Taking the Plunge: Is the Grass Always Greener?

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Financial Plan

Why is it in life that when we have one thing, the complete opposite can seem so appealing at times? This can be seen in many, many areas of life – thus the phrase the grass is always greener on the other side. Many times it’s true and many times it’s not true. I guess a lot of it comes down to a matter of perspective, how reflective you are and what is going on in your life at a particular moment. As a small business owner, it’s easy (for us at least) to look at how the absence of things like a 401k match, health insurance, and paid time off and think it might be better to be employed by a company big enough to offer these things (a.k.a. “the other side”). Well, about two months ago, something happened that caused us to really look at if the grass was greener on the other side and if we should shutter our business. As I’ve taken a bit of a breather from my Taking the Plunge series, you can check out some of the posts in the series if you’ve never had a chance to read them:


An Offer Out of the Blue

As with any business, especially a small business, a solid client base is essential to keep the lights on and be profitable. With our business, we have a number of consistent clients that we’re basically on retainer for each month. They send us a certain amount of work and we can to a certain extent depend on income from them each month. The next level of clients are ones that we do work for regularly, but the amount of work varies from month to month and we invoice them individually for the work done for the month. The final level are clients we’ve done work for a number of times but can go months without hearing from. As a regular practice we email those clients about once a quarter to touch base, tell them a little about what we’ve been doing and bring us back to the top of mind. Well, at the end of June we heard back from a client that Mrs. Frugal Rules did work for several years ago, and not only did they have freelance work for us, they also had a job offer! Suffice it to say, we were not expecting the latter and quite honestly it caught us off guard. Our initial gut reaction was no way on earth do we want one of us to go back into the corporate world and be in a position where we have to answer to someone or have no control over what work we do, but…the benefits and “dependability” of the regular paycheck was awfully tempting after we gave some thought to it. After several meetings, they essentially offered Mrs. Frugal Rules a position within their company. She was honored to be offered the job, but still, the offer took us aback a bit and was the dominant topic of discussion for several weeks as we looked at the offer from all sides we could imagine.

The Devil is in the Details

As an analytical person by nature, I wanted to look at the details of the offer before instantly shooting it down. There were a number of factors at play, most importantly, with our business. Would we have to close our business for good? Would it be something I could manage on my own? Would Mrs. Frugal Rules still be able to do some freelance work on the side? With the number of agreements we have in place, these all became very important and vital questions to be able to answer. That is also not to mention the fact if I was ready to be a full-time stay at home Dad. I love my kids and would do anything for them, but was that something our family wanted – or would I have pulled my remaining hair out in a few short weeks? That said, we were also looking at the benefits of what a job could provide us and saw ourselves wanting that on one level, which really is not surprising as many crave to have that stability. After several weeks of introspection, discussion, and looking at the offer, something just did not feel right about the offer. With that, we decided against having Mrs. Frugal Rules take the offer, for a number of reasons, mainly because we saw that the grass was not greener on the other side for us. The straw that broke the proverbial camel’s back for us was that they wanted us to essentially shutter our business – which was something we were not willing to do.

Was it a Waste of Time?

Now that we have about six weeks of separation from the final decision, I ask myself if the whole thing was just a waste of our time. We felt early on that it wasn’t going to be something we were going to pursue, but still gave time to it as we like the model of the business in question and were honestly tempted by the benefits. It would be easy to say that it was a waste of time, and we really did feel that way after it became obvious what our decision would be. However, we both feel that it was a constructive exercise to go through. At the very least, it gave us a renewed fervor for our business, particularly to see it grow beyond where it is now. We also learned that just because something seems good, it does not mean it’s the case and to not be so quick to give up on our vision to create something that is ours, something that benefits our local economy and something that benefits our family. Essentially, we want something more than being stuck in a 4×4 prison cell…err…cubicle and create something that is bigger than ourselves. Sure, that means that we don’t have the “benefits” that others do, but being able to work from home, make our own schedule, work in our PJ’s if we choose, or have a cold one with our lunch is a pretty nice benefit too.  🙂


Do you think that it can be constructive to see if the grass is greener on the other side? Is there value in going through the process, even if you feel you know what the conclusion will be before you start?


Photo courtesy of: Kevin Wong

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John is the founder of Frugal Rules, a dad, husband and veteran of the financial services industry whose writing has been featured in Forbes, CNBC, Yahoo Finance and more.

Passionate about helping people learn from his mistakes, John shares financial tools and tips to help you enjoy the freedom that comes from living frugally. One of his favorite tools is Personal Capital , which he used to plan for retirement and keep track of his finances in less than 15 minutes each month.

Another one of John's passions is helping people save $80 per month by axing their expensive cable subscriptions and replacing them with more affordable ones, like Hulu with Live TV.

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  • Pauline says:

    Looks like it was a great way to realize what you have. I think a job offer would have had to pay me at least twice what I was making freelance to consider it. There is more time away from home than 40 hours a week and expenses like gas and commute that aren’t on the package so that reduces the offer.

