Kevin Howard

The advisor I wish I had at 25 | Tax-smart wealth systems for Millennials & Gen Z

[Kevin Howard @KevinOnPlanning]

At 25, I had investment accounts I'd inherited.

I had no idea what they were, how they worked, or what I should be doing.

I stumbled into financial planning, and what I learned changed everything for me 🧵

[Kevin Howard @KevinOnPlanning]

"I'll start investing once I pay off my student loans."

Meanwhile:
401k match goes uncaptured.
HSA sits empty.
Roth contribution window closes.

Debt payoff and wealth building don't have to be mutually exclusive.

Most high earners can do both. The sequence just matters.

[Kevin Howard @KevinOnPlanning]

Things high earners should automate to actually build wealth:

- 401k to match on day 1 of new job
- HSA contribution set to annual max
- Roth IRA/backdoor on January 2 each year
- Quarterly estimated tax payments (if self-employed)
- Taxable brokerage the day every paycheck comes in

Don't make these decisions manually each month – make them one time. Automate them.

[Kevin Howard @KevinOnPlanning]

I had a mentor early in my career who told me: "You're not managing money. You're managing decisions under uncertainty."

That changed how I thought about planning.

A financial plan isn't a prediction. It's a framework for making better decisions around life's constant changes.

[Kevin Howard @KevinOnPlanning]

High earners are often surprised to learn they owe a 3.8% tax on top of their regular rate.

It's called the Net Investment Income Tax (NIIT).

Kicks in at $200k single / $250k MFJ.

If you have dividends, interest, or capital gains – it applies.

Most people learn about it when they file, which is too late.

[Kevin Howard @KevinOnPlanning]

For me it was prioritizing which accounts to contribute to first.

Before I got into the industry, I knew very little about the differences between them, and the thought of prioritizing one over another honestly hadn't occurred to me.

You don't know what you don't know.

[Kevin Howard @KevinOnPlanning]

If you're making $150k-$300k, what's the one financial decision you wish someone had walked you through earlier?

I'll share mine 👇

[Kevin Howard @KevinOnPlanning]

I've watched people get a $50k raise and feel richer for about 90 days.

Then the apartment upgrade happened. Then the car.
Then the subscriptions.

By month 6, the raise was gone.

The window to capture a raise is the month you get it.
After that, lifestyle fills the gap.

[Kevin Howard @KevinOnPlanning]

Making $200k+ with W-2 and side income?

TurboTax can technically file your return. It cannot:

- Identify your optimal retirement acct structure
- Model Roth conversion windows
- Flag NIIT exposure ($200k single / $250k MFJ)
- Plan around your equity comp

Filing and planning are different jobs.

[Kevin Howard @KevinOnPlanning]

The financial advice that would help you at 25 is not always as helpful to you at 35.

At 25: Automate everything, don't touch it, time does the work.
At 35: Optimize the tax layer, sequence matters, comp complexity is real.

Many advisors give 25-year-old advice to 35-year-olds.

[Kevin Howard @KevinOnPlanning]

I don't see myself ever truly retiring.

The closest thing would be scaling back, and only working because I want to, not because I have to.

That 'work optional' distinction matters more than any retirement account balance.

What does your 'retirement' actually look like to you?

[Kevin Howard @KevinOnPlanning]

Got RSUs vesting this year?

Your employer will withhold ~22% federal tax. Your actual rate might be 32-37%.

The gap is your estimated tax problem, and you won't feel it until next April.

If you're in the 32%+ bracket, adjust your W-4 or sell some RSUs at vest to cover the shortfall.

[Kevin Howard @KevinOnPlanning]

Most high earners don't have a savings problem.

They have a sequencing problem.

Here's the order that actually maximizes what you keep: 👇👇

Step 1:

401k to the employer match.

This is a 50-100% instant return.

Nothing else can compete with that. Do this before anything else.

Step 2:

HSA max ($4,400 in 2026).

Triple tax advantage – deduction going in, tax-free growth, tax-free out for medical.

Most people delay this (or skip entirely) and go straight to maxing their 401k.

Step 3:

Roth IRA or backdoor Roth ($7,500).

If you're over the income limit, the backdoor is still available.

Most people making $200k+ would qualify for backdoor only – and many don't even know this exists.

Step 4:

Finish maxing the 401k ($24,500 total).

Between these three accounts, you're now capturing $36,400 in tax-advantaged space annually.

And that's before a mega backdoor Roth if your plan allows it.

Step 5:

Taxable brokerage.

No contribution limits.
No early withdrawal rules.

But make sure you've captured every tax advantaged option first.

The mistake:

Most high earners max the 401k and go straight to taxable.

They skip steps 2 and 3 (the HSA & the Roth IRA).

That's $1,500-$3,000/year in missed tax savings.
Every year. For decades.

The sequence isn't about the amount you're putting in.
It's about the order.

Get the order right and the rest is just simple math.

[Kevin Howard @KevinOnPlanning]

My wife didn't go back to work after our son was born.

We went down to one income. Out marginal rate dropped significantly.

That was the best Roth conversion window to date.

Life events can change your tax picture. Don't miss the opportunity to plan around them.

[Kevin Howard @KevinOnPlanning]

I've met people making $500k with $200k saved.

And people making $80k with $300k saved.

High income is great, but it's not what builds wealth.

The gap between income and lifestyle is what builds wealth.

High earners are usually just better at hiding the gap.

[Kevin Howard @KevinOnPlanning]

Things that matter more than picking the right index fund:

- Contribution rate
- Account type (Roth vs Traditional)
- Asset location (what goes where)
- Tax on the way out
- Sequence of withdrawals

The funds inside are the last decision.

[Kevin Howard @KevinOnPlanning]

I've talked with people making $350k who had never heard of a backdoor Roth.

It's not that they weren't smart. It's just that nobody told them.

Their CPA filed the return. Their advisor managed the portfolio. Ok fine.. but nobody did planning in between.

That gap is expensive.

[Kevin Howard @KevinOnPlanning]

Tax season hot take:

Your refund isn't a bonus.

It's proof your paycheck was smaller than it needed to be all year.

Adjust your W-4. Redirect that cash every time it his your checking acct. Let it compound for 12 months instead of sitting with the IRS.

[Kevin Howard @KevinOnPlanning]

I used to think budgeting was the answer.

I tracked every dollar. Built color-coded spreadsheets.
It felt productive.

Never moved the needle.

So I automated my savings and stopped thinking about the rest.

The spreadsheet was procrastination. Automation was an actual plan.

[Kevin Howard @KevinOnPlanning]

You don't have an income problem.
You have a system problem.

Most high earners making $200k+ aren't overspending.
They're just not capturing.

Don't rely on habits to build wealth.
Build a system, and let it capture for you.

This is how wealth gets built with ease.

[Kevin Howard @KevinOnPlanning]

The order high earners actually get their tax deductions wrong:

1. Contribute to 401k ✅
2. Skip the HSA ❌
3. Taxable brokerage ❌

The right order:

1. 401k to match
2. HSA max ($4,400)
3. Roth IRA ($7,500)
4. Back to 401k max ($24,500)
5. Taxable

Sequence is a tax decision.