Get the Confidence Boost You Need to Plan a Backpacking Trip

A journey of 1,000 miles begins with a single step.Lao Tzu

But that first step can be a biggie!

That’s why I’m here (Greg Rodgers from to help new travelers by getting them sorted and motivated with a backpacking coaching/mentoring session.

One or two live calls can really get your momentum going and confidence building. Plus, you get real-time answers to questions about backpacking travel from someone who has lived on the road as a digital nomad since 2006.

Planning a Backpacking Trip

When I was planning my first budget backpacking trip (Thailand) in 2005, there were only a few reliable resources for info about backpacking travel. Now, the opposite seems to be true: There is too much out there!

Information in forums and Facebook groups is conflicting. Some of the trolls are rude. Advice on travel sites becomes outdated quickly. What worked last year may or may not work now. Places change faster than travel writers can keep up!

I know firsthand. I’ve been living, working, and writing from the road for 13 years now. Sure, I return home, but since leaving my “real” job at IBM in January 2006, I’ve made a new life as a travel writer.

If you feel as though you’re rotting away in a cubicle, don’t worry, you aren’t alone. I’ve been there, too.

Someone to Call

I had plenty of inspirations for my first trip but no real mentors. I hacked my way through quitting my job, uprooting my life, and learning to live and work on the road.

I understand very well the nervousness of leaving a job, selling everything, and stepping out with only a backpack and a one-way ticket. I was terrified. Friends warned that I could be making a big mistake. The Fear took hold. I wasn’t sure if I was doing the right thing.

I wished I could have spoken to a real traveler before I left home, if nothing else, just for some reassurance that I wouldn’t end up on an episode of Locked Up Abroad.

And I wish someone experienced had told me not to leave home with a bulging backpack full of stuff that I didn’t need anyway!

One-on-One Backpacking Travel Coaching

There are plenty of trip-planning resources online, but nothing really beats the real-time sanity check that only talking to a fellow traveler provides.

I speak on the phone with travelers (or sit down with them if we’re in the same place) and answer questions, quell nagging fears, and provide specific answers to questions they have.

I’ll be glad to answer follow-up questions or help with issues via WhatsApp if something comes up days, or even weeks, after our call.

Long-term travelers become happier, healthier versions of themselves. I am here to support you during that transition. Travel makes the world a better place, one person at a time.

How It Works

  1. You contact me via
  2. We schedule a time to talk
  3. I research your itinerary if necessary
  4. You pay (via PayPal)
  5. We talk on the phone for a backpacking coaching session
  6. We follow up (I email you resources and takeaways from our chat)
  7. You kick butt on your trip!

One Backpacking Coaching Session or Two?

For obvious reasons (other than I can buy more pad thai), booking two sessions has some advantages. Here are a few:

  • Things you forgot to ask about during the first call can be covered during the second call.
  • New questions are sure to arise as your departure day approaches. (e.g., “Hey, should I pack this?”)
  • The second call can be made if you’re already on the road, freaked out, or need some last-minute advice.

Want to Call Later?

Nothing says you have to schedule now. Once you’ve signed up, we can wait until you are ready.

Let’s Go!

2021 Update: My travel coaching has now been integrated into my courses on

Now most of your basic questions will be answered before we speak, that way no time gets wasted. Plus, you’ll learn all you need to know about escaping the Rat Race or taking a career break to travel extensively.

Click below for the details.

Escape the Rat Race course

My Qualifications

Greg Rodgers the backpacking coach

I’m not into bragging about country counts, but I’ve been to quite a few. I prefer to travel slowly, return places, and learn more.

But if you want to read a bit about my 13 years of backpacking experience, you will find details and resumes on my homepage.

Many of my craziest adventures and experiences on the road since 2006 can be found in my vagabonding travel blog.

Don’t let the long hair fool you: I’ve got a solid presence online and am very accountable. I won’t disappear into the jungle with your funds, well, until after we’ve had our consultation.

