There are at least 3 steps towards learning to be Comfortable with Success.
The first is making many mistakes and admitting to them.
Discover: I am not talking about being sloppy. The universe is relentlessly complex. Try many things and admit when it is not working out as you expected. “Reflect early & often“. Most people and organizations I encounter actually have a hang up with being able to look straight in the mirror and say that they made a mistake. The fall into a trap of predictive thinking for complex stuff. They think they can tame complexity easily. In both cases of people or organizations, not being able to admit and make mistakes shuts down the whole approach to learning. By not admitting we made a mistake we drop the practice of the scientific method and shut down simple open inquiry. Said another way we stop seeking feedback and shoot any messengers with bad news. Innovation and creativity are born from a sea of attempts and most of those attempts will not pan out (call them mistakes or whatever word works for you).
The second step is to never stop trying.
Persistent: ”It dosn’t matter how many time you get knocked down it only matter if you get back up.” Even when you cannot succeed at something a committed person or organization will keep trying. Trying in an almost mindless way. And sometimes still succeed (the hard part is we just don’t know where success will show and it is hard to know when to stop and try something else). The difficulty is learning how to back off and point your energy elsewhere. Again a habit of reflect early & often. For organizations this can be especially trying and can create a tension in tying to redirect energy elsewhere. Often people take it as a personal failing and feel like their position is being undermined by being asked to stop working in a direction that has not yielded any favorable results. The classics response is to get tough with them but, this fails to engage them fully on the next task because they never deal with the regret. An emotionally healthy thing to do is to help them let go and transition. The other end of the spectrum is organizations who behave so frenetically that they never really try because they are changing direction all the time. They trample their own ethics into the ground.
The third step is learning to be comfortable with success.
Win: Is perhaps the most fuzzy and elusive of the three steps. It is not about enjoying the after effects of success. It is more about being in the moment and amplifying that success and seizing it instinctively when it is at hand. For some, being in the lime light is the only thing they desire and they flourish at this step but, the above two steps constantly befuddle those types of people and organizations. Really the above two steps are sequential for those who are not innately comfortable with success. You almost need permission to give it your best and be dramatically successful. Being told you are good at something creates a state of affirmation that empowers those who are uncomfortable with success. The person or organization who is uncomfortable with success is chronically humble. Now the interesting thing is that “Reflect Early & Often” does not apply. It applies afterwards but, you have to learn to be comfortable in the moment and there is no time to learn as success is happening. Simply smiling and saying thank you is a right display of behavior but, you have to do more than that you need to feel comfortable in your skin at that moment in time so that your instincts respond correctly. If you do not feel comfortable in your skin you will dampen your instincts on what is working and not react smart when opportunity passes by.
Learning to be comfortable with success.