Taking the Plunge: Why I Love Being Self-Employed

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Welcome back to another post in the Taking the Plunge series as I discuss leaving my corporate job to run a business with my wife. If you’ve not read those earlier posts, then I highly encourage you to do so in order to get an insight into my thinking. Mrs. Frugal Rules and I have been self-employed and running our business for almost a year now. To be fair though, my lovely wife started it two years prior and has since taken off to the extent we can both manage it. While being self-employed is tough work and anyone considering it should give it full thought, I have to say that I have quickly learned one thing among many…I love being self-employed! As I do not know the future, it’s entirely possible that I may re-enter the corporate world at some point; but, my hope and vision is to create a company that sustains itself and opens up further entrepreneurial opportunities.

Being Self-Employed Creates Freedom

We all crave freedom to a certain extent, some more than others. Being self-employed, I have quickly learned that it breeds freedom. Sure, you can take that freedom and sleep in until Noon every day in order to catch the latest Jerry Springer episode in your sweats and eat Cheetos while doing it. However, if you’re looking for that type of freedom in self-employment then I suggest you find yourself a Sugar Daddy/Momma as you’ll not last long. This is not the freedom I am talking about. The freedom I am talking about here is working on what I want to work on. Sure, there are some activities you must do in order to pay the bills, but what type of work you focus on is up to you. That freedom, once you taste it, is incredibly contagious and I found that I wondered why I waited so long. The other big freedom is that you can create your own schedule. To be honest, my wife and I bust our backsides, especially my wife, but we get to schedule it how we want. A perfect example of this was surprising my three year-old son a few months ago by taking him to go see Finding Nemo in 3-D for his birthday. It was in the middle of the day and we were the only ones in the theater. He had a blast and I have memories that will last me a lifetime. Sure, I might have been able to do that when I was at my former employer, but the point is that I had to check with no one. I was able to schedule my week so I could take the afternoon to be with him and no one could tell me no. That freedom is priceless.

You Learn A Lot About Yourself

Being self-employed has taught me a lot about how I tick. What gets me motivated, what gets me down and what I want in life. I knew much of that before I was self-employed, but it’s much clearer now. One of the toughest aspects, and one of the last things we considered when we were making the decision to move to self-employment was health insurance. We knew we would lose all of our health insurance when I left my corporate job and being married, with three little ones it was no option not to have health insurance. We had no clue what it was going to cost or what to expect. Thankfully we were able to find an insurance plan that was only $75 more than what I had been paying, so it was nothing to worry about in the end. The great thing is that we found we had many more options than the few given by my previous employer and something that was a greater benefit for us. This is just one of many things we’ve found that being self-employed opens up more opportunities for us and ones that we can use for our benefit. I love having that freedom and is one that regularly teaches me more about myself which will help me as a person, a husband, a father, and a business owner. As a side note, I do plan on covering self-employment health insurance in a future post.

You Benefit From What You Create

If freedom is what I love most about being self-employed, then benefitting from what we create is a close second. At my corporate job, anything I created went to benefit their bottom line. Being a leader in the financial services industry and sitting on $1.7 billion in cash alone I knew that at the end of the day they benefitted from me and not the other way around. Sure, I got a paycheck and benefits, but the enjoyment and fulfillment was not there. Not to mention the fact that I was not being mentally challenged and was in a job I detested. In running our own business, we see directly how our work benefits us. It benefits our bottom line and is extremely rewarding to see the outcome of something we created. That feeling is awesome and one that that we strive for. Why work for years in a dead end job and not getting noticed when I can create something of meaning, something of substance and value? I see what’s possible now, and it drives me. Additionally, doing it for myself is far more enjoyable than for some cold, impersonal corporate firm.

I will close with the same disclaimer I have given in the previous Taking the Plunge posts, if you’re looking to run your own business then go into it with your eyes WIDE open. It’s not the get rich scheme that many make it out to be. It is hard work and takes a TON of time and it is not for everyone. That said, if it is something that you’re longing for, there are numerous self-employment opportunities to be had, you just need to know where to look and what you want to do.

What are your thoughts? Do you think you’d love to be self-employed? Or, is it something that has no appeal to you?


Photo courtesy of: Tim Barrett

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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.


  • Glen @ Monster Piggy Bank says:

    I would like to be self employed, but I am not sure how I would go at staying focused. There are so many distractions at home.

