Alex Tiffany On How We Need To Redefine Success

Make sure you get enough sleep, do regular exercise and eat healthily. It sounds basic, but these things are absolutely essential if you want to live a happy, successful life. Have you ever noticed how often we equate success with more? Whether that’s more products, more profits, more activities or more accomplishments, we buy into […]

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Make sure you get enough sleep, do regular exercise and eat healthily. It sounds basