Fact #1: There’s never a perfect time to do something.
Fact #2: Often, right now is the perfect time to do something.
These two rules will be our guiding light for this column, because when we’re talking about bucket list things, sweating the details is what’s kept you in the planning stages and the “one day I’ll do it” mindset.
Today, we say “fuck it” to all that. Today, we outline how and when to take that bucket list trip.
Why am I writing this now?
Because I am on the heels of a weekend destination golf trip with my dad and my brother that reminded me we all need to take these trips more often, when we can and while we can, because tomorrow is promised to none of us.
To begin, there are three types of bucket list trips: Evergreen, Timely and Bonding.
We’ll tackle Evergreen first because it’s the easiest to plan.
An Evergreen Bucket List trip is one that can be done almost any time because the destination is likely not going anywhere.
Think: Hawaii or Iceland or the Aurora Borealis or the pyramids of Giza.
When it comes to these types of trips, they often begin with a fascination and end with a “One day I HAVE to go see the pyramids”. But too often, that day never comes because you have “too many priorities”.
Well, what if, just once, the trip you’ve always dreamed of becomes the priority? (We’ll get back to this in a moment).
The second type of bucket list trip is the Timely Bucket List trip.
Think: Your favorite team is in the NBA Finals or your favorite artist or comedian is playing one last show at a hallowed venue. Or maybe your kids are the perfect age to enjoy a week in Yellowstone and you want to do it before they’re screen-obsessed teens.
Or maybe you and your son are diehard WWE fans and your favorite wrestler is fighting two legends for a title at WrestleMania. Yeah, that one’s specific, but my son and I took that trip last Spring to watch Cody Rhodes face The Rock and Roman Reigns and it was amazing (you can read my column on that here.)
These are Bucket List trips that happen once, or during a certain time in your life, and you need to make a quick decision if you’re going to be there.
Again, too often your day-to-day priorities stand in the way.
After all, who’s going to handle [fill in the blank with kids, coaching, work commitment] if you run off to catch the Celtics play an NBA Finals game at home in the Boston Garden, something you’ve wanted to do since you were 11-years-old?
Here’s a refreshing thought:
What if it doesn’t matter who handles all those things, as long as it’s not you?
The third type of bucket list trip, the Bonding trip, doesn’t revolve around a specific destination or event, rather, it revolves around the people involved. People you’re close to. People you love. Family. Friends. People who you always say, “we should plan a weekend to do ‘X’ together” but never do.
Often, these types of Bucket List trips morph into traditions that get put on the calendar yearly. They may not seem like bucket list trips because of that, but it all starts with the first one.
These could be father-son trips, college buddy trips, best friend trips, father-daughter trips, even long overdue vacations with your spouse.
The point of these trips isn’t so much ‘what you do’, it’s that you do something you have a shared passion for, away from your normal routine, just the two or three or ten of you.
Example: My dad has loved golf his whole life. He taught my brother and I to play (and at 75 he’s still better than both of us), so we’ve planned and gone on a few big golf trips, just the three of us. It’s a rare thing when we get extended time together without spouses and kids/grandkids and we treasure it. We played Pebble Beach a while back. We just played at Streamsong this weekend.
These trips are priceless. Golfing happens to be the thing our trip is based on. My wife has started a yearly trip down to Miami with my daughter, just the two of them, chilling at the pool, beach and restaurants. I have friends who hit up different baseball stadiums every year with their childhood buddies. Other friends who do the same with college football games. I know brothers who do marathons in a different state every year or two. Bonding bucket list trips with people you want to bond with. Such a simple, rewarding concept.
When it comes to deciding whether to take a bucket list trip, your decision comes down to two things: money and mindset.
No, not time. You have the time if you care enough. As Greg Scheinman always says, “show me your calendar and I’ll show you your priorities.”
The money side is a much more concrete indicator:
Can you afford it or not?
We realize “afford” is a loose term. We’re going to assume you’re not weighing whether to pay your mortgage one month or drop $5,000 for a seat behind home plate at Wrigley for a playoff game.
We’re talking about what else you’d do with that money if you didn’t spend it on your bucket list trip. This is where mindset comes in. In fact, this is the key to the entire decision.
Rather than viewing a bucket list trip as an expense, you must view it as an investment in your happiness.
How much joy would you feel this weekend, right now, if you took your dad and your kids to your favorite baseball stadium? Or to the one you’ve never been to? Or you did that Grand Canyon hike with your best friend?
How much joy would you and your wife experience if you FINALLY just booked the damn trip to go on an African safari for your 20th anniversary – something you’ve talked about since before you were married?
By viewing the bucket list trip through this lens, everything shifts.
Let’s say the trip you’re contemplating costs a dollar amount you’re hesitant about spending.
Question: What else would you do with that money?
If you’re a responsible guy who is responsible with money and you’d otherwise put this sum of money into some kind of investment for your future self…
Then all you’re doing is taking some of that money you’ve allocated for future happiness and putting it to work towards today’s happiness, when you can guarantee you’re feeling good and will have fun.
Feel guilty? Don’t.
Remember, like we said up top: tomorrow isn’t promised to any of us.
We’re all a phone call or doctor appointment away from shitty news.
With this in mind, the question goes from “can I afford this trip now?” to “can I afford NOT to take this trip now?”
This is how you decide whether to take your bucket list trip or not, with these three questions:
Are you healthy now? Can you afford it now? Would you enjoy it to the fullest now?
If the answer to these three questions is “yes”, “yes” and “yes”, then you’re all out of excuses. Quiet that little voice in your head. You deserve this trip. Let this be your priority for once.
Book it. The “future you” will thank you.
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Jon Finkel
Editor-in-Chief, Midlife Male
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Check out my latest books at jonfinkel.com
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