10 Things I’ve Learned From A Year Of Self-Employment


Today is officially the first day of the rest of my life. I am finally free of the cubicle and all the crap that goes along with it. I no longer have to be the “tech” guy that everyone comes to for problems and stupid questions.

The above quote is from a post I wrote a year ago entitled A New Journey Starts Today. It was officially the first day of my new life after leaving my cubicle job. Well guess what? It’s been a year since that happened!

I can’t believe a year has come and gone. When I first quit my job, my main goal was to make it a year without having to get another job. All I wanted to do was work for myself for a year without having to commute, sit in a cubicle, or answer to a boss. Luckily, I managed to do just that. I learned a lot along the way and wanted to put together a list of some of the things I’ve learned from a year of self-employment.

1. Hard Work: You Can’t Escape It

When a lot of people make the jump to working for themselves, they often assume they will be able to work less and set their own hours. While this can be true to some extent, it’s not likely going to happen this way. Instead, I’ve learned that hard work is necessary to build a successful company (or career). I’ve easily worked more than twenty 75 hour+ weeks since I quit my job.

Heck, I often work more than 12 hours a day. It’s one of the sacrifices I made in making the move to working for myself. However, the hours you put in are much different from clocking 12 hours at your day job. Working for yourself means you can take breaks when you want, work on the projects you want, and work when you want. That’s why I often split my work up and do some throughout the day and some at night.

Plus the work I do is fun so it doesn’t really feel like work to me. It feels more like playing video games did back in high school. You don’t even realize the time is flying right by.

2. Trial And Error Is Necessary

While spending all that time working, I’ve noticed that some things work well while others fail miserably. If everything worked the way we wanted it to, I probably would have retired already. But things fail and this is where we learn a lot about business, as well as ourselves.

So don’t be afraid of trail and error. It’s not as simple as finding a book with all the directions in it because not everything works for everyone. You need to find the things that work for you. Once you do, take baby steps to scale them to be much larger. This is where you will start to see success.

3. Sleep Will Be Lost

With working long hours and failing constantly, you will no doubt lose sleep. I often find it hard to sleep when I can’t get something off my mind. I even wrote a post about my unplanned experiment with sleep deprivation, where I ended up staying awake for more than a day straight.

The good news is since you can set your own work hours, you can easily catch up on sleep by giving yourself the enjoyment of sleeping in.

4. Sacrifices Will Be Made

Regardless if you plan on it or not, you will eventually make some sacrifices when working for yourself. It might be as simple as skipping an event with a friend to catch up on work or saying no to something you really want to buy. It’s just part of life and anything worth having requires some sacrifices.

As I mentioned above, one of the sacrifices I made was working far more than I used to. I also sold my car and got rid of a lot of things I no longer used. These things made it easier for me to make it a year without any problems.

5. Money Isn’t Everything

A lot of people go into business to make money. While obviously this is one of the goals of a company, it should not be the only one. What you should be focused on is proving some sort of value, making a difference, or creating something unique. The goals will lead you to the money you were hoping for.

However, working for myself quickly made me realize how unimportant money is. Yes we need it to survive, but that’s it. Other than food/water, clothes, and a place to sleep, we really don’t NEED much else. Instead, we WANT everything we see on TV. The key is to use your money wisely.

Do you absolutely love watching television? If so, then go grab a badass TV. But if you’re only buying the TV to have a bigger one than your neighbor, think twice before you get it. If you’re like me, you’re happy with a 23 inch screen and some rabbit ears. It’s important to decide what you want in life and then focus your money on it.

Neil Patel over at Quicksprout summed it up perfectly in this quote:

So what has all of this taught me? It is easier to save money than it is to make it. You can’t always control how much money you make, but what you can control is what you spend your money on.”

6. Benefits Are Nice, But You Can Live Without Them

One of the things that everyone pointed out to me was “if you quit your job, you will lose your benefits!” I think other people were worried more than I was. It was probably due to that fact that I was just out of college and barely had benefits prior to landing my first two office jobs. So I knew what it was like to not have them.

But the truth is, benefits are overrated. This is coming from someone without a family so I’m sure things would be different if I had a family to support. When you’re young and single, you don’t really need benefits. As soon as I quit my job a year ago, I grabbed a health insurance plan online for less than 90 bucks a month. 6 Months later, I ended up cutting that plan down to a 60 dollar plan that covers me in case of an emergency. Guess what? I haven’t used my plan in over 12 months.

If it’s retirement you are worried about, you can also setup a retirement plan for yourself. This can provide a nice tax break since you can put some of your income into a retirement account.

The key is to do your research prior to quitting your job. Learn as much as you can about your current benefits and see what you can get on your own. This will make the transition a lot easier for you.

