Rule #1: There’s never a perfect time to do anything.

Rule #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.

To begin, there are two types of bucket list trips: Evergreen and Timely.

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.

These are Bucket List trips that happen once, or during a certain time in your life, and you need to make quicker decisions if you’re going to drop some serious cash to be there.

Again, too often your priorities stand in the way.

After all, who’s going to handle [fill in the blank with a 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?

When it comes to deciding whether to take either of these types of bucket list trips, your decision comes down to two things: money and mindset.

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 son to a championship game for your favorite team?

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 $15,000 all-in.

What else would you do with that money?

If you’ve got your rainy day fund covered and you’ve got your debt taken care of and you’re a responsible guy who year after year puts that money in  an investment fund 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.

Feel guilty? Don’t.

Remember: 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.

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.