Why I Chose Self-Employment: Part 1

Part one of why I chose self-employment and my mistakes that brought me to where I am today.

Part one of why I chose self-employment and my mistakes that brought me to where I am today.

I don’t talk about self-employment much on the blog and to be honest, I’m not really sure why. Back when this blog was After Nine to Five and not Hello Nature, it’s nearly everything I talked about. That was the whole point. But when I made the switch to Hello Nature, I think I realized I wanted to be about more than self-employment. And instead of balancing life and work, I swung the other direction. I’ve missed it though. And I’ve learned a lot of lessons since then so I’m excited to get back to the fun (and scary!) business stuff!

I figure the best way to get back into it is to share my story. But the why for me really starts with the how. And the how is messy.

It’s long. And honestly, it’s made up of a lot of wrong turns. A lot of bad decisions, but ultimately – these decisions brought me to where I am today. And I’m pretty happy where I am today so I don’t regret any of these decisions.


I didn’t always know that I wanted to be self-employed. I knew that I wanted freedom and creativity to be the building blocks of my career, but what that career was? I was clueless. I also wanted to make a difference. So I dabbled. Everywhere. In high school, I spent most of my elective courses in art. I tried pottery, graphic design, mixed media and more. It provided me freedom to create what I pleased and gave me an outlet for my creativity. I also joined the LGBTQ group and became the leader of it. I was making a difference. And on top of that, I took extra English classes so I could do more than draw with a pen. I wrote and I felt free.

But once high school ended, I stopped doing it all. I went through retail jobs in high school and shortly after I graduated, I switched to a desk job at a health insurance company. I loathed it. It was boring, required few skills and it was also temporary. Being a temp made me feel powerless in a job I already disliked. So as soon as I could, I found a more permanent job. Unfortunately, the next job was even worse.

I worked at a call center for health insurance and it became my life. I hated my job so much that it was all I would think about. Being screamed at, being ignored, and watching the class of trainees I started with slowly dwindle down from the mid-twenties to single digits was too much for me. There was negative freedom, my creativity was being zapped by the constant stress of the job and it was rare that I made a positive difference in someone’s day.

So I left for another temporary job at a manufacturing plant.

I became an Administrative Assistant and while the job wasn’t glamorous, I was given a lot of freedom. Creatively and otherwise. It was then that I finally started to realize more of what I wanted. Prior to this, I simply knew what I didn’t want. I created newsletters, organized files, and put together color-coded spreadsheets. I helped people and felt responsible for important tasks. I was never yelled at and very rarely saw anything negative happen.

Eventually, I was good enough at my job that I actually replaced the person who I was working for and got a permanent job. This was my high point. This was the moment when I thought 
I’m finally doing what I was meant to do. Unfortunately, I was wrong.

This was my high point. This was the moment when I thought “I’m finally doing what I was meant to do.” Unfortunately, I was wrong.

The job was never bad, but the responsibilities didn’t change all that much from when I was an Administrative Assistant. I got bored. Quickly. There was little room for growth, my boss didn’t act upon ideas I had for my position or the facility and I felt stuck. I was going to a local community college for graphic design and this was my only salvation. It encouraged my creativity and pushed me to work towards something I loved doing. Unfortunately, I stopped going for numerous reasons and never got my degree.

During this time, I broke up with my ex and felt a deep dissatisfaction with my life. I joined eHarmony and met my husband, which is definitely a story for another day. But he was the reason I finally realized I was not going in the right direction. It took me a little while to figure out what the right direction was after this, but he helped me get there.

Shortly after this, I left that job for a Customer Service position at a trucking company. My dad worked there and as fate would have it, my husband got a job there in a different department the same week I did so we did onboarding together. This was our first glimpse at working together. I was super bummed when we’d completed the company training and we headed off to our own departments.

Why I thought another job answering phones would be better is beyond me. I’m convinced I had wedding brain and I wasn’t focused on the right thing for me. Instead, I was caught up in working at the same company my dad had been at for years and working with my husband.

Why I thought another job answering phones would be better is beyond me. I’m convinced I had wedding brain and I wasn’t focused on the right thing for me. Instead, I was caught up in working at the same company my dad had been at for years and working with my husband.

Big surprise: I hated it.

It wasn’t nearly as bad as the first one, but I hated answering phones. I hated being the person everyone blamed for everything going wrong. I was hired on the lowest team in the customer service floor which meant all of my loads were the first to get pushed. Which led to unhappy customers. And that led to some of the worst days in my life.

