My First Mistake as an Entrepreneur [Don’t Do This!]

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It’s officially been more than a month now that I can call myself a business owner/”entrepreneur.” It’s weird – but also exciting, fun, and terrifying all at the same time.

I’ve learned a lot already, and am seeing myself grow in many ways. I’ve also watched myself make some pretty decent mistakes already.

Honestly, I made my first big mistake before I even left the corporate world….when I put in my two weeks notice.

Now, contrary to what you immediately thought just now, I’m not saying leaving was my mistake. Read on.

June 1st, 2017

I had known for a few months that I was planning on leaving my job around June 1st. I had picked a date before to leave and never followed through. So I prepared as much as possible by saving up 8-12 months expenses, and having a few clients already in the works so I could really hit the ground running. Essentially, I left myself no more excuses to not leave the middle of that year.

While I knew I was planning on leaving, I was waiting to tell my employer until closer to the date to “CYA” if you know what I mean. I didn’t have quite enough money saved up just yet, so getting let go would have foiled the plan a bit.

Anyway, a little more than a month before June 1st, I learned that an employee on our team got let go – which for our department was kind of unheard of.

On top of that, their last day would be…….June 1st.

I felt awful knowing that I was going to quit soon and leave practically the same day they were going to lose their job. I thought maybe I could have saved their spot if I had given my notice earlier.

No time like the present!

Handing in My Resignation Letter

In an effort to potentially save this person their job, I sat down with my boss the next day and gave her my resignation letter. I even mentioned that they should give the person their job back and they could take on some of the projects I was managing.

I don’t think it worked – but the coincidence around June 1st was a definite motivator for me to hand in my notice, as honestly I kept putting it off.

My First Mistake as an Entrepreneur

So what did I mean when I said my big mistake happened when I was handing in my resignation letter?

My mistake was the date I gave as my last date of employment with the company.

May 31st.

Why is this so significant? Well May 31st happens to be the last day of the month. You know what also ends on the last day of the month for people leaving a company?

Health Insurance.

Now, I was able to get health insurance through (we won’t go into the debate about this program). Getting a health insurance policy wasn’t a problem at all. I got a decent policy for a pretty good price of $284.42 a month.

I had been under the impression that you have healthcare coverage with your current job until the end of the month following when you leave. I’m really not sure why this was in my head – and even after looking at the policy on the company’s intranet, I still got it wrong.

You know what would have happened if I had put in that letter that my last day was going to be June 1st?

I would have had healthcare coverage through my previous employer until June 30th.


Entrepreneurship: 1
Chenell: -$284.42

You live and learn folks. And my big tip for those getting ready to leave your job: do your due diligence and make sure you know when your health coverage is going to end once you leave.

[Photo credit: @atlas_green]

5 thoughts on “My First Mistake as an Entrepreneur [Don’t Do This!]”

  1. Congratulations on leaving the 9 to 5 to work for yourself! Healthcare coverage is expensive no matter where it’s coming from in the US. But, lesson learned!


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