What 19 Job Changes Teaches You About Being Optimistic - Part Two

How an '80s kid survived 19 Job Changes, became his own boss, and is redefining retirement.

Welcome back to an examination of my crazy work history and how I went from a pessimistic loser to an eternal optimist:

Last week we went through my first eleven jobs.

We left off on a pretty sad note…

I was jobless, smoking a lot of weed, and feeling pretty worthless. (If you missed it, you can read part one here.)

This week, things start to turn around.

Let’s dive in.

The Turn-A-Round

Growing up, I went to a Lutheran School from kindergarten until 9th grade. We studied the Bible every day.

But it wasn’t until this period of my life that I started to believe in divine intervention.

At my lowest point, I had less than $10 to my name. I had to tuck my tail between my legs and ask my dad if I could sweep his shop floors for a few bucks.

With the $10 in change that I had, I needed to take a cab to get to my dad’s shop. But. I wanted a pack of Marlboro Red’s too (priorities ). So I had the cab drop me off at a convenience store, and then I’d walk the rest of the way.

I bought the smokes and a lottery scratch-off ticket.

The ticket ended up being worth $5000.

Still have the big check they gave me!

That ticket, along with the disgust and shame that I felt about my life at the time, triggered a turnaround.

12 - Gorman Foundry (Laborer)

I worked at Gorman Foundry for three years until I returned to college. It is hands down THE most demanding physical labor job I’ve ever had.

Working with molten metal in the summer is brutal. And they don’t do air conditioning in a foundry. If it was 95 degrees with 100% humidity, you could tack on another 10 to 20 degrees easily. I could drink a gallon or two of water and never have to take a leak because I would sweat it out.

Very few new employees lasted more than a couple of days. Sometimes not even a day. I convinced a friend of mine to try it once, he said, “FUCK, this. You guys are crazy.” and asked me to take him home at lunch.

I doubt I would have stuck around if I hadn’t needed it so badly. It paid well, and I wasn’t going back to rock bottom.

Of all the jobs I’ve had, this is one I wear like a badge of honor. I learned much about mind over matter and that I could endure more than I thought.

I also learned how to turn doubters into fuel.

In my 3rd year, I told my boss I wanted to return to 2nd shift because I was back to school in the mornings (Nobody went back to 2nd shift because it was entry-level and harder).

With a slight grin, he asked something along the lines of…

“Are you sure? Because everyone before you tried and ended up back on first shift.” 

There was smugness in that comment that really pissed me off.

I mean, here I was excited, and thinking he’d be encouraging, but no. He was being a dick. Either way, it worked out because it was like pouring gas on the fire already lit under my ass.

Less than a year later, with a slight grin on my face, I gave him my two weeks’ notice. One of my best feelings ever.


13 - Benchmark (Circuit Board Inspection/Repair)

My confidence was really starting to grow at this point. I was 3 months from graduating. I just needed a second-shift job so I could go to school.

Enter, Benchmark.

The line work there was brutal in a different way than Gormans. Sitting in one spot, staring at circuit boards for eight hours. Mindless work is extremely difficult for somebody like me.

But thankfully, after a week, I was offered the chance to take some soldering and circuit board inspection classes, and jumped at it.

I was there for about four months until I finished my degree in Drafting And Design.

That lead me to…

14 - Winona Lighting (Draftsman/Estimator/Marketing)

I was offered this position less than two weeks out of school. This would turn out to be the longest job I’ve ever had (from 1997-2013).

This was huge for me. I felt great.

After all, less than four years before that, I was at the lowest point in life. I was unemployed and had to work in a brutal factory while attending school. Now, I get to work in the office with all the big dogs.

I was a draftsman. I worked in product development and managed standard product documentation. The first 6-7 years were some of my best working years up until that point.

Finally able to afford nice things, I bought my first “newer” car around this time. Behold the Olds Cutlass Supreme.

Eventually, the feeling of content would wane as I started to gain more and more confidence.

I started realizing how much value I was creating for the company. My redesigns and product/process improvements were saving and making the company quite a bit of money. I started feeling underpaid.

I realized I had a couple of options;

  1. I could bitch about how unfair it is and how much I’m not getting paid (while standing there with my hand out begging for money).

  2. OR I could look for a way to make it so that I can capitalize on my value and create leverage.

I chose the latter (although I did bitch a little too).

All these revelations started happening about the same time the internet started taking hold. I could educate myself. I was able to devour podcasts while I worked. Those podcasts lead to books, blogs, newsletters, etc.

This is where I developed a love of learning.

Long story short, I started learning how to build websites, publish podcasts, run pay-per-click ads, AND make money online.

These skills actually helped me move up in the company too. I spent time in a higher-paying sales support role and eventually ended up in the marketing department.

The reason I ended up in the marketing department was that someone in upper management noticed I was building websites on the side. Next thing you know, I am helping on their website, running Google Ads for them, and more.

I never went to college to learn any of this stuff. I learned it all on the web, in books, and by doing it. I am proud that I was able to do this. I am very grateful for living at a time this is possible.

This was when my optimism was really growing.

“If I can do this, I can do anything.”

Eventually, after 17 years, I was able to walk away.

On July 3rd, 2013, I would walk away from Winona Lighting and start my own business.

For a little context as to how I was feeling around this time, here’s a song that I wrote, recorded, and released a couple of months after leaving.

The Bump In The Road

Fast forward to about 2015. I had been self-employed for two years at this point.

I was living the dot-com dream… I thought.

I ended up losing a couple of decent-sized clients. It was a massive hit to my income.

