Things I Wish I Knew Before Quitting My Job

I quit my 9-to-5 job almost ten years ago. I hope to never go back to it.

Here are 7 things I wish I knew before quitting…

What you need to know before quitting your job

Everyone paints the picture of entrepreneurship being glamorous, independent, making tons of money and living the life. Parts of it can be like that but, there are things working a 9-to-5 job offer that just won’t be available as a business owner, and you’ll need to get used to it.

Before you pull the plug and quit your day job for your dream life as a business owner, keep these things in mind..

1. Your health insurance is gone

You can get business owner’s health insurance.

There’s the health insurance marketplace you can go through and if you’re married and your partner has health insurance, you might be able to be covered under your partner’s health insurance.

If you’re looking at getting health insurance as a business owner (not on your partner’s plan), it’s not going to be quite the same as the coverage you had as a 9-to-5 worker.

I don’t want to speak generally about all health insurance plans and I’m no expert but, I’ve had a few different plans and I can say they are all much different than my health coverage when I was a W2 employee.

Is it worth it?

It very well might be.

Consider the benefits you gain being a business owner like freedom, flexibility, unlimited income potential and other perks. These may outweigh this drawback — the crappy health insurance insurance options for business owners.

2. You have to be diligent

This means you have to police yourself and prioritize your work.

When you don’t have to wake up at 6am, commute to the office and be monitored doing work all day, all that new found freedom can be overwhelming and as a result, you could slack in doing your work.

Sleeping in until noon, taking yourself out to a long lunch, shopping, exploring during the week in your city instead of working, etc.

It’s important to be diligent and have self-control.

Some people can master it, others cannot. Just something to think about.

3. Taxes

I’m not going to talk at length about this since I’m not a tax advisor but, as an entrepreneur, you’ve got to work harder to get your taxes in line.

Taxes aren’t automatically taken out to pay the government like your W2 job paychecks.

This means either hiring an accountant or bookkeeper to manage your taxes for you, investing in software for tax prep, saving 20% to 30% of your income or more for tax purposes, etc.

It can be a lot and part of the price to pay in becoming an entrepreneur.

4. Income can be unstable

As a W2 employee you know that if you work your 40 hours per week then you’ll earn your full paycheck and get paid.

As a business owner, sometimes you work and don’t get paid.

Sometimes you are working toward the opportunity to earn income and you go without for weeks or months before landing that paycheck.

Also, your pay can fluctuate greatly from one month to the next.

Your income one month could be $10K and the next month be $1,500.

5. There’s no sick pay

Unless you build up an emergency account or sick day fund for yourself, if you get sick, there’s no sick pay.

You don’t work, you don’t get paid.

6. It can be hard to explain what you do to others

This isn’t a real big deal but it’s something I have dealt with and something others deal with too. That’s explaining what you do for a living.

With a W2 job, when someone asks you what you do, you can tell them your title and that pretty much explains it, most of the time.

It’s a little different as an entrepreneur.

I think it’s because a lot of people don’t know how entrepreneurship works and how you can make money to support yourself as a business owner.

They just don’t get it.

And a lot of titles you try to give yourself may not accurately describe what you do.

When people ask me, I say digital publishing.

And, they instantly think, marketing.

Which it’s not.

It’s publishing on digital (or online), like content creating and writing.

I usually have to spit out a few more lines explaining some examples of what I do.

Again it’s not a big deal but, your introductions to new friends and peers will probably take a little longer.

7. Getting a home loan will be tough

This, along with other kinds of credit will be a challenge as a business owner. Many companies won’t even extend credit to entrepreneurs unless they have a two year history documented with tax returns.

So, if you’re a new business owner (less than 2 years), don’t count on getting that house loan or car loan any time soon.

Is being an entrepreneur worth it?

Heck yes!

I’d give up my W2 job with all the amenities, benefits, my $60K/year salary any day for the freedom, flexibility, personal and job enrichment, and unlimited paycheck I get as a business owner.

It’s a lot to take in, all the changes that will happen when transitioning to business ownership full time but like all change, you’ll get used to it and you’ll probably find that the tradeoff is very worth it, just like I do.

So, what do you think?

Are you a business owner? What are some things you wish you knew before quitting your 9-to-5?

Want to read more stories like this? Check out my Substack where I talk about side hustles, social media, content creation and business.