The Big Dilemma: Retire Early or Travel Now?

I recently met with a fellow Bay Area parent over lunch and he told me how he was debating between retiring in 10 years versus saving up to travel with his kids in 5 years.

His dilemma is something we all wrestle with. Most of us want to retire early and travel sooner than later, regardless of if you have kids or not. However, because both of these goals are so far in the future, they aren’t actionable. They’re so distant that achieving these goals is almost impossible.


What you need to do is reframe the questions.

Instead, you should ask yourself, “What can I do today to travel more for the rest of my life?” If travel is a major priority in your life, then you’ll do everything you can to make it your lifestyle.

And is early retirement really what you’re after? If you look at it from the perspective of doing work that you are passionate and energized to do in a sustainable way, then you’ll probably never want to retire. The better question you should be asking yourself is “How can I get more freedom and flexibility in my work to have the lifestyle that I want now?”

The reality is you’ll probably never have enough money, time, and energy to take a big, long trip around the world.

The only people who actually do it are the people who make a conscious effort to make the most of their situation—and actually make it happen.

If you want to travel more and live better, start where you are.


First, do a reality check. 

Take an assessment of where you are financially, mentally, physically, and emotionally.

  • Do you have enough money to travel the way you want to?
  • Are you really satisfied with your work and career?
  • Are you at a point in your life where you need a healthy break?
  • Will you regret not traveling now (with your kids)?

Second, figure out how to make it work. 

Don’t get mired in analysis paralysis, but ask questions that are actionable—immediately.

  • Instead of taking one big trip around the world, can the trips be split up into smaller, more manageable blocks of time over a longer duration?
  • How much time off could you get from your employer without losing your job?
  • Could you negotiate a remote working arrangement for an initial trial period?

Finally, do it. 

You start with one step, then another, then another, and eventually you’ll have the momentum you need to get what you’ve always wanted to achieve.

At the end of the day, you have to ask yourself what’s most important to you. Figure that out, then put an action plan with small steps that you can work on now to eventually achieve your goals.

Start where you are. Then go.


Cliff Hsia is a writer, husband, and father, who is determined to live a better than normal life by traveling the world, slowly and purposefully, with his wife and two young daughters. His writing has been featured on MSN, TODAY, The Huffington Post, The Good Men Project, and other publications. He writes about travel, parenting, and lifestyle design.


  • Giovanni Gonzalez

    Hey! That fellow Bay Area dude is me! 😉

    Great advice!

    • Giovanni, Thanks for lunch and the inspiration for the post. Wishing you and your family all the best!