Travel, Freelance, Science: How to Live Life with No Regrets

Okay, the title says “no” regrets. Maybe you’ll have a few minor ones that creep up on you with the occasional wince-inducing flashback.

But the real question is, how many of those serious, major, heartbreaking life regrets will you have by the time it’s too late to do anything about them?

Specifically, how many of those highlighted in a meta-analysis conducted by Prof Neal J. Roese of the Kellogg School of Management and Dr. Amy Summerville of Miami University? (Sources below).

The paper was written after analysing 11 ranking psychological studies on regret. It collates information from multiple data sets that were gathered using “hypothesis-blind” judges to ensure impartiality, among other scientific best practices.

The studies even employed cunning tactics to try and manipulate the outcomes to see if people changed their minds about what they regretted most based on how the scientists framed questions and otherwise interacted with the subjects.

But nothing changed…

The six most “regret intense” areas of life that are most likely to have us moping around and wondering “what if” are, in descending order:

  • Education
  • Career
  • Romance
  • Parenting
  • The self
  • Leisure

It got me wondering… Could Freedomlancing be a powerful tool to live life with no regrets?

A key focus of the study: loss of “perceived opportunity”

The study uncovered a common denominator between these six factors. It’s super important, so we’ll put it in a nice chunky block quote.

“Overall, these findings show that people’s biggest regrets are a reflection of where in life they see their largest opportunities; that is, where they see tangible prospects for change, growth, and renewal.”

Wow. Change, growth and renewal. We’ll come back to that later.

The study also found that there’s a difference between a lot of minor regrets which are usually based on action rather than inaction.

For example, when we make a decision to take action and it doesn’t go well, naturally we’ll regret making that decision. But, because we can explain away, justify or otherwise make ourselves feel better about that mistake, it tends to be less of a big deal.

Also, as we know the outcome already, there’s less room for imagining the potential upside and how great it might have been.

It’s when we have opportunities to positively affect aspects of our lives that result in “change, growth or renewal” and that offer massive upside potential where the biggest regrets are likely to rear their ugly, looming heads.

Provided of course, we don’t take action…

What might be a relevant example I wonder? Hmm… How about, open-ended world travel and a freelancer lifestyle?

Should you book that ticket?

1. Education

I love learning (read: “I’m a nerd”). It’s a love that developed only after I’d left school and didn’t have a terrible education system run by even worse teachers ramming it down my throat with a particular lack of finesse.

All the time I’ve freed up working just a few hours a week to cover all my living expenses has afforded me the opportunity to indulge this love of learning. At some point in the next few years, it’s likely I’ll take up an Open University degree just for the sheer joy of it.

So far though, I’ve developed multiple new work-related skills, read more books (largely educational) than I ever could before, learned a second language, rediscovered my love of drawing and enlisted in a course, started a blog and learned one heck of a lot about myself and other, very different cultures.

What steps would you take towards your education if you had plenty of time on your hands and fewer distractions than you do right now?

2. Career

Naturally, freelancing is a career (with the option for world travel as an epic benefit).

But, more importantly, because you can cover your living costs with just a few hours a week in parts of the world such as Southeast Asia, India or South America, you can (in the words of best-selling author, Rolf Potts) find the time to “indulge in passions that you never even knew you had”.

One of your interests might be starting a company in something you love, whether you know you love it yet or not. Either way, Freedomlancing gives you almost boundless career opportunities, whether starting a business or learning an entirely new skill.

If you freelance the way I teach (I.E, in a way that positions you to work with only top-tier companies in your chosen sector), you continually meet interesting and successful people through work.

You build relationships with them, and entrepreneurial doors constantly open to you that simply don’t exist if you’re grinding away in a job you hate.

After a couple of years looking for business opportunities I recently started one that I’m excited about. I have the time to freelance, write this blog and start on other business projects.

If you could freelance to cover expenses and had plenty of additional time to further change your career path, what would you do?

3. Romance

I remember reading a book in which the eminent philosopher, Friedrich Nietzsche said something to the effect of “you cannot successfully be with someone before you can successfully be with yourself.”

I couldn’t find a verified source for the quote, but if anyone reading has one, feel free to let me know. However I did find this one which I believe holds the same truth.

“Remember that a successful marriage depends on two things: (1) finding the right person and (2) being the right person.”

