Introducing Work life

So I have had great opportunities within my job. I have been at the same company for 6.5 years, starting as an admin assistant and ending up as the production manager. It's been fantastic.
I am now, kind of, in between jobs. I have resigned from the company earlier this year, looking forward to a new challenge of doing my own thing. But my boss asked me to stay within the group on as they don't want to lose me. I suppose that is a very nice thing to hear from a company, but I kind of feel done with what I've been doing. The season has passed.
The new challenge will mean a lot of travelling by car and not seeing my family that often. I also have to work with people who tends to have big egos and who is already not happy with my involvement because I have to change systems already in place, which is not working. Yay.
I can't say I'm overly excited about the new challenges.
I decided to stay on with the company for a few reasons, as well as conditions.

1. My boss insisted I stay on, having asked numerous times after I said no. I got tired of saying no and started thinking maybe they see something in me which I'm not seeing in myself and it will only be a matter of time when they stop asking.... Will I then regret it? I suppose I wanted to "see" the value he saw in me.
2. I wouldn't be in charge of managing 130 anymore, which was DRAINING. Data would need to be given to me by individuals from each company of the group, which meant I would be working with 7 people .
3. Let's face it, it's a permanent income. One of the issues I had was not having enough time to grow my own thing. I put a lot of hours and energy into my job and never paid enough attention to what I wanted to do for me. This was part of the reason I quit as well. The salary didn't make a difference as I though my emotional well-being was more important at that stage. My good friend encourages you to grow your own business while being employed. It does make a lot of sense, but not having enough energy at the end of the day to spend 4-5 more hours behind the computer after a long day of physical work just didn't work for me.
4. Why then stay, you ask? Because, as mentioned in #1. They kept asking me to stay. So I told my boss that I will accept the new challenge, but then do it for 6 months only. If it isn't what I want to do, or if it's not working out, then I'm done. They have actually created a job for me to stay. So yes, I have postponed what I want out of life for another 6 months to do something for someone else. And I have to include at this stage, the relationship with my boss is starting to unravel quickly. Too much office politics!!!
5. My boss offered me a pilot's license. Now let's be honest, what am I going to do with a pilot's license? (The company is wanting to buy a plane to shorten travel time between units). It will cost a lot of money to maintain the license, should I no longer work for the company. I told my boss we can discuss the pilot's license after the 6 months. I know very well that they will make me sign a contract to stay with the company for a certain number of years if I go for the license. Which is understandable, it is quite expensive. But I would then, again, post pone what I want out of life.
6. The new challenge would remove me from my place of comfort, allowing me to get involved with other people, and allow people from here to move on with their lives. It's complicated :)
7. I have very little confidence in myself that I will make a success from my own challenges. Obviously that will take work to do, which I'm well aware of, but I have SO MUCH practicing to do! So I suppose in a way I "failed" by giving in and allowing other people to influence my decisions because I know it will take a lot of struggling and cussing and irritation, and maybe I was just procrastinating.

But I've had a month off. Or supposed to have had. I was sent to France, again, for a week for work, in my OFF MONTH. Don't accuse me of being ungrateful. I'm not. I just had plans for myself that did not include work at all. I've had to go in to the office 4 times during the month and will start 2 days earlier than agreed. So, I'm really not happy about that. So.

But I've paid some attention to trying my hand at graphic design. I must say, my stick figures are looking good! I'm next going to try and add pants to the stick figure, maybe a shadow. Challenge accepted!
Wish me luck!