5 Reasons I Will Never Have a Normal Job Again

What this morning looked like.

This morning as I was driving down the freeway headed to buy a washer and dryer, I was overwhelmed at how much I love working for myself.  Here it was, just a beautiful sunny day here in Portland. I’d already hit the gym and run my four miles.  Had a nice breakfast, coffee and time with my family.  Now I was sitting in my nice warm truck with two of my boys in the back, listening to music and driving down the highway.

Just over five years ago you would have found me along the railroad tracks down in Southern Oregon where I worked for a short-line railroad.  That was one of the hardest of my approximately thirty or so jobs I’ve had in my 31 years of life.  The worst part of the job was the uncertainty of what I would be doing each day.  One day I might sweating away changing out railroad ties in the pouring down rain.  The next, I would end up working 16 hrs late into the night on a derailment.  It was a miserable job, but I’m thankful for it.  It taught me what hard work was.  It’s also made me thankful every day for the situation that I’m in now.

Here’s my 5 Reasons I Will Never Have a Normal Job Again

1.  I want to decide how I spend every minute of my day.  Working for yourself gives you that freedom.  I need to exercise 3-4 times a week.  I like bringing my boys with me when I’m working.  I love meeting friends for coffee in the middle of the day.  I cherish having breakfast, lunch and dinner with my family every day.  Some days I don’t want to work.  Others I shouldn’t.  I want to be able to travel when I want to.  Just this month, I’m going to Hawaii again for a week.

My four kids sitting on the beach at my favorite surf spot.

2.  I don’t want to work 40-50 hours a week ever again.  I’m not against work.  I think work is great and much needed.  However, especially with our efficiencies, I don’t believe we should be working as much as we are.   The work-like-crazy now, so I can enjoy it one day in retirement doesn’t make sense to me. Why not set your life up so that you enjoy it today?  Why work so hard for your children’s “future” when all your children want is your attention today?  Or work all those overtime hours to buy your wife some expensive gift when she would rather spend time with you today.  It might also mean cutting out frivolous items from our lives that we spend half of our working hours paying for.

I’m not saying we should never work long hours or work our tails off.  There are seasons for everything.  I’m suggesting that we write down what we want our dream life to look like and then do whatever it takes to make it happen now.

3.  I would rather be a good boss than work for a bad one.  I’m not saying that all my bosses have been bad over the years. Some were good.  All had their weaknesses, some more than others.   Working for a bad boss is like living in a cage.  It’s one of the most frustrating and exasperating things in life.  Complaining about bad bosses doesn’t help anyone.  We need to start businesses and become good bosses.  That’s been a good thing having had so many jobs in my life.  I’ve learned what not to do.  I hope that in the coming years as I employ more people, that I’m looked back upon as the best boss any of them ever had.

4.  I don’t have a college degree.  I might as well have three or four felonies on my record.  I’m not going to get the job.  I wouldn’t be called in for most interviews.  It doesn’t matter how smart or talented you are.  Our system is setup for the conformists and those that get in line.  It’s not for the “dreamers”, as Steve Jobs would call those that didn’t quite fit the mold.  Maybe our system of vetting and discovering talent is broken.  Hopefully the student loan bubble ushers in some reform towards our approach to education.

5. I would probably get so depressed I would want to die.  I once worked for a lumber mill pulling sheets in the plywood plant for exactly 2 weeks. Before that job I had never been depressed.  I didn’t know what depression felt like.  That changed when I stood with earplugs in my ears, standing for 8 hours a day putting veneer on plywood.  Sheet after sheet.  Over and over, all day long.  Everyone hated their job, or at least none were happy, and all looked like they hated life.  It was physically demanding work.  I would go home at night and I could barely pick a fork up my hands hurt so bad.  I was so exhausted that I usually just went straight to bed.  In the mornings, my time off was wasted because I couldn’t stop dreading going to work.  But all that was nothing compared to what it did to my mind.

I was paid to focus on one task. To do it well, it took full concentration.  I couldn’t think.  I couldn’t dream.  I couldn’t wrestle with ideas.  It killed me inside.

Homer talking to his Dad

The movie October Sky, which is one of the greatest entrepreneurial movies of all time, captures very well what I’m trying to communicate.  One of my favorite lines from the movie is when Homer is talking to his Dad about what he wants out of life.

Homer: No. Coal mining may be your life, but it’s not mine. I’m never going down there again. I wanna go into space.

Me too.  Normal jobs may be ok for many, but not me.  I’m never going back there again.


  1. Haven’t made the plunge yet, but I yearn for when I can work solely for myself. I make a good chunk of change reselling electronics I buy on Craigslist, but it’s not enough to where I could replace all my income with it.

    Cool post, I’m glad you’re living the dream.

