Reflections on 4 Years of Working for Myself

I’ve been working for myself for 4 years and have learned a lot. Here’s why I love to work for myself and will continue to do so.

Four years in, I can say with confidence that quitting my job changed my life for the better. I’m a doubter by nature. I see what others are doing, the successes they have and think it’s not possible for me to experience something similar. Those were the voices that were going through my mind for years.

I knew I wanted to work for myself. I knew there was something beyond the fabric prison of a cubicle. I was tired of sitting under the glow of fluorescent lights feeling like I was going nowhere.

Not only did I deserve more, but more importantly, my family deserved so much more. After having hit what felt like every brick wall the corporate world could throw at me, I decided to change the story and chart my own course.

Freedom is Intoxicating


As I sit here typing this I’m watching my young children color and play in the backyard. I’m sitting on our deck enjoying the sun-filled day. Later today I’m going to go pick up a craft beer I’ve been waiting to come in to our local bottle shop. Tomorrow we get to go take a day trip as a family.

Those were not things I was able to do while in the corporate world. I know they may seem trivial, but to me it’s about freedom and getting to do what I want in a day and not what’s going to make some company more money on my back.

That simply is not for me.

We’re accustomed to accepting that we get two weeks vacation in our society, if we’re lucky. You have to fit life and all that it throws at you in that 80 hours per year. That simply is not enough time.

As the Steve Miller lyric goes in Fly Like an Eagle, “Time keeps on slippin’, slippin’, slippin’ into the future.” Time simply goes by too fast and I want the freedom to take back as much of it as possible to spend with my family and friends.

If we’re not doing that, then what’s the point?

Freedom isn’t simply about choosing what to do with your time. It’s also about what kind of work you do. Working for yourself opens up the ability to work on what you want with the partners of your choice. Anyone who is an entrepreneur will tell you that is one of the best things about working for yourself.

You get to pick and choose what you work on, assuming you can pay your bills of course. Coming from a job that compromised my morals, that’s not something I’m willing to give up.

Freedom Can Be Deadly


Freedom has a flip side. When you’re free to do what you want, you can choose to do too much. Like a sugar crazed kid unable to put down that candy, it’s easy to over consume.

I know I’m guilty of it. You want to make more and more work equals more money. Working for yourself shouldn’t be about killing yourself, but finding a balance so you can enjoy the fruits of your freedom.

Quitting My Job Changed My Life


I heard it all when I quit my job. Friends and family members thought I was nuts. Here I was with three young kids, with a “good” job and decent benefits and I was snubbing my nose at the establishment to go it solo. Hell, I’d be lying if I didn’t say I was repeating some of those criticisms in my mind.

However, I firmly believe that we can only judge someone if we’re in their shoes. I knew there was something more out there. I knew that if my wife and I gave it our all that we’d make it big.

It wasn’t that way in the beginning. She was writing for content mills. I wrote for free – all as a way to get noticed and grow our business. Something happened over that time.

We built something, from the ground up, and succeeded beyond my wildest dreams. We’ve been able to significantly increase our income over a few short years.

It wasn’t easy. We busted our tails to do that, but it’s something we created and can’t be taken away from us. Of course, this could mean we could blow up our lifestyle and freely spend. Yes, there are a couple of things we’ve increased in spending – but only things that bring us value. To do otherwise would be a waste of our hard work.

Instead, we’re saving like crazy for retirement, saving for our children’s college and working to pay off our mortgage in ten years or less. The ultimate goal is freedom, not gluttony and slavery to the commercialist mindset.

More Are Killing the Status Quo


This isn’t to say that we’re going to become a nation led by the self-employed, because we won’t. I’ve talked about this before, but Pew Research Center reports that 30 percent of the workforce works for themselves or for someone who does.

I love this and believe it will grow in future years. As we move away from corporations doing less for us – fewer offering real retirement plans, fewer subsidizing health care plans like in the past, etc. we’re going to see more people take a chance on themselves. Which, in my opinion, is what it really comes down to in many cases – taking that chance and believing in your ability.

Opportunity is out there for the taking and if you put in the work it is possible to break free of the status quo and build something for yourself.

This isn’t to say that all will see success, because they won’t and many do fail. Working for yourself is hard. It can take significant time to build traction. You don’t have the framework of a larger entity supporting you. However, as more look outside the confines of tradition and change their paradigm, more will take that plunge and see success.

You’re Only As Good as Your Team


In most professional roles you’re a part of a team. In very few circumstances do you have a choice of who is on that team. That’s both good and bad. One of the things I’ve come to appreciate in running our business is the ability to build the kind of team we want.

I wouldn’t have it any other way and, ultimately, being a team helps us achieve the kind of balance we seek. However, the key player in that team, and the one that drives it is my beautiful wife.

The creativity and determination she displays is the engine of our business and, quite honestly, I wouldn’t want to do it with anyone else. That aside, if you’re seeking to become an entrepreneur or grow your small business, don’t take lightly the task of who you choose to be on your team.

I’ve been working for myself for 4 years and have learned a lot. Here’s why I love to work for myself and will continue to do so.