    • John says:

      That is a struggle Glen, especially now that you have a little one at home. It requires thinking creatively about when you can get your work done as well as being flexible.

  • AverageJoe says:

    I think you nailed my favorite, John: you reap what you create. I don’t need my boss to tell me (through a raise) that I did a good job. My client either tells me or doesn’t, and there’s a direct correlation between how well I do and my paycheck.

    • John says:

      That’s exactly it Joe. It’s a very intoxicating drug to see the result of your hard work. It does require hard work and commitment, but it is so worth it in the end.

  • Jason @ WSL says:

    Being self-employed definitely has positives but it also has a lot of negatives. After having been through it myself for the past 3 years, I’d have to say that it doesn’t appeal to me much any more. Frankly, the grass isn’t always greener. lol.

    • John says:

      It does Jason, and I’ve covered some of those and will be covering more in future posts. It can be incredibly difficult as well if you might be in a commission based field.

  • Roger @ The Chicago Financial Planner says:

    Great post and I can relate having been self-employed since the mid 90s. It is a great lifestyle and affords a lot of opportunities. It can be a financial challenge at times, though. Thankfully my wife has a “real job” (she went back to work about 10 years ago after having stayed home with the kids). so we get medical and other benefits.

    • John says:

      Thanks Roger! It does afford a lot of opportunities, but that also comes with great responsibility. I would imagine that having your wife being able to have a job like that would bring a certain level of peace. You’re right that it can be financially challenging at times, thus why watching your money, as you well know, is so vital.

  • DC @ Young Adult Money says:

    I would like to be self-employed/small biz owner someday. Right now there is no way I could justify leaving my 9-5 job and I honestly have a lot of incentives besides monetary gains to be there (mainly the training and exposure I get to software and systems). But I absolutely agree with you on this “The freedom I am talking about here is working on what I want to work on.” That’s the kind of freedom I would like some day.

    • John says:

      That’s a great point DC! You lose out on that when you run your own business. Sure, you can write it off most times, but it’s still money out of pocket. That freedom, though, is a pretty nice thing to have. Once you get it you’ll find it’s hard to give up.

  • Money Bulldog says:

    The thing I love most about self-employment is creating something from nothing. To start with an Idea, create a brand name, win clients and earn a living from that business gives you such a feeeling of satisfaction. Great post John!

    • John says:

      That’s exactly it Adam! If you’re successful, then you get to see the fruits of your labors and it’s very rewarding in the long run.

  • Grayson @ Debt RoundUp says:

    Being self-employed requires a lot of discipline, but also requires you to take on things that you might not enjoy, just to pay the bills. I am not sure I would love to be self-employed at this point in my life, but maybe one day down the road. I like my full time job, but also like running my business on the side. This works for me right now, but I do have the entrepreneurial bug and have had it since I was about 20.

    • John says:

      You’re right on Grayson. It requires boatloads of work and can be extremely time consuming most of the time. That is not to mention the fact that a work/life balance does not exist. But, if you’re able to take it and you’re aware of the challenges you can possibly become successful. Having a business on the side is a great way to go at it as well.

  • Budget & the Beach says:

    I have my ups and downs with it. It’s very hard..VERY and I don’t think people realize it. Or maybe they are lucky ones who ease into it effortlessly and have a stead stream of income. However, I know I would have a hard time going back to full time after being a freelancer for over four years. I do like having those times where I can run to the grocery store in the middle of the day. And I LOVE working from home!

    • John says:

      It is VERY hard Tonya, and many do not realize it. They think you can just come up with a business name and fall backwards into a pile of cash. It does not work that way and it does take a ton of work. I would agree though, that it would be hard for me to go back to the corporate world after seeing the possibility this freedom brings. I LOVE working from home too. 🙂

  • Kim@Eyesonthedollar says:

    I should have been looking for the sugar daddy all along. How did you know my life’s ambition was to eat Cheetos on the couch and watch Jerry Springer? Is he still on?

    I loved owning a business for many of the reasons you mentioned, but mine was a bit different in that we had an actual brick and mortar building with office hours, so not quite as flexible. I also got really tired of the employee struggles, so I’m looking forward to leaving all that behind. With your occupation, I think it makes perfect sense, though.

    • John says:

      Right on Kim! It’s your life’s ambition as well?! 😉 Sadly, I think Springer is still on.

      I would imagine that dealing with employees can be a challenge to deal with many a times. That’s part of the reason why I am hesitant to hire one ourselves. But, there’s only so much time in the day with only two of us.

