Daniel trained for 900 miles. Then race day came 20 degrees warmer than ideal, his wife hit an injury at mile 19, and the plan went sideways. A lesson from the Chicago Marathon on why dynamic planning — adjusting, not abandoning — is what makes the finish possible.

Starting this tax year, non-itemizers can deduct up to $1,000 single or $2,000 joint for cash gifts to qualified charities. Jordan Richert, CPA, on what’s new in 2026, the 0.5% AGI rule for itemizers, and why year-end giving deserves a little planning.

The best time to plant a tree was 20 years ago. The second best time is now. This summer, Daniel’s daughters opened Four Sisters Flower Co. with backyard zinnias and scrap wood. They made less than $30, but planted something bigger. What’s the tree you’ve been meaning to plant?

Stamps cost 23¢ in 1996. Today they’re 82¢. Tim O’Connor uses that simple benchmark to show why a diversified portfolio of great companies has consistently outpaced inflation. Plus, a reminder on why you probably don’t need to worry about that Roth conversion your favorite podcaster mentioned.

In 1973, a young Steve Jobs filled out a job application and under transportation wrote "possible, but not probable." Jack O'Connor on why that line is a great reminder for financial planning — stay grounded in what's probable, but leave room for optimism. Case in point: Tim Cook grew Apple from $348 billion to $4.28 trillion.

Inflation, conflict, political upheaval, disruptive technology, tough housing — 1970s or 2026? Trick question. There's always something to worry about, but there's also plenty to be hopeful for. Five reasons for financial optimism, from surging productivity to record-breaking entrepreneurship.

Reaching the summit is optional. Getting down is mandatory." A mountaineering truth Daniel can't stop thinking about. Retirement isn't the finish line — it's the halfway point. Why decumulation is the technical, less forgiving half, and why the descent deserves the same care as the climb.

Around this time each year, we pause to remember the heroism of September 11, 2001. This week Daniel shares the story of Welles Crowther — the man in the red bandana — through ESPN's 14-minute feature. Worth carving out the time to watch.

In 1968, Paul Ehrlich predicted mass starvation and became a celebrity. Economist Julian Simon bet him it wouldn't happen — and won. After 35 years, Tim O'Connor keeps coming back to the same lesson: never invest based on a forecast or prediction. The experts are wrong far more often than we remember.

Daniel has played golf his whole life and never made a hole-in-one, while beginners do it all the time. It's a good reminder that luck and risk are siblings. What actually builds a life — or a portfolio — is the unglamorous work of focusing on what's in your control.

Ben Franklin warned that keeping our freedom would be the real challenge. The most valuable real estate to protect it? The space between your ears. Tim O'Connor returns to Ecclesiastes for a timeless framework — enjoy, accept, toil — and why grateful living is the antidote to lifestyle creep.

Daniel and Hannah made a pact in 2024 — if they weren't pregnant in 2026, they'd run the Chicago Marathon together. Somehow, here they are. What training has reminded him isn't about the miles. It's that meaningful growth almost never comes from a breakthrough — it comes from stacking ordinary days.

The 1990s Bulls didn't win championships until Phil Jackson brought in the Triangle Offense. Financial planning works the same way. Jordan Richert, CPA, introduces O'Connor Tax Partners — a sister firm bringing tax preparation and strategy under the same roof, so every decision works from the same playbook.

Tomorrow, America turns 250. For a quarter of a millennium, generations have built, sacrificed, and left things better than they found them. Daniel Westergaard on the freedoms we too often take for granted, and why witnessing what people do with them is reason enough for optimism.

Every July 1, the Mets still cut Bobby Bonilla a $1.2 million check. The reason traces back to Bernie Madoff, fake 15% returns, and one of the worst contract deals in sports history. Jack O'Connor on why intelligence doesn't protect us from overconfidence — humility does.

After 35 years of helping people build financial wealth, Tim O'Connor has seen lives fall apart even when the money was buttoned up. The people most satisfied in their relationships at 50 were the healthiest at 80. A reminder to invest in more than just a portfolio.

Daniel Westergaard's son Rory thought twenty bucks made his dad poor. The question stuck. Cash has a real role — tips, emergencies, short-term goals — but Fidelity data shows even the worst-timed investor since 1980 left a cash holder ten times behind. Some dollars need to work harder.

