’t been necessary in the past few years. 

Striving to be a better professional is part of a more complete plan to constantly improve all aspects of my life. There is no rising tide in self-improvement.

Cushy Photos Courtesy of Ryan McGuire via Gratisography

Do you have a cushy job? Why do you stay there? Have you ever declined the opportunity to grow your career because you just didn’t have it in you?

Cushy Worker

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  1. It’s very true that aspiration with your job tends to fade with age. On the plus side though, I’ve noticed that although I’m not as eager to expand my role at my office anymore (I’m 40), my aspirations with other opportunities that are specific to finances are stronger than ever. I spend any time I have figuring out more ways to bring in as much passive income as I can while at the same time look at cost-cutting avenues.

    The goal to retire early gives a lot of drive back to those aspirations!

    — Jim

    1. Jim,
      Yes, I can agree with that. I am more passionate about not working in my “old” age, even though I’m working harder now. Most parts of my life I take more seriously now. Perhaps it’s wisdom. Or maybe a recognition of what is important.

  2. I left a stable job to start my own business a little over a year ago. I don’t consider it to be that risky because I had no debt and decent savings. I knew if I didn’t do it then, it’d only get more difficult as time passes. I recently married and having kids may be a couple years down the road. It is a much tougher decision when you have little ones to care for. If you are seriously considering a business idea, don’t have debt and/or a family to support, now might be the least risky time in your life to pursue it.

    1. George,
      Thanks for sharing your story. Now that i have kids, dropping everything to start a business would be riskier than five years ago. That is a deterrent. Most people don’t realize that until after they have kids. So I commend you for taking the plunge.

      I would be comfortable from a risk perspective, starting a business in my professional field because my foot is already in the door. But it’s not my passion. I don’t want to own a business I don’t love.

  3. I’m the “side hustle” kind of guy. My 9to5 salary supports my wife and 2 kids, so I wouldn’t jump into my side gig full time. It has proven to generate less revenue (on a per hour basis) than my daytime job, but on the other hand it’s been steadily generating 10% more each year, to a point that it is now a significant amount of money that will dramatically accelerate my FI date.

    So then comes the question, would you rather invest energy into your daytime job for a 5% increase, or in your side gig for a 10% increase (of a smaller starting value)? I chose the side gig, because I know I’ll want to keep working on the side gig in the next few years, while my day job is not motivating anymore to me

    1. Stockbeard,
      One cool thing about this new gig is I can still pursue side gigs. It won’t totally wipe me out. If it does take up a lot more time, I’ll make overtime pay. 10% is a nice side income. I don’t necessarily want to pursue side gigs full-time either. It would have to really grow prior to leaving a full time job before even considering it.

  4. Bryan,
    Good to hear. I know you’ve shared a lot of employment situations with your readers. I haven’t switched positions for the past 7 years. Now I’m getting used to it and I do already miss some of the old work. But still think it’s worth it in the long run.

  5. FV,
    I suspect I won’t hold this job into retirement. I milked the cushy job for a while there, but needed a change. Things should work out, if they don’t, I don’t need this stinkin’ job, so I’ll find something else, or drastically cut expenses and take some time off!

  6. Great post RBD. I’ve felt the cushy job syndrome set in a bit for myself, but that all changed last year when I lost my job. I have a new outlook on things now. Totally agree on being surround by the right motivated people. Miserable co-workers can suck the life out of you if you let them.

    1. Brian,
      Good to read that you bounced back and found something new. I’m guessing you’re going through some learning curve too, even with your experience. I wouldn’t say my coworkers were miserable. Most were quite happy to have a job. It was me that was becoming miserable. People would come ask me for help and I’d roll my eyes to myself, because I just wanted to be left alone.

      This new position, I’m always helping people, but it’s eager 22-year-olds instead of late career folks who don’t like the newer technology. The verdict is still out on whether it was the right move.

  7. I’ve worked for multiple employers over the past 10 years and have often taken on jobs outside my compfort zone in order to advance both my career tragectory and my wallet. Although I have been able to learn and grow into each new position, the next level up (project management) is a much different skill set that what I have been doing and takes essentailly learning an entirely new field. One of my concerns is fulfilling the Peter principle and becoming one of those stagnant people who are incompetent at their job. Once I make the leap I will give it a couple years, but make sure that the door is still open to returning to a Supervisory/Co-ordinator capacity.

