Email to an Aspiring Artist

I recently received an email from a friend of a friend who's growing as an artist.  She had a few questions for me that I thought might be beneficial for any and all aspiring artists out there.  Here is the interaction...
1. How did you start your career as an artist? Did you work multiple jobs and do art on the side or dive right in?
I've been painting and drawing my whole life, then went to art school.  During that time I started putting my art in cafe's and doing little group shows.  Then as I started having more and more art to display I found places that I could do solo shows at.  People started asking for commissioned pieces and I would make those and sell them.  Eventually I got asked to do a mural here and there.  All those things have just continued to develop into where I am today.
I had side jobs all along the way.  I worked in restaurants and bars as a busser, server, bartender..  I had a few different construction gigs.  I tried to go all in with my art 3 different times, unsuccessfully before I figured it out.  You have to make money.  One problem for me was that I wasn't really aware of how much I actually needed to survive and thrive.  So I was just optimistic that it would work, but I didn't see that I needed to clear X amount per month, and I definitely didn't have any clue on how I was going to do that through art.  Another problem was that I didnt' realize that a lot of my sales would come through connections that I made through those side jobs.  Without the side job, I didn't have the connections.
But, with good financial awareness and the use of social media, email marketing and getting yourself out there as much as you can, you can create the connections that you need and make the money you need.  Although, I would recommend weening yourself off side jobs as it makes financial sense to do so.  I was in my ego wanting to "be an artist" and not wanting to work another job at the same time, so I just went for it, failed, and had to go back to the job market with my tail between my legs multiple times.  Had I just been humble about it and built me art business as I went along, while working a side job to cover the bills, things could have been more smooth and comfortable.
2. Did you go to grad school and if so do you think its worth it?
I haven't gone to grad school yet.  I'm planning on it, but only when I can afford it from my artist income and not have to take out student loans and go into debt.  I feel that grad school is very valuable.  It connects you with high level art students (who become professionals), professors (who become your professional mentors, advisors and connectors), and your artwork and content deepen.
I think it's worth it in the long term, but I definitely don't think you need it to have success as a working artist.  And definitely not at the expense of going into big debt.
3. How did you decide the price to sell your paintings at? 
This one's a tough cookie.  To each his or her own really.  Art is worth what you can sell it for.  I always feel that it's good to hold your work in high regard in terms of price, but not too high.  Especially as you're getting started.  At the beginning, selling art is more about the connections and the experience than the money.  I think here, self awareness is really important.  Look around at places you want to sell your work and check out the prices there.  See who's art is comparable in size and quality and see what they're charging.  If you have a market where you can sell it and you're going to get lots of eyes on it, it'll be easier to sell, so you can have the prices higher.  If you don't, you're going to need to have them a bit lower.  That's the beauty of being in a good art market vs a stale one.  You really have to feel this one out.  For me though, I feel it's way better to have a competitive price and sell it (Maybe lower than you could have if you held out higher), than to just have it on the wall as this high hanging fruit that only a few can grab. Sell the art, get it on people's walls, get the energy moving, make more art, sell more art, raise your prices incrementally over time.
So color is your jam.  No one sees the world exactly like you do.  Exploit that.  Go big with that.  Make art about this every day.  Push your concepts and your vision.  Work, work, work.  If you do this, after a bit of time, you're going to have a solid body of work that is you.  Completely you.  That's what you make your portfolio from.
Follow your gut.  Start in nature and build yourself and your work from there.  Do what you love.  Be what you love.  Paint what you love.  Great things will happen from there.  And don't worry about having to paint like that forever.  If your feeling for what you love the most shifts at some point, shift with it!  All true artists go through phases and reinvent themselves many times over.  But go all in with where you are now until you completely exhaust it.  You will know in your gut when it's time to change.  Until then, go big with this.