I’m afraid to ask for certain things. It’s an embarrassing feeling to have since I pride myself on being able to say whatever I want. Maybe it stems from doing a lot with a little as a kid, who knows. That attitude doesn’t work in business, or life for that matter. I was involved in a situation a couple years prior, with a great client of mine, who acted very paternal towards me. He mentioned a couple times that if I needed money to fund my new venture to always ask. I didn’t have the confidence to ask, so I would become passive aggressive towards the issue and mention “we could use money, but I don’t know how much”, which was complete bullshit. If someone offers you money, you throw out a number and work with them. In order to gain any investment, I need to be transparent and explain in what ways the money could expand my business and how it could benefit the investor.
Maybe it’s my penchant for keeping things smooth. I enjoy ruffling feathers, but for people I care for, I keep the ruffling to a minimum. Something as stupid as food; as I type, my biz partner asked what I want for lunch, I play the passive aggressive part by saying “oh I could do Panera or the other place”, instead of just saying let’s do Panera, since he doesn’t care either way. I know it's trivial, but if I continue this behavior, it will leak onto major parts of my life.
How do I fix this? Well I got to tell myself that it’s ok to be honest with people when it comes to touchy subjects (including lunch! Kidding) and that the truth is not going to offend them. Being passive towards them is more disrespectful (wastes time) and Lord knows that I despise when people aren’t upfront with me.