Have you ever encountered a situation at work where you got the message “show initiative” and then when you do take the initiative and it doesn’t go as planned (according to management) the response is “why didn’t you ask first?”? Some supervisors communicate mixed messages. They say they want new ideas, but apparently only their new ideas. They are apparently afraid of too much change or afraid of losing control.

If you want people to show initiative, you have to let go. If you yourself want to take initiative, you have to let go. And that means allowing for failure. Trying new things or new ways involves the risk of failure. And that’s okay because not everything will fail, and you can learn from failure.

I did a presentation recently on leadership for our Spring District Toastmasters Conference. The subject was reimagining and reenergizing leadership by taking risks. My lead point was “don’t be afraid to crash”. I told a story about my roller-skating days where I was able to learn new skills when I got over my fear of falling. To the point where I decided if I wasn’t crashing at least once or twice a night I wasn’t trying hard enough.

Initiative is scary and can be painful when crashes happen. But regret from not trying can be painful as well. I like the saying “mistakes are just a sign that you are trying”. Or the saying “better to ask for forgiveness than to ask for permission”. The problem with asking for permission is that you have to wait and you are giving the person asked the opportunity to say “no”. Yes, there are times when you need to ask, but not nearly as many times as you may think. Like for instance, when requesting time off from work, I have found that yes there are procedures and time constraints. But I always put my requests in the form of “boss, I need to take x amount of time (days) off for (fill in the blank)” I am assuming it will be fine, and if he has a problem with it he will let me know.

I know the times that I have been the most successful are the times I took charge and did something based on my confidence to do it. Like the time that I hiked the Grand Canyon rim to river and back up in one day. It was pretty audacious, totally exhausting, and yet fully exhilarating. And every time you take the initiative and succeed it will build your confidence to try it again. And this from a confirmed laid-back introvert.

Whatever you do, do not hesitate. There is a time for contemplation, research, and consultation. But when the options are clear there is no place for hesitation. Yoda was wrong – there is always try. All we do is try. We cannot guarantee that are actions will succeed (do) but we can always use all the skills and abilities at our disposal and make a good faith effort.