I’m a sensitive person by nature and being blamed, yelled at, and treated like I personally sought out to destroy someone’s day on a regular basis sucked. If there is a word that is stronger than sucked, that is what it was. Thick skin is not something I have and this job took it’s toll on me. It led to deeper depression, stronger anxiety and a dark cloud that loomed over me every single morning I woke up. I started to loathe traveling as I’d see their trucks and feel an immediate sense of overwhelm for what I was going back to. I started to hate visiting my family because I knew the company would come up. It took over my dreams, my moods, my weekends and every corner of my life.

During this time, I did go back to school – but for Environmental Management.

See a pattern here? I was struggling to grasp what I really wanted. I liked (and still do) too many things. So I tried to do it all with no plan in place. I just jumped from ship to ship, hoping that one day it’d blow in the right direction and I’d land on happy island.

See a pattern here? I was struggling to grasp what I really wanted. I liked (and still do) too many things. So I tried to do it all with no plan in place. I just jumped from ship to ship, hoping that one day it’d blow in the right direction and I’d land on happy island.

I was certain this route would led me to a position I loved with this company and would leave me feeling like I made a difference. I thought for sure this time was the right time. And as I’m sure you can guess, it wasn’t. Not even close. I couldn’t stick with it long enough and right around my six month mark, I caved.

In October of 2010, I quit. Not for another customer service job. Not for another office job. Not for another temporary job.

I just quit.

No job lined up, no idea what I was doing. I just knew that was it. I was done with the grind, the struggle and the frustration. I was done with drifting in a sea of possibilities and hoping something stuck. I was done with watching my marriage be torn apart by my career and watching my depression get a stronger and stronger hold of me.

No job lined up, no idea what I was doing. I just knew that was it. I was done with the grind, the struggle and the frustration. I was done with drifting in a sea of possibilities and hoping something stuck. I was done with watching my marriage be torn apart by my career and watching my depression get a stronger and stronger hold of me.

So I just quit.

I lied and told people I was going to focus on my studies. Nathan was the only one that really knew I was just flat out miserable and needed to rethink my life before I got to the point that it was too much for me to handle.

Luckily, I had better things on the horizon. In April of 2011, we got married. The months in between me quitting and us tying the knot were blissful. I focused on the wedding, we jetted off to Jamaica and had the best wedding/honeymoon I could imagine. I soaked up the sun and we were happy again. But I knew that when I set foot in the states again, I would need to focus on work.

So I started my journey in self-employment. Blindly.

I started blogging shortly after I quit, merely as a hobby. I needed to connect with the real world and this was a way I could do it while I was preparing for our wedding. I contemplated monetizing it and briefly tried, but didn’t treat it like a business at all. Then I had a jewelry shop on Etsy. (Truth be told, I have zero explanation for this one. I hardly ever wear jewelry.) That turned into a prints and decal shop that eventually ended because it wasn’t generating enough income and I didn’t see a way for me to turn it into a full-time job. (I probably could have, but once again – I didn’t treat it enough like a business.)

I did all of this in about a year.

By Fall of 2012, The Gnarly Whale was born. And this is where it kills me. It was created strictly as a hobby.

I did a bit more research to make sure it would be profitable and even made a break-even analysis, but it was only because I wanted to make some money while I figured my life out. I was ready to go back to the corporate world and do something that made me feel like a productive member of society. I was ready to stop making poor decisions that were fueled by high hopes. I just wanted to do what was right for me and needed to make sure I contributed to my marriage while I did that. I was ready to get serious.

And the next chapter is lengthy. Because what started as a hobby, now generates a full-time income for me. And Nathan. And it led to this blog which is a whole story on it’s own. This was already long-winded enough so I’ll save the rest of the story for another day.

But I’d love to know:

If you’re self-employed, was your journey easier than mine? Or if you’re on the way to self-employment, what has your journey looked like so far?

And if you have ANY questions about my journey or even self-employment – feel free to ask! Either in the comments or contact me via email: [email protected]. I love connecting with people who have big dreams for themselves and I’m an open book!

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Did you find my story inspiring? Think it might help someone else out? Please share it below! Self-employment can be a scary journey and it always helps me to know that not everyone knows what they want to do right away. Or that sometimes, everything doesn’t fall into place immediately.

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