Taking Risks with your Small Business

Yesterday, I was catching up on some reading, and I stumbled upon this article from Tara Gentile about the reward of taking risks. It made me think back to my own “Big Risk” when I left my full time position as a high school art teacher to pursue papernstitch full time. That was just over a year ago.

I had been running my business on the side for almost a year already at that point and it was growing. Really growing. So, I knew it was feasible. I had crunched the numbers over and over again. Spent endless hours coming up with a plan of attack. And all of that. It was a calculated risk.

But the REAL risk, the BIG risk, (which I didn’t realize until later) was what would have happened if I hadn’t quit that teaching position. I was unhappy there. I felt confined and unable to truly express my thoughts and ideas. “But at least I had a stable income,” I would say to myself. But what is that really worth? Your happiness? My happiness? No. Absolutely not.

So, even if I fell flat on my face, I decided it was worth a shot to go after something that I really believed in. “Give it a try,” I thought. And if it doesn’t work out, I’ll just do something else. Simple as that.

And now, more than a year later, what has happened? Well, I am still here. Still chugging along. Making a living doing something that I absolutely love. I am happier than ever before. I can work from anywhere. I am my own boss. I control what happens in the future. Never been better.

This isn’t everyone’s story though. I understand that. Sometimes we take risks and they don’t pan out. We fail and are left wondering why. But at least now we know. Right? That is the point of taking risks in the first place. Isn’t it? To roll the dice and take control, instead of waiting on the sidelines for “it” to happen to you.

What risks have you taken or struggled with lately?

Image c/o Rosie Hardy

27 comments | Click here to reply

I love the picture. It captures perfectly the spirit of this post. I know that there are many, many people like the author, who quit their careers to do something they love (I basically left my PhD program to take this risk). But no matter how strongly I believe that this was the right choice for me, it’s always such a comfort to hear of another person who “made it to the other side.”


That’s good advice. I’ve been on the fence about making the leap.


Thank you for this article, it sums up all the thoughts that were going through my head. I recently also quit my ‘day job’ to pursue the finer things in life. 🙂
It is scary, stepping out into the unknown, but with like-minded individuals like you and everyone else here, its a little less frightening.

Thanks again.


Brill! Will find this usefull and will add it to my bloglist

Emanuel Meras

I had no idea that this is how your site started. Thanks for the article. Hope to read more like these in the future.


This could not have come at a more clandestine moment! My hubby & I have been talking about how miserable my job is making me – what a toll it is taking on not only my mental & emotional well-being, but on my self-esteem too. My hubby said “give your 2 week notice! Do your Etsy shops full-time!” and I keep saying “but it’s a stable check”.
Okay. I hear you! 🙂


Thanks for sharing your success story. I am glad that risk paid off. I am chugging along here too.


Thank you for sharing, this is really an inspiring article. Makes me think of my plunge in taking the leaps from a system analyst into a full-time artist.

Yes, it is a big risk, but I couldn’t think of what will happen if I didn’t make the changes.

And, now there is another big risk that we are taking, we are in the plan of moving to other country. Hope our dream will come true!

🙂 Life is like a roller coaster.



Thank you for your short but sweet inspiring experience! To take the big leap from a stable paycheck to the unknown is what being an entrepreneur is all about. I, myself, am trying to figure out if I want to find another job when I lose mine sometime this year or take the leap too. I am looking at jobs that are 3 to 4 days a week so I can work my business on the other days. Congrats to your ongoing success!

Michelle Martinez

Thank you for reminding us of the real reason to pursue our dreams – a lifetime of wondering “what if I had…?”

My big risk right now is pursuing my art full time too. When I sold my house this spring I was lucky enough to make some money, and though the practical part of me was screaming, “You need to invest that in something and keep working this job you hate!” I listened to the quieter voice of my heart, and lo and behold…it was telling me to believe in myself and focus entirely on my business. I worry about making an “irresponsible” decision, about the money running out and falling flat on my face.

But I’m proud of myself for listening to that soft voice of the heart, no matter what happens…

Thanks for being an inspiration!


What a great read! Thank you for sharing your experience. I too have the dream of expanding and becoming my own boss. I love to read success stories because it inspires me. My BIG risk was pursuing my craft career. It’s hard to put yourself out there but when you see the delight on people’s faces it makes it all worth it. I am looking forward to my next risk and the learn from it as well.

Leslie (LeslieGallery)

Thanks for sharing about your story and the article, very inspiring. I quit my job six years ago to pursue my own creative business and I’ve never once regretted it. Never. Even in moments when things were difficult, I never looked back. The risks that I’m facing now are questions on where to go and grow from here. It is easy being comfy in what I’ve been doing, risky to take things to another level. Plus, now that I love what I do I’m more hesitant to take those risks.

