The questions I keep coming back to are:
1) Am I better off ramping up the % I contribute through work rather than opening up a fresh account on something like TD Ameritrade?
2) Do I open up a separate Roth IRA on TDA where I can control what is in it more and it grow for retirement?
3) Do I open up a regular trading account and invest in whatever I want as I want with the option to liquify when I see fit?
4) A combination of the above?
5) Go see a professional and let them figure this out for me?
I honestly don't know what is the best route here. My goal is for retirement in 15-20 years not to get filthy rich and retire in the near term.
Just saw this post thanks to
@ChicagoCavFan bumping the thread with his post above. I'll add my thoughts FWIW, as a guy who has made a LOT of mistakes, but has recovered from them nicely.
I think
@Lee's advice above (contribute in 401k/403b up to the match, then IRA, then back to 401k/403b up to the limit) makes a lot of sense. The IRA gives you the advantage of being able to invest in pretty much anything you want (stock/bond/mutual fund wise at least), and not being limited to the choices in the 401k/403b plan. Personally, my wife and I max out our 401k/403b, but don't have IRAs (not counting rollovers from prior jobs).
I don't do individual stocks, and wouldn't suggest them other than (a) it's something that interests you, (b) you have an amount that you can invest after exhausting other options like 401ks, and (c) you could lose every penny and not have it affect your life. Part of the reason I don't invest in them is risk -- single stocks are volatile. For me, just as big a reason is that it became way too much of a time suck for me. I was constantly checking stock prices, researching new stocks to buy, fretting over the ones I already owned, etc. It took way too much of my time and energy, and was distracting me from other, more important parts of life.
So what do we invest in? Low-cost stock index funds. They aren't sexy, but their results over time have been. To peg it to your time frame -- my wife and I really got serious about our finances about nine years ago, when we barely had any net worth. Today, we could probably retire (i.e., never have to work for money again) if we wanted to. (For perspective, I'm in my early 50s, she's in her 40s.) Doesn't mean we would -- just that we could.
Bottom line -- your goal is very doable, in my opinion. Feel free to ask any more questions along the way. You can get there.