How to Finally Pull the Trigger on Your Travel Dreams

 In Badassery, Planning, Skills
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In a past post, we talked about how there’s no perfect time to plan a trip.

If you wait for the travel stars to align, you’ll never get off the couch. There will always be problems at work, hard times for family members, scary stuff happening in the news, and love interests who want you right here.

If you want to travel the world, you’re going to have learn to fearlessly plan a trip even when the timing sucks.

And you can totally do it.

In today’s post, I’ll show you how to be a kick ass trip planner who powers through procrastination and worry and gets that flight booked fast.

The secret? You have to create momentum and excitement that’s bigger than your doubts.

Here’s how.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Are you ready for a leap of faith?

1. Dream bigger

If can’t get yourself to sit down and plan a trip, you probably aren’t excited enough about it. (Yet.)

Excitement is a great motivator. I’d consider quitting my job and renting out my house for the opportunity to climb a 7,000-meter peak in Central Asia.

Compare that to my annual obligatory holiday trip to Cleveland, which I usually put about zero energy into. (Last year, I was so apathetic, I ended up driving there from Denver with my cat, which I don’t recommend.)

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Plan a trip you’ll remember on your deathbed

Over-the-top goals are easier to achieve.

So let’s take your travel dream and think of at least one way to “big it up.” How can you make this trip into a life-changing experience you’ll be proud of on your deathbed?

Here are some ideas:

  • Stay longer. If the idea of visiting Paris for a week doesn’t get you off the couch, imagine yourself moving there for three months. Or a year.
  • Do something epic. Sometimes a major challenge like climbing Mount Fuji, taking the Trans-Siberian Railway, or walking across Turkey can provide a rush of motivation.
  • Go for an experience. Examples might be Oktoberfest in Bavaria or the Mass Games in North Korea or the next launch at the Baikonur Cosmodrome. In addition to creating excitement, aiming for a time-limited experience gives you a hard deadline to work toward.
  • Give back. Adding a volunteer element to your trip is a great way to increase your motivation — and can sometimes drastically reduce your costs, too. So if you’re passionate about hiking, do some trail work in Patagonia. If you care deeply about education, build schools in Nepal.

Radical “Plan a Trip” Tip: Write down three ways to make your trip more exciting and meaningful. Allow yourself to be unrealistic. Then spend no more than an hour researching your favorite. Decide how you’ll translate this passion into your next trip.

For example, maybe you want to climb every country high point in Africa. You probably can’t do that in one trip, but you could start with Kilimanjaro to create some momentum.

2. Set a date 

Now that you’ve built up some excitement, it’s time to up the ante by setting a date.

In 2012, my friend and I decided to backpack across Central Asia. She was a teacher, so we set our dates to cover her entire summer vacation. We bought plane tickets 12 months out without knowing what would be happening in our lives, jobs, families, or the world. We weren’t even sure which countries we’d visit.

But we knew that setting the date was the key to making the rest of it happen. So we locked it in early as possible.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Get your ideas on the books

Why is the date such a big deal?

A date is an important symbol. It makes your dreams feel real, gives you a deadline to work toward, and gives you psychological insurance against doubt and anxiety.

It’s totally OK to set your travel dates even if you don’t have all the details yet. You can take a quick look at what’s the best time to visit your destination. (For example, you probably don’t want to attend Oktoberfest in April.)

But don’t feel like you need to plan your entire trip and then bracket it with the perfect dates. Quite the contrary; having time constraints to work inside can make your planning much easier.

Another tip: don’t set your dates too far out. Even if you’re dealing with the most Byzantine developing-nation bureaucracies that never answer their embassy phones (cough, Uzbekistan), you can usually sort out visas and travel arrangements in 6 to 12 months. Stretching your timeline any longer is just an excuse to procrastinate and lurk permanently in the “someday” zone. In general, the closer your trip, the more urgency you’ll feel and the more motivated you’ll be.

Radical “Plan a Trip” Tip: This one’s really simple. Pick actual dates. Mark your trip in your calendar and phone. Start living life as if you’ll be gone during that time.

3. Announce your intentions

It’s one thing to be excited by yourself. But when other people are excited for you, it feels good. And it’s also harder to back out without looking like a giant flake.

Depending on what you’re planning, you may also encounter people who think you’re misguided, soft-headed, an incurable dreamer, completely mad, or lying. In a way, that’s even more motivating than well-wishes. You’re going to have fun proving them all wrong.

Another reason to announce: call me crazy, but I’m a big believer that putting your intentions out to the universe tends to make those intentions come true. I think it probably has more to do with you than with the universe. But if the universe wants to lend a little cosmic help, why the hell not?

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Tell the world what you’re up to

What about work?

