Be Bold. Be Daring.


When you think of taking a risk, what do you think of? Putting a weeks worth of earnings on red in roulette? Jumping out of a plane? Learning to ride a motorcycle? Walking over hot coals?  I haven't done any of these things - and I'm not sure I will since I've never been much of a risk taker or thrill seeker anyways. But I am a big believer in getting curious and trying new things - sometimes against the good advice of the people around me and regardless of whether I know what the hell I'm doing. 

My most recent (calculated) risk was investing a crazy amount of money on 358 new camping mugs. Yikes! I had so much anxiety not knowing the things I wanted to know; What would they look like? When would they arrive? How much tax would I have to pay? Would they even sell?! There were no answers and no guarantees so I was at the mercy of the universe - which I never like! Luckily, it has (so far) turned out OK and am really happy with them. I also feel more comfortable jumping into things like this moving forward because I'm confident in my decision-making on bigger ticket items so that, in itself, is valueable. So, mugs aside, how does one go about learning to get comfortable with taking a 'risk'?

Decide that you'll do something you've always wanted to do, and try it! Even if it's just a small attempt. 

Well, I'm no expert. But I can share some thoughts here and I think it all starts in getting curious and being more excited about it than you are fearful of it. Decide that you'll do something you've always wanted to do, and try it! Even if it's just a small attempt. Especially if you may not have a good idea of what you're doing.

A marathon is a good example. You've always wanted to run a big marathon but feel uncomfortable jumping into a 20K right away. You've never trained to run. You've never been athletic but it's something you've wanted to challenge yourself with. So...start small by hitting the gym or joining a running group. Then step it up with a small 5K and work up to those big runs. Maybe after that 5K you decide that marathons aren't your jam; And that's cool too. You're allowed to change your mind. And please don't think that's a failure! Think of it as something new you've learned about yourself.

A good adage that has served me well is to say "f**k it". Instead of me making risk out to be this scary thing, I like to turn it on its head and think of it more like an experiment. I want to see what happens even though I may not have 100% confidence to know that I'll crush it.

For some that would be the thrill of jumping out of a plane. For others, it's trying a new fashion style. For me, it's getting married at 21 (and divorced at 23). Taking a 3-week European vacation by myself. Running 3 Tough Mudders'. And starting a business at 37. At first read, they may seem silly or stupid or careless. Heck, maybe not even risky at all! But for me, these were outside my comfort zone to some degree yet they proved to be some of the richest experiences of my life. One of the reasons being that I stepped beyond the threshold of who I thought I was, which helped me define who I am by learning likes, dislikes, abilities, limitations, etc.

Business risk is a little trickier and I'm sure I haven't even brushed the surface of everything I'll face. I know that sometimes you have no choice but to take those big risks whether you like it or not. Other times, you have the luxury of choice. When it's the latter, I can't stress enough how important it is to do your research. If you sell product, get a small run done to test the market before you order 1000s. Talk to people and get advice. Ask questions. Work out the kinks. 

My dad always taught me that if you're going to do something, do it right and do it well so that's the compass I use for a lot of my business decisions. Am I thinking it thoroughly or being careless? Am I in love with the design I'm sharing or am I sharing it for the sake of sharing? Some decisions are easier than others but I think they should all start in the basis of knowledge and research. This will help you make an informed decision without having to bet the farm on a hopeful idea and lose.

So how do you guys approach risk? And what kind of risk are you thinking about taking?