How can you manage medication and self?

I have ADD, I've known since I was in 3rd grade.  It was then I was put on Ritalin and just shy of 4 years later I stopped taking it - I felt that as a child it was having an extremely detrimental effect on my ability to develop a sense of self as I seemed to be two completely different people.  On ritalin I had no interest in taking risks or having fun.  Off ritalin I was only about risk taking and being impulsive. 

Flash forward to now, I'm 30 years old and I've never seriously looked back at going on medication because, to be honest in all this time I've learned a lot of ways to cope and live with my behavior patterns and I really do believe that they are a part of who I am.  That said I'm tired of hearing girlfriend after girlfriend complain about the same things.  I am habitually late, my organizational skills are minimal, I'm professionally not as successful as I am in my personal life.  All things I have long known, understood and coped with being ADD.

The reason I am posting this is that I am seriously considering, after reading posts here, of putting myself back on medication to see if it helps certain areas of my life.  I'd like to be able to muster the willpower to go to bed before 1 am, I'd like to be more focused and productive at my job and I'd like to be able to get a grip on organization, my finances and being late which aren't things I'm proud of.  But the fact of the matter is I am terrified of losing my sense of self to the medication.  I'm a very creative person and I'm impulsive.  I am extremely caring and good at relating to people and have a high level of emotional intelligence for a man.  These are the things I want to keep.  I mountain bike as my main hobby and I'm a little afraid that the medication will effect this.  When I was a kid I remember describing being on ritalin as thinking of doing something and stopping to consider the vast array of consequences that action could have, and ultimately not doing much of anything because the consequences of almost any action dwarfed the reward.  My biking is a great metaphor for my life, I just do and act without thinking and handle the consequences. 

How do I get the best of both worlds?  It may seem like a silly question but how do I preserve my sense of self and not become dependent on a pill that in many ways will cause me to act contrary to how I would act otherwise?  We are defined by our actions to a great degree in life and I do work to constantly improve myself.  I'm just afraid of exactly what I was afraid of 18 years ago, that when on the medicine I will be the same person I was then, 18 years back.  Calm, disconnected, extremely rational but not me. 

I'd love to hear from anyone who's gone back on the medication and how they handle it or people who know people that have.  Or ideas and suggestions from anyone.