Philip Morris was the best performing stock from 1957 to 2007, but the product killed 100 million people. So they changed their name to Altria and kept selling. Tim O'Connor on why O'Connor Financial Group's values-based models start with a different question — does this business promote human flourishing?

Sir Isaac Newton was a genius, but even he couldn't beat FOMO. After taking a 100% gain on the South Sea Company in 1720, he jumped back in and lost millions in today's dollars. A reminder that intelligence isn't enough — emotions can wreck even the most prudent investors.

Turning 33 got Daniel Westergaard thinking about what we're really building. A meaningful life, like a good financial plan, isn't built on dramatic moves — it comes from aligning your time, money, and energy with what actually matters.

Ferris Bueller learned that driving a Ferrari in reverse doesn't take the miles off. Life works the same way. The time you don't spend with family, or the savings you put off — you don't get that back. A simple reminder to use today well.

Pensions were built when people died before they ever collected. Today we live decades longer, and many retirees find the missing piece isn't money — it's purpose. A look at the history of retirement, and why minding the gap matters as much as funding it.

Spring has a way of pulling us toward a reset — open windows, clean garages, a fresh start. Your financial plan benefits from the same treatment. A simple review and a few thoughtful adjustments now can bring real clarity before summer arrives.

What's happening in the world — and what does it mean for your money? Three charts tell the story: why cash is barely beating inflation, how reinvested dividends added 63% to returns over a decade, and why investing globally is paying off right now.

AI, war, headlines — none of it makes for a rational investment policy. After 35 years, Tim O'Connor has never seen a client who followed the plan fail to reach their goals. The secret isn't reacting to the news. It's diversification, patience, and tuning out the noise.

The Masters never changes venue, and most champions spend years learning Augusta before they ever contend. The biggest goals work the same way — financial independence is built through small, consistent steps long before the results show. So don't measure the distance. Just focus on the next step.

Somewhere along the way, investing became a spectator sport. After 35 years, Tim O'Connor has seen how stock picking, market timing, and chasing track records hurt people who treat their money like a game. The wiser path is far less exciting: follow the plan.

Baseball's best hitters got on base before they ever scored. The same goes for money: lasting financial success rarely comes from home runs, but from simple habits repeated for years — spending less than you make, investing consistently, and staying grounded in what you value.

Netflix won the streaming wars. Disney owns the world's top theme parks. McDonald's leads fast food everywhere. Yet over the past five years, each one trailed the S&P 500 — a clear case for why we diversify instead of betting on individual winners.

We spend years working toward major goals, then barely pause when we reach them. A client's story about buying hunting land for his son reminds us why milestones deserve celebration — not just a quick glance in the rearview mirror.

From the 1980 Miracle on Ice to 2026 gold medals, the Winter Olympics remind us to play our game. Tim O'Connor shares how discipline, habits, and investing in your life produce the greatest returns of all.

Giving to charity, building new friendships, starting an exercise routine — every worthwhile habit feels strange at first. Here's why the discomfort is a sign you're heading in the right direction.

The most successful investments aren't exciting — they're boring. Companies like Visa, Costco, and Casey's quietly power everyday life and compound wealth over decades. Here's why boring done well becomes extraordinary.

Bonds returned 6-8% last year, but that doesn't tell the whole story. Discover why maintaining purchasing power over a lifetime requires owning companies — and how healthcare inflation silently threatens your retirement.

Think the S&P 500 is all you need? Two companies you've probably never heard of — TSMC and ASML — power the entire global digital economy. Here's why international diversification matters more than ever.

Indiana football's perfect 16-0 season mirrors how compounding works in investing. Small, steady steps — not dramatic moves — build extraordinary outcomes over time. Here's why patience is your greatest financial asset.

Two gifts that cost nothing but change everything: perspective on 50 years of extraordinary global progress, and the optimism to keep building toward your goals. The data will surprise you.

What if there were a fourth law of motion — one that applied to your money? Jack O'Connor explains how financial resources multiplied by positive financial habits create unstoppable momentum toward lasting wealth.

Indiana football's historic turnaround from decades of losing to a national title contender holds lessons for your finances. Learn how raising your standards and refusing to be limited by the past can transform your financial future.

Start 2026 with two powerful principles: margin and mantra. O'Connor Financial Group shares how discipline, kindness, and investing in great companies can make this your best year yet — regardless of what stock prices do.