It’s About Taking Back Your Life


I touched on this a bit earlier, but so much about working for myself has taught me one thing – you need to take back your life. We get asked by people how we do it, or we hear “there’s no way I can do what you do.” In some cases that may be true, for one reason or another.

I used to give into the same self-defeating belief – that I couldn’t do it. That you have to be special to go it on your own. We’re proof that you don’t have to be “special” or “lucky” to be successful. Maybe luck plays a particular role, but by and large, in my opinion, it comes down to hard work.

We wanted to take back control of our lives. We wanted to create our own narrative and not one that’s bound to the confines of a 9-5 job. It took me being backed into a corner and seeing the only way out as taking charge to change the paradigm.

After four seemingly long, albeit fast, four years I’m so thankful to have taken control and live the kind of life I want – not one that fits someone else’s definition of what I should do.


Do you work for yourself, and if so, what’s the one reason that you do? Did you always think you’d be a success, or did you doubt yourself? Do you believe we’ll see more workers take the plunge into entrepreneurship?

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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.


  • I’ve worked for myself since starting my first business in 1996 – and love it! Stress and all. 🙂

    I’m curious about your “team” that was mentioned. It would be interesting in the comments, or maybe in a separate post, to understand the team roles you’ve filled to help make your venture successful.

    Keep up the great posts! 🙂

    • John Schmoll says:

      Very cool Brad! I love it, mostly, myself as well. 🙂

      Oh, it’s my wife and I (as well as a VA) but we do have a team of individuals we work with that have skills we don’t have and we offer things they don’t. We’ve all worked together long enough now to trust each other & refer projects/clients and have seen all of our businesses grow as a result. Much of that is local, so it’s cool to see the result of the growth for all.

  • I lucked out and found a job I can do from home. If we are able to have kids, both my husband and myself will be around them all day. Though I may have to hide out a bit when things get slammed. By and large, my job is pretty low-key and I can take an hour off (or a little more) if I need to run an errand.

    Unfortunately, we aren’t able to take vacations much, since I’m technically a contract worker. It means that I don’t get paid for days I don’t work, and with my husband on disability, that’s not a blow we can handle. So we take very short trips that last 3-4 days and mainly take place over the weekends.

    Still, not working in a cubicle means the work isn’t as draining. Well, at least until the worst retail season hits. Then things get a little hairy.

    • John Schmoll says:

      Relatively speaking it sounds like you’ve got a pretty good setup! There’s a lot of freedom, as I’m sure you can relate to, with working from home. Freedom from a cubicle is a great thing. 🙂

  • Freedom is awesome and that picture you painted is doubly awesome…sitting on the deck on a warm day watching your kids play. That is what I want. However, I have a traditional job with a long commute but the pay is good, hours aren’t bad and great benefits. It is hard to give up. It is a pair of golden handcuffs.

    • John Schmoll says:

      Can definitely understand Andrew and, from the sounds of it, you’ve got a really good job that you enjoy. Not everyone has that unfortunately and can understand not wanting to give it up – don’t think I could myself. 🙂

  • John it has been so inspiring following your journey the past four years! My wife and I have seriously discussed what it would take for me to work from home full-time. I don’t think we are even close to getting there, but she graduates with her masters in a couple years and will be making a higher income. I have a number of things in motion as well as ideas, but limited time to work on them due to my 9-5. Plan is to see how far I can get with some of them over the next couple years and whether any take flight to the point that it replaces my full-time income. Anyway wanted to make sure you knew you definitely have inspired me!

    • John Schmoll says:

      Thanks DC, I appreciate it! That being said, if anyone can do it I know you can. The great thing you have going for you, in my opinion, is time and ideas – not to mention an already solid foundation as it is. Too many make the leap thinking it’s just going to fall into their laps or don’t fully think through everything. Working for yourself is hard enough, but if it’s not thought through then you might as well be tying both hands behind your back.

  • Now about to graduate school so I want some work experience first but opening up my own firm is my dream. Many of the reasons are highly correlated to what you said in this article. Life will us up too quickly if we work with limited vacation. Luckily I am not American so we embrace vacation. Unluckily I will be working in America to start off but hey the money is good.

    Fun fact: I think I saw somewhere that an estimated 60% of millennials want to work for themselves, will be interesting to see how that plays out.

    • John Schmoll says:

      I think everyone should have experience in the corporate world. It’s never going to go away and it can provide valuable lessons. Who knows, you may find a job you really enjoy. That stat doesn’t surprise me at all, I’d think it’d be higher – but, yes, it will be interesting to see how that plays out over the next few decades.

  • I love working for myself but like Abigail, it’s frustrating not having paid holidays or paid sick days!

  • Hannah says:

    Congratulations on reaching the 4 year mark! I keep trying to convince my husband to drop out of school so we can flip houses together, but that’s not his idea of teamwork (as he would have to do the hard part of the labor).

  • Ahhh, I am so jealous. Mr. Picky Pincher and I are working to be completely independent. It takes a lot of work, but it’s doable for anybody. Thanks for sharing your thoughts on what it’s like on the other side. 🙂

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