You don't need to go crazy about things, you can just use a few guidelines

• Calculate expenses (especially discretionary expenditures) against the amount of time you are trading (in terms of earnings or potential savings).
• Keep things in perspective as your net worth or net investable grows. You should have an idea of what the equivalent dollar-amount is for what you have no problem spending as your net worth increases. Have a good idea of what your daily expenses and earnings are (based on salary or investment earnings) as well.
• Remember, making money is trading your (limited) time and energy to support your material needs and desires. Don't lose sight about that and think long and hard about the tradeoffs and about what you really need and want.

Basic rules for financial literacy:

• Always take the money you owe for taxes straight off the top, leave it in cash (savings, money market, short term bonds). Really, skip the painful lesson of not doing that.
• Have 6 month cash buffer (really!) first - make sure you actually know how much you're spending each month, how much of that is discretionary, and how much is not. This (or a fallback, like parents) is the safety net you need to be able to make potentially make life-changing decisions without worrying too much about your day-to-day. Tools can help (try Copilot, Monarch Money or Personal Capital). If you aren't good at having a feel for what your spending is like, try something like Trail Wallet even just for a couple weeks. It's a pretty good way to get an idea of what's going on. You can also use free accounting tools like https://www.waveapps.com/
• Pick a simple asset allocation for your investments and stick with it (it’s a capitalist cliche, but if you ever don’t want to actively work for your money, your money has to work for you)
  • If you don't want to ever think about investing, choose a Vanguard Target Retirement Fund: https://investor.vanguard.com/mutual-funds/target-retirement/#/
  • If you want a simple low cost fund but don't want to deal with rebalancing pick the LifeStrategy Growth Fund and then shift over some to a Bond Tent strategy to taste in the decade leading up to retirement
    • https://investor.vanguard.com/mutual-funds/lifestrategy/#/
    • https://www.kitces.com/blog/managing-portfolio-size-effect-with-bond-tent-in-retirement-red-zone/
    • https://www.reddit.com/r/financialindependence/comments/5y13ue/the_bond_tent/
    • https://www.reddit.com/r/financialindependence/comments/9b3vwr/the_sp_500_did_not_give_a_positive_return_for_12/
  • If you want to get in the weeds, go for it, just remember to actually stick to a strategy and to re-balance regularly (once a year or so is fine, especially if it’s in a taxable account). If you are optimizing for maximum growth, be aware that long-term, stocks always outperform bonds but that there have been multi-decade periods where investment performance has been miserable so you need to take that into consideration during your draw-down period. DYOR.
• Maximize your tax-advantaged investment accounts. Over long time horizons, it's a lot of "free money" at stake:
  • If you have a 401k, 403b, especially one that has employer matching, be sure to maximize that first. These programs might not have the best investment choices, be sure to roll them over to standard rollover-IRA accounts after you change jobs
  • Roth accounts are always preferable to non-Roth accounts - they let you invest more tax-free and have more flexibility for withdrawals (they also go away once you make too much money so be sure to rollover, etc while you can, although you are able to backdoor Roth (rollover traditional accounts into Roth accounts))
  • Try to max out your IRA (Roth if possible, if not Traditional). You can backdoor Roth if you want but IMO those advantages are questionable.

If you get to a point where you are climbing up tax brackets, start to think about tax-loss harvesting, making sure your most tax-inefficient investments are in tax-advantaged accounts. Ask your similarly well-off friends for recommendations on financial advisors. At the very least pay for a decent accountant, and maybe get a business/tax planning lawyer as well. You may want to sit down and chat with some registered financial advisors to see what they can offer you (I recommend a good fee-only vs someone that takes bips. Make sure they are a proper fiduciary - meaning they are legally obligated to work in your interest).

• https://www.kitces.com/blog/understanding-the-mechanics-of-the-0-long-term-capital-gains-tax-rate-how-to-harvest-capital-gains-for-a-free-step-up-in-basis/
• https://www.kitces.com/blog/harvesting-losses-or-harvesting-gains-planning-around-four-long-term-capital-gains-tax-rates/
• https://www.kitces.com/blog/evaluating-the-tax-deferral-and-tax-bracket-arbitrage-benefits-of-tax-loss-harvesting/
• https://www.kitces.com/blog/using-systematic-partial-roth-ira-conversions-and-recharacterizations-to-fill-the-lower-tax-bracket-buckets/
• https://www.kitces.com/blog/tax-managed-mutual-funds-avoid-tax-drag-but-cause-higher-tax-rates/

Just a thought: 60% of US federal discretionary spending goes towards military spending, so optimizing your tax bill via donations at that point might let you redirect those funds to things that align better with your values.

One FIRE (Financial Independence Retire Early) concept I find useful is the rule of thumb that 4% is the standard safe withdrawal rate (SWR) and really gives you two knobs for reaching your financial goals:

• Increase your net investable
• Decrease your cost of living