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Taking the Plunge: Why I Hate Being Self-Employed

Why I hate Self Employment

You read the title right – there are days where I absolutely hate being self-employed and running our own business. Last week I covered why I love being self-employed, and today I’ll discuss why the grass is not always greener on the other side. Starting your own business is a ton of hard work. To put it lightly, it’s not the “lollipops and rainbows life” that the late night infomercials would have you think. One of the things that’s easy to miss when you’re self-employed is the benefits you receive from being an employee.

Health insurance, nope. Free money for retirement, nope. Paid vacation days, nope. Those are all things that are easy to miss and anyone would miss those. What I am talking about in hating self-employment is all of the nasty things that those infomercials do not tell you about. I share this all with you, my readers, so if you’re considering running your own business that you go into it with your eyes WIDE open to the benefits of being self-employed, but also the drawbacks that need to be seriously considered.

Being Self-Employed Means It’s ALL up to You

 

It is nice to go to work every day and be told what to do, or at the very least, have a framework of expectations that you need to fulfill by the end of the day, week, etc. There is nothing at all wrong with liking that; heck, we all crave some amount of structure in our lives. If you’re self-employed then that framework is out the window. Any framework you do have is because you have created it. That demands that you be extremely disciplined with your time and cut out the fat.

In most office settings you have meetings, inner office politics and the like that are time wasters. Such time wasters are not absent from the world of self-employment. Time drainers must be kept to a minimum, otherwise the day will easily get away from you and you’ll see at the end of the day that nothing has been accomplished. This, though, just covers the day in and day out activities. Added to that is the aspect of bringing in additional business, managing workflow and handling client invoicing. Those can be extremely daunting tasks if you have a lot of work and it can play on your mind if you have no work. You also have no human resources area that will prompt you to improve yourself and grow professionally so that gets thrown on the pile too.

As you can see when you run your own business it’s all up to you…I could write an entire post on that, but I’ll leave it at this section.

People Do Not Keep Their Word

 

Ok, to be bluntly fair, I already knew this before we became self-employed. However, when you run your own business, you really and truly begin to feel it. We’ve met with numerous potential clients who have said the right things and told us, without a doubt, that they wanted to do business with us. The sad thing is that many of those times they fall off of the face of the earth after they tell us yes.

On one hand, we could be thankful for that as we probably would’ve had to hire two people to help us with all of the work, but it still sucks. I like to pride myself as being a man of my word, though I am not perfect I do like to follow through when I give someone a yes. Sadly, this is not always the case when you manage your own business. I don’t know if the people out and out lied or if they just chose to go a different direction, but you learn very quickly to not count business until you sign on the dotted line and see the first job come in. This can be a drain on finances as well as a mental challenge as it can be difficult not to worry about why they chose to go a different direction. Ultimately, when it does happen, and it will again, you need to assess the situation to make sure nothing was/is wrong with your approach and go on. Otherwise, it can really take a mental toll on you.

What Work-Life Balance?

 

While many people have to take work home at the end of the day, countless others get to leave their work on their desk when they leave for the day. What about when you’re self-employed? Well, there is no such thing as a true work-life balance. This becomes readily apparent when you run your business out of your home. When you’re self-employed there is almost always something that “needs” to be done, it just comes with the territory. This can result in a horrid work-life balance. It is very easy to find yourself working at 10:00 or 11:00 at night, knowing full well that you need to be up at 5:00 the next morning. Add to that the reality of being reachable at nearly any time of the day and you have all the ingredients for an unbalanced work-home life. This ultimately means you need to find a happy medium and set boundaries, which is a topic I’ll be covering in a future post.

If You Hate it, Then Why Are You Doing it?

 

After all of my belly aching, I know it begs the question of why are we doing it. Truth be told, being self-employed and running your own business is a lot of hard work…A LOT! You work long hours and have to create a whole business on your own. Please do not forget that if you think self-employment is for you. If you do, then you will likely flame out in the end.

