I’m not racking up miles from business travel. I rarely take work-supported trips. I’m just someone who enjoys getting travel perks and strategizing to maximize them.

So today I want to share how I’ve been funding a good chunk of my travel budget through credit card signup bonuses. This isn’t about churning cards irresponsibly or carrying balances and paying interest. It’s about being strategic with applications you might make anyway.

The Game, Briefly

Credit cards want new customers badly enough to offer substantial bonuses for opening accounts. We’re talking 60,000 to 100,000 points for spending $3,000 to $6,000 in the first few months. For context, 100,000 points can easily cover multiple domestic round-trip flights or one nice international ticket.

Over the past few years, I’ve accumulated several hundred thousand points this way. I apply for a new card roughly every six months, meet the spending requirement through regular expenses like groceries, utilities, and insurance, then collect the bonus.

Two Cards That Have Worked for Me

The Chase Sapphire Reserve gets a lot of attention, and for good reason. Yes, the $795 annual fee makes you wince. I winced. But here’s the math that convinced me:

The credits add up fast. There’s $300 back through the annual travel credit that applies to flights, hotels, and more. Another $300 in dining credits. $300 for StubHub if you go to concerts or sporting events (even if you don’t think you would use this, you can buy a ticket and resell it to pocket the money). $250 for Chase Travel hotel bookings. $120 in Lyft credits.

Not all of these will fit your life. Some require activation and attention. But even using half of them offsets that fee pretty quickly. Add in the airport lounge access, which I didn’t think I’d care about but now genuinely appreciate (free drinks!), and the card starts looking different.

The British Airways card has been my other workhorse. I love Europe. Direct flights leave from Las Vegas on British Airways. After spending $30,000 in a year on the card, they give me a companion voucher. This means my wife flies along for just the taxes and fees on her ticket.

I combine saved points with that companion voucher to book premium economy or business class for roughly what coach would normally cost. This summer’s Athens trip? Business class seats are currently selling for $6,300 each. We’re paying $800 per person.

Is This Worth Your Time?

Maybe. It depends on a few things.

First, you need good credit. These cards require it. Opening a new card might cause a small, temporary dip from the credit inquiry, but the added available credit can actually boost your score over time.

Second, you need to pay your balance in full every month. The moment you pay interest, you’ve lost the game. The credit card companies are betting you’ll carry a balance. Don’t prove them right.

Third, you need to actually use the points. It sounds obvious but people sit on hundreds of thousands of points waiting for the “perfect” trip and then the points devalue or expire. Book the trip.

If those conditions work for you, this approach can add real flexibility to your travel budget. It won’t replace your savings, but it can meaningfully supplement them.

Making This Work for You

Start with one card. The Chase Sapphire Preferred is a gentler entry point than the Reserve if the big fee feels intimidating. Right now you can earn 75,000 bonus points after spending $5,000 in the first three months. Meet the spending requirement through expenses you’d pay anyway. Never carry a balance. Learn the transfer partners and booking strategies. Then decide if it’s worth adding another card to the rotation.

I’ll probably write more about specific booking tactics in future posts. For now I just wanted to get this idea on your radar in case, like me, you spent years not knowing this game existed.

Hit reply if you have questions or if you’ve been playing this game yourself. I’m always interested in what’s working for others.

Until next time,

Art

PS: I use these cards and recommend them. In a future post, I’ll share referral links that can be win-win offers benefiting each of us.

I recently revisited a classic book that tackles this exact dilemma: Your Money or Your Life by Vicki Robin and Joe Dominguez. While often cited by young people wanting to retire at 30, the core message hits even harder when you are 55 or older.

Spotlight: The Wall Street Analyst Who Walked Away

To truly understand the book’s power, you have to understand Joe Dominguez. He wasn’t just a theorist; he lived this philosophy to the extreme.

Joe retired in 1969 at the ripe old age of 31. He had worked on Wall Street as a technical stock analyst, but unlike his peers who were chasing endless wealth, Joe had a specific “enough” point. He walked away with a nest egg of just $70,000 (about $600,000 in today’s dollars) and lived comfortably on the investment income, roughly $6,000 a year, for the rest of his life.

Even more strikingly, he didn’t write the book to get rich. In fact, he and co-author Vicki Robin donated all the proceeds to their non-profit, the New Road Map Foundation, to promote sustainable living. Check out Vicki’s Substack.

However, I was disappointed to learn that Joe passed away quite young, in his late 50s. It is a sobering reminder that the goal isn’t just to have a pile of cash at the end. The goal is to ensure the time we have left is spent on what truly matters.

The Core Concept: Life Energy

The book posits a fundamental truth: Money is something you trade your life energy for.

Joe and Vicki believed that modern conveniences, especially credit cards, created a screen that separated us from this reality. We stopped seeing money as the “sweat of our brow” and started seeing it as plastic magic.

