The Ultimate Personal Investing Playbook

Unlock the artistry of unruffled investing with my Ultimate Personal Investing Playbook — one of the most expansive, trustworthy (not tied to any fee or commissions or customized AI engines) and most importantly, uniquely simplified online literature you will ever find on personal investment in US 🧘‍♂️

I often get asked:

🧩 Who is the target audience for this?
A. Serious DIY investors, families & long-term planners. I will call out special considerations for beginners, young professionals as well throughout this post.

🧩 Why should you or anyone spend time on this when you have gazillion other known sources on personal investing?
A. What sets this blog apart in a sea of retail investing content isn’t extraordinary credentials or flashy promises. I’m an above-average investor at best. Where I do excel is in absorbing large volumes of information, distilling it into clear, practical insights, and presenting it in a way that’s both thoughtful and visually engaging.

🧘‍♂️ My goal is to curate the signal from the noise — and make smart investing concepts accessible, actionable, and enjoyable to read.

What you are about to read, is aimed to empower every thoughtful, serious investor to build wealth with confidence and discipline. It will take you days or even weeks to get through all this, so be ready for the grind 📚

From taxable accounts to tax-advantaged strategies like Roth and HSA, I break down the vast personal investment ecosystem focusing on how each investment option works, matters, and how to align it with your long-term financial goals — and be unruffled while doing so 🏝️

Knowing how to efficiently leverage these investment options should be the cornerstone of your long-term retirement strategy. Mastering them can accelerate your path to hit that magical financial independence number 🎯 — the point where work becomes a choice, not a necessity.

This mega post will be regularly updated as I learn more — be sure to bookmark it to turbocharge your investing strategy 🚀

First, How To Prepare Emergency Funds

📌 Before you start investing, you should have 6-9 months of emergency savings for sure. Single earners for families, self-employed should aim at the higher end of the range. Young professionals with lesser dependencies would do fine with 2-3 months.

👉 For optimal emergency savings plan, divide the emergency savings into 2 tiers:

Tier 1:
Use a high yield savings account to have immediate access to emergency funds. Use a reputed, mobile-first, stellar bank like Sofi. I highly recommend Sofi due to following reasons.

Tier 2:
Use extremely safe bond ETF which invests in treasuries. I use SGOV.

🧩 In case you are wondering, what is SGOV and how is that extremely safe?
Use this Bogleheads post which has everything you need to know about SGOV safety but in short – SGOV is great as it offers higher rate of return than cash, is liquid, low cost & you get state tax benefit on dividends & is extremely safe. Of course, it is not 100% safe as cash and it will take you couple of days to sell, settle and get cash but if world’s biggest economy defaults on their treasuries, even your bank’s FDIC insurance might be in question (it is backstopped by USA Treasury as well). And guess what, treasury bonds are what most of the banks use as well to get higher returns on the money you keep in your accounts.

Now that you got some emergency funds parked, let’s get into investments.

#1 Taxable Investments

Your brokerage accounts fall under this category.

The key to success as a retail investor is having a written Investment Policy Statement (IPS) that aligns with your emotions (most important), investment horizon, and risk tolerance — and then sticking to it.

In short: protect yourself from yourself ⚠️

Here’s what my IPS looks like:

50% Growth
20% Dividend Income
10-20% Very Strong Conviction Individual Stocks
10-20% Dry Powder/Excess Cash Parking Spot

This reflects a U.S.-centric, high-risk-tolerance strategy targeting a strong mix of growth and sustainable income over the next decade. My portfolio details:

#1 Growth:

High-quality, low-cost ETFs: Blend of VGT, VOO & VXUS
US Mega Caps: All the Mag 7 and Netflix

#2 Income:

High-quality, Low-cost Income ETF: SCHD
Stable Income Stocks: ABBV, AEP, BMY, CVX, DUK, ENB, ETR, MO, NEE, PFE, PM, PRU, RF, UGI, USB, VZ, T.
High-quality BDC: ARCC, Main

#3 Very Strong Conviction Individual Stocks:

Divided into 3 Tiers:

Tier 1: Ultra high conviction: HOOD, RBLX and SOFI.

Tier 2: High Conviction: RDDT, RIVN.