There are two main reasons why we chose to go down the path of starting a business: the freedom that comes as a result and we see direct results of our hard work. Those two things on their own can be incredibly intoxicating. Mind you, they should not be THE only reason why you should pursue self-employment but they are major factors. When we were in our decision making process we looked at the pluses and the minuses of going all in with our business idea. In the end we saw the limitless possibilities of what we could create and knew we had the background to be able to accomplish something big. We are doing it because we have a place we want to get in life and that was not possible with the then current situation. Things had been going nowhere for too long and a change was needed. Simply, we are doing it to better our family and improve our lot in life.

I’ll end this post with the same disclaimer I have given in all of my other Taking the Plunge posts…If you think running your own business is for you, great! However, go into it with your eyes WIDE open to the fact that it is A LOT of hard work and that it rarely, if ever, comes by easily. Running a business is not for everyone, so please make sure that if you’re debating it now please do so with that in mind.

 

If you’ve made it through the near 1,300 word post, thank you for sticking around. I covered just a few of the ugly warts of being self-employed. What are some of the things you think you’d hate?

 

Picture courtesy of: Luke – rative

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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more. If you're wanting to learn how to monetize your blog, check out my blog coaching services to see how I can help you take your site to the next level.

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81 Comments

  • I’ve found the only real answer to the work-life balance is just to create one. I have A LOT of difficulty switching my mind off and running a business makes it even harder because there’s always something to do and even if there isn’t you can find yourself making new work by dreaming up new ideas and projects. These days I give myself a cut off point and just say enough is enough, kind of like your stop loss John 🙂

    • John says:

      That’s a great point Adam! It’s also one that I’ll be covering in an upcoming post. It’s about having boundaries and sticking to them. It can be difficult to turn that switch, which is why it’s so important to have boundaries.

  • I hate those infomercials as well. They sell you on the idea that owning your own business means you don’t really have to work at all. That is only true if you plan on going out of business very quickly.

    I think the hardest part for me would be creating the framework. It’s along the same lines of not knowing what you don’t know. You might not know you should be doing this or that which would really grow your business. Instead you are focusing on what you do know and that might be limiting the growth of the business.

    • John says:

      That’s a great point Jon, those infomercials are completely baseless in my opinion.
      Creating that framework can be very difficult, especially if you’re not administratively minded or not reflective on changes you should make. Thankfully my wife and I balance each other well, so the framework has come easy to us as opposed to other things.

  • I think there’s a fine line between love and hate. Some days you might love getting to slip a little bit of work in between stuff in the evening if it meant you could slip in some fun in the middle of the day. But other days all you see is hating the time coming out of the evening. At least that’s how it feels with my days, and I’m not self employed. =)

    • John says:

      You are very right Mrs. Pop! It can be a challenge to find that balance, which is why it’s so important to regularly analyze what you’re doing to see if there are things you can do to make life more efficient.

  • I’ve thought about self-employment and it’s not in the cards for me, for at least the next few years, because of the very points you made in this post. The work-life balance would be VERY difficult, because it’s all on you to work as hard as possible and if you don’t work, you don’t get paid! No paid time off. With that being said, I really respect you for taking the plunge.

    • John says:

      That balance is very difficult DC, we still struggle with it from time to time. We’ve come to the realization that we simply have to create it. If we don’t then it simply will not happen.

  • I’m sure it is better than working a 9-5 job that you hate. Afterall, you only get out what you put in and so provided you put in the time and effort you will most likely end up succeeding and retiring far earlier than someone like me who works for the man.

    • John says:

      Yes it is Glen! It is so much better, especially with the fact that we get the direct benefit of our hard work. You do definitely get out of it what you put into it. It’s hard to see that while going through it, but that’s why having a long term view is so important.

  • I would love to be self-employed and we will probably shoot for it once our house is paid off. However, the exact things you mentioned are the things that would hold us back – particularly the health insurance thing. That is one more reason that I think our healthcare system is a joke…but that is for another time:)

    Great roundup here! Thanks for your insight. We don’t always see people talking about the other side of self-employment, so good job!

    • John says:

      “We don’t always see people talking about the other side of self-employment” You’re exactly right Greg. Most often we see people say that you put little work in and then you fall a$$ backwards into cash and you’re drinking drinks with tiny umbrellas for the rest of your life. That simply is not true, though it would be nice if it were. 😉

      The healthcare issue is a tricky one and that was actually our final hurdle before we made our decision.

