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Three Questions To Ask Yourself Before Leaving Your Day Job

I wrote this post almost a year ago, but never put it on my blog. I don’t know why I let it sit in my folder of unpublished writing for so long. (There is loads of stuff in there).  Looking back at it, I think it has some helpful tips for anyone interested in entrepreneurship and is still worth sharing.

I want to note I definitely think I sound super dramatic about “corporate” in posts I used to write.  I don’t think twice about those types of jobs anymore and I’m not sure why I acted like I did something so noble by leaving. It is not courageous to leave a job. Anyone can quit something – It’s what you do next that is what counts. And having an office job is not something to feel bad about. Many people make great, happy livings from these careers. But I guess that’s what happens when you’re in the wrong job type: you feel like you’ve escaped and met freedom once you leave. Sorry for being obnoxious about it.


If you’re thinking of leaving your day job to become an entrepreneur or follow your passions, that is amazing, But, there are three things that are worth asking yourself before making any extreme moves. Now, onto the original post. This was written in November 2016.


A little over a month ago** (now one year ago), I left my full-time corporate job to create a living on my own. I felt completely out of character in a corporate environment, and couldn’t understand why I would work so hard for something I didn’t love. Did I really want to speed through life working for the weekends? I knew to my core this wasn’t the lifestyle for me and that being an entrepreneur was my true calling.

For the 6 past months, I knew I was going to quit, but I thought I needed a solid and sensible plan before leaving behind a steady paycheck. While I planned to stick the job out until sometime in 2017 to save a decent amount of money, one Friday in September I made the decision to quit. It was random but smacked me in the face like a bag of bricks. I am a huge believer in taking life into your own hands and creating your own opportunities, but on the outside I was paralyzed by fear of doing so myself. At the same time, I couldn’t stomach working so hard towards something that was, at the end of the day, someone else’s dream, when I could be working to follow my own instead. So why wasn’t I? That Friday I decided to practice what I preached, and once that thought came into my head there was no turning back. My last day was two weeks later.

I did not save nearly as much as I’d hoped for this and had no concrete plans of what I would do. I still don’t. But, I’m living a much more present lifestyle, one that is a complete shift from that of the corporate world. I wake up everyday choosing what I will do with my day, and if I don’t put in the work, I don’t get paid. I have always been somewhat comfortable with risk and am self-reliant, so this may be helpful with my transition. But it still is fearful (and exhilarating) jumping into the unknown.

There are so many positives to becoming an entrepreneur, but leaving a 9 to 5 for this is a huge lifestyle change. One some may not be able to handle. When is the right time to follow your passion project and leave the office behind? While a lot of people just know in their gut it’s time to leave, like I did, some may be stressed and confused about the right timing (I have been there too).

If you’re thinking of leaving your day job behind, consider the questions below before you go.

Is a consistent and reliable paycheck important to you?

The biggest, and most obvious, transition from a 9-5 to being on your own is the lack of financial security. Though I believe relying on yourself instead of a corporation is much more secure in the long run, short term leaving a steady paycheck is a financial risk. If not knowing when or how much you’ll get paid each month makes you uncomfortable, leaving your day job at this time may not be for you.

Do you get lonely?

Though there are many benefits to working on your own that outweigh this one, the life of an entrepreneur can be lonely. This is one part of entrepreneurship that probably doesn’t get talked about as much as it should. If you are working to build something to call your own, there will be times of loneliness. There is no work culture or camaraderie. Often times, even if you don’t like your job, the people you work with make it worth going to. Think about being alone all day while mostly everyone else you know is at work. Does that sound lonely to you? If you aren’t in a place where you’re comfortable spending A LOT of time alone, leaving your current work environment may not yet be for you.

Are you disciplined?

One reason why many people fail at being entrepreneurs is lack of discipline. No matter how much flexibility you have in your corporate job, you are ultimately being told what to do. You have a job title with set responsibilities that you’re expected to complete in exchange for pay, and you have a boss that will monitor this. But can you handle being your own boss? Being your own boss may sound amazing on the surface, but many people can’t do it. It can be tempting to sleep in everyday and take long lunches with friends when you’re out on your own, but these actions will never get you the success you left your steady job for. Learn how to be disciplined before leaving your current job.


After all this has been said, it can be argued that there is no right time to leave your day job. Sometimes, you have to just wing it, and in times of desperation you will learn to be strongest. I completely agree with this as well. It is kind of what I did. There is no right or wrong way to do it. But, being comfortable with risk, feeling okay with being alone and having self-discipline will make the journey of entrepreneurship a lot easier.

I urge everyone to follow their passion project, whether this requires you to leave your day job or not. There is no greater feeling than “being paid to live”. As long as you are being true to yourself, the rest in life will follow.



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