<prompt> Human: Hello PF. Below is my story. Looking for some feedback on investing moving forward with a specific FI timeline goal. The story of how I got to here is below.BackstoryIm at the beginning of my FIRE path. Ill be 31 years old in a few weeks and am trying to get my FI date to my 40th birthday over the next 9 years. I graduated in 2013 with a B.S. in Financial Economics as the economy slid off a cliff and down a toilet at the same time. My degree was basically worthless. I was not going to enter that field amidst the turmoil and uncertainty. I was lucky enough to have a job waiting for me in IT when I graduated, even working full time before graduation as I polished off some bs courses for my final credits. My first 5 semesters were spent in Computer Science and computers are kinda like riding a bike that keeps breaking and always needs a tune up - hello job security.Common Sense? Nope.As someone else said on one of these FI resources there should be a home economics class... about finances. Cooking?! Uh weve got Youtube and Jamie Oliver on Netflix for that crap. Education system, please teach young people about debt and savings and how to be successful managing money. The lack of knowledge and fear of open discussion for money makes my head spin. Even with a firm grasp of portfolio management, the black scholes model and other various statistical and math concepts there is zero instruction on common sense economics anywhere in your standard school curriculum and certainly not in a economics degree. Needless to say when I graduated I did some pretty stupid things.Bad Decisions1. Got bored after 6 months post-college and bought a house. Basically got paid to purchase the house. 10k home buyer credit. 3 down requirement on a FHA loan on 188k. Yep, I put 3 equity into a house and was like, cool I just made money! Somehow this was smarter than living at home with the rents where I had it far too easy and paying off student loans.2. Property taxes got jacked 70 3 months into owning that house. I was living in the red for 2-3 years. During this time I was paying down my student loans 20k balance at the minimum payment rate.3. Didnt really have a firm grasp on why spending more than I made was financial suicide and I did this day after day, weekend after weekend.4. Traded in a 2008 model year car in 2011 for the 2011 model of the SAME EXACT CAR because due to the value of the car and balance of the loan there was 5k of equity in the car oh and I was bored on a Saturday.5. Bought a timeshare. A timeshare Ive never used. Ever. Period. Still paying off that loan. About to just dump it for dirt cheap to get out of the yearly maintenance fee, exchange fees etc. and chalk it up to my stupid youth.The Turn Around BeginsSomewhere in all of there I found Mint one day, made a budget and started monitoring things a little better with envelope budgeting. I was paying down credit card debt slowly but quicker than minimum payments. I started to turn things around. I switched to Simple for my bank and man has that been a big help. The goals section just made tracking my spending a piece of cake. Combined with some budgeting Simple has gone a long way to helping me get a grip on my expenses.Housing ChangesI met my SO almost 3 years ago and being as strapped as I was I took on a little more debt in the beginning to keep us busy with something to do every weekend. We moved in with each other a year ago. Two mortgages. I just in June rented out my house. The market wasnt the greatest for selling in the spring early summer so Im attempting to mitigate as much as I can of my mortgage payments while not living there anymore. Im cash flow positive for the lease year even after the management fee, brokerage fee.Out of Debt and BeyondI stumbled upon MMM Mr. Money Mustache in rpersonalfinance. After the Zero to Hero article I pretty much drank the kool-aid and read the entire blog in 2 weeks. Holy crap did I want to punch myself in the face for my previous sins. Upon finding his high holiness MMM I broke out Google Sheets and started crafting the climb out of debt and the life afterwards in an attempt to accurately model our combined take home, expenses, savings rate, and stash growth. Long story short Ill be out of all debt 30k 112017 minus the house. We carpool as much a possible work 2 miles from each other when our schedules line up 45mi round trip. Trying the adjust the definition of fun times that dont include driving 60 miles, spending tons of for temporary experiences. After the check engine light came on in the car two weeks ago I picked up an Automatic sensor and man has that been and eye opener. Ive taken my MPG from 25 to almost 40. Theres been a bunch of other FI inspired changes to behavior in the last month that are still in their infancy.Investing the question for you, FIThis is the part of my story where I need some feedback feedback on the rest is fine too!. Ive got a Roth with Vanguard, Simple-IRA from previous job, 401k with new job. Im looking to transfer the Simple-IRA over to my Vanguard account, opening up a tIRA in the process. This is where my pride, ego, and hubris comes in. Ive crushed it picking stocks since 2008. Looking at my Personal Capital charts the SP has done 43.6 between 1108 and 72915. My total investments have done 100, my Simple-IRA 113. Id really like to liquidate my individual stocks and have a more passively managed, balanced portfolio full of various index funds. Ive been reading the Bogeleheads wiki among other resources. The idea of buying bonds given such an aggressive timeline for FI is a little counter intuitive to me. I would most likely stick age2 in bonds. Even 15 seems drastically conservative. If I needed to tolerate some serious volatility I can. If it all hits the fan I can work more, its not the end of the world, FI will still be there waiting when the stock rebound comes. All signs point to me losing the stock picking game sooner or later but 6 years of more than doubling the stock market has given me a false sense of confidence. Do I continue to ride the individual stock train or cash in my successes and invest across various index funds to create a balanced portfolio? Any and all opinions are welcome. Thanks!TLDR; Ive more than doubled the stock markets performance over 6 years but am looking to get my investments in line with FI goals. Should I ride the individual stock picking rocket ship Ive been on or cash out my success and invest in index funds, bonds.  <response>: Do I continue to ride the individual stock train or cash in my successes and invest across various index funds to create a balanced portfolio?The answer to this one should be pretty obvious. Gambling on individual stocks is a poor strategy for any retiree, and certainly for one that desires FIRE. 