  • Of course, John, the grass is not always greener. I appreciate you celebrating the best and worst of self-employment. It is a tougher road to travel for sure. I have been self employed, then a government employee, and about to go SE again! Bottom line is that you have to follow your passion and your calling. If that means working for someone else, that’s cool too.

  • Your first point really keeps me out of the self employment world. I’m a hard worker, but that doesn’t mean that I’m fully competent to perform every aspect of running a business. For example, I have no talent for or desire to do business development. But without it, where am I going to get clients?

    • John says:

      That’s what keeps a lot of people out, as well as what a lot of people do not realize. Business development can be difficult, especially if you’re working without a base. That’s why networking is so vital.

  • This was the article I was waiting to read John. I knew it was coming, but just wanted to read it. Since I have been there, I know exactly what you are saying. You can love being self-employed one day and really hate it the next. You work harder being self employed because you are the only one that can bring in the money. They paycheck is not waiting for you at the end of the week. You have to create it.

    • John says:

      Well, I hope it lived up to your expectations Grayson. 😉 You’re exactly right, everything you have is because you created it. That can be a very overwhelming thing if you allow it to be.

  • I can agree with every point here. As you know, I’m a bit different because we have an office and office hours, etc. Last night we had kind of an open house, meet the new Dr., celebrate Kim’s cutting back sort of a thing. It was amazing how many people came out that I’ve know for years just to say good luck. It makes me happy that I was able to do things my way and cultivate a wonderful patient base. Those kids of things are priceless.

    On the downside, most of my troubles over the past few years, aside from working too much, were with employee issues. I’m sure you will have your share when you start to deal with them. I am amazed at the things people will do and won’t do. I could write a whole book about it.

    • John says:

      I imagine there are some things that are unique to running a brick and mortar, though many of the same basic issues. That’s awesome so many people came out to show you support. That really speaks to the service you provide and the great resource you are to the community.

      I am not looking forward to employee issues, which is part of the reason why I am putting off hiring someone.

  • Michelle says:

    Great post. I will most likely be entering the self employed world within the next year and am hoping it all goes well. I am afraid of not having a good work-life balance!

    • John says:

      Thanks Michelle! Best of luck to you, I know what you’re going through right now in your decision process and it’s not really an easy process. That work-life balance can be a tricky one, which is why it’s so vital that you create it…otherwise it will not happen.

  • and you didn’t even mention the inconsistent income!

  • Everything you said is so true. I work with one client 90% of the time, and I find I have to literally become a huge bitch when it comes to boundaries and when he is crossing them (we go way back to it’s OK. 🙂 ) You have to hold your ground when it comes to balance, otherwise it’s like a cancer that takes over. I think it’s because freelancers fear clients will go elsewhere with their business, but it’s not worth slowly killing yourself. Right now I’m in probably the most hectic time of the year. But it’s “mostly” my choice because them money is really good and I want to save as much as I can for the slower summer. That being said, I SILL have to make time to do things like exercise and get sleep. If those things are compromised, then I have to scale back.

    • John says:

      I can totally relate Tonya! Setting AND keeping those boundaries can be very difficult, yet VERY important to have. The fear of losing a client is there for many in our role, but at the end of the day you can only go so far to keep them.

  • Every thing in life has a good part to it and a pad part. It comes down to, as the saying goes, pick your poison. Hard work has never scared me and I like working alone (discovered THAT way too late in life). That, and the fact that I’m naturally self-disciplined makes working for myself overall a good thing.

    Of course, it helps A LOT that in my earlier working life we saved like crazy in order to have investments to fall back on…

    • John says:

      You’re exactly right William and it’s important to realize that. I am naturally self-disciplined myself as well, so it does make things a bit easier.

  • Mackenzie says:

    A good work/life balance is important, especially when you’ve got children. They require a lot and it’s a fine line to make sure that work and family life don’t get too out of balance.

  • pauline says:

    You can’t have it all… although I’ll take self employment 1000 times over a 9-5 job. What I struggle with most is balance and having specific times for specific tasks. A day of procrastination and then working at 11pm is not good!