Great question. The perfect approach probably depends a little on your organizational culture. Some tips:

  • Go ahead and take time off, so long as it’s not going to lock you into anything irrevocable before your ready.
  • Try to avoid asking for permission. I’m a big fan of telling work, “Hey, I’ll be gone these dates. Please let me know what paperwork I need to fill out.” An announcement is harder to refuse than a request.
  • If you’re going to need more travel days than you have paid vacation days, look into options like unpaid time off, personal leave of absence, sabbatical, or a remote work arrangement.
  • If you expect resistance, draft a proposal outlining your plan, the benefits to the organization, and how you’ll help to ease the transition.

Radical “Plan a Trip” Tip: So now that you’ve got a big dream and a date, get the word out. Tell your friends and family. Tell your work. Posting to social media can be great, but sometimes it’s better to wait until you’ve got things sorted out with work — especially if you’re going to be taking an extended trip.

4. Invite a friend

Inviting someone into your travel dream benefits you in a few important ways.

First, it’s insurance against cold feet. It’s kind of like a wedding proposal that way. Once you’re committed to traveling together, it’s a lot harder to back out.

Second, planning a trip with someone else can be a lot of fun. It feels less scary. And you can feed off the other person’s excitement on days when you have doubts.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Everyone needs a wing-woman

What if he says no?

It’s still totally worth asking.

For one thing, it’s a good test. You’re not going to ask unless you’re pretty committed yourself. And because you asked, there’s now one person out there who knows you’re really super serious.

What if she says, “I’ll think about it”?

That’s OK, but don’t let her procrastination become your procrastination. Assume she has the same human weaknesses and doubts that you do. She might resist going until the timing is perfect or she gets a green light from the universe.

So keep the door open, but don’t wait on her. Keep the planning ball rolling.

Remember, this is your dream. Your first goal is to get yourself there.

Radical “Plan a Trip” Tip: Ask a friend to travel with you on the dates you’ve set.

5. Invest

Telling people your plans puts your ego on the line. So now you need to do the same with your money.

When it comes to motivation, money sometimes works better than praise. It’s really hard to nag a smoker into quitting. But sometimes when the smoker sees in black and white how much they’re spending on cigarettes, they’re shocked straight forever.

So what should you buy? I usually start with books. Buy the newest Lonely Planet or Rough Guide for your destination.

If you’re doing something obscure and can only find an expensive self-published travel guide on Amazon, that’s even better. (Check the Look Inside feature first to make sure it’s not total crap.)

Don’t cheat and go to the library. You want something you can take on the road with you.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Be a shameless gearhead

Next, buy something especially for this trip

Going to Italy? You’ll blend in better if you bring at least one designer outfit and some nice shoes. Or maybe it’s finally time to upgrade to a four-season tent so you can be cozy on New Zealand’s high peaks.

You can also invest time. Taking language lessons is a great example.

During this exercise, spend enough money to push yourself outside your comfort zone. If you feel anxious, remind yourself that you’re investing in your dreams. The things you’re buying will help make them happen.

Radical “Plan a Trip” Tip: Make your shopping list and get busy. Try to include at least one item that costs more than $100.

6. Pull the trigger

So the day is here. You’ve set exciting goals, set your dates, announced your intentions, and invested in your plan. You’ve also done some basic research to ensure that your dream destination is safe, that you can get the required visas, that you’ve got enough money to feed yourself, and that you’re unlikely to land in monsoon season when all you want to do is surf.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

Leap with maximum enthusiasm

It’s time to get real.

Think of an action that is going to send you over the event horizon. Once you do this thing, there will be no going back on your plans. (Well, not really. We tend to overestimate the permanency of our actions. But find something pretty damn close).

Some ideas:

  • Buying plane and train tickets
  • Booking a tour or expedition
  • Renting out your home
  • Selling your car
  • Renting a home in your destination country
  • Quitting your job

And then, as soon as possible, not knowing everything about the future but having faith in yourself and the universe …


Your hands may sweat and your heart may pound. That’s OK.

The great thing about pulling the trigger is that you’re going to get a rush like no other. Its going to be so easy to dive into the research and nail down all the small details when that trip is irrevocably written on your future.

You might feel scared. But if this is your dream, you’re also going to feel truly alive. And probably a little proud of yourself for making it happen.

Radical “Plan a Trip” Tip: Finish your basic planning, decide on your trigger, and pull that sucker.

So that’s my radical planning process for travel, which is very close to my heart because I’m doing it right now! (More on that soon.)

How do you plan a trip when life gets in the way? Comment below to share your tips.

How to Plan a Trip Even When the Timing Sucks: Tips for Ending Travel Procrastination

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