A lesson on regret, anchoring, and making thoughtful decisions with incomplete information.
One of the most mentally taxing activities for me is booking flights.
Booking flights online is both a modern blessing and a constant curse. The blessing is transparency and access. The curse is that you can always compare prices and wonder whether you’re booking at the right time.
One of my biggest fears is booking at the wrong time. Recently, that fear came true.
Katie and I were looking at flights for a bucket-list trip to New Zealand. A rainy weekend kept us indoors and gave us time to dig deeper into our itinerary.
The scale of New Zealand is hard to comprehend. For some perspective, the South Island alone is about nine times larger than Oahu.
Panoramic view of the road leading to Mount Cook National Park, South Island New Zealand. Image Credit | Lab_Photo | Adobe Stock
Between debating whether to fly into Auckland, Christchurch, or Queenstown and mapping out drive times, the price of plane tickets became a lower priority. After some quick searches on ChatGPT and travel blogs, we settled on flying into Christchurch and out of Queenstown. Google labeled the flight fares as “low,” so we booked them.
For the next few days, the excitement of our dream trip took over. Lodging, motorhomes, and campsites, all booked. Everything felt great… until it didn’t.
We had just missed a flight sale. Tickets dropped roughly 25%.
Buyer’s remorse set in immediately. We explored every option to rebook outside the 24-hour window. Short answer: no luck.
While I still feel a few dollars poorer, I can now write this from the bargaining-and-acceptance phase. (Not sure the same can be said for Katie.) With emotions still a bit raw, my overthinking financial-planner brain couldn’t help but connect this experience to market timing and the lessons it reinforces.
1. Be confident in what you’re buying.
Image Credit | zvkate | Adobe Stock
What gives me some comfort is that I still really want to go to New Zealand. Even though we paid a premium in hindsight, the decision still aligns with what we value.
The same principle applies to investing. We don’t invest simply because something looks cheap. We invest in stocks and bonds we believe have long-term value and that we’re comfortable owning, even when prices move against us.
2. What if prices had gone up?
Plane ticket prices fluctuate daily, much like the stock market. We have limited insight into short-term movements. Historical data and price indicators can guide decisions, but they don’t eliminate uncertainty.
Katie’s version of acceptance was simple: “Prices could have gone up.” She’s right. If prices were higher today, we’d be celebrating and maybe upgrading our motorhome.
Investing works the same way. It feels bad when you invest and markets drop shortly after. But the alternative is that prices rise and you miss the opportunity entirely.
3. Losses hurt more than wins.
Image Credit | kleberpicui| Adobe Stock
Do I remember every plane ticket I’ve bought over the years? Of course not.
But I’m certain there were times when I booked a flight and the price went up afterward. Did I write a blog post about those moments? Definitely not.
Losses are more emotionally powerful than gains. That’s why the fear surrounding the tariff shock in April 2025 still feels stronger than hearing that the S&P 500 finished 2025 up 16%.
4. Anchoring changes how outcomes feel.
The frustration we felt didn’t come from the trip suddenly becoming less meaningful to us. It came from seeing a lower price and mentally anchoring to it.
The recent plane fare became the new reference point, even though it didn’t exist when we booked our flight. The only thing that changed about the trip was our perception.
As investors, we experience this all the time. We anchor to recent market highs, account balance milestones, or the price we almost invested at. When markets move, it can feel like something was lost, even though no real loss occurred.
Anchoring doesn’t change outcomes, but it does change how we feel.
Moving Forward
Kiwi road sign and volcano Mt. Ngauruhoe at sunset, Tongariro National Park, New Zealand. Image Credit | NMint | Adobe Stock
This was a reminder that meaningful decisions rarely feel perfect in real time. Whether it’s booking a trip, investing cash on the sidelines, or planning for retirement, waiting for absolute certainty often costs more than acting thoughtfully and moving forward.
The goal isn’t to avoid regret entirely. It’s to make decisions you can stand behind, even when the outcome isn’t exactly what you hoped for.
And maybe… wait until Tuesday to book the flight.
Scott
Investment advisory services offered through Andrews Advisory Associates LLC, a registered investment advisor. This blog is not meant to give investment advice. Before investing in any advisory product please carefully read any disclosure documents, including without limitation, the firm’s Form ADVs. The information herein is provided for informational purposes only, and does not constitute an offer, solicitation or recommendation to sell or an offer to buy securities, investment products or investment advisory services. Nothing contained herein constitutes financial, legal, tax, or other advice. These opinions may not fit your financial status, risk and return profile or preferences. Investment recommendations may change, and readers are urged to check with their investment adviser before making any investment decisions.
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