    1. John C,
      That is the way to grow a career. I haven’t been doing it, mainly due to comfort. Until now. I am already learning a new skill set as I must delegate a lot of work because I can’t handle it all due to meetings. Luckily, I have some youngsters eager to do it for me.

      This early, I don’t see myself staying in this position for longer than 5 years. After 5-6 months I should have a better idea of where it’s going.
      Thanks for your input.

  8. RBD,

    Great article there. I am looking at my job the same way, except a change will likely lead to a massive salary bump. I’ve put in my grind including taking on jobs out of my comfort zone, but now I want it to get me that fastest route to FI, and sadly that is not through my current employer due to their set up and structure. Also like you stated, I’ve gone out and gotten extra certifications and taken all of the trainings my employer wanted to add, giving me a much sweeter resume. In fact it has started to lead to a few interviews that are looking really bright.

    I’ve also started pursuing a real side job over my blog, potentially working at a local brewery on the side. So if that happens perhaps you should stop in, it would be in the VA side of the Potomac.

    – Gremlin
    PS – like the use of the electrical ‘path of least resistance’ as a science person and sometime engineer.

    1. Gremlin,
      I like hearing about the hustle, especially when it involves beer. Contact me and maybe I’ll stop by to check out the local suds if it’s not too far away.

      Didn’t know that was an electrical term. Learn something new every day. I like it because I’m choosing the path that leads to the highest income with as little work. Of course, I’m working harder up front to catch up on the new stuff, but it should pay off in a number of ways, primarily in income. But also so my brain doesn’t deflate.

  9. What is “paid overtime?” (Said like the Dowager Countess on Downton Abbey asks, “What is a week-end?”) 🙂 I just did my time entry for last week (68 hours — no overtime), which reminded me that my “cushy” job is not actually cushy at all. I work my tail off. Mr. ONL both talk sometimes about how we’d be willing to earn less if we could have a cushier job, just because the stress is taking a major toll on our health, and making us feel like we HAVE TO quit soon if we don’t want to end up with major health problems related to work. So that’s the flipside. But we also recognize that we’re outliers on this, and are also golden handcuffed because we live in a small town where we could not replicate our income, and are fortunate to have brought our now-telecommuting positions with us from a much larger city.

    Congrats on taking the leap and finding something that’s a great fit for you. I hope the higher earnings potential part pans out, and also hope that you enjoy the thrill factor of a more demanding job. For all of what I just said, I also wouldn’t trade a lot about my job, including the fun parts which wouldn’t be possible without the stressful stuff. 🙂

    1. ONL,
      Oh, the Countess of Grantham. I was afraid she was gone for the season, then she comes back to somehow turn Mary from mega-bitch to married in less than an hour (we’re a day behind on the finale, should get to it tonight!).

      Yes, paid overtime. Sounds strange doesn’t it? My company does pay it. However, most of my coworkers do not receive it, and are expected to work long hours. It’s a bit uncomfortable. I work for a small business that subcontracts to a more traditional consulting firm. Sounds like you work for one of those. I understand your urgency. I’m still working 40 hours a week, but I’m hoping that number goes up so the extra pay starts coming. I say that, but then again, once the summer gets here I’m not going to be happy working long hours. I try to work the on the early side of the day. So far the new job is mixed. Miss the ease of the last project, but enjoy the greater purpose of the new job. I do admit though, I dread Monday’s now more than I used to.

  10. evenstevenmoney says:

    For the past five years, I became comfortable in an increasingly easy and low-profile position. I was a subject matter expert, but the position didn’t require a lot of brain power anymore. My intellectual capacity as an IT consultant was not being fully utilized. For a while I was OK with that. I channeled excess cognitive capacity toward personal finance and writing.

    We live the same lives, just toss in operations instead of IT. I’m catching up on posts but I like the big moves!

    1. ESM,
      I think a lot of us are in a similar situation! I did move on from my old position and my brain is being exercised again. It was tough at first, but I’ve caught up to speed and things are good. Customer is more difficult to deal with though. No regrets, and I’ve increased my earning potential.