Tier 3: Ultra High-Risk: I also hold very limited ultra high-risk stocks which have long-term moonshots as core theme:

Air Taxi Industry: ACHR, JOBY
Energy: OKLO, PLUG
Modern Defense Tech: AVAV
Space Tech: RKLB

#4 Cash and Treasuries:

Finally, for dry powder, I use SGOV Treasury ETF. I have a rule where the last allocation of my dry powder is used only when Nasdaq or SP500 is in the bear market (drops more than 20%). I also use SGOV when I am closing out positions and need a parking spot before the next investment. SGOV is great as it offers higher rate of return, very liquid, low cost & you get state tax benefit on dividends & is extremely safe.

🧩 Admittedly, my dividend generating bucket is the most puzzling aspect of my investing philosophy—and arguably an anti-pattern since it involves individual stocks and the dividends are taxable. That said, the steady cash flow gives me a real-estate-like experience without the hassle of owning and managing physical properties. This approach may not align with everyone’s goals, but that’s exactly why the word “personal” matters in personal finance.

📌 Note that all of the income stocks pay qualified dividends and NOT ordinary dividends, very important and frequently missed knowledge nugget to optimize your tax savings.

👉 Use dividend.com portal to know if a dividend is qualified or ordinary. You can also find this information into your brokerage’s monthly/annual statement.

❇️ Super Tip: Once you have your IPS created, you can use your favorite AI chat engine to ratify whether buying or selling a particular investment is in line with your IPS. I have heavily trained ChatGPT & Gemini on my IPS and use it to further vet my decisions, knowing it is going to be much more consistent and save me from making emotional, irrational investment mistakes, on the lines of expansive case studies like this great Knowledge Project podcast.

#2 Tax-Deferred Investments

This covers your retirement accounts like 401(k)s and IRAs. If you’re self-employed or in certain sectors, this may also include SEP IRA, Solo 401(k), 403(b), or 457(b) accounts.

These are a bit different – you contribute pre-tax, your investments grow tax-deferred, and you pay taxes only on withdrawals — ideally during retirement, when your taxable income may be lower.

👉 Here’s how my IPS for tax-deferred looks like:

60% Growth ETFs
10-20% Bond ETFs
10% Dividend Income
10-20% Dry Powder

#1 Growth:

For IRAs where you have entire ecosystem to invest – I favor passive, large market cap, low-cost index like VGT, VOO with some allocation to international ETFs like VXUS.
For 401K accounts where you have restricted funds to invest in, I mostly go for most passive, low-cost, large-market cap index based funds.

#2 Bonds:

I just go for high-quality, low-cost bond index funds.

#3 Dividend:

For IRAs where I have entire ecosystem to invest: I also invest small portion in the non-qualified dividend payers (best for tax-advantaged accounts) such as:

REITs: O, NNN, VICI

BDC: ARCC, MAIN

Random: MPLX.

⚠️ Note that MPLX is a Master Limited Partnership company which generate UBTI for investors. If held in retirement accounts with UBTI exceeding $1,000 per year, you must file Form 990-T and pay taxes on the amount over $1,000. For non-retirement accounts, you need to file K-1 forms each year, which make MLPs a hassle to own individually. My UBTI for MPLX is below 1000$ an year so I am covered.

❇️ Super Tip: I have accumulated some of these individual stocks over a very long period of time and just have some inertia to let them go. If I’d start new, I’d just go for passive, low-cost diverse index funds. The compounding effect will take care of everything.

#3 Tax-Exempt Roth Investments

Roth accounts are a bit peculiar:

✅ Contributions are post-tax.

✅ Growth is tax free

✅ Withdrawals are tax free- as long as you meet the rules

This includes Roth IRAs and Roth 401Ks.

👉 Considering the tax-free growth and withdrawals, Roth accounts should be a core part of your retirement strategy.

You can either contribute directly or if your income is too high for direct Roth IRA contributions, you can try Roth conversions like Mega Backdoor Roth or Backdoor Roth

My investment approach here mirrors my tax-deferred strategy — focusing on low-cost index ETFs for long-term, tax-free compounding 🧘‍♂️

Advanced Tip: Roth conversions are a great tool to turbo-charge your Roth pool and reduce your deferred tax number but require a ton of expertise, would be best to consult a reputed CFP to cover all angles.