  • Michelle says:

    I definitely want to be self employed, and with this next thing I have going on, it will pretty much force that upon myself. I can’t wait!

  • Catherine says:

    Great post! In my industry I have the option of being self employed and work autonomously but I have no desire to do so. I like going to work and getting paid never having to worry about the financials and maintaining a dental practice. I would however work FT as a freelancer if I was ever able to.

    • John says:

      Thanks Catherine! Not having to worry about getting paid is a big thing, one that I can totally understand. Freelancing can be a pretty nice gig, especially if you can get a nice network set up.

  • Jennifer Lynn says:

    I love reading these posts, John. It was such a courageous leap for your family and I believe you will succeed phenomenally. The unsteady bursts of income are difficult when self-employed (or while freelancing). However, that is balanced with much greater freedom.

    • John says:

      Thanks Jennifer! From your lips to God’s ears. 🙂 The ups and downs can be difficult, but as long as you have a good financial backdrop that freedom is quite intoxicating.

  • pauline says:

    I love to be self employed, to reap all the rewards mainly. You can only blame yourself for failure as well, which teaches you about humility and hard work. Inside a big company, it is hard to see what your concrete use is, and everyone is replaceable. On your own you have to fight to survive but it is worth it.

    • John says:

      Right on Pauline! It does, to a great extent, come down to you and how much you’re willing to put on the line for it. You do have to fight to survive, but the end result (assuming you’re seeing some success) is a great motivator.

  • Melissa says:

    I love being self-employed and watching my business grow. I don’t miss boring meetings and office politics. It can be challenging juggling caring for kids and working at home, but the pay off is the schedule flexibility that you mention. I don’t have much trouble motivating myself to work; instead, I have trouble disconnecting sometimes because work is always there.

    • John says:

      I don’t miss those things at all either Melissa. I always found it to be such a waste of time. We have the same trouble to unplug as you can always find work to do most times.

  • My Money Design says:

    “Being a leader in the financial services industry and sitting on $1.7 billion in cash alone I knew that at the end of the day they benefited from me and not the other way around. ”

    That’s a great quote. I have been asking myself the same sorts of questions. I know that I work very hard and have a unique set of talents. Could they be better served being directed towards my own efforts? How badly do I want to find out?

    • John says:

      Thanks MMD! To be honest, those were all questions that ran through my mind as we were making our decision. Actually, they had been running through my mind for several years. At the end of the day, a big firm is only going to care about one thing…themselves and not those that bring them to where they are.

  • Suba says:

    I am currently self-employed. There is a great sense of satisfaction when you can build something from ground up. I probably earn less than 10% of what I was earning before in my regular job, but the freedom it provides and the potential to grow is unbeatable. I am also very very (I can’t emphasize this enough) fortunate to have a husband who supports emotionally (in whatever business venture I start on) and financially (he has a regular job and we live on his income).

    • John says:

      You’re right Suba, there is quite a sense of accomplishment when you get to see the fruits of your hard work. Having a spouse to lean on as well as provide for living expenses can be huge. Thankfully I was working still when my wife started it. I know that was vital as we started out and did not move until we saw sustainability.

  • Lance at Money Life and More says:

    I think I would enjoy being self employed but I would definitely be worried about the lack of stability. I would have to have a big chunk of money in the bank before I made the jump.

    • John says:

      That can be a valid concern Lance. Which is part of the reason why it’s so vital you have a good framework in place before taking the leap. We also have a good sum set aside in several bank accounts to cover for shortages, thankfully they have not needed to be tapped.

  • My Financial Independence Journey says:

    I would not want to be self employed. I like not having to waste time with sales, marketing, or business development. I’m not good at (or interested in) those kinds of things. Having an employer lets me focus on doing what I’m good at . Admittedly, I can’t do it while watching Jerry Springer in my underwear, but at least my job security isn’t at the mercy of performing tasks I have no talent for.

    • John says:

      That is a valid concern MFIJ. Thankfully, we deal mainly with other businesses, so the “sales” aspect is a bit different, especially when you have a portfolio to show what your capable of and what you can bring to the table. I would argue, though, that job security has become a bit of a misnomer lately. At the end of the day a firm is going to look out for themselves when push come to shove and not their employees in many situations. I think the growing entrepreneurship we’re seeing is pointing to that.

