Five Key Take-Aways on Taking Risks

Today I’m sharing what 40-something women have learned about risk that they would tell a 20-something.


You think the risk is in doing something, leaving a job or a relationship or a friend but the biggest risk is not doing it.

We often fear the unknown. The relationship may not be great, but it’s someone to come home to. The job may not be great, but it pays the bills. You are doing the same thing over and over again, but it’s daunting to change. You may afraid of what you will miss if you leave a job or a loved one or a city, even for just a trip or unknown adventure. But you may be missing out on more than new experiences.

1. When you give up the known to try the unknown, the rewards can be greater than the risk

“If I look back on my twenties, I was trying to make a relationship work that wasn’t going to work. I was trying to make a job work that wasn’t going work.Everyone knows when a relationship is over and everyone knows when you aren’t going to advance at your job or make more money because the company has said, ‘We were not giving any more wages for the next 10 years.’  Whatever it is, there are signs. Trust them. It’s over. I need to look elsewhere. Walk away and try something else. Give up on some stuff and you will get more in return.” – 40-something, Washington, DC

2. Don’t wait too long to find out that taking risks is empowering.

“There are things I wish I had left but I was afraid of the risk. Now I realize the risk was me accepting a situation that wasn’t right for me, and then two years later thinking “Oh my gosh, I knew it wasn’t going to work when I did it.Unfortunately it took me until my mid-thirties to learn that taking risks was empowering. In all sorts of different ways, whether it was getting in a helicopter in the Grand Canyon or quitting a job, I became better for having taken those risks.

I’m not suggesting anything irresponsible but you should always get what you want out of whatever situation you’re in. You shouldn’t feel like “I’ve been here and it’s easy. Don’t be complacent. Change what you can change. – 40-something, working woman, Washington DC

3. Keep calm before you take risk on.

“Don’t stay too conservative. Take risks. But be calm. Don’t succumb to the panic that the train is leaving the station. Sometimes you make choices because you are afraid of missing whatever it is. You aren’t really choosing you are just choosing by default because you don’t want to miss it. Give it a little thought. Seek some advice and then listen to your gut. Any bad decision I made happened because I was talking myself out of a gut feeling. –40-something, Cleveland, OH

4. Build up your confidence by taking risks…one step at a time.

“If you could just tell people in their 20s to have self-confidence. It’s so hard because you can’t just get it. There are still 40 years olds that don’t have it. But in retrospect the things that you are petrified of doing, except fears like death and things like that, are so miniscule and meaningless. I have always had self-confidence. Even when I didn’t have it I had some of it. It led to some awkward moments but it was worth it. I remember in high school when I asked a guy, a football player, to go to a dance and he was like, what? But at least I had the confidence to do and it and now he friended me on Facebook so I think that is hilarious. But I think it is taking that risk, doing it early and often to build yourself up. – 40-something, Brooklyn, NY

5. Don’t be afraid to try taking risks….all you have to do is try to be successful.

“As I’ve gotten older taking risks has become more a natural part of my life. I decided, “I want to start to climb. Okay I’m climbing Mount Rainier. I want to do a marathon. I will do that.  I think that’s part of how you trust in yourself as you get older. You realize you’re capable of doing things and as you attempt those things and become successful at them you trust yourself more. I don’t mean you either did the summit or you didn’t do the summit.  I mean successful in trying. Some people can’t even decide to try. Their risk of failure is so high and that doubt is just so permanent. Don’t be afraid to try for fear of failure. It will get easier. – 40-something, Santa Monica, LA





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