Here’s to Keeping It Real

My girlfriend has grown impatient with my lack of progress.  We have no doubt hit rock bottom.  I say that this is rock bottom because no matter what I can wait tables anywhere and sustain this level of existence and unless I commit a felony I can always get a job waiting tables somewhere.

Today I submitted a couple of ideas I’ve had rolling around in the back of my head for a while to a fast pitch event that connects entrepreneurs with angel investors.   I bounced some of the details of my ideas off her and she was clearly annoyed by it.

Tonight we had a good talk after a few drinks.  We started out talking about her goals.  She’s at that point in life when she realizes she is going to have to make a decision about what she wants to do with her life but hasn’t found her calling.  I can relate because I’ve been there.  I try to be sensitive but I also try to challenge her to think it through and work the problem without talking down to her, making her feel stupid, or pissing her off.  Usually I piss her off.

As usual the conversation turned to me.  What have I accomplished?  Why am I so special?  She is reserved and it’s rare that she opens up about what she really thinks although I can usually tell what she thinks before she admits it.  I love the real conversations.

She admitted that has grown impatient and weary of all my ideas.  No surprise to me because it’s no secret that she wants to get married, buy a house, and start a family.  She feels that every new idea means failure of the current idea and further delay.

She came at me hard.  She said that as this drags on she increasingly doubts that I will be successful.  I can see why she thinks that.  She sees other guys my age with stable salaried careers.  I tried to defend my choices by arguing that the experience I’ve gained is far better than any of our peers/friends who have chosen a stable career.  I added that although I they may seem better off right now, in the short run, in the long run I have better positioned myself for greater success.  She countered, “why do you think you’re so special.”  Using my own words against me.

It cut deep but strangely I loved that with one simple question she was challenging everything I believe in, everything I’ve ever done, and everything I’m striving for.  It forced me to do some soul-searching.  Why am I special?  Damnit, I’m special because I have ideas, the courage to give them a go, and some savvy to execute them.  Instead of wavering I am now even more entrenched in my conviction that building my own successful business is my path to happiness.

But how do long do I have before she leaves me?  I have always wondered but never asked.  Given her rare brutal honesty it seemed like time to ask so I did.  She roundaboutly said 5 years although I suspect it’s really much less.  Judging by her increasing impatience and frustration I give it 2 years at best.  Can’t blame her, wouldn’t blame her, that’s just real.

It’s tough to swallow when those closest to you don’t think you’ll succeed and may leave you if you don’t.  On the flip side, I am more motivated and energized to make something happen and for that I am grateful for her brutal honesty and implicit challenge.  If she continues to challenge me in this way it will be far better than her benign complacency, pretending to listen or care about my latest idea.

Here’s to keeping it real.

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