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You are here: Home / How to Travel Alone / Solo Travel Planning / Successful Trip Planning: Address the Obstacles First

Successful Trip Planning: Address the Obstacles First

Janice Waugh

June 4, 2018 by Janice Waugh

Toronto. My home town. My option for a micro-vacation. trip planning
Toronto. My home town. My option for a micro-vacation.

Few of us live life free of all restrictions.

The same goes for travel. This post is about managing to travel despite the obstacles. For, really, who among us has unlimited funds, unlimited time and no responsibilities? Who can travel anywhere, anytime, for any length of time and as luxuriously as desired? A rare, rare person to be sure.

When it comes to trip planning, most of us have to be realistic about our limitations while pursuing our travel dreams. To successfully balance life and travel, start planning from the point of greatest pain – the point that holds you back the most. Ignoring it will lead to either paralysis and no travel or a trip that causes undue stress.

In my mind there are three possible pain points and, therefore, three different approaches to trip planning. One of these may be right for you.

A micro-vacation destination can simply be a hike in a nearby woods. trip planning
A micro-vacation destination can simply be a hike in a nearby woods.

Table of Contents

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  • If Your Pain Point Is Time
  • If Money is Your Obstacle to Travel
  • If Your Pain Point Is Responsibility

If Your Pain Point Is Time

Time is a huge issue for most people. We live in busy times. With mobile phones, social media, and texting we are (if we allow it) accessible 24 hours a day, seven days a week. By nature, most people will fill all the time available. If a responsibility falls off, we'll replace that commitment with another.

So how can you deal with the issue of time if you want to travel? It's all about setting priorities and designing your travel to fit your lifestyle. When the issue is time, travel will fall into four possible categories.

  • staycations
  • micro-vacations
  • short getaways
  • a week to yourself

When planning to travel, start with the category that fits your life. Then choose destinations that are appropriate. Staycations cause you to approach your town as a tourist. On a micro-vacation you might get out of town for an afternoon. A short getaway may mean going only a few hours away, whether by car or plane, for a weekend. And, if you're lucky, you might get a week away. Maybe you'd prefer to travel longer, but it's not always possible within our personal constraints. The bottom line is that you may have to save your bucket list destinations for when time is less of an issue.

Read:

  • How to Find More Travel Time – 15 Tips
  • When Travel Is the Goal, Not Destination
My stay at Anand Prakash ashram was an experience that I will never forget (and one I'd like to repeat.) trip planning
If money is your pain point, consider going to a place that is inexpensive. This ashram in India was less than $20 per day for food and accommodation. The flight was expensive but at that daily rate a two-week trip could come in just slightly under $2,000. This is Anand Prakash Ashram in Rishikesh.

If Money is Your Obstacle to Travel

Money is a challenge for many people but unless you are in very serious financial difficulties, it should be one that you can get around. There are three possible ways:

  • Save to take your dream trip.
  • Choose a trip that matches your budget.
  • Schedule your trip when the prices are lower.

Let's talk about saving for your dream trip first. It can take time. It requires delayed gratification – not something that our credit-laden society is particularly good at. But it can be very sweet to reach your dream destination this way. Research shows that the satisfaction of having saved for a trip, the planning time that this allows, and the lack of stress from not being financially in debt after the trip, all contribute to getting more happiness from your travels.

Of course, the second way to deal with money issues is to travel to destinations within your budget or at a time that makes a destination within your budget. Consider:

  • Places you don't have to fly to.
  • Destinations that are less expensive such as South America or Southeast Asia.
  • Traveling on the off or shoulder season.

Read:

  • Best Budget Destinations for Solo Travelers
  • How to Save Money for Travel: Top Tips to Save
  • No Money to Travel? Here’s What You Do.
These are the "Pained Ladies" of San Francisco - one of my dream trip destinations. trip planning
These are the “Painted Ladies” of San Francisco – one of my dream trip destinations.

If Your Pain Point Is Responsibility

Personal responsibilities are a more difficult challenge than either time or money. Family or work commitments can definitely get in the way of travel. But it's important to remember that you will live up to those responsibilities better if you are a happy, satisfied person. So set aside any guilt, make yourself a priority, and plan the solo trip you want.

Once you have your head around the balance of your travel desires and your responsibilities, communicate clearly with family, friends, and work to negotiate your personal time and travels. Be confident that taking time for yourself is good for everyone.

Read:

  • Separate Vacations: Travel Solo for the Good of Your Relationships
  • A Journey of Self-Discovery: Be Great at Being You
  • Why Travel Solo? 15 Reasons Going Alone Makes Travel Better

Last updated: 28th September, 2025

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