Two Questions I'll Ask Myself For the Next Decade

I am turning 40 this coming week so there’s been a lot of time for reflection on my life and choices. This episode isn’t going to focus on that. But, I have landed on a couple of questions that I want to keep asking myself this year and throughout the next decade. So, in this episode I am going to share these two questions in the hope that they might help you wherever you are on your own personal journey.

• What am I afraid of?
• What will I regret?

What am I afraid of? This is a great questions to ask yourself because it may help identify things that are holding you back or things that you want to do. It might also reveal whose opinions and approval hold sway over you and your choices.
Are you afraid of failing as a parent?
Are you afraid of being your full self?
Area you afraid a pursuing work or a hobby that you love?
Are you afraid to stand up for yourself?
Are you afraid to ask for help?

Once you identify 2-3 things that you are truly afraid of. Then you can use a technique that you might be familiar with called the 5 whys. You just keep asking yourself “why”?

What will I regret?
This is a powerful question if you are someone like me who learns a new piece of wisdom and then goes back to my earlier self and regrets that I didn’t use it. Or recognize that I was given wisdom/advice that I didn’t follow at all, fully, or soon enough.

For many, financial education and literacy or a career you love come to mind as things you regret today from yesterday. Maybe it’s a relationship or friendship that you let fade (or stayed in too long).

But, instead of focusing on the past, I have started reframing this question to look at my current regrets and use them to help me jump forward 5, 10 and 20 years into the future to think about what is currently before me and what I will regret when I look back on today.