    • John says:

      No you can’t Pauline, though that would be nice wouldn’t it? 😉 After being at this for a year or so I’d take this any day over a 9-5 job. The procrastination can be a real issue, thankfully both of us have become very disciplined with our time.

  • When you work for somebody else, you have a small set of responsibilities that are your job. As a flagger, I don’t have to worry about purchasing new equipment, hiring, getting new contracts, writing out daily logs and chasing down the three people that need to sign it.
    If I struck out on my own to start my own flagging company, all of the sudden, I’d have my job, plus all of what I mentioned above.

    • John says:

      I would agree that is generally true Edward, though not for all jobs. Starting your own company teaches you VERY quickly that everything is up to you. That said, I enjoy that aspect (most days) as I like having that control.

  • I couldn’t agree more, John. There are lots of good points to being self-employed, but it is definitely not all rainbows and lollipops (I wish!). For many years I coached financial advisors who were franchise owners and it fascinated me because the most successful advisors weren’t always the “best” financial advisor. They didn’t necessarily pick better funds or write better financial plans (some admittedly did!) but they were a better business owner. I think some people have a natural knack for leadership and are comfortable making decisions and sticking to them. Others were better suited with some structure and guidance, but they wanted to be their own boss. I also think some people forget about marketing and building their brand when they leap into the self-employed world too.

    • John says:

      You’re very right Shannon, there are a lot of perks to running your own business, but also many downsides. I would also agree that there do seem to be those two categories of individuals and I would say that I am definitely in the first camp. I love the decision making process and then implementing it to see where it takes us.

      Great point on people forgetting the branding/marketing aspect. That is so vital and is needed so you can differentiate yourself.

  • Justin @ The Family Finances says:

    It takes a certain kind of person to be their own boss, and I’m not that kind of person. I know I’d rather work for a corporation with employer-sponsored health insurance and a nice 401k match. To each their own! Different personalies are better geared for different things. Kudos to you for enjoying (for the most part) self employment and being able to make it work.

    • John says:

      I would definitely agree Justin, and I never thought I would be that type, but I have found that I am. Those things are nice and I miss some of them, though the income aspect can be limited in relation to running your own business (generally).

  • I agree with all of your points! The one that jumped out at me is the one about chasing new clients, meeting with them, thinking you have a new client and then they disappear. It is emotionally draining. Many people will say “well that’s business” but when it is your own small business it starts to feel quite personal. One of the other things we learned early on is that companies would often ask for a long proposal with ideas on how to solve their problem. From speaking with other business owners we learned that many times clients use these proposals as a way to get a lot of free ideas and suggestions on how they should do things. After that we limited what we said in proposals and kept things very high level until the client signed our contract.

    • John says:

      It really can be emotionally trying Sicorra, which is why we don’t even count it until we got a job and actually see money coming in. We’ve also heard of companies doing that to get ideas and is part of the very reason we limit what we say in meetings.

  • Part of the reason I took the plunge was purposely to instill a sense of work-life balance. Doing so was a choice and a deliberate sacrifice because I know I’m not going to make as much money as I could if I were working 50+ hours a week. The thing is, I’ve already replaced more than my full-time job’s income and I have more hours for life so it’s a decision I’m not yet regretting!! I think you have to figure out what matters most to you in the long run. For me, peace of mind and balance is far too important 🙂

    • John says:

      You do have to figure out what’s best for you in the long run Jen, I completely agree with that. I’ve found that we have to choose to have that balance otherwise it just won’t happen…thus why having boundaries are so important.

  • It’s definitely not easy. I wrote a post entitled, “A Day Job Is So Much Easier Than Entrepreneurship” last year when I first started.

    But I gotta say, w/ almost a year under my belt, being free is worth it.

    The #1 thing I dislike is bookkeeping and taxes.

    • John says:

      You’re exactly correct Sam, it is not easy. That said it is totally worth it in my opinion. The direct results from your hard work is quite addicting and I love it the more we get into it.

      Bookkeeping and taxes are not my favorite thing either.

  • Jose says:

    Being self employed would be a challenge for me. I can be disciplined but have an inclination to stray and bounce around from task to task. I may find myself spending four hours commenting on blogs and doing an “Oh Crap” when I saw how much time has gone by!