This period was another all-time low for me, but this time it wasn’t because of partying and low-self image.

This time it was because I sucked at running a business, I got lazy, and I had three young kids and a wife to help support. I was failing as a provider.

At one point, my wife asked me if I had any money to help with the house payment and other expenses.

I didn’t have it.

It was one of the worst feelings a dad, husband, and provider could ever have: 3 young kids, a wife in tears, and no money.

It was a huge lesson. The loser-sick-to-your-stomach feeling was back. This time I named it; I called it “The Pit.”

But no time for crying, I needed money, and I had to get a job (and that really sucked).

15 - Machine Shop (Draftsman)

I jumped back into the drafting seat for the first time in a while. Not sure how long I was there, six months, maybe?!

I’m not naming them because we didn’t part on the best terms. The work was challenging, and the owner was super smart, but the environment was dreary and stressful. Especially when people stand over you, questioning everything you do.


16 - Wood Product Company (Laborer)

I took this because I could work part-time and still work on my business. I sanded and stained doors and trim.

Again, I’m not naming them because, other than some of my great co-workers, I don’t have many nice things to say. What I will say, though, is that when you have to bother your employer for your paycheck repeatedly, it’s not a good sign.

Good thing I didn’t have to stay there for more than six weeks because a better opportunity popped up…

17 - Kendall Lumber (Materials Delivery)

I worked part-time at a lumber yard, loading trucks and delivering materials to job sites.

Getting out from behind the desk was nice, being outdoors and doing physical labor again. I gained a ton of respect for everyone who works in the trades.

18 - Oz Lifting (hoist inspection)

While at the lumber yard, a client needed some help in their shop. It was an opportunity for me to get to know their products on a much deeper level (huge for my marketing work). Plus, it paid better than the lumber yard, and the hours were more accommodating.

But after a couple of months, the work was getting very repetitive. I can put up with a lot, but like with the Benchmark job above, the mindless monotony crushes me. Hard to explain, but it is unbearable.

I needed to mix it up and started looking for something else.

19 - Universal Marine and RV (Sales, Marketing)

I answered an ad on Craigslist looking for someone to help with their website.

After talking with them, they also liked that I could run Google Ads.

At this point, I recognized that my weakness in my business was my lack of sales skills.

So, I told them I’d help with the website and run ads for them. In exchange, they train me to make sales. And the kicker, I told them I would do it all for commission. I wanted to make an offer they couldn’t refuse. It worked.

This was a big step for me. It was a gamble. Until that point in my life, I never had the confidence to gamble on myself—big step.

I ended up selling enough to keep our heads above water. But the real payoff was immersing myself in this type of sales environment and learning from sales pros. I learned so much by watching them and listening to every piece of advice they gave.

At some point, it dawned on me that if I could sell campers and boats without knowing a lot about them, I sure as hell could sell digital marketing, which I had been geeking out on for almost ten years at that point. And that’s what I did.

After a long talk with my wife, the hardest person to sell at this point, I took another gamble on myself. I devised a plan to get clients, quit the dealership, and was back in business full-time with a much greater focus.

Long story short, it worked out.

Here I am 8 years later, talking to you, making a very comfortable six-figure income, and very optimistic about the future.

Big Takeaway

So, what did I learn after all this?

Here are a few:

  1. Always follow your curiosity and never stop learning.

  2. Always be optimistic. Anything other than optimism is just counterproductive.

  3. You don’t have to hate your job. If you can’t find a way to like what you do for work, you can find another way to make money.

  4. Don’t listen to people, who have never done something themselves, tell you what you can or cannot do.

  5. Choose yourself. There’s a great book by James Altucher with this title. Basically, don’t wait for someone or something to pick you. Pick yourself, get started.

  6. “Whether you think you can or think you can’t, you are right.” Henry Ford said that and he’s right. Stop telling yourself reasons for why you can’t do something because you’re not even giving yourself a chance. Instead, start looking for ways you can.

  7. Doesn’t matter how much you think you fucked up your life, you can get back on track if you truly want to.

  8. Savor the wins. Even the small wins are building blocks. Let them sink in. They’re liberating and empowering.

  9. Be an evangelist. Helping others achieve the same feeling is really awesome.

For someone who never took chances and never believed that good things happen to them, I can’t put into words how liberating these discoveries were.

Wrapping It Up

There you have it.

You just read how I went from unemployed to employed.

How I went from blue collar to white collar to “know” collar (more on that next week).

You watch me transform from a pessimistic loser to an eternal optimist.

I hope my failures, followed by equal or greater comebacks, prove there is always a way out and a way up.

It’s all about mindset.

Looking back, most of my issues were from a lack of direction, low self-worth, and low expectations.

It is sad to look back and think that one of my biggest goals when I was young, was to turn 21 so I could legally drink. How fucked up is that?

But I can't be too hard on myself. I was just doing what I thought I was supposed to be doing. Playing it safe for 40 years doing work I could tolerate until I could retire and do what I really want to do.

When you realize that you don't have to settle for someone else's version of the future, you can get to work on your own future. And when you get to work and start stacking your wins, your belief in your ability to overcome grows.

Each win leaves less room for pessimism. You start to see that pessimism is shooting yourself in the foot.

Optimism is the only way.

And to complement this feeling of optimism, I have the perfect song…

Love that song. Great for working out, while driving, or just to pump up the motivation.

Now, if you want to fast forward to the time I realized I didn’t want to retire, click the link below, and I’ll tell you all about that too.

See you over there,


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