As a general rule of thumb, should people with ADD go on their own? I am trying hard at my third thing in three years and I am finding that I still make a lot of mistakes. It gets to a point where I space out and lose time. I try focusing and buckling down, but things still go bad.

I moved to Spain with my parents when I was 11.

I have severe ADHD and dyslexia.

I didn’t finish high-school.

I opened a bar when I was 22 years old, and lost a ridiculous amount of money before it closed a year later.

I started a software company with a friend of mine. I got tired of the friend and soon got tired of the company.

I started doing freelance work in “online marketing” very generally. Did some work with some local fashion boutiques to get them online. I learned a lot, but I felt I was being dishonest with my clients and not delivering the results they needed.

I decided I ought to go back to work, that I still lack a lot of experience and discipline and might be able to get this by working with more seasoned startupeers.

I joined a start-up that dealt with online fashion sales. I was fired after one month. They said they couldn’t afford me, and that I’d oversold myself.

I joined another start-up and got fired.

I find myself losing faith in myself, not sure what I’m doing wrong. I’ve often times when reading your blog feel like your brutal honesty and ability to cut through the bullshit is something that would help me out. I feel that I am very strong at some things (thinking outside the box, risk taking, sales, schmoozing) but really bad at other things (planning, “sticking with it”, networking with people I don’t automatically like).

In my heart what I want to do and be is an entrepreneur. I enjoy the thrill of creating something from nothing. But I don’t really have an “idea” now. My family urges me to keep looking for a job, even if it is one I’m not too excited about.

I feel like I’m at a crossroads, and that if I compromise now I’ll lose something intangible.

I haven’t felt this lost and directionless in probably at least a decade, and I think I’m at the point where I could benefit from your advice.