5 Things You Can Do to Become a Risk Taker in Business

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Risk Taker: Someone who does something that involves danger or risk in order to achieve a goal.

Would you define yourself as a risk taker? I sure wouldn’t! I play it very safe in life and in business. But that doesn’t mean I think about everything all the way through before I do it either. In fact, most times, I get an idea, just jump right in and then calculate the risks. There is no risk taking involved at all, but rather, thoughtlessness. And thoughtlessness is only going to get me so far.

In my day job I am an analyst. I should know about benefits and risks, right? I mean I do analyze stuff. I may understand it for my 9-5 however learning to being a thoughtful calculated risk taker in my own life and business is another thing entirely.

So I rummaged around the internet for a while, determined to learn how to become a risk taker. I used our very favorite tool, Google and came up with five things I could do to help me be more of a risk taker and I thought I would share them with you!

5 Things You Can Do to Become a Risk Taker in Business

1. Fake it ’til you make it

So this saying gets tossed around a lot, but I absolutely believe it. Whether it is starting a business or trying to work through a hard relationship, sometimes you just have to fake it ‘til you make it.

You must believe in yourself and be confident and unapologetic in your abilities. Everyone is going to see right through you if you don’t think you can make this thing work. Have a strong, confident presence even when you don’t feel like it.

2. Work ON your business, not just in it

You’ll never be able to make big waves or dream up the next big thing for your business if you’re always working in it. Don’t let the admin tasks wear you down.

Use as many free systems, softwares, and websites as possible to start automating your admin tasks. Then start paying for systems you’ve been using for free, if you need to. Bootstrapping and leverage free systems until paying just a little bit for them makes using them even easier. Some free systems that I use are Mailchimp for email marketing, WaveApps for expense tracking and invoicing, Trello to manage all platforms and everything I do, Google Drive...oh where would I be without Google Drive!

3. Just Do It!

Haha, I have never had a problem here. This may not be the best advice, because well, you want it to be just a little thought through, but sometimes if you overthink things you will never do the thing you actually want to do!

You can make saying yes or no to a risk easier by first sitting down and jotting down what kinds of risks you are and are not willing to take, just don’t dwell or be wishy-washy on your decisions. You are wasting precious time! Just say yes or no and move on. If you have any interest to do the thing, JUST DO IT! Doing it will be so much better than feeling regretful later. BUT, be mindful. If taking this risk and just doing it has money involved, make sure you have talked it through. I wrote about how to budget in business here.

4. Set goals + reward yourself

I struggle with setting goals and keeping them. Instead I create laundry lists and hope things get done. I am really going to try and take this step to heart and you should too! Sit down for 30 minutes and set your goals for the year, quarter, or month. It is ok if these goals change throughout that time, but having set goals will help you to keep on track!

Try to have at least one small goal every day. It could be something as small as eating breakfast or not checking your email before 8am. (Waaaaa?!?!) Write out the 3 things that MUST get done and do them before lunch. This will motivate you to get the most important things done first and then you’ll have the rest of your day to be creative and work on your business!

Did you set a goal for the end of the month that you reached? Celebrate!! You took the time to set the goal and you achieved it, now sit back and have a glass of wine or go out and treat yo’self. Seriously, you will get tired of the grind if you don’t step away and celebrate your wins, no matter how small.

5. Get rejected 100 times + The secret to success is failure

The first secret to success is failure….what? Blue Oak Farm is not my first business. Sarah Todoroff Designs existed at one point (yes the initials are STD), then there was The Bold and Creative (not sure what I was doing there) and last but not least the My Simple Life Blog. I was a web designer and social media manager. I was a social media educator for a while and then turned blogger. With the exception of My Simple Life, the other two businesses fell flat. Although I could do the business, my heart just wasn’t in it. I just wasn’t excited about it and my customers could feel it also.

The second secret to success to get rejected. Getting rejected isn’t easy, especially when you’re pitching something you’re really excited about. Man, do I know it. It hurts a ton but it helps you to grow because of it. Just as you say no to things that don’t bring you joy, others are doing the same thing. Being rejected doesn’t mean they don’t value you. There are a million reasons they could have told you no. Don’t take it personally. Keep going and keep asking.

The key to rejection is this - learn from it! Ask why they said no and try and improve your service or product from there. It is probably the most risky thing to put yourself out there with the knowledge that rejection might happen, but it also might be the most worth it!


Are you ready to be a risk taker? Let’s do it together! I am going to be taking a lot of risks (hopefully calculated and thought through) with Blue Oak Farm and you can follow me over on my Instagram account while I do it! I may fall on my face a bit, but it will sure be a fun journey!

I am so excited for you to start being a risk taker in your business! You’ve got this and I will be here to cheer you on!!

here is what i have been taking risks on!