  • Shannon Ryan @ The Heavy Purse says:

    I’m a small business owner too, even though my office is not at home – it’s only five minutes away, which I love! Especially since I no longer have to brave the congested LA freeways to get to work. And yes, even though my day is probably a bit more 9-5 than yours – I still have more freedom. Mid-day school concert – no problem. I do agree with you that being self-employed isn’t for everyone and it’s a lot of hard work too. It’s easy to romanticize the notion when you’re sitting in a cubicle how great it must be to be self-employed. I’ve done both and enjoyed both, but right now, self employment work best for me.

    • John says:

      That freedom is nice to have Shannon, especially when it involves activities for your children. You bring up a great point about romanticizing how great it is. It does require a ton of work and many do not realize it.

  • Mackenzie says:

    I hope to one day get to a point that both my husband and I can be self-employed. But that’s awesome that you and the Mrs. were able to do it and are continuing to be successful at it 🙂

    • John says:

      That’s awesome Mackenzie! It does take a lot of work but, in the long run, it has been quite worth it for us. Good luck to you as you possibly pursue it in the future.

  • Tackling Our Debt says:

    I find your point about “You Benefit From What You Create” to be the biggest benefit for me. I love seeing a project through from beginning to end instead of just focusing on one piece, which sometimes happens when working at a job for someone else.
    The part we found most difficult was finding an insurance company in Canada that offered benefits to self-employed individuals. Yes, they are available, but with a high premium. I had to really search to find something affordable and even that is costing us $150 a month.

    • John says:

      I totally agree Sicorra! That really is a big benefit. There is such a sense of accomplishment in seeing your ideas and plans work out in the end to create something workable and effective. Getting health insurance was a major concern for us. To be honest we would not have taken the plunge if we could not have gotten good insurance at a reasonable price in comparison to what I was already paying.

  • Kay Lynn says:

    It is definitely hard work and those that put in the effort are the success cases we hear about. Will you write about retirement savings as an self-employed person?

    • John says:

      Right on Kay, it is a lot of hard work. I will be covering retirement saving in a post, that is a great suggestion btw. I am still learning about it myself, but it will be coming at some point in the near future.

  • Canadian Budget Binder says:

    My parents were both self employed for as long as I can remember and owned a business. I worked at the business every day I could and so did they. It took alot of work on my parents part but in the end just like you say you had the freedom. They worked for themselves, had themselves to answer to and the rewards of good work came back to them. I learned alot from my parents and their business and they are now benefiting from it. Weeks on end trips around the world, and enjoying the good life, so yes it was worth it but hard.

    • John says:

      I didn’t know that about you Mr. CBB! You have a great perspective, to be sure. It is a lot of hard work… A LOT! But, it can be worth it in the long run of you’re able to find success. We aim to be like your parents and be able to benefit from our hard work later in life.

  • Edward Antrobus says:

    I’m not interested in full time self-employment. When you work for yourself, no matter the industry or what you do, you really work in sales. I hate sales. I’d rather let somebody else worry about that.

    • John says:

      That is a valid point Edward, though I would have to disagree with you in regards to being able to blanketly apply it to all industries. If what we did were truly sales, then we’d not be successful as neither of us care to do it.

      Our work involves very little sales, very little. The only real sales is simply going to networking events and that is a very small part of what we do. When we meet with a prospective new client it is because they have reached out to us for a reason. They have either heard about us from another client or looked at our website. They already have a need and we meet with them to see what we can do for them. It really is much closer to consulting than anything else.

  • Tony@WeOnlyDoThisOnce says:

    Love the series of posts, John. I’m going to be joining you soon (for the most part) and I’m reading as much as possible. You are doing the right thing, and I’ll be in touch for advice along the way!

    • John says:

      Thanks Tony! It’s amazing when I started out this series I only had five or six posts and it’s quickly growing into double digits. That’s awesome you’re looking at this in the near future! If you do not mind me asking, what line of work are you looking at? I am open for questions anytime, just shoot them my way.

  • Jim says:

    John, I totally agree with you that self-employment is freedom and don’t think that we place enough value in freedom. In the US we have always been “free” so we often take it for granted and place more emphasis on money. Freedom, to me is more of a commodity than money!

    • John says:

      That’s a great point Jim and one I would tend to agree with! Money is great and all, but time and freedom are much more important in my opinion. You can almost always get more money, but not time.

  • Jose says:

    Being self employed requires a tremendous amount of discipline. I’m a little challenged at that sometimes and get easily sidetracked (you can call it ADHD extreme). But all in all, if I had the option, I would pursue an income being self employed. Hopefully that will be part of my semi-retirement in 5 years.

