The worst regrets are the ones you have about holding yourself back, about hesitating to put yourself out there, about playing it safe and remaining inside your comfort zone.
The worst regrets make you feel like a coward, like a fraud, like a failure. They make you wish you would have had the confidence to chase after what you wanted. They make you wish you would have picked a different path because there’s no telling what could have happened if you believed in yourself a little more.
Even though risks are scary, you cannot always choose the easiest path. After all, the easiest path is rarely going to lead to the most fulfilling results.
Think about it this way: If you take a risk on yourself, then there is a chance it won’t work out, there is a chance you’ll feel awkward, there is a chance you’ll end up regretting your decision. But if you do nothing, then the regret is guaranteed.
It’s always better to regret something you did because at least you can say you tried.
Besides, if you take a risk and end up regretting it, at least you’ll learn a lesson along the way. If you ask someone out and they reject you, at least you’ll know they aren’t interested in dating you. If you end up in a bad relationship, at least you’ll learn this person isn’t the right one for you — and you’ll learn to raise your standards in the future.
Meanwhile, if you end up regretting something you didn’t do like not asking out someone on a date or not applying for your dream position, then there’s no lesson learned. You have no idea whether you would have succeeded or failed. You have no idea whether you made a mistake or made the correct decision. The what ifs will eat away at you. They will slowly make you angry with yourself. They might even make you hate yourself.
It’s better to regret trying than to regret sitting around and wishing you tried. It’s better to put yourself out there and risk making a fool of yourself than it is to hide yourself away and wish things worked out differently. It’s better to take a chance on yourself than to doubt yourself.
If you take a risk, even the worst case scenario isn’t that bad. No, you might not get the results you were hoping to get, but there are silver linings. You might regret asking someone out who turned you down, but you can also be proud of how brave you were and how confident you acted in the moment.
On the other hand, if you’re regretting something you didn’t do then you’re probably mad at yourself for your lack of confidence and bravery. You’re probably annoyed that you didn’t have the guts to do what you really wanted to do.
No matter what path you choose, you’re always going to have some sort of regret. So make your regrets good ones. 