    • John says:

      That can pose a challenge. I’ve found that if I allow myself some time to take breaks that goes a long way in terms of avoiding that temptation to not be disciplined.

  • krantcents says:

    As a consultant, I face some of the same issues you mention. When I had apartment buildings, I could delegate some of the work to the resident managers. As a sol blogger, it is all on me. There are mes I wish I could delegate certain things and I do.

  • Self-employment isn’t for me since I don’t have the work ethic that you and your wife have 🙂 But you two seem to be doing great at it and I wish you both continued success!

    • John says:

      I’ll be the first one to say that it’s not for everyone. I never thought it would be for me, but thankfully it seems to be working out. 🙂

  • It’s no secret working for yourself is hard work but these businesses that are making the big bucks had to start somewhere. Sometimes sweat, agony, and long hours is what it is needed to get a business off the ground and on somewhat of a straight playing field. Growing my parents owned a couple of businesses and I’ll be honest we didn’t always see my parents at the dinner table every night together or we were all working every hour at the business to make it as successful as we could. They are retired now, in comfort and won’t have to worry about money for the rest of their lives but it’s all because they didn’t complain, they enjoyed what they did, they took the good with the ugly and they pushed towards their goals. Success is in the eye of the beholder and it’s not always about money. Great post mate.

    • John says:

      You’re exactly right Mr. CBB, it does have to start somewhere. It can be a lot of work and staying busy, but anything worthwhile takes work and does not come easily…otherwise everyone would be doing it. I agree that success is in the eye of the beholder and should be what makes you happy and help you sleep at night.

  • Justin@TheFrugalPath says:

    Great post John. Running your own business is far more difficult than many people give credit. I still want to start my own business for other reasons, but it’s something to think about.
    The one thing I would hate the most would be no days off. I mean, it’s up to you and if a job needs to be done on a Sunday, well then you’re working because there aren’t as many people to fall back on.

    • John says:

      Thanks Justin! It is difficult, though worth every moment of it for us. The balance can be a difficult one. We do our best to take weekends off so we’re not going every day of the week. I am usually more guilty than my wife than breaking that though.

  • Running your own business assumes you have a marketable skill or product and basic skills in running an organization, something most people do not have. Hiring expert help is a must and very expensive.

    • John says:

      I agree that you do need to have a marketable skill and some business sense, most people start small when they start a business. As the business grows they learn how to do those things themselves if they do not know them already.

  • Jim says:

    Great post John, I truly believe in the Freedom of being self employed and I dont think working for the man offers that. I am still working for the man, but hope that one day I will have enough income streams to be able to work for myself. Great post, well articulated!!

  • Kay Lynn says:

    I plan to start a small business once I “retire” in six years. Until then I’m reaping all the benefits of being an employee.

    I hope your post makes people considering the jump think it through. I can’t tell you how many people I work with were self-employed at one point.

    • John says:

      That’s exactly what I am hoping Kay Lynn! Running your own business is great and can be freeing. But, there are many things that need to be considered before taking the leap.

  • I know what you mean about people not keeping their word. They think that just because you are not working in a fancy office, they can do whatever they want and it will just be okay.. That is one of the cons. But, the pros always outweighs the cons. 😉

    • John says:

      You’re exactly right KC, which is part of what frustrates me about it. But, like you said, the pros do outweigh the cons. Thanks for stopping by!

  • It’s hard work, but all your effort goes to the bottom line. I never liked making other people rich. I’d rather be my own boss and live with the consequences. It depends on your mentality too. If you can follow direction, then it’s probably good to work for a company.

    • John says:

      Great point! I always hated working for someone else making them money but getting so little for myself. That’s part of the reason why I made the switch.

  • I definitely understand this love/hate relationship with being self-employed. That’s the life of my BF and sometimes it’s great but most of the time it’s tiring and stressful!

    • John says:

      It can definitely be a very fine line to walk when self-employed. We’re often tired, but it’s a good tired because we’ve worked hard and see direct results from that work.

  • Thanks for shedding light on this John. I always tell people at work starting your own business is very hard work and it’s why so many businesses ultimately fail. Additionally as much as people gripe and complain, they love being employees and getting all the perks you mentioned!

