Matt Harris, Financial Analyst

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Tinley Park, IL
Matt Harris, Financial Analyst

Helping Aviators Grow & Navigate Retirement with Confidence | Financial Strategies for Pilots

Our mission is to empower individuals to achieve financial security and peace of mind by providing educational strategies and guidance. We are dedicated to helping you avoid outliving your income by crafting personalized financial plans tailored to your goals and circumstances, ensuring a stable and fulfilling future.

09/04/2026

62 y/o. First Officer. $473,000 salary.

$501,000 sitting in an old 401(k) he was afraid to touch.

He understood just enough to know one wrong move could cost him. So he left it sitting there, invested exactly the way it was the day he left his last airline.

Every time he got close to making a move, a new question appeared. Will I owe taxes if I roll it over? Should I wait til I'm retired? What if I pick the wrong provider?

Analysis paralysis had become his plan.

We walked through what was actually his to move and what needed to stay put.
The difference between a rollover and a withdrawal. And what it would take to protect what he'd built before retirement.

He's now got an IRA consolidated in one place, part of it positioned into a fixed indexed annuity to lock in guaranteed income down the road, and a maxed out Roth IRA every year.

Each year we review it and take action.
The fear of touching it, gone.

09/03/2026

My retirement plan just dropped....

It takes money to make money. 😂

09/02/2026

Proof you don't need a $2M portfolio to enjoy retirement.

09/01/2026

59 year old airline captain. $612,000 in his 401(k).

Six years out from mandatory retirement at 65.

Told me his risk tolerance was a 7 out of 10. Called himself "moderately aggressive."

Sent me his statements. 68% in bonds. ~12% in international small cap. The rest scattered across funds he couldn't name.

His portfolio was nearly the opposite of what he told me his risk tolerance was.

"I just picked whatever the default allocation was when I got hired."

Then we found an old 401(k) from a prior airline he flew for early in his career. $89,400 total, still sitting in the same target date fund from 2011.

The plan:
Rolled the old 401(k) into an IRA and positioned part of it into a fixed indexed annuity to lock in guaranteed income starting at 65. Reverse-engineered exactly what he needs saved to hit his number, then built the income plan around it.

He told me he probably would've flown right past retirement without ever knowing where he actually stood.

If you don't know what's actually inside your 401(k) right now, that's usually the tell.

Comment FLIGHT and I'll send you my retirement guide.

08/31/2026

Delta pilots have the best on-time performance in North America.

It doesn't buy them a single extra year in the cockpit.

Every US pilot hits the same wall at 65.

Federal law
Unchanged since 2007
No exceptions for seniority, performance, or which airline signs your paycheck.

The airline spends 20-30 years building your seniority number, pay scale, and 401(k) around that fixed date. Most pilots never run the actual math on what month one looks like.

I've watched a pilot realize his spendable income was $3,000 a month lower than what he'd assumed for a decade.

He hadn't done anything wrong.
It was avoidable.
Nobody caught it in time to fix it.

Comment FLIGHT and I'll send you the guide to building your real first-year income number, before you're standing at the wall with no runway left to fix it.

08/30/2026

Ripped shorts, toddler sunglasses, zero shame.

Out doing dad stuff.

Shorts didn't survive the day.

Sunglasses confiscated by someone who decided they were hers now.

Nobody tells you how much of parenting is just rolling with whatever just happened.

Some days, you just lose your shorts.

08/28/2026

Most retirees think their will controls everything.

It doesn't.

Life insurance, 401(k)s, and IRAs generally pass by beneficiary designation, not by your will.

TOD accounts, POD accounts, annuities, and jointly held assets work the same way, passing by titling instead.

Assets held in a trust follow the trust document instead.

If your beneficiary forms haven't been updated in years, your will may be the least important document in your estate plan.

I see this constantly with people who changed jobs, got divorced, or added grandkids, and never circled back to the paperwork.

The fix isn't complicated. It just requires checking every account, not just the will.

When's the last time you actually looked at your beneficiary designations?

08/27/2026

A captain retired with $1.4M saved, a military pension, and zero debt.

One withdrawal cost him $11,400 in unnecessary taxes.

Six months before mandatory retirement, he had a plan:
Pull $8,000/month from his 401(k) starting in January until Social Security kicked in at 67.

Add his $4,200 monthly pension, and that strategy pushed a large portion of his income into higher tax brackets.

But he had a taxable account sitting untouched.

Pulling some income from there instead could have reduced his taxable income.

Nobody combined the two income sources before he made the withdrawal.

By the time the tax bill arrived, it was too late.

A first-year mistake like this doesn't cost you your savings.

It can cost you $10k+ you can't get back.

If you want to avoid this mistake, I built the Retirement Income Flight Guide for pilots approaching retirement.

Comment FLIGHT and I'll send it to you.

08/26/2026

A father passed away last year with a $340,000 retirement account.

He'd been divorced for seven years. Never updated the beneficiary form.

His ex-wife got every dollar. His new wife found out at the funeral home, then spent the next year in probate court fighting for money that was supposed to be hers.

Beneficiary forms override wills.
The custodian doesn't read your divorce paperwork, they read the form on file.

Same blind spot shows up in:
Old 401(k)s from a job you left years ago.

A will naming guardians for kids who are now adults.

One form is the difference between your family getting what you intended and fighting for it in court.

Make sure to double check yours.

08/25/2026

Last month, I got the opportunity to fly with my brother. ✈️

Pretty cool experience, but even better getting to share it with him.

Really enjoyed every minute of it.

Some memories are worth more than anything you can buy.

Address

Tinley Park, IL

Telephone

(708)5057686

Website

https://go.redstoneretirement.com/incomeguide

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