Friedrich Nietzsche

It may be true that Nietzsche was a misanthropic recluse who was single most of his life. But many would agree that it was all this time alone that helped him achieve his most powerful work to make such big contribution to philosophy in the first place.

What’s the best way to get your ideal partner so you don’t end up with someone you’ll later regret? Could it be to focus on yourself and “[be] the right person” or even “become who you are” as Nietzsche also said?

Well, I think it’s fair to say that travelling the globe and getting some time alone will help you do that. And chasing arbitrary relationships to make yourself feel better about life certainly won’t.

4. Parenting

I’m not yet a parent, but I’d like to be someday. I’d not only like to be a parent, but I’d like to be the kind of truly awesome Dad who raises a well-adjusted, super smart and freethinking individual into the world.

I study psychology partially for this reason. Also, if you have kids already, remember that being a travelling freelancer is not just for the individual. Families do it too.

Watch this space for a post interviewing a number of highly successful global travelling families.

5. The self

“The self” is a trickier thing to pin down and it’s only actually mentioned twice in the whole paper. Let’s look to Wikipedia to get an explanation of what the study might be talking about here:

“The psychology of self is the study of either the cognitive, conative or affective representation of one’s identity or the subject of experience.”


Naturally, all of the above subheadings tie in closely with this idea of the self.

Surely making better decisions, being a better, more fulfilled and rounded individual who’s had incredible experiences is inevitable after multiple years of incredible experiences travelling the world and understanding both yourself and its inhabitants?

Might that contribute to less regret about “the self” later in life?

6. Leisure

Finally comes leisure.

When you’re at the end of your days, lying on your hospital bed, looking back on your life and thinking how ridiculous it is that you spent so much time worrying or procrastinating that could have otherwise been enjoyed on the perceived opportunities of potentially incredible life decisions, leisure is around the sixth thing that’ll spring to mind.

My world travel has only spanned three years so far. But whether it’s regular snorkeling in mind-blowing coral reefs, having incredible meals and long island iced teas on palm beaches with friends, hiking up jungle-encrusted mountains, swimming with whale sharks or any of the other incredible things I’ve done so far alone, these bucket-list nominations can be every day experience before you, too.

I love London. But even if choking on human fecal matter as it slipped down your airtube wasn’t an issue while snorkeling in the Thames (which it would be), there are no coral reefs to see through the murk, anyway.

Next-level leisure is affording to the travelling freelancer. Which countries would you visit? What activities would you do?

On change, growth and renewal

Surely the life of a travelling freelancer is all about change, growth and renewal? If Roese and Summerville are correct, I wonder how Freedomlacing might affect these apparently essential components for aiming to live a life without regrets?

What if you booked the ticket and took the ride?

  • Change

    Not only will you change your current environment and break free from the daily grind, but you can change environments regularly, experience as much of the world as you want, constantly open yourself up to opportunities meeting people though both business and travel.

    Also, you can settle down somewhere you genuinely love, not just the country you happened to be born in.

  • Growth

    Don’t take my word for it, why not take a look around the Internet at how much travelling the world and putting yourself outside your comfort zone seriously contributes to your, self-esteem, confidence and personal growth in general.

    There’s a lot of science behind this one, too. Travelling has helped me grow in so many ways, and I’m confident that just about any one of my fellow travellers would back up that sentiment.

  • Renewal

    See that tropical palm beach in the feature image? That was the first Instagram I took when I started travelling outside of the UK (I spent several months in the Scottish Highlands before I left).

    I take time to renew myself at locations equally stunning to this on a regular basis. Not just because they’re there. But also because I have the time. See the office? That’s actually where I used to work. I can assure you, there was no renewal. Only a David Brentalike.

The loss of opportunity

If you’re reading this right now, there’s a good chance you’re a freelancer (or considering becoming one) and have at least considered booking a one-way ticket.

If that’s the case, make sure that you properly weigh in these science-backed considerations when deciding whether or not to do it.

It takes guts. But you simply cannot put a value on the payoff.

P.S – Want some help becoming an established freelancer and travelling effectively? All the links to the Freedomlancers Udemy course from the website are 50% off.

What We Regret Most … and Why by Prof Neal J. Roese and Dr. Amy Summerville

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