Amber (woodmouse)

I must say, its been so wonderful to read over everyone’s responses here. I wasn’t really sure how much personal info people would be interested hearing about little old me. But this is great. Suki, you are so right! A lack of confidence can really hold a person back from accomplishing their dreams. The only person who can stop you is you.


Thank you very much for writing this post Brittni! I am now doing exactly the same thing that you were doing one year ago. I work full time a the hospital and at home I am doing all these crazy stuffs. Hopefully next year I can work full time at home, part time at the hospital. Sometimes we know we want it, and we know we can do it, but it’s just that lack of confidence or the uncertainty of the future that hold us back.


Thank you Laura. Michelle, I know exactly how you feel. And Ruth, I love your perspective on this. You’re absolutely right…with success comes failure and vis versa. Failed obstacles along the way are part of the journey.


I love this post, Brittni, it really speaks to me. I believe that you can’t be successful if you’re not willing to take a risk. And failure is a part of success, too. I’ve been learning that you have to see failure as a part of the process in becoming successful – it’s just another step in that long journey of doing what you love. 🙂


I don’t know whether articles like this are popping out at me because I just took the risk, or not, but thanks for sharing this. I did not calculate, I just knew that it was now or never, and I chose NOW! That same voice in my head kept saying the same thing….stable income…but to risk your soul/life/happiness just for a stable income, not worth it! It has been 2 weeks tomorrow that I took the risk, only time will tell if I sink or swim!! 🙂

Michelle @ Sweet Something

Brilliant post! Turns out you are not alone as my ‘big risk’ follows a strikingly similar pattern to yours! Enjoy your freedom and well done on your success!


Aw, thanks so much Missy. And Darlene, congratulations on your upcoming craft show. Sounds like it could be a great opportunity for you and your business. You know the old saying, it takes money to make money, is true more often than I’d like to admit. Hope everything works out for you!


Thank you so much for this post. It’s so inspiring to read about people who are making a living on their craft.

The risks I’m taking, and struggling with, now mostly have to do with investing in my crafty business. I’m naturally an extremely frugal person. When I started out, I was really careful not to buy any supplies or tools I needed unless I sold something, and to only spend what I’d made on the sale.

I’ve since realized that my business cannot grow if I don’t invest in it appropriately. For example, I just got accepted into a large craft show, and in the past I probably would’ve declined it because I haven’t made enough sales recently to pay the table fee. Instead, I’m going for it!

This is really scary for me but I am taking a deep breath and doing it anyway!


I’m so glad you took the risk, because your website provides me hours of entertainment and inspiration. 🙂 I haven’t quite made the leap to quitting my day job, but I did take the risk to start my own business. It’s still small but I have big dreams for it one day. Thanks for the article, I’ve been in need of some inspiration lately.


Hi Mayi! Congrats on quitting your day job in January. As an artist, I can only imagine what a HUGE leap that was for you. To be able to work on your art full time really is like living a dream. Huh?


Great, inspiring article. Thanks for sharing…!

Jen Z

So glad I could help Kara. Good luck with your getting your business off the ground. And Linda, although I was only speaking on those BIG risks, I think “smaller risks” can be just as important sometimes. Just taking those small steps for your business when you’re starting out can be scary, and those small successes are worth mentioning as well. 🙂


Brittni… what a great note!!! I didn’t know this about you. I’m so happy you shared your personal journey with us. I also quit my “real” job in January of this year to allow myself to be happy + pursue my passion (just like you). And, I did all the calculations + risk research too, lol. But in the end, those analysis didn’t matter. All that mattered was my soul + my happiness. Today, I’m a happy camper living my dream of being a full time artist. So, my story is a happy one too… 🙂

Mayi Carles

i really really really love short and sweet business stories and advice like this. they really feel personal and to hear how people got to where they are is so inspiring to me.

i haven’t really taken any big leaps (same level as yours) for my business, yet, but i’ve definitely taken a big chunk out of my income to invest in tools and supplies. but i’ve never looked back and regretted any of those purchases, because each thing means something to me, to what i do that makes me happy, and to my overall passion of making handmade things for people.

i applaud you for pursuing your passion and love and it seems like you enjoy every second of it. hooray to that!


This is an insightful article. I went over to Tara’s site and read the article you referenced as well. I feel inspired now to get off my ass and stop feeling sorry for myself. I am hoping to get my own business off the ground here shortly. This is exactly what I needed.

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