    • Thanks for stopping by Chris. I think the easiest way to get started is to buy an item that you need. Maybe it’s another computer or laptop. Then get competitive about finding the best deal you can on Craigslist. Figure out which make/model you want to get, what type of condition you want it to be in etc. Then do a little research about how to test it out before you buy. If you get a good deal on it, it’s relatively easy to put it back up for sale for $75-$100 more than you paid. Then you wait. You can even use and enjoy the product while you wait for someone to buy. It might take a few days or a week, but everything eventually will sell.

      You can even start smaller. The next time you need any product, try to buy it on Craigslist first. Once you start realizing how much money you can save, you will be hooked. Best of luck man!

      • I believe even if you work for someone , You should always consider yourself , self employed . Its you who is responsable for your work ethic , attitude, productivity and customer. (boss) satisfaction. Every customer is your boss and , self discipline , it takes a lot to be self employed. Try to give every customer something extra , it is hard but in the end the payoffs are beyond what we envision for ourselves. You may only be the plywood slinger in some factory, But be the best one with the best attitude, work ethic , productivity, and boss satisfaction , make em cry when you leave . You shortchange them you shortchange yourself

  2. great post- Me too Ryan. Now I have multiple sources of income, multiple business ideas going on in my head. One of the hard parts of the jump is getting that monthly mortgage/rent out of the picture, either by subletting or buying cheap or whatever. I could not even pursue some of my ideas if not for that freedom. see you in a couple weeks in Hawaii!

  3. I stumbled upon a post on Google and this site is awesome. I’ve bought on and off from craigslist and China selling on various sites and flipping a profit. this exactly the lifestyle I want to live and its great to know there are other people like you Ryan that exist… and making work. Thanks for putting up the site and keep the ideas coming. Definitely bookmarking your site and looking forward to hearing more about your methods. – Josh

  4. Cool post Ryan! I could not agree more, once working for yourself there is no going back. Once that sense of freedom is attained it is hard to imagine having a boss again. With a college degree no longer being key to a guaranteed job I hope we see more young people strike off on their own. -Jordan

  5. I agree with all 5 of your reasons, Ryan. Although a bit older than you, I’ve felt the same way in my work life. But a lot depends on the type of person you are. Some folks need the security and routine of a daily job. After working at a large corporation for 3 years (and hating it) I saw people forced into retirement or downsized after 40 years. They left practically kicking and screaming because they didn’t know what they would do. With the recession you see stories of people laid off and still searching for a job for two or three years with no success. They are so used to working for someone other than themselves. The college education requirement for many jobs puzzles me. When you see how manufacturing companies want college grads and then they pay $10-12 dollars an hour which no one can live on. That doesn’t even take into account how they’ll have to pay off student loans. For most folks, the days of counting on one employer to meet your needs are gone.
    I enjoy reading your posts, Ryan. Keep up the good work.

  6. I agree there is a paradigm shift in way we think about work. The recession ignited an era of entrepreneurism. The key is it set up some form of passive income because you can not actively run so many things (unless they clone you). My ultimately goal is to have 4 separate business making in 1,000 – 1,500 range and be totally diversified in case google or some other source of income does a dance on you. Online and offline.

    • I think that’s very wise Carl. I’m working on the same thing. It’s a bit dangerous, or riskier, to have all your income from one source. When you start, you do what you have to do. But it is somewhat wise to diversify the income. Once you have multiple business’s going, or streams, build up the ones that are doing the best while simply maintaining the others.

  7. I have been hooked on your website for the past four days. It has given me a lot of inspiration because just like you I have had all kind of odd jobs and none really satisfied me and I have always considered having my own unusual way of making a living for my wife, daughter and myself . I became a father for the first time 16 months ago and ever since I don’t want to spend more than a few hours away from my lovely daughter. I think spending time with our family can help build solid foundations for the future we can play a very important role in the way our kids’ personalities develop. Now I’m struggling to provide for my family but your stories give me motivation to keep pushing forward and striving to materialize my dreams.

  8. Sometimes I feel like your posts are straight out of my own head. I’ve held a few jobs and I never did well because I’m a dreamer. I couldn’t focus on any tasks. One of the last jobs I had was in my field and was exactly what I thought I wanted, but it was very production-oriented, though very technical. I watched all the other guys in my department doing their processing and they could sit there and focus for 8 hours straight. It was later on in the 18 months I worked there (before having my position cut, which led to selling on Craigslist!) that I finally said something to another guy about my issues with focus and he didn’t really relate. He was able to sit there for hours on end working through the process, but all I could do was dream and think. Some of these guys even had masters degrees (I have half of one….long story) but could sit there and process stuff all day.

    Now I sell mainly drum sets and associated gear on Craigs, teach lessons, detail cars (advertising on Craigslist; something I want to scale back on due to the “processing” challenge I have as mentioned above), and I’m looking to start an organic farm.


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