I've got a 5 month old and I want to start some investments. I got a brokerage account started but I was wondering if a 529 would be worth my time? I'm in Illinois so upto 20k/y can be a state tax deduction.

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Stupid not to, especially in IL. 5% return on top of the market. And I say no to individual stocks. I put $60 in Robinhood a year ago and picked 5 stocks - it’s worth $40 today.

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Thank you. People are different and all. Come from different angles. What you did was good in the sense that it provided education and experience. This happens to nearly everyone at the beginning. Yes, you went to cannabis - risky. Yes, you went into companies that are not great - Ford here. Have not followed GE lately.

The good thing is you started with a little amount of money. I would say do not let your experience deter you. Many have lost more at t hff e bgg beginning but are now doung well. Try using a simulator. If you had bought PayPal or Square you would have been amazed now. It takes some time to get the hang of investment thesis and philosophies you want to pursue in individual stock. Do not give up. I posted a reply to OP about Integrator on Seeking Alpha( not advertising here. Check his investment categories. I learnt a lot from him. We all start from somewhere. It is important to learn how to invest your money.

Yes, do the 529!
My dad did it for me and a 100% of it was in stocks. While i was in high school, it doubled in value and we were essentially able to pay for most of my undergrad with it

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Just think long term. You will be able to more than double what you put in by far in a brokerage account. It looks like you are comfortable with picking stocks considering what you have done so far and research on 529 and starting a brokerage account. You could split into 2/3 brokerage and 1/3 529 if you do not feel comfortable. In my comfortability I would go with a brokerage account with no hesitation at all even given that it is Illinois.

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Absolutely. I do it and don’t even get a state tax exemption.

From an education standpoint, a great tool. There’s always the risk they don’t go to school or something else, but you can still get the money back less taxes and penalties.

But really depends on your goal.

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Not 529. Not good returns. Put it in stocks unless your 529 allows use to choose stocks which is usually not the case.

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Do IL 529 brightstart and select the vanguard total market fund for at least 80%. For the remaining select some international exposure(10-15%), and or a limited amount of bonds or inflation protection products

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The distributions if used for education are tax free, so I did the 529. Not sure if that was the best move, but my investment grew fine and I didn't really watch it regularly. What I would differently is perhaps change the date my child will go to college so that the investments are more in stocks for a longer period. Now that my child is getting closer to college age, the investments are more heavily in bonds so I am missing out on the recent growth but not losing any sleep either.

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OP. Let me direct you to something "tangible". Check Integrator on seeking alpha. See his articles. See his portfolio categories and his goals. Definitely worth looking into this. You will see how some make a killing on individual stocks.
Goals are good. Have a number in mind you want to achieve? The devil and the motivation lies in the detail. 529 is vague but a number as a goal is detail. See his project $1M also.

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