    • John says:

      It would have to be at least that much for us to even consider looking at it as a viable option. We’d also like to keep our business running too, which was the ultimate nail in the coffin with this situation.

  • DC @ Young Adult Money says:

    I absolutely do not think it was a waste for you guys to spend time looking into the opportunity. I’m confident that I would have looked into it as well because I like to evaluate all my options. It is funny, though, how the grass always seems greener and I’ve seen that in my own life.

  • Holly@ClubThrifty says:

    There’s nothing wrong with considering your options! And, sometimes the grass really is greener. It sounds like you did the right thing.

  • AverageJoe says:

    It’s great to be wanted, isn’t it? For that reason alone it clearly wasn’t a waste of time.

  • Michelle says:

    Love this post. I don’t think I could ever go back to working for someone else. I am making the switch soon and cannot wait.

    • John says:

      Thanks Michelle. Yea, I think both my wife and I have been ruined for corporate America. We just don’t want it on so many levels.

  • Matt Becker says:

    I definitely think it’s valuable to explore your options. It’s easy to stay in your groove but life changes and it’s important to re-evaluate from time to time. At the same time, I think your understanding that different is not always better is a good one. And it’s not just the financial benefits that have to be considered, it’s the lifestyle benefits as well. Sounds like you guys made a good decision for your family.

    • John says:

      Right on Matt – the lifestyle benefits are huge. It’s easy to look at the paycheck and think that’s it when it really is only the tip of the iceberg.

  • Mrs. Pop @ Planting Our Pennies says:

    It’s always nice to have options and to be able to consider them carefully. Sometimes we learn just as much (if not more) from the things we considered, but didn’t do, than the things we jumped into head first.

    • John says:

      Totally agreed Mrs. Pop. I love to learn things the hard way and that often happens when I dive in head first. I much prefer lessons like this and hopefully we can draw on them if the situation happens again.

  • Grayson @ Debt Roundup says:

    I think you guys did exactly what you should have done. One it is a great feeling to know that you are wanted by another company. That usually gets you going when you are an entrepreneur. Also, analyzing what it could be and seeing if it is a good fit needs to be done from time to time. Nice work!

  • Mr. Utopia @ Personal Finance Utopia says:

    When an opportunity presents itself to you in that manner, I think you’d be be foolish not to at least do some cursory exploration and analysis. In the world of sports, you always at least listen to the other team’s trade proposal even if you only consider it for a brief moment. As for the “grass being greener”, that’s a tough psychological thing to battle. It’s almost always made worse when you’re not happy with your current situation.

    • John says:

      Agreed Mr. Utopia. It is tough to look at the grass being greener issue, especially if you’re not happy. Thankfully we are relatively happy and I think that helped us in this situation.

  • Joshua from CNA says:

    The grass is very seldom greener on the other side. It’s nice to have your options and, I love to know what my options are so, I would dig a little into finding information but, actually taking the plunge, I don’t think so! Thanks for the great read!

  • Alexa says:

    I want to desperately be on my own. I know there is a ton of hard work that goes along with freelancing but I am up for it! I want to be able to pick my kids up from school everyday and talk to them about their day. I want to have flexibility to keep them home when they’re sick without feeling bad for calling off work. I want to be proud of what I create myself. For me, the grass is looking greener on the other side and I just can’t wait to take that plunge!

    • John says:

      I can understand that feeling Alexa. That is where we were last year and that flexibility issue is a huge one. Being on this side, it’ll be clear to you when you should take that leap – not necessarily easy, but clear.

  • Andrew@LivingRichCheaply says:

    I don’t think it was a waste of time. You never want to just say no to an opportunity without knowing the details and thinking it over. My wife and I had a similar issue, but different circumstances. With a newborn, my wife was going to leave her job at the preschool and take care of the baby. We talked about starting some type of business once she had a little more time, but there was no concrete plan. A job interview then offer came out of the blue and the benefits, etc were too good to pass up, well at least my wife wanted to check it out. We did not have to leave a business…though we do have to figure out childcare. I think you guys made the right decision…wouldn’t want to shutter my business.

    • John says:

      Agreed Andrew. I think it’s those situations that come out of the blue that not only test us, but allow us to learn so much from.

  • Kim@Eyesonthedollar says:

    We always look at every opportunity, and I probably over think it way too much. Having good benefits is certainly nothing to sneeze at. We’ve had an expensive medical year, and there really wasn’t even that much that happened. It’s just expensive to go to the doctor. I can’t tell you how many times over the years that I’ve said I should just screw it and go work at WalMart. It would be easy money and no headache, but I would lose some of my soul every day. I would certainly do it if that was the only option, but I think job happiness with some uncertainty is usually better over the long run, at least for me.