When you buy a new car or a second home, you aren’t just paying dollars. You are paying with the hours, days, and years you spent working to earn those dollars. At our stage in life, this calculation becomes critical. If you are thinking of working for another year to pay for a luxury renovation, ask yourself: Is that renovation worth another 2,000 hours of your limited time on Earth?

Financial Corner: The Rates Have Changed, The Principle Hasn’t

It is important to note a key difference between Joe’s era and ours. In the 1980s, Joe could invest in Treasury bonds yielding over 10%, sometimes as high as 15%. Today, those rates are significantly lower, fluctuating closer to 4% or 5%.

This means we can’t just rely on high-interest bonds like Joe did, but the principle of widening the gap between income and expenses remains rock solid.

The Strategy:

• Identify “Enough”: The book introduces the “Fulfillment Curve.” Spending money increases happiness only up to a point (survival, comfort, modest luxury). Beyond that point, more spending actually decreases fulfillment because of the stress of managing “stuff”.

• The 4% Rule: The book touches on the “safe withdrawal rate.” Generally, if you can live on 4% of your total investments annually, your money should last 30 years. We’ll revisit this in depth in a later post.

Action Step: Calculate Your Real Hourly Wage

If you are still working, or perhaps working a “retirement job,” try this exercise from the book.

Don’t just look at your salary. Subtract the costs of working: commuting, professional clothes (aka costuming), convenience meals because you are too tired to cook, and the decompression time you need after a stressful day.

You might find that your “high paying” job effectively pays very little per hour once you factor in the costs. This might give you the courage to downshift, work part-time, or fully retire sooner than you thought.

As Joe Dominguez famously said, we have to ask ourselves: “Do I want to use these hours of my life just spending it on more crap and more stuff, or do I want to start getting a handle on it and using my life more intelligently?”

Make sure you are enjoying the time you bought.

Best,
Art

If you’re not familiar, Frankl was a Viennese psychiatrist who survived Auschwitz. But before the camps, he faced an impossible choice. In 1941, he held an American visa. Freedom. Safety. The chance to continue his work on meaning and psychology. At 36, he could escape Vienna before things got worse.

His parents couldn’t leave.

So Frankl wrestled with what to do. Then he noticed a piece of marble on a table at home. His father had salvaged it from their synagogue after the Nazis burned it down. One Hebrew letter was visible, part of the Ten Commandments.

“Which commandment?” Frankl asked.

“Honor thy father and thy mother.”

Of all the commandments that could have survived the fire, his father happens to salvage the one about respecting your parents? If I didn’t know better, I’d say that’s some world-class guilt delivery.

Frankl let the visa expire. He stayed with his parents.

He couldn’t have known his parents would die in the camps anyway. He couldn’t have known he’d survive to write one of the most important books of the twentieth century. He just made a choice and moved forward.

What I Keep Coming Back To

Every time I read Frankl’s story, two things hit me.

The first is gratitude.

I know that sounds obvious. Of course reading about Auschwitz makes you grateful you’re not in Auschwitz. But it’s more than that. Frankl describes standing in the freezing cold, starving, watching fellow prisoners work themselves to death. He describes the daily humiliations. The random violence. The complete uncertainty about whether you’d survive another day.

And then I look at my life. My biggest complaint this week? The internet went down in the middle of the football game this weekend.

Reading Frankl doesn’t make the frustration disappear. But it does put it in perspective. It’s a reset button for my brain when I start spiraling about first-world problems that, in the grand scheme of things, barely register.

The second takeaway is even more powerful: no one can take away your mind.

The One Thing They Couldn’t Touch

Here’s what gets me about Frankl’s experience. The Nazis took everything. His possessions. His profession. His name. They tattooed a number on his skin and treated him like livestock. They could starve him, beat him, work him to exhaustion, even kill him.

But they couldn’t control what he thought.

Frankl would march to the work site in the predawn darkness, freezing and exhausted, and he’d think about his wife. He’d imagine her smile, hear her voice, have entire conversations with her in his mind. He didn’t even know if she was still alive. But in his thoughts, she was there. And in those moments, he was free.

He writes: “Everything can be taken from a man but one thing: the last of the human freedoms - to choose one’s attitude in any given set of circumstances, to choose one’s own way.”

The guards controlled his body. They controlled whether he lived or died. But his thoughts? His outlook? Those were his.

What This Means at 55 and Beyond

I think about this a lot in the for the third phase of life.

Not because I’m facing anything remotely comparable to a concentration camp. I’m not. But because this stage comes with its own losses and limitations that can feel overwhelming if you let them.

Your body doesn’t work like it used to. Your career trajectory has plateaued or ended. Your kids don’t need you the same way. Friends move or pass away. The future feels shorter than the past.

You can’t control any of that. Just like Frankl couldn’t control being sent to Auschwitz.