7. Bookkeeping And Taxes Suck

One thing I cannot stand doing is the books. I hate accounting and always have. Taxes are a whole other ballgame. When you go into business for yourself, these are some of the things you will have to learn about. You don’t need to know everything, but the more you learn the easier it will be to meet with an accountant.

I’ve slowly been learning more as I go and I’m finally to the point where I have a good understanding of how things work. However, when I just started I wanted to pull my hair out.

You can check out my podcast on bookkeeping and tax tips for bloggers and freelancers for some useful tips.

8. Office Politics Are Shit

If you’ve been here before, you’ve probably read my post about hating office politics. I used to hate everything about them. The gossip, the power tripping, and the alliances that employees make. It used to drive me absolutely insane. Even the whole idea of “climbing the ladder” made me want to cry.

After spending an entire year as far away from an office as possible, I can tell you one thing: office politics sucks. I don’t miss them one bit and I really hope I can continue to work from my home rather than an office.

9. You Will Learn (A Lot)

Of all the things I’ve mentioned so far, nothing has been more enjoyable than learning. It’s absolutely amazing how many things I have learned over the course of one year. I can easily predict that I’ve learned at least 5 (maybe 10) times as much as I did from high school and college combined. I’ve learned valuable things about business, life, and everything in-between.

If anything, I recommend trying out self-employment for the learning experience. It forces you to quickly adapt to what’s happening around you. I think one of the reasons it works so well is because you don’t have a lot of people around to ask questions. If you need to figure something out, you find a way to make it happen (the best saying ever). Whether it’s from reading online or visiting the public library (a lifesaver), the answers are always out there.

10. Freedom Is What Matters

Last but not least is freedom. Freedom is the one thing that made me want to work for myself, as well as build an online business. Why? Because I love to travel and be anywhere at any time. I also enjoy moving fairly often, which might be happening fairly soon.

Having a normal job makes it difficult to live the digital nomad lifestyle because you always have to be at work. Yes you can take vacation but you only get so much time a year. Instead, I decided it would be far more beneficial to create a career that can move around with me.

So the most important thing anyone can have is freedom. The ability to do what you want whenever you want. This is far more important money. People with high-paying jobs have plenty of money, but they don’t necessarily have freedom.

It Was A Great Year

Overall, it was the best year of my life. Not only was it fun and rewarding, but it was also challenging and difficult. I learned a lot and have been making progress since the first day I started. I can only hope that this upcoming year can be just as fun and rewarding. So far, it has been just that.

Photo Credit: St3ve

23 thoughts on “10 Things I’ve Learned From A Year Of Self-Employment

  1. Robby G

    Self employment is the way to go. Still really enjoying your blog and happy I was able to interview you a few months back, if you still remember. By the way, this whole year you’ve been surviving off this blog and your Zoop Media company? Has this blog been bringing any steady income for you that is of any actual help?
    Cheers! :)

    1. Justin Wright Post author

      Hey Robby,

      Yeah I managed to live off the income from this blog as well as ZoopMedia. This blog has been bringing in some really decent Adsense checks lately so it’s been great so far. I hope to continue making progess.

  2. Pingback: Justin Wright Survives Self-Employement | The 42nd Estate

  3. Candi

    Your option for health care is only good if you don’t have a medical injury or illness. My son recently broke his arm severely and needed surgery. The cost just to take the rods out of his arm would be over $15,000 if we didn’t have insurance. The cost for the initial hospital stay and surgery was probably to the tune of $30,000 or more. Unless you have some form of insurance or unlimited income, bills like that would take you down.

    I am a huge advocate of healthy living. My family is rarely sick but we have had freak accidents that without any insurance we’d be quickly put on the train to homelessness. So I don’t necessarily agree with number 6. Benefits are necessary to some extent unless you can guarantee you will never have a major injury or illness.

  4. Carla

    When in comes to benefits, I don’t agree with you there. Some of us do need health insurance, and with “pre-existing conditions” our options are very limited. I was in a way forced out of work due to disability, otherwise leaving a job to become a full-time entrepreneur would not have been on the radar unless I married someone with group insurance!

    I really had to learn and embrace #2. You will make mistakes no matter what. Sure, if I had to start over, there are so many things that I would have done differently but we don’t have a time machine! You live, learn, move on and dont be afraid.

  5. Jenn

    I think it’s very awesome that you’ve made it an entire year working for yourself. You should be proud that you haven’t given up yet, it takes a strong soul to do what you do.

  6. lissie

    I could have written this post LOL I so agree re the office politics – I don’t even miss the people – I now know I have no option to make self-employment work as I could never work for anyone else again!

    I totally agree with you re the insurance thing – its a major downer for Americans because your healthcare is so over-priced. I would seriously look at the price of having anything done in nearby countries (Mexico, Costa Rica) – the price of the airfare would be nothing compared to the saving in premiums.

    I am unlikely to be insured again – moving countries loses you your coverage too – and once you have preexisting – nothing that you are likely to need treatment for is going to be covered anyway – so whats the point?