    • John says:

      I totally over think options when I am looking at them. I think for us we’d be in the same situation as you (if you worked at Wal-Mart) in that we’d lose some of our soul every day. Our happiness just is worth too much to do that.

  • Shannon @ The Heavy Purse says:

    I think it was incredibly wise for you and Mrs. Frugal Rules to take your time to think over the offer and examine it from all sides. Otherwise, the first time she or you had a bad day in your business, you might have thought you made a mistake. But now you know – even those days where a salaried job sounds likes heaven – owning your business is right for your family.

  • Roger @ The Chicago Financial Planner says:

    Good post John. I’ve been self-employed for some 15 years and occasionally I am approached with employment opportunities. I’ve never taken any of them but I’ve looked at a couple. I think we are all free-lancers whether truly self-employed or working for an employer. Your decision was just a form of career management and I don’t think it was in any way shape or form a waste of time.

    • John says:

      Thanks Roger! I imagine that’s typically the case the longer you work for yourself and the more successful you are. That’s a great point about it being career management, I totally did not look at it in that way.

  • Girl Meets Debt says:

    I don’t think it was a waste of time to carefully consider other opportunities. I do think it’s awesome that essentially you and Mrs. Frugal Rules are content and proud of your business! That must feel great! ๐Ÿ˜€

  • anna says:

    That’s pretty controlling of them to want you two to shut down your business if Mrs. FR accepted, so it sounds like the both of you made the right decision!

    • John says:

      It can definitely seem that way Anna. A big part of it goes back to non-competes and wanting to make sure we weren’t doing work for competitors to their clients, which I can understand. My issue is that they were wanting it shut down completely, meaning I couldn’t even continue it.

  • The Warrior says:

    My first reaction was, “Screw the offer.” That was a horrible reaction and you guys took the right steps by analyzing the offer and letting the decision sink in. That is a huge decision and not allowing it to overwhelm you in the moment was smart.

    The Warrior

    • John says:

      That’s what I wanted to say as well, but thankfully cooler heads prevailed. This was a time where taking our time and being patient helped us out in the long run.

  • Marissa@Thirtysixmonths says:

    I agree with what everyone said. It was not a waste of time. I believe it was something you had to go through. It was an essential phase that you needed to overcome to appreciate what you already have. I love what said that “just because something seems good, it does not mean itโ€™s the case” Sometimes taking a break, stepping back and looking at how we started and how far we’ve come is a big motivation on its own. I would love to have that feeling one day that I’m finally at a place where I am confident and contented. Kudos to you and the Mrs.

    • John says:

      I agree Marissa, I think it’s something we had to go through and I think will benefit us in the long run. The important thing is to remember these experiences when things aren’t going the way we would like it and motivate us to continue.

  • Nick @ says:

    I definitely think it was worthwhile to pursue the opportunity. You never know what people are going to offer you until they do

  • Budget and the Beach says:

    I think there was probably value in going through the process, if only to think “hey if the shit hit the fan I’m still really employable!” People want me! ๐Ÿ™‚ I think it’s also times like those where you are forced to evaluate your situation to see what is best for you. Always good to have options!

  • Stefanie @ The Broke and Beautiful Life says:

    I think it’s essential to consider all the options. Sure, it can be time consuming, but without weighing all the benefits and drawbacks and how they’ll affect not only your work but your life as a whole, I’m not sure how you could make an informed decision. Either way, you get a little ego boost from the offer ๐Ÿ™‚

    • John says:

      That’s a great point Stefanie, you really can’t make an informed decision without looking at the options and situation as a whole. And yes, it was a nice little ego boost. ๐Ÿ™‚ Thanks for stopping by!

  • Mackenzie says:

    I think you guys made the right decision, John. There is a freedom that can’t be matched, in working for one’s self.

  • Brian @ Luke1428 says:

    Yes, yes and yes…there is huge value in going through the process. We all have a path in which our life is headed but we don’t really know what is right around the corner that could change our perspective and then the direction that path takes. Things are brought into our life that could open doors to possibilities we had not considered before. It’s a must to evaluate them. In your case John, it sounds like the process only helped to cement your convictions that what you are currently doing is best for your family right now. I say kudos for having the courage to evaluate the option instead of just blowing it off. You guys will be stronger people for having gone through it.

    • John says:

      I could not agree more Brian. Right after it happened it al felt like a waste of time because we had just spent all sorts of time talking about it and analyzing it. Now that we have separation we know there was a ton of value to be derived from it. I agree as well, that it’s vital to evaluate reasonable opportunities as you never know what’ll come of them or what door might be opened.

  • Simon @ Modest Money says:

    As many have pointed out, I think its totally worth it to consider opportunities even when you have an idea at the back of your head of what your decision will be. You never really know what the excercise might unearth, ideas that may come out as a result or even other opportunities that might arise out of your consideation.
    The grass may not always be greener on the other side but when it is, it doesn’t hurt to see whats being done to keep it that way ๐Ÿ™‚

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