But you can control how you think about it. What story you tell yourself about this phase of life. Whether you see it as decline or as something else entirely.

I catch myself falling into the decline narrative more than I’d like to admit. Poor me, getting older. Poor me, not as sharp as I used to be.

Then I read Frankl and remember: if he could choose his attitude while starving in a concentration camp, I can probably manage to choose mine while sitting in my comfortable house with a full refrigerator and indoor plumbing.

The circumstances are mine. The outlook is also mine.

Making This Work for You

Here’s what I’m trying to practice:

When I catch myself complaining about something trivial, I pause and think: “Frankl dealt with worse.” It’s not about feeling guilty for having problems. It’s about perspective. Most of my problems are actually pretty manageable when I’m honest with myself.

When I face something I dislike, I ask: “What can I control here?” Usually, the answer is my response. My attitude. My next small action. That’s often enough. As my wife likes to say, ‘Now what?’

Frankl survived by focusing on two things: love (the image of his wife) and work (imagining his future lectures). He couldn’t control anything else, so he didn’t try. He just held onto those two threads of meaning and let them pull him through.

What are your threads? What can you focus on that gives you something to hold onto, regardless of circumstances?

You probably have more control over your life than Frankl did over his. But the principle is the same. Your mind is yours. Your outlook is yours. That’s not nothing. That’s actually everything.

Worth Noting:

If you haven’t read “Man’s Search for Meaning,” it’s short - you can finish it in a day or two. But it will stay with you much longer than that. Fair warning: it’s heavy at times. In spite of that, it’s also oddly hopeful.

Best,
Art

There’s a subtle shift that happens as we age. A tendency toward crankiness. An impulse to monitor minor irritations with forensic precision. I’m 55 now, and I can feel the pull. Part of my motivation for starting this newsletter is to actively resist becoming that cantankerous old man. To maintain curiosity and generosity instead of succumbing to needless irritation.

The newsletter’s name came to me after my recent birthday. 55 Times. It brought back Sammy Hagar’s “I Can’t Drive 55,” which was everywhere when I was a new driver in high school. That age seemed impossibly distant then. Now here I am. The name also reflects my commitment to at least 55 weekly issues of the newsletter. We’ll see if I make it.

The Disorienting Part

It’s strange to look back on a career spanning over 30 years and realize that memories feeling relatively recent actually happened decades ago. When we’re younger, purpose seems clearer. Get into college. Do well. Get a job. Get promoted. Have kids. Build a family. For the most part, I’ve checked those boxes.

But purpose doesn’t end there. I still need to be a good husband, a decent father, a responsible son. Beyond those core commitments, though, I’m in new territory. My children have reached independence. The demanding years of practices, school runs, and constant presence are largely behind me. The time commitment has shifted dramatically.

Last Saturday morning I woke up with nowhere to drive anyone. No games. No events. No obligations requiring my presence. Just open time. I sat there for twenty minutes trying to remember what I used to do with Saturday mornings before kids. The feeling was simultaneously liberating and unsettling.

What Comes Next

For many of us, this period marks a transition. Retirement is close enough to merit serious attention. I’m looking forward to continuing productivity but also to greater independence and more time for personal projects. Health has become a bigger focus as I manage a few moderately serious conditions. These challenges, paradoxically, push me to think seriously about making Phase Three fruitful and productive rather than just comfortable.

I’ve been thinking a lot about Viktor Frankl’s Man’s Search for Meaning lately. The book centers on finding purpose, which feels especially relevant right now. Frankl observed that even in the most extreme circumstances, people who maintained a sense of purpose survived the concentration camps. Not always physically, but psychologically. That idea keeps surfacing for me.

What does purpose look like when the traditional markers are checked off? When your kids don’t need you at every soccer game? When your career trajectory has plateaued or concluded?

What to Expect Here

This newsletter will examine questions and choices around Phase Three. I’m thinking about personal finance (making the final push toward retirement and financial independence), personal growth and philosophy (what it means to be productive and useful in later years), productivity and technology (including observations on artificial intelligence), and family dynamics (what I’ve learned and what I might have done differently).

Some upcoming topics I’m planning:

I’ll dig into Frankl’s book and why it changed how I think about Monday mornings. I’ll look at “Your Money or Your Life” by Joe Dominguez and Vicki Robin, a personal finance cornerstone I keep revisiting. I’ll share what I’ve learned about frugal travel and credit card rewards, particularly for trips to Europe. I’ll discuss exercise and diet as they relate to energy and motivation. And I’ll examine other books and ideas that have shaped my thinking about this transition.

The goal isn’t to cover everything. It’s to be useful. To share honest reflections on navigating this phase as it happens, not after I’ve figured it all out.

Thanks for being here at the beginning.

Art V.

PS: If you’re in a similar life phase, I’d love to hear what you’re wrestling with. Send me a note and let me know what questions you are struggling with.