One of the most common questions I’m asked constantly is why I decided to strike it out on my own as a self employed freelancer. I usually answer with the predictable responses of, “I wanted to pursue my passions,” and “I wanted to work on my own terms,” both of which are true statements. But recently I read a blog post by Chris Guillebeau that really resonated with me:

“For better or worse, I learned that I was a terrible employee. I was unreliable and unskilled.” – Chris Guillebeau

Whoa. It may sound like a harsh self assessment, but this was entirely true and one of many reasons why myself and many others have ventured into the world of self employment. Some of us just aren’t meant to be employees, and that is totally okay.

From First Job to Eighth Job

My first paying job ever came when I was 18 years old. As a fresh high school graduate at the top of my class, I had spent my entire life dedicated to academics and sports, and while it meant I had a stellar report card, I had zero applicable job skills. Even so, a friend of the family managed to hook me up with my first paid job as a file clerk at a Honda and Acura car dealership. My next few job roles weren’t any more glamorous, especially as I became a food service employee at McDonald’s, and then my college cafeteria. However, working in food service helped me discover that there was a skill I was pretty damn good at: operating a cash register for $6.00 an hour. While all of these first jobs were definitely not career jobs, they were highly interactive and fast paced and I was really really good at them. These elements made me actually enjoyed these jobs very much.

When I left the manual labor workforce and transitioned to corporate office life, my outlook on the idea of work completely changed. Once I graduated from college, I was extremely fortunate to earn a full-time job as a corporate financial analyst at Boeing. While it was very high paying and challenging, it also involved sitting at a desk for 8+ hours a day, working on spreadsheets and databases, or sitting through meeting after meeting. It was hardly fast-paced, and it definitely wasn’t interesting, but my coworkers had been there for decades and were convinced that this was the only job I would ever need for life. After a year and a half at that job, I shocked my coworkers and family by resigning. I took a mini career break, spending a month backpacking through Costa Rica and Germany, before returning home and repeating the same process over again. Over the course of 3 years, I held 8 different corporate desk jobs at different companies (including a brief return to Boeing), before I reached my breaking point. I couldn’t stick it out at any job for longer than 1 year before I would freak out and resign. What was my problem?

Accepting My Bad Employee Status

During my third attempt at establishing a career at Boeing, I had a manager who finally sat me down one day and asked me what my career goal was. She was concerned that I wasn’t as engaged as I should be and wasn’t climbing the corporate ladder according to schedule. It was during that candid, honest meeting that I verbally confessed for the first time ever that I simply hadn’t been fully happy in any job I had ever had since my summer stints at McDonald’s. This was one of the most difficult realizations I had ever come to terms with, but it was a very important one as it set me on the path to becoming a self employed, which has to date been the longest I’ve ever stuck with a job role in my life.

Signs It’s Time for a Change

My personal disgruntlement over a period of time lead me to my solution of becoming my own boss, but this isn’t necessarily a mandated outcome. It’s completely normal to go through periods of discontent at your current job role, and the way you solve this problem could be as simple of changing your routine or attitude, or it could be as extreme as changing your career and entire surroundings. Either way, these signs below should indicate that something’s off and merits a change of heart or lifestyle.

1. You can’t fully buy into your employer’s brand and mission.

Do you respect the company you work for, and almost everything it stands for? If not, this may be a sign that you aren’t working for the best company.

2. You don’t respect your manager or the people running your company.

While it’s important to believe in the company you work for, it’s equally essential to trust in the leaders at the top of the company. Good intentions are nothing without solid execution.

3. You’re not engaged at work.

In many companies, it’s incredibly easily to fake productivity for a period of time. I recall one job in particular where I would catch my colleagues blatantly watching Netflix or editing vacation photos while they were in the office in the middle of a busy work day. We were all incredibly disengaged due to bad management, and it came as no surprise when the company eventually folded. Lack of engagement, whether voluntary or not, generally indicates a poor fit.

4. Your job is no longer your top priority.

Most people have side passion projects that eventually become the basis of side ventures. If you find that you’re spending more of your time and effort working on your side project rather than your main paying job, it may be time to consider a job change.

Don’t Quit Your Day Job Until…

Realizing and accepting you have a problem is the first and easiest step. The hardest part is actually doing something about it. As someone who has made several career changes, my advice for making any kind of professional change is as follows:

1. Research and learn about a new skill online.

Before I left the corporate world, I decided to give it one last shot by transitioning from finance to marketing. This ended up being a difficult switch to make when my resume had extensive references to Excel and SQL, but none for marketing. So I did the one thing that could easily add marketing qualifications to my resume: took classes at a local community college and earned short-term marketing certificates. While they don’t offer certificates, I highly recommend Lynda.com as a starting point for learning creative or technical online skills. Sure, they didn’t carry the weight that a bachelor’s degree or actual work experience did, but it was enough to get me to my next launching point.

2. Get experience in a new field by interning or volunteering.

Once you have something on your resume that indicates skill in another field, it’s time to get verified work experience using that skill through interning or volunteering. This is the best way to gain valuable work experience that can easily be added to any resume and used in any job interview. Volunteering or interning is also a low investment for yourself and the organization you’re working with as there’s usually no money or high value item at stake. Personally, I took my newly formatted resume and used it to get a marketing internship at a local startup, which ended up being a very humbling experience that also beefed up my resume.

3. Do the math — don’t quit until you’re generating enough income.

While completing my certification and internship, I was still pursuing entrepreneurial passions on the side, biding my time and trying to figure out when to take the leap and become fully self employed. That moment came 9 months into my internship, right when I was starting to get antsy for something new, but the catalyst was purely financial. It was around this time that I sat down and did the math, realizing that I was making as much income off of my side projects as I had been as a corporate employee. There was still some risk since I couldn’t verify if these income patterns would stretch into the future, but it was enough evidence for me to quit my internship and go full-time self employed. That happened in September 2012, and I haven’t looked back since.

Conclusion

If you’re stuck in a miserable situation, there are many ways to begin identifying and combatting the situation, but the first step is just to realize that there is indeed a problem that needs fixing. The solution often times won’t be evident or fully implemented very quickly, but if you start working on it little by little while keeping the end goal in sight, you’ll get there sooner than you might expect, and it will be completely and utterly worth it.