I was having a discussion with my friend Gus (names changed to protect the innocent) not too long ago and he was extremely supportive of me going to explore other career alternatives (within or outside of my current employer).  Gus even went so far as to offer up his services  to help me craft and shape up a new business, connect with contacts for existing business, or anything else I may need.  In short, Gus’ services are at my disposal when I want to take advantage of them.

It is very comforting to know that I have friends and associates like Gus in my corner; many times we allow our value to be defined, measured, and determined by others vs. allowing our value to be measured simply by who we are, how we are made, and how we operate.

Back to the story — As a part of the conversation, I asked Gus why he wasn’t off starting and running his own business.  Gus is super talented, super driven, and clearly would make many good things happen in his own business if he chose to do so.  Ultimately, Gus responded as said something along the lines of “been there, failed at that, not gonna do that again”.  Being that Gus and I are open to challenging questions, I asked him a very pointed question; “Why are you so eager, supportive and confident in my abilities to go explore options for myself, but when it comes to exploring options for you that same eager, supportive, and confident nature is not evident?”

Gus didn’t have an answer, but I did (I guess it is good to know the answer to the question before you ask it), and it boils down to a several things (2 of which I’ll share):  Offense, Investment, and Awareness.

I once heard the question asked “Why is it so easy to give to someone you don’t know, but when it comes to giving to close friends and family it can be a very difficult proposition?”  The answer is that people that we do not know have not offended us in any way, thus there’s no reason to hold back.  We can invest in them freely and have no reason to second guess anything that we do for them because of anything they may have done to us in the past.  In addition to this, there is no rationale or reason for us to be invested in the outcome of the investment we place in them.  It could be chalked up to a random act of kindness on our part; if it works, then great, but if it doesn’t then no skin off of our backs.

Well, the opposite is true when it comes to ourselves.  The reason we are so unwilling to gamble or bet on ourselves is because we HAVE offended ourselves, we are VERY invested in the outcomes of our activities, and we are EXTREMELY sensitive to our own vulnerabilities and limitations (to a fault in most cases). We have hurt ourselves, we have done things that have set us back years, and we are very unwilling to do that knowing that we have to reap the outcome of any of those activities / actions.

Success and bravery are more linked than people realize.  Successful folks are willing to be brave enough to push through any offenses they may have committed against themselves and ultimately drive towards whatever goal is in front of them.  They are no less invested in themselves than anyone else, but they also are very willing to forget past hurts they have caused themselves and move forward.  They are able to recognize that the end game / goal is far more important and far superior to the ramification of not moving.  Plus, in some cases, the reason they move isn’t even for them; it’s for someone else, and maybe the possible up side to helping someone else close to them is worth them moving ahead and ignoring the past self-offenses.

Gus told me of a past startup venture he did that failed, and it took him into a deep depression.  At the time he was single and no one else was really affected. Now he has a wife and two children and doesn’t want to risk / gamble their situation for him going to start something up.  But I reminded him that he’s not the 25-year-old Gus that started that business; he’s the 42-year-old Gus now. The lessons that the 25-year-old Gus learned are still a part of him, but there is no way that he will re-live what happened in the past.  The past experience shaped his intellect and wisdom, and now he knows how not to fall into the same traps.  In addition, his level of critical thinking and problem solving are far beyond 25-year-old Gus’.  Thus, while there will be some unknowns he’s faced with, Gus is more prepared and ready to address those concerns going forward.

With any offense we have committed there is a lesson we should have learned from the offense.  Many tend to carry / hold onto the offense, but what we need to do is carry the lesson from the offense, but release the offense itself.

If we learned this, we’d be much better off; and maybe we’d bet on ourselves more often.

Oh, the picture?  Yes, I took that.  On my way to the top of Kilimanjaro; I bet on myself, and I made it.  Can’t make it to the top of the mountain if you don’t try.