  7. Tracy

    I took the leap over 10 years ago and have loved every minute. Yeah, you are right the bookkeeping sucks but luckily I have a very good CPA that makes it as easy as possible for me.

  8. Marketing Ideas

    I couldn’t agree more with your list. I find myself in the same boat with the good comes the bad and things you never knew how to do like taxes. But on the flip side you are building something that is yours and completely yours not just some hour slave for the good of someone else’s pocket.

  9. Girdle Woman

    I walked away from my career about eight years ago now. I have never looked back over my shoulder nor felt a single moment of regret. As you said ‘Freedom is what matters’. I may have less money but I have freedom.

  10. Huey Harden the Get Paid For Your Opinion Guy

    I am with you on this Justin!

    Once you’re in business on your own, its less scary for you than to the thousands of other people on the other side of the fence in their cube farms. :)

    And it will always be scary for people who have not made the leap. And what a leap it is. Of faith and trust in your ability to succeed. Krakens may lurk around the corner, but they are easily avoided by an alert mind.

    If you cube rats find making the leap a bit daunting, how about working on something on your off time or down time at work. Something that will make it easier for you to make the leap.

    Some things like finding out what it takes to do what you like doing, or finding what’s online that pays, or get together with your friends who are business minded for lunch (you’re buying) and pick their brains for advice.

    The possibilities are endless. I hope I’ve inspired all of you. :) Good luck.


  11. Ascentive

    I think this pretty much sums it up right there. There are very few people I know that have the goal of this type of freedom… I wish they would see there are different options available to them!

  12. another justin

    not to be too political, but health insurance in US is seen as a privilege, when it should be a right…I have several friends right now who fly overseas and get surgery, etc…it is much cheaper, they say, even incl. airfare…

    It is a bargain and many ARE self-employed who will be drastically affected by having to have health insurance..their more import. concern is why is it so expensive in the US to get any treatment or go to ten diff. ‘specialists’ for one thing when overseas one professional can do everything for 1/10 the cost?

    I tell them I don’t know, and it doesn’t make sense.

    I am also exploring other careers via adult ed. to hopefully get out of rat race at some point, as well. I just need some actual skills like Mr. Wright here whereby people can value my services enough to pay me for them.

    every single day, I see people who slave their life away and THEN retire and I don’t understand it at all….it shouldn’t be this way at all….and, once again, I don’t have the solutions myself. I just know it is wrong. However, 99% of indiv. reading this blog or thread, if like me, were coerced into college and professional careers and steered away from ‘vocational’ fields, notwithstanding personal aptitudes, and after obtaining two masters’ degrees in totally separate fields, it is still the same old baloney incl. the aforementioned office politics…it never changes.

    1. Barbara

      @anotherjustin – You wrote “However, 99% of indiv. reading this blog or thread, if like me, were coerced into college and professional careers and steered away from ‘vocational’ fields, notwithstanding personal aptitudes, and after obtaining two masters’ degrees in totally separate fields, it is still the same old baloney incl. the aforementioned office politics…it never changes.”

      Amen, amen, amen.

      I’ve thought many times that a trade would have been an easier route to a fulfilling life than the solo entrepreneurship that’s all the rage for knowledge workers now. Benefits, work that at least has a minimal point (instead of ridiculous make-work), better wages than many “professional” (read, glorified clerical) jobs in business.

  13. Barbara

    Gotta join the chorus about the benefits. Have a pre-existing condition and you may not be able to get that emergency plan for less than $1,000 per month. More and more people will fall into that category as they get older, whether from “poor lifestyle”, a work-related injury, genetics, an accident that leaves a permanent health issue (even a minor one.)

    1. Carla

      I totally agree. I am paying about that per month in health care related costs (premium + out of pocket expenses). Thankfully I live in a state where I can even have the option to have a plan with a pre-existing condition in the first place, though its hard to be “thankful” for anything having to do with this…

  14. Theo

    You really do have to be willing to work hard and sacrifice a few things if you want to become successful at being self employed.

    Deciding to become self employed was the best decision I ever made but it certainly hasn’t been easy and stress free!

  15. Kesenia

    Hi Justin, you sound like one happy camper.
    Congratulations on deciding to jump off of the proverbial merry-go round called a job. I’ve been self-employed for a long time and agree with most of your 10 things that you mentioned above.

    However, you stated that money isn’t everything, I’m not 100 percent with you on that one. In my opinion it’s right up there with oxygen. Without it life can sucks.

    It’s not the point of money but it’s what money can buy. I had 2 close family members to die because of the lack of money… that hurts.

    Never the less, but you don’t have to have a job in order to purchase insurance.

    So my suggestion is for those that have great self employment ideas, move forward but set it up like a legit business, with insurance, retirement funds, etc..

    Good Luck Justin,


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