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Stregger on Strategy

John Stregger | Mar 6, 2026

A More Flexible Way to Think About Retirement

Retirement
Finance
Lifestyle
Risk Management

Many retirement plans are built on a quiet assumption: that spending stays roughly the same from year one to year thirty.

It sounds reasonable. But research

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Toddler standing at the bottom of a stone staircase
John Stregger | Feb 27, 2026

Investment Strategy: Where You Are Now vs. Where You're Headed

Investments
A gap analysis can help you see if you’re still on track to pursue your financial goals.
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John Stregger | Feb 20, 2026

5 Financial Crossroads That Could Reshape Your Future

Finance
Retirement
Family
Tax Planning
Risk Management

You know how life tends to throw in a few plot twists?

They don't ask if you're ready. They just show up—with potential financial consequences tagging along.

A

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John Stregger | Feb 13, 2026

When the Weather Hits: What Natural Disasters Actually Mean for the Economy (and Your Finances)

Finance
Investments
Risk Management
Insurance

A major storm rolls through. The headlines light up. Power outages. Travel chaos. Damage estimates climbing into the billions.

And somewhere in the back of your

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John Stregger | Feb 10, 2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Tax Planning
Finance
Retirement
Investments

Many people think about taxes once a year — when April rolls around and it's time to file.

By then, the year is already in the rearview mirror. The decisions

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Parent reading a book to their newborn child
John Stregger | Jan 20, 2026

What does "Wealth" Mean to You?

Finance
Lifestyle
A clear understanding of what wealth looks like to you may help you build a financial strategy.
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John Stregger | Dec 12, 2025

What 2025 Taught Us About Staying the Course

Investments
Finance
Risk Management
Retirement

Some years pass quietly. 2025 wasn't one of them.

Between market swings, geopolitical shocks, and a news cycle that never seemed to pause, this year tested

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John Stregger | Dec 8, 2025

Common Retirement Regrets—And Proactive Moves to Consider

Retirement
Finance
Savings
Risk Management
Insurance
Health
Family
Estate Planning

Many people don’t regret being retired. They regret how they got there.1

“I wish I had saved earlier.”

“I didn’t think long-term care would matter.”

“I should’ve

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John Stregger | Nov 7, 2025

How to Talk to Your Aging Parents About Estate Planning (Without Making It Tense)

Estate Planning
Family
Health
Disability
Insurance
Risk Management

These conversations aren’t easy.

Bringing up long-term care or estate planning with aging parents can feel like stepping on a landmine—awkward, emotional, maybe

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John Stregger | Oct 31, 2025

What Recent Inflation Signals Mean for Financial Planning

Finance
Savings
Investments
Retirement
Tax Planning
Credit
Risk Management

Inflation has been the boogeyman of the economy for months.

Sticky prices. Rising gas costs. A looming rate hike.

The latest report provided useful data for

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John Stregger | Oct 14, 2025

Rethinking Retirement: Why True Wealth Is More Than Money

Retirement
Lifestyle
Health
Family

Rethinking Retirement: Why True Wealth Is More Than Money

You’ve mapped out your dream retirement. Maybe it’s a cozy beach town, golf twice a week, time with

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John Stregger | Sep 11, 2025

Overlooked Retirement Expenses (And How to Plan for Them)

Retirement
Finance
Health
Tax Planning
Family
Real Estate

A comfortable retirement doesn’t come with a fixed price tag.

Expenses can change over time, and some of the most important ones are easy to overlook.

That’s one

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M: 416-884-6332
F: 905-232-9075
E: john@discovery-wealth.com

    

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