This past month entailed some light traveling and I can say without a doubt once you get to a certain point in your life, paying for things like early boarding and GASP…first class can be more than worth it. Before you think it’s unattainable, let’s dive a little deeper about whether you are spending or making an investment. Plus, I may have a confession from a travel dilemma a few weeks ago.

When it comes to traveling, do you have a carry-on bag you absolutely need to stow versus being forced to check? Well, that extra $20 for enhanced boarding will keep you from stowing your bag somewhere away from where you’re sitting and embarrassingly trying to wade through a crowd to get it while deplaning. Perhaps you need to perform on the other side of your flight and make sure you give an incredible presentation or be on top of a job interview? I’ve certainly seen the jet-lagged, sleep-deprived version of people coming off a flight. Tim Ferriss once told this story where he got a speaking gig in Australia where they paid a few thousand for his travel budget. He decided to book a commercial flight and pocket the difference. Once he felt like absolute trash during his keynote, he realized he had learned a life lesson the hard way. 

My Travel Confession

I had a pretty frustrating travel day when I flew to Boston in late August for a friend’s bachelorette. It wasn’t the worst by any means, but at the lowest point I kept saying to myself, “saving $150 was not worth it.” I wanted to book an earlier flight to get into Boston to meet a friend before the bachelorette trip officially started. The earlier flight was $100. I opted to decline. The night before when picking seats, I saw a preferred seat for $50. I stuck with my original seat. My flight ended up being delayed 1.5 hours and when I got to my seat, there were middle metal supports for the seat in front of me. My Tumi backpack didn’t fit.

Coupled with a few frustrating work things, I ended up texting a friend my American Airlines loyalty information and asked her to upgrade me. Whether it’s to business or first class on the flight back so long as it cost less than $200. I realize $200 is a lot of money. But for me, I had a lot of stuff in my backpack (including my handbag) and the fact it didn’t fit and I had to stow it overhead was enough. Plus, I have a broken tailbone and since I was in the middle seat, I didn’t have a lot of room to shift around during my flight. Let’s just say I landed with more tailbone pain. When I landed I got a text from my friend. It cost $88 to get me into first class on the way back. I felt so stupid. My time, a clear head and less frustration are worth more than $88. I should have made the investment in either booking the better flight with better seats from the beginning or waking up a little earlier to call the airline for a last-minute upgrade.

So which is it? Spending or investing?

It got me thinking about an overarching subject many of you have been sending DMs about. Are you spending money or making an investment in yourself? Sometimes it comes in the format of this cheap thing or this seemingly more expensive thing?

This can manifest itself in a few questions buzzing through your head over this past year:

• Did I buy something I regretted later?
• Did this polyester sweater actually keep me warm?
• Are these shoes actually comfortable and fashionable?
• Who won in a fight between my couch and my kids or dog?

The framework I use to answer “am I spending or am I investing in myself?” is by asking myself a more clarifying, but deeply personal question: 

Will future me thank past me later?

There’s a big element of regret minimization embedded in answering that question.

Johnny and I find ourselves asking this question a lot this year as we invest in turning our house into a home and with our wedding. A lot of these decisions can cost a pretty penny. Not only do you have to live with them, but so do a lot of other people.

Johnny’s going to jump in with a story from his POV. One example of this is with the DIY project in the guest room. I was shortsighted and made a boneheaded decision with our backboards as a newbie. This will probably mean we’ll eventually need to refinish the wall. I love the work we did…and it was perfect as a learning experience. But a simple $100 decision could’ve saved a whole lot of headache in an eventual rework. Now, I have to look at it every day and it drives me a little crazy.

On the flip side, a decision our future selves continue to thank us for is waiting and saving for six months for the dining table we have today. It’s an investment into our home for sure. We endured a few embarrassing tours without a dining table. We shared some good laughs while turning it into a multipurpose project room where a lot of furniture got assembled. Hoang-Kim even did a few try-on sessions there before she got her new arch mirror. In the meantime, we used the kitchen island and ate in the living room while saving. We outright refused to buy something “temporary” because to us we would rather spend that money on something we love and will have forever.

I can say without a doubt, we thank our past selves every time we eat on the table. It’s gorgeous and most importantly effortlessly expandable. The times we cherish the most are when we’re hosting for the holidays and can expand the table to fit 10-12 guests. We thank ourselves a little more those times. Did we spend too much on this dining table or did we invest in a dining table that brings us joy every time we use it? I think the latter.

What are some times you’ve felt guilty spending? If you asked yourself, “Will future me thank me later?” and answered it honestly, would you make a different decision?