Want to Work For Yourself? Think Again!

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work for yourself

As many of my regular readers know, my wife and I run our own business. A little over two years ago I got the pleasure of being able to tell my boss I was done with the job and left to go out on my own. Ok, truth be told, my wife had already started our business three or so years prior and was now at the point where I could help her run it.

To say it was a dream come true would be putting it lightly. For as long as I could remember I had wanted to work for myself. I don’t know why exactly, but it is something I had always wanted but just couldn’t find a way to make happen. Well, my excitement was brief at best. Yes, I could do what I wanted but a crazy thing happens when you work for yourself…it’s ALL up to you. Everything, as in anything you can think of is on you.

You want new business? You have to go get it. You want to take a month long vacation? You have to bust your hump to do it. You want some sort of work-life balance? It’s a challenge at best. As for health insurance…I’ve already touched that one!

That’s not to say I don’t love self-employment, because I really do. However, what many don’t realize is the work that goes into it. Simply put, many don’t realize what’s entailed in working for yourself. That’s not to say it can’t be done, because that’s obviously not the case – just not the life of puppies and rainbows that gets glamorized by many.


If you’d like to read more about why you want to think twice about self-employment, then check out my article at AOL Jobs.


Photo courtesy of: Reyner Media

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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.


  • There is nothing wrong with slapping us in the face with some real reality. I am planning on becoming self employed and have started working on it a year and a half before leaving my current career. I realize it’s not going to be easy and maybe at times I will wonder what was I thinking, but like you I know it can happen and I’m gonna go for it. Just keep the good advice coming on your blog to school us newbies around here. I really enjoy your articles. Hope you had a great Thanksgiving

    • Yes, reality can be a good thing at times. 😉 Best wishes Petrish, it can definitely be a challenge but it can be well worth it – especially since it sounds like you’ve put some good planning in it.

  • There’s definitely a slew of misconceptions around self-employment and blogging in particular. I don’t know if you’ve seen the latest progressive commercial around the dinner table, but bloggers are the butt of the joke.

  • Congrats on the article for AOL John! I’d love to work for myself. There are drawbacks, that’s understandable, but for my personality I feel like the benefits would outweighs them. Hopefully I can give it a try in the near future.

  • dojo says:

    I have been working ‘for myself’ for 5 years now. There’s absolutely NO reason why I’d preach caution to anyone, it’s amazing to do it, you can be very successful, as long as you are good in your business and know how to work. I have worked hard, I have played hard. Finding the right work-life balance is really easy, you just need to know your priorities and work accordingly 🙂

    • I’d respectfully disagree Dojo. There is so much that goes into self-employment and running your own business and many don’t stop to realize it. As such, I’d be lying if I wouldn’t share the reality many can face. While I agree, on one level, that work-life balance is easy for many that run their own business it’s not. That said, glad it’s worked well for you.

  • Ben Luthi says:

    Self-employment used to seem like a paradise, but the more I grow my freelancing career, the more I realize just how scary it can be. I’m still planning on taking the plunge eventually, but I’m taking more steps now than I was then to make sure I don’t screw it up.

    • I can definitely relate to that feeling Ben. It can be scary, but it can also be very rewarding. That said, you’re doing the right thing by planning it out and since you have that solid base of freelancing it’ll help you out in spades once you do take the plunge.

  • Congrats that you made the right choice to leave your job. It must take you courage to do that without even knowing if the business you were getting would be a success. Now that you’re self-employed and enjoying its advantages or benefits. That’s something I’ve been dreaming of! I’m planning to be self-employed soon, and I have actually started partly, but still I cannot find the right timing to leave my stable moderate-paying job.

  • John I appreciate this perspective as I am transitioning into the world of trying to balance a “real job” and other projects. I’ve started to more appreciate some of the “real job” benefits, health insurance being one of them as my family has seen its share of medical bills this year.

  • Tre says:

    What? You mean you aren’t sitting on the beach all day? I’m so disillusioned.

  • The biggest impact when beginning a life of working for yourself is you no longer have an established business to rely on for your paychecks every month. Instead, YOU are the business. You get your job done or you’ll find that your checks keep getting smaller. The responsibility shifts onto you, and in many cases, other people’s livelihoods might depend on YOUR hard work.

    I dipped my feet into starting my own analytics business. I was up until 2 or 3am virtually every night while still working my day job. It was stressful and a lot of work. It’s not for the faint of heart, but it is definitely rewarding if it begins to turn a profit.

    Self employment is wonderful, but it takes a LOT of work, typically, to get off the ground. Be prepared, stay true to yourself and your ethics, and succeed.


  • Wow. That must have felt crazy and scary to tell your boss that you’re quitting to start a business 🙂

  • Scott says:

    It all depends on what industry you get into. Personally I write website content. It’s incredibly flexible, and is so much easier than having a “real” job. However, I know it’s not the case with all those who are self-employed.

    Personally I rarely have to get anything done TODAY, so if I need to take a Tuesday off to go hunting, that’s what I do. I can work any time, not just office hours. I set my own schedule, set my own prices, have a vast array of tax write-offs, and get to spend most of the day with my son.

    I would caution people that it’s still work, and when you are responsible for EVERYTHING it gets tough, but I would say go for it to anyone looking to get into business for themselves… just do your research first.

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