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3 Lessons I Learned from Quitting My Job and Starting My Own Business

Mommin' is hard, but entrepreneurship is a close second.

Let’s get really real here for a second – being a mom is hard work. Up until 4 years ago, I didn’t know what it meant to be a mom. Babysitting and being a super cool aunt was as far as I had gotten, and let’s just say that isn’t anywhere CLOSE to being similar. 

I learned a lot about who I was both inside and out – there are things I kind of wish I hadn’t learned about my body, but that’s a different story for a different day (or never.. whichever comes first). 

But you want to know what’s even harder? 

Being an entrepreneur. 

Sure… it looks like fun and games. And sometimes, it is. Other times, it’s like willingly sticking a fork into your eye, repeatedly. 

For the most part, though, I’d say that being an entrepreneur is HARD but worth it. And the funny thing is, people see me thriving and growing as a person and as a professional and they WANT my “secret”. 

“Jen, how’d you quit teaching and start your own business?” 

“Oh man, I wish I could do that!” 

By all accounts, it looks like a sweet gig. 

I don’t HAVE to shower every day if I don’t want to (judge me…). I don’t have to brush my teeth if I absolutely don’t want to (again… judge away). And, I don’t have to put on real clothes for DAYS at a time… yoga pants and a sweatshirt suffice most days for the pickup line at my son’s school. There are those days when I don’t change my clothes from the day before and have to walk into school both days. That’s when I hang my head in shame…

On the other side of things, it’s a scary, hairy, fuzzy world. 

I have always (and by always, I mean literally always) been hard on myself. Messing up on something sends me into a tailspin of emotions ranging from I should quit my job right now to I wonder what life in Antartica would be like. 

This entrepreneurial thing is no joke people. It’s not for the faint of heart. And it’s not for those who suffer from any of the following:

– Comparisonitis

– Anxiety

– Low self-worth

– Low self-esteem

– Minimal self-care practices

And by saying all of that, I’ve just put myself in the “not qualified” category. Sweet.

But along this journey, I’ve found that even though I suffer from ALL of those God-forsaken things + have a family to take care of + have bills to pay + have a business to run + have to be a human being + have to be a friend and daughter and and and and… I have still found a way to be highly successful and live the life I always dreamt about. 

Here are the top 3 lessons I (begrudgingly at times) learned in the last year of infant entrepreneurship. 

Find a mentor. Attach yourself like a baby leech. 

Alright, maybe don’t attach yourself quite like that, but you do need to find someone you can hang onto for a while. This someone will be there for you whenever you need a shoulder to cry on, someone to scream at (or with), a swift kicker of your butt when you need it, and a cheerleader to remind you how awesome you are when you don’t think you’re even good at cooking toast (because… cooking toast? really?). 

Get super-de-duper clear on what you want to do! 

This one might sound like a bit of a “no duh” statement, but hear me out! When I started my online business, I thought I was just coming in to be someone’s virtual assistant. I remember the exact words that I said to my husband upon my epiphany: I can totally be someone’s assistant! Yep. That’s right. I just knew I was going to be amazing because being someone’s assistant couldn’t be that hard. Could it? 

Well no, it wasn’t that hard. But what WAS hard was figuring out that a) that was just too dang broad and b) if I didn’t narrow down I’d be stuck creating graphics for the rest of my life (which I suck at, by the way). 

So I got really intentional on figuring out what it was that I wanted to do and what I was good at! Turns out, I’m not so terrible at this copywriting thing. Call it a hunch, but maybe my two college degrees + years of teaching English had something to do with it. And once I got really clear, it was like the floodgates opened and a whole new world (a la Ariel in “The Little Mermaid” mind you) was upon me! 

Be OKAY with failure. 

Oh boy… this one was a tough tough tough one. Why? Because the thing is: I don’t like failing. Not even one little bit. There was never a time in my life that I felt “okay” with failing at anything – not losing an argument with my husband even if I was wrong, not getting a B on a test that I didn’t even study for, and not even getting in trouble for being a sassy pants to my parents when I knew I was being a big ol’ bitch. 

There just was nothing inside of me that accepted failure – until I met this little thing we call entrepreneurship. Failing is a big word with a lot of negative connotation behind it, I know. But it’s a real word that we need to say more often. There are going to be times in this entrepreneurial world where we fail – sometimes miserably and sometimes just a teensy bit. And that is OKAY. Literally. More than okay

Because guess what failing does for us? It teaches us lessons and shows us a) how strong we really are and b) what not to do in the future (like me creating graphics). Once I got over that hissy fit of mine (and I’m still working on it daily), I was able to see that life goes on and things will get better. I can’t be everyone’s cup of tea all the time, and that’s perfectly fine! 

It’s okay to want to quit sometimes – just don’t. 

Being an entrepreneur for the last year has been an eye-opening experience. As a teacher, it was pretty set in stone for me how my life was going to turn out. I was going to teach for 28 years, maybe become an assistant principal or curriculum coach, and then retire. That was it. Sure, I was going to impact students’ lives and make a change in their world, but I was sacrificing a lot in the process. (Please do not get me wrong… I’d never trade my years of teaching for anything. Who knows… maybe one day I’ll go back?!?) 

With the way education was headed when I was teaching (and it is NOT any better, trust me), I knew that I couldn’t sacrifice my family or my happiness for anything. So I made a decision that was best for ME and my family. But this journey is anything but easy. It’s really freaking hard. And sometimes, when people say that they want to jump into this online business world for a few months and hop back out, my skin crawls. 

I have worked really freaking hard to get where I am today, and that means I’ve stepped out of my comfort zone and marketed myself in ways I never knew was possible! And without these lessons + incredible community support from many people, I would not be where I am today. But this is not something you jump into and jump back out – this is NOT the lazy river people. 

There are days when I want to quit… days when I think that teaching would be easier and much more secure. Then, I reel myself back off the ledge and remind myself that I chose this life because I wanted something more for my soul. I wanted to be lit up every day when I thought about the work I got to do – not dread a classroom full of teenagers who could think of a million other places they’d rather be (like the bathroom) than sitting in class reading To Kill a Mockingbird (it’s a classic, though… so I don’t feel bad about that one). 

So take my lessons for what they’re worth (approximately $5.25 if you want to know) and roll with them. Learn not to quit even when you want to, and keep being the amazing person you are for taking this leap! It’s not for the faint of heart, I’ll tell you that! And you, my dear, have no fainting heart… and if you do, you might want to get that checked out! <3

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