#4 HSA – Health Savings Account

HSA, the high-deductible health plan accounts tied to High Deductible Health Plan (HDHP), are the most underrated — and the only one offering triple tax benefits:

✅ Tax-free contributions

✅ Tax-free growth

✅ Tax-free withdrawals (for qualified medical expenses)

✅ The money never expires – even if you change employers

✅ You can invest excess money and use it later for qualified medical expenses.

Given above ridiculous benefits, I would highly recommend every family to strongly consider having HSA in their investment armory.

⚠️ Important – HSA is tied with high-deductible health plans which, as the name says, come with higher out-of-pocket expense so in general, if you are making frequent doctor visits and have high medical expenses and your employer HSA plans are not lucrative enough, HSA may not make sense for you. There are insanely detailed blogs like this and this to help you make that decision For young professions in their 20s and 30s, check this.

👉 Best way to contribute is to have pre-tax contributions get deducted automatically from your payroll. But incase you are short of the max limit, you can make your post-tax contributions until federal filing deadline of next year (April 15 typically) but then you would need to claim tax deductions on your federal return. I max out my HSA contributions (8.5K$ in 2025) each year. I don’t use FSA since we are obligated to use that money at the end of the year, so it doesn’t align with my unruffled theme 🧘‍♂️.

📌 Note on HSA Rollovers – Keep an eye on the investment fees charged by your HSA admin. I noticed the HSA admin tied to my employer charged pesky investment fees and had limited investment options as well, so I use HSA Rollover trick to move money to a brokerage with lower costs and better fund options.

Which HSA admin did I choose?
I wholeheartedly recommend Fidelity as the HSA admin. Reason? Fidelity is the undisputed king of HSAs – zero fees (yes zero!), access to every stock and ETF under the sun, highly reliable & reputed brokerage with great customer experience. They have been rated #1 HSA admin for many years in a row by Morningstar. What’s more, if you are already hooked up with Fidelity through your employer (401K etc.), then using Fidelity for HSA simplifies your personal finances too.

Important: I don’t get any commission from them for writing this.

❇️ Super Tip: After age 65, you can even use HSA funds for non-medical expenses without penalty (though they’re taxed as ordinary income) — making it a stealth IRA of sorts.

#5 College 529 Savings Plan

For those with kids, contributing to 529 college savings plan early is extremely prudent and tax-friendly decision in my opinion. You contribute post-tax but the earnings and withdrawal are tax-free as long as the funds are used for qualified education expenses.

👉 Every state has some benefits tied to their 529 plan. For example, Illinois provides generous $20K of state tax deductions for using their in-state 529 plan. With around 5% Illinois state tax, I feel not contributing anything to 529 plan and then later paying college fee out-of-pocket is akin to leaving money on the table.

🧩 Many have asked me for investment options on 529 plans and my advice again is to go for low-cost, diverse funds. I live in Illinois and use my state’s Bright Start 529 college savings program. My selection of Bright Start 529 funds:

30% – Principal Plus Interest (no expense fee, safest capital appreciation, very handy if you are nearing withdrawal period)
20% – Total Stock Market
20% – S&P 500
20% – Equity Portfolio
10% – Fixed Income Portfolio

Investment Allocation Strategy

Now that you’ve built a strong foundation of investment options, learn how to put them to work by allocating your money intelligently.

Final Thoughts

Master these five essential investment options — Taxable, Tax-Deferred, Roth, HSA, 529 and investment allocation strategies — to upgrade your retirement planning, optimize taxes, and accelerate long-term wealth building 🏝️

👉 If you’re short on time, expertise, or just motivation to self-manage your investments, automated investing (robo-investing) is an excellent alternative — it offers low fees, automatic rebalancing and truly simplifies portfolio management.

🧘‍♂️ Unruffled Life Pro Tip

The real test of an investor isn’t on good days, but when markets hit hard. 👉 As Mike Tyson put it, “Everyone has a plan until they get punched in the mouth.”

As always, stay rich and unruffled!

Disclaimer: The intent behind this post & any other material on this portal is to help our readers cultivate total wealth of health, money, time & social life (in that order) – essentially amplifying the joy and contentment in life. None of the content substitutes professional financial, tax, legal, health, home care or any other kind of advice. Please perform your own due diligence before acting on any of the ideas & material shared here.

RICH & UNRUFFLED