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Self-Employed: Epiphanies From A Former Newspaper Boy

Self-Employed: Epiphanies From A Former Newspaper Boy

Artwork from original Paperboy Arcade

Do you spend time reflecting on your progress as a self-employed entreprenuer?

I’ve spent some time reflecting today on how far I’ve come…

…and how far I still have to go…

It got me thinking about my first taste of working for myself by delivering newspapers in 2012…

My Self-Employment Journey Begins…

Delivering newspapers is that halfway point between working a job and being self-employed…

You are contracted by the newspaper company and have a boss…

But, you’re responsible for all aspects of delivering the papers…

As a newspaper carrier it was my responsibility to:

    1. Deliver all of my papers before the 6 am deadline every day…
    2. Keep my car properly maintenanced and pay for gas…
    3. Manage a payment book and send out bills to my customers who weren’t directly paying the newspaper office…
    4. Chase down customers who didn’t paid their bill and make the decision to cut them off…
    5. Redeliver wet or missed papers after my route was finished…

In the beginning these things didn’t bother me because I had a lot of freedom…

I would go home after my delivery and sleep about 4 hours…

Then I would get up and do what I wanted the rest of the day…

With the free-time, I started building a side business as a freelance web designer…

Also, my customers loved me and I gave some great Christmas tips…

But after my first year, things weren’t so rosy…

The Downward Spiral


This was a 7-day a week gig and my body and my car took a beating…

The problem is If I wanted a break, I had to pay someone to take over my route…

I made decent money delivering papers…

But, paying someone to run my route so that I could take a family vacation…

Not cool bro, not cool…

I did find someone and pay them so I could take a vacation…

The thing is I couldn’t enjoy myself because I was so worried about them messing up my route…

Which, they did and I had to fix when I came back…

Shortly afterwards, the awesome district manager who gave me the job left because he was over worked…

The new district manager ended up being a real prick…

He made some new policies about growing the number of newspaper subscribers on the route…

This made the work even tougher because not only did I have to deliver my normal papers on time…

I had to give non-customers sample papers with an offer to subscribe at a discount…

But, he was the boss whether I like it or not…

All of this led me to a few epiphanies about being self-employed…

My Self-Employment Epiphanies

With all of these issues and the constant feeling of being tired…

I knew that I couldn’t deliver newspapers much longer…

As I dwelled on my current circumstances, I realized a few things…

Epiphany 1: Be Self-Employed And Set My Own Rules

I loved the challenge of being on my own and having to stay self-motivated if I wanted to succeed…

But I didn’t like that I had a district manager who could boss me around…

So, I knew I wanted to be self-employed and be in full control of how things operated…

Epiphany 2: Work When I Want As Much As I Want…

I loved the few hours of work each day and the freedom to do what I wanted when I was done…

However, I didn’t like being forced to work 7 days a week…

I needed to get a full nights sleep and not have to worry about waking up at a certain time…

I wanted to set my own work hours…

Epiphany 3: Make More Money Without Trading Time…

I understood that I was only able to make more money by trading more time…

If I added subscribers to the newspaper route, I’d have to get up earlier and spend more time delivering papers…

Or, I’d have to try to find more side work to grow my income…

I knew there had to be a way to make money without having to trade more of my time…

Epiphany 4: Take PAID Vacations

Finally, I wanted a way to take vacations where I was still being paid instead of having to pay someone…

But I also didn’t want to have to work full-time somewhere for 2 – 3 years just to earn a week of paid vacation…

I knew that being self-employed was the answer, but I wasn’t sure how yet…

It took 4 1/2 years but I finally found a way to make all of those things happen…

Self-Employed Journey Continues…

So, before I tell you about my solution, let me tell you how I stumbled across it…

I worked another year doing the paper route and in the Summer of 2014 a new opportunity opened up…

This would allow me to work for myself full time as a web designer…

So I put in my notice, and struck out on my own as a freelance web designer…

Things seemed to be going good for the first year or so (notice a pattern?)…

But, I got myself in the same position of working all the time and being too tired to really enjoy my life…

Work was overwhelming as I took on more than I could handle…

This led to me dropping the ball on a few projects and losing a couple of good clients…

It got to a point where I fell into depression towards the end of 2015…

I ended up going to counseling for 5 months…

The counseling along with discovering a great marketing book helped me recover…

But, I’m grateful for this low point in my life because it ultimately led to the solution I want to tell you about today…

The Solution That Is Working For Me…

Working for the local newspaper wasn’t a long-term solution…

Working as a freelance web designer was better but still had limitations on my time and freedom…

But, the solution that is fulfilling all of my epiphanies is affiliate marketing…

With affiliate marketing I get to:

  1. Be self-employed and decide what I focus my time and energy on
  2. Work as little or as much as I want
  3. Put in some upfront work and make a recurring stream of income month after month
  4. Be paid while I’m on vacation, go to a movie with my kids or just chilling out on YouTube

I still have to spend time managing my numbers and making adjustments to improve my offers…

But, that is just a few hours a week vs having a set number of hours I have to work in order to get paid…

Uh Oh I Said A “Wordy Dird”…

I remember as a kid my youth pastor used to call dirty words “wordy dirds” and I never forgot it…

Unfortunately, the word affiliate marketing is considered a dirty word by some people…

I blame slimy marketers who pitch a false lifestyle of success…

You won’t be hearing that from me…

I’m still on this affiliate marketing journey and have a ways to go before achieving all of my financial goals…

But I am so much closer now since I started this journey 2 years ago…

So, affiliate marketing isn’t a four letter word to me, but it’s generated a four figure monthly income for me…

I’ve learned the hard way how to build an affiliate business and I’ve had some good success

But, also some failures…

Thankfully, I’ve taken these experiences and developed my own system…

If you’d like to find out more about the system I’m using for my affiliate marketing then click here

Wrapping It Up

So, that is my journey so far…

From a newspaper boy to a self-employed entrepreneur…

Its been a roller coaster ride for sure but I’ve learned a lot along the way…

I hope my experience inspires you to take action in your own life…

Leave me a comment and let me know about your own experiences or if you are just getting started!

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