Sample Topics for Your Session

Of course, you can ask whatever you like—it’s your backpacking coaching session! But to get your brain busy storming, here are some sample topics that I am often asked:

  • Am I making a huge mistake by quitting my job?
  • Are there any safety concerns for solo travelers?
  • Is traveling alone a lonely experience? What is the best way to meet people?
  • Is it possible to earn money while traveling?
  • How should I tell my family/romantic partner/employer that I am leaving?
  • What should I expect the first week away?
  • How do I deal with burnout, culture shock, or homesickness?
  • What happens if I get sick or injured?
  • What is romance like on the road?
  • I hate my cubicle! How do I escape?

What Should I pack?

There’s no shortage of packing lists for backpacking travel to be found online. Every travel website has one or two. But a lot of the information is outdated or conflicting.

If pre-trip stresses such as what to pack are a real concern, you can send me your packing list. We will invest some time going over it, or you can ask about specific items you plan to carry.

How Much Money Should I Take Traveling?

This is, by far, the most frequent question by new travelers. I can go ahead and save us some time on our mentoring call by saying: the answer depends entirely on you!

As you can imagine, some people spend more money on drinks and socializing than food. Some travelers demand privacy while others prefer to stay in cheaper dorms. If the money issue is the most pressing for you, we can discuss a bit based on your travel style. I am very much a budget traveler and know how to save money.

Figuring out how much money to take for a specific trip duration (e.g., 1 month, 3 months, 1 year) requires knowing about the travel “budget dance”—ask me about it. If you really want to add time to a trip, consider doing some side work along the way or offsetting costs with WWOOF (working on organic farms).

I can also provide real-world examples (I journal a lot of stuff) for exactly how much I spent in places (e.g., my first two days in Bangkok).

Are You Traveling to Asia?

I’ve traveled in Europe, South America, Egypt, India, and many other places, but Southeast Asia is my second home. If you’re coming this way as many travelers do on their first trips, I’ve got you covered. If our paths cross, I’ll even pick you up at the airport!

There are plenty of websites that already cover the best places to eat, stay, etc. But if you would like a deeper understanding of a destination, particularly in Asia, I can help. I have been the Asia Expert for TripSavvy since 2011. I definitely know the best ways to get a foothold in popular entry places such as Bangkok, Bali, Kuala Lumpur, etc.

Looking for Adventure?

I know where to find it!

If you’re in the market for some serious adventure on your trip but are wondering how much you can bite off, let’s talk about diving, trekking, climbing, volcanoes, the Himalayas, jungles…

How to Call

In my experience, the popular phone app WhatsApp produces the best calls. Microsoft didn’t do Skype, the old traveler standby, any favors when they took over. Sorry, I don’t do FaceTime.

Regardless, I can meet with you using on a variety of platforms (excluding FaceTime). Video calls are an option, but these can be noisy and distracting, especially if the connection isn’t good. If you’re serious about having a good conversation, a voice call is the way to go.

My guarantee to you: If a connection is poor, the Wi-Fi gods are frowning on us, or we have trouble communicating, we will reschedule for a later time. You won’t be charged. It’s as simple as that.


Time zones don’t hold vagabonds back!

I am pretty flexible when it comes to scheduling mentoring sessions. If I am in Southeast Asia, the time is 11 or 12 hours ahead of Eastern Standard Time. No matter where you happen to be, we’ll find a time window to accommodate.

If something comes up for either one of us, sometimes it happens, we can easily reschedule via a quick email.

Give Backpacking Coaching as a Gift

Give the gift of knowledge! And also adventure, experience, and memories.

If someone you love is going to be traveling, you can gift them a backpacking coaching session. I’ll provide a nifty certificate and code that you can print and give to them (or just email the code). They can schedule a session whenever they are ready.

Still Have Questions?

Shoot me an email:

See you on the Road!


Photo credits: Featured image, Steven Lewis; Rob Paetz for the portrait