    • John says:

      “Being self employed requires a tremendous amount of discipline.” Truer words have never been spoken Jose! It does require a lot of self-discipline, otherwise things simply do not get done.

  • The First Million is the Hardest says:

    I’d love to be self employed, I’d be much more motivated to bust my ass to help myself than I am to do it for my employer who will barely notice. The real appeal of self employment to me is the flexibility to make my own schedule and not have my work schedule be a rigid force that dominates the week.

    • John says:

      Knowing that you’re responsible to provide for yourself can be quite the motivator. Add having a family to the equation and it can be very powerful. That flexibility can be awfully nice as well.

  • Brian @ Luke1428 says:

    I have to believe at the end of the day the fact that you are able to personally benefit from what you create gives you a higher level of satisfaction than anything you did in the corporate world. Thanks for sharing your journey…it is encouraging!

  • Justin@TheFruaglPath says:

    This is something that I’ve been giving a lot of thought to lately. I’m a little fearful of putting myself out there, but I know that there are great rewards as well.
    I’ve got the idea and I think that it will work. I’m just going to wait until the debt is paid off. I’m glad that it’s working out for your family.

    • John says:

      Those are all very valid issues Justin. I know I was scared half to death when we took the plunge, but believe it was based on research and logic. That said, the rewards can be great. I would definitely encourage you to have your debt paid off before considering making the move.

      • Justin@TheFrugalPath says:

        The debt isn’t an option. My wife wouldn’t allow any other ventures until it’s gone. She still gets on me about spending money on The Frugal Path. So there’s no way I could spend a couple thousand dollars starting up a company until it’s gone. Although I’m in the planning stages now.

  • Brick By Brick Investing | Marvin says:

    Great points John! I love and respect how you are honest about being self employed and instantly crush any falso hopes of staying home just to watch tv and play video games all day. I don’t work at home but I know just from working on my off hours that if I did stay home I would likely work longer days than I do now. The difference is it will be doing something that I love and not something just for a paycheck. Hopefully one day I can get there with you.

    • John says:

      Thanks Marvin! It definitely is not that type of lifestyle. If that one is even possible, I’d love to find it. 😉 I am actually writing a follow up post for next week on the reasons why I hate running our own business to help further communicate that it’s not for everyone. I can vouch for working longer hours but, for me, it is well worth it at the end of the day.

  • Cat Alford (@BudgetBlonde) says:

    Great post! I definitely realize that being self employed is a huge, huge undertaking. I know a lot of people do romanticize it, and I’m sure you and your wife work harder than you ever thought possible. I am definitely toying with the idea of going 100% freelance. I think if my husband was working right now and not in school, I would take the plunge. I know I have the work ethic and the stamina to seek out the staff writing opportunities that I would need to get in order to make it work, but right now I’m limited by time. Next year, we’re moving to New York for my husband’s school, and again, I wish I could take the plunge but I fear that NY is too expensive to go 100% freelance being the primary wage earner. Maybe one day. It’s on my mind all the time! Great post!

    • John says:

      Thanks Cat! I definitely agree that many romanticize it, and often times people think the grass is greener on the other side and often times it is not. I am actually writing a post for next week that will go over why I hate running our own business as a means to help further dispel the myth of it being all lollipops and rainbows.

      You’re right though, we do bust our humps…my wife especially. While it is a ton of hard work and VERY long hours it is well worth it for us at the end of the day. Thanks for stopping by Cat!

  • Buck Inspire says:

    I see the appeal, but I may be more suited for working in the corporate world. With the new mouth to feed, the steady paycheck helps me sleep at night. Who knows, perhaps I’ll take the plunge one day. Loved your warning that it may not be for everyone and that it is not a get rich quick scheme. Too many people are unrealistic. May I ask what type of business did your wife start up two years ago?

    • John says:

      You have to go with what works for you Buck, and I can definitely understand the desire to have a steady paycheck with a new little one to provide for. You’re exactly right, that many are unrealistic and do not fully comprehend the work behind running your own business. I actually have a post going up tomorrow on why I hate being self-employed that’ll point to that.

      In terms of y wife’s business that she started, she simply started with freelance copywriting. She had been a copywriter for 5-6 years and wanted to be able to stay home with our kids. What she started has since developed into basically helping create and manage marketing campaigns.

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