Pillar Financial Advisors

06/22/2026

A savings balance tells you what you've accumulated. A retirement cash-flow analysis tells you whether it actually works.

At Pillar, a cash-flow analysis maps every income source against every projected expense across the full retirement timeline. Social Security timing, withdrawal sequencing, tax bracket management, and healthcare costs all get modeled together rather than in isolation.

Retiring on your terms requires knowing exactly where you stand today. Let us help you get that clarity: https://pillar.net/contact-us/

06/21/2026

Today, we celebrate the dads and father figures who raised us. Who worked hard, always had a life lesson ready, and never once let anyone touch the thermostat. Ever.

We appreciate all you've taught and given us over the years.

Happy Father's Day from the Pillar Financial team.

06/18/2026

The timing for claiming your Social Security benefits matters just as much as how much you’ve earned over a lifetime. Learn key factors that can help you make more confident retirement decisions and strengthen your long-term income strategy.

Learn how to maximize Social Security benefits with smart claiming strategies. Greg Curry is a financial advisor at Pillar Financial Advisors in Louisville, KY.

06/17/2026

Is your advisor reviewing your taxable accounts for tax-loss harvesting opportunities right now?

In a volatile market, declining positions in a taxable brokerage account can be converted into a tangible tax benefit. Selling a position at a loss offsets capital gains from other sales dollar for dollar, or reduces ordinary income by up to $3,000 per year with any remaining balance carried forward indefinitely.

A similar fund or ETF can be purchased immediately to maintain market exposure during the required 30-day window before repurchasing the same security.

The window to act is while the losses exist.

06/15/2026

Even the most thorough retirement plans tend to overlook this one detail: the people who would need to act on it have never met the advisor behind it.

When something happens, your family will need to move quickly and make decisions under pressure. A financial advisor who already knows your family, your accounts, and your intentions is a valuable resource to have in that moment.

At Pillar, introductions to our clients' families are part of how we work. A single conversation now means nobody is starting from zero when it matters most.

If your family hasn't met your advisor, we recommend making that introduction a priority this year.

06/10/2026

Does your retirement income plan account for inflation by source, or just as a blanket assumption? The difference matters more than most projections show.

06/08/2026

An HSA is the only account in the tax code that gives you a deduction going in, tax-free growth, and tax-free withdrawals for qualified expenses.

For pre-retirees still contributing, that triple advantage makes it one of the most efficient places to accumulate assets for healthcare costs in retirement.

A few things that change the math significantly:

-> After 65, HSA funds can be used for any expense, not just medical, and are taxed like a traditional IRA withdrawal.

-> Medicare premiums, long-term care insurance, and out-of-pocket costs all qualify as tax-free HSA distributions.

-> Investing HSA contributions rather than holding them in cash compounds the advantage over time.

The account most underused by pre-retirees is often the one with the most tax efficiency.

06/04/2026

Markets move and goals evolve—so should your investment strategy. Learn when and why it’s important to realign your portfolio to stay on track and manage risk.

Discover when and why portfolio rebalancing matters. Ben Allison is a financial advisor at Pillar Financial Advisors in Louisville, KY.

06/03/2026

Are you within 5 years of retirement and considering a job change? Check your vesting schedule before you set a departure date.

Employer-matching contributions and profit sharing often vest on a cliff schedule, meaning leaving two months before the vesting date forfeits years of accumulated employer contributions.

A single calendar adjustment can change that outcome entirely. If you have a job change on the horizon, let's make sure the timing works in your favor: https://pillar.net/contact-us/

06/01/2026

What separates investors who stay the course from those who don't?

The investors who make the fewest emotion-driven mistakes tend to share two things:
1. They understand exactly why their portfolio is structured the way it is.
2. They have enough liquid runway that a bad market quarter doesn't force a bad decision.

Selling into a decline and waiting to feel comfortable before getting back in almost always means missing the recovery.

A plan specific enough to trust in advance is what keeps that from happening.