    • John says:

      Not a problem Marvin. Many see it as a way out from working for the man and at the end of the day it’s just not for everyone. While it can be quite freeing to work for yourself the nasty truth is that it’s a lot of hard work.

  • Love the honesty here, John. When Rick was laid off in 2010, we looked seriously at several self-employed options, but in the end, Rick decided that it just wasn’t something he was ready to tackle at the time: with a wife and 4 kids to feed, he needed the security of knowing he’d have a paycheck every week. Now that he’s a bit older and more confident in himself, he’s starting to look into it again. I’m so proud of him for knowing what the best decision for his psyche was, you know?

    • John says:

      Thanks Laurie! I think it really says a lot for your husband that he was self-aware enough to see that it was not the right thing for him and you family. Many would jump just in head first without giving much thought to it. It’s not a decision to be taken lightly and should be treated as such.

  • I don’t hate anything about self-employment. I am new to being self-employed and I’m loving it. It is liberating to not having to go to an office and deal with an alarm clock and traffic jam everyday. What I quickly learned about self-employment is that it is hard work. You have to work just as hard, or even harder as when you were an employee. Discipline when it comes to using your time productively is very important, too. When you work at home, there are lots of temptation to take little rests that could affect your productivity negatively.

    • John says:

      I completely agree with your points. It is hard work and there are many temptations to not stay busy. My larger point though was to communicate that it’s not all it’s cracked up to be (meaning it’s hard work) and not the get rich quick scheme that infomercials would have you believe. Basically, just to communicate that the grass is not always greener.

  • As someone who is also self-employed, I agree most with your point about work/life balance. Because it’s all up to me to generate my income, I am known to work whenever, wherever. At 9pm on a Saturday night, at 4am on a Tuesday morning, even on vacation.

    • John says:

      I can completely relate Elizabeth! That balance can be one that is difficult to find, especially if you do not have boundaries. We have learned that we simply need to make a choice to stop working and have some of that balance….of course that is easier said than done.

  • I hear you on this one! My fiance runs his own business and I don’t understand how people can just not do what they say they’re going to! When I say I’m going to do something, or make a commitment to something, I follow through! Not everyone is like that though, unfortunately.

    • John says:

      I know exactly how you feel Jordann! It just makes you wonder whether the person was lying, something came up, or just could not afford you. I’d much rather be told the truth as opposed to being strung along. Like you said though, thankfully everyone is not that way. 🙂

  • I’m a big believer in the fail fast and fail often philosophy and as a result I’ve churned though a bunch of businesses of varying levels of profitability (or lack thereof). While I don’t mind everything being up to me and I think I thrive in that environment, the fact that most people say things and never do them is a killer to me. Be it counting on help from business partners and employees or even sales from clients, I’ve learned to “believe it when I see it.”

    I think the one thing you missed which Sam hit on is book keeping. Between itemizing every single expense and tracking a billion metrics for your business to see if what you are doing is working, it’s a huge time sink (and it’s real easy to get obsessive over). There are times when I’ll spend more time on metrics then actually making the changes necessary to improve them :/

  • Jackie says:

    Great article.I actually googled I hate being self employed – because that is exactly how i am feeling after 16 months of running our own business. I crave Mon-Fri, 9-5, retirement funds, paid holidays and sick leave. Definitely things you need to consider if you are thinking about becoming self employed.

  • I have been working for myself for three and a half months now.

    You are absolutely correct about people keeping their word; I have learned to not count any money until it is sitting in my PayPal or other account, and it really does help to shift thinking this way. So far things have been very good. I finished up several large projects all at the same time, and had a sort of void for a week or two where I wasn’t sure how to move ahead, but now I have some solid plans in place and am happily working away at them.

    And yes, you just have to create your own work-life balance. I can be a workaholic, so this is a big challenge for me. But I am getting much better at it, mostly because I have realized that the reins are in my hands.

  • liz says:

    I have a very demanding job so I feel like my work life balance is already not great. I think I would adjust to that part of it. I am vey interested in becoming self employed. Looks like a wild adventure!

  • I can definitely relate to the “people lie” portion of the post. It is something I deal with on at least a weekly basis. I think most people go into those decisions well intended, but for reason (probably some of the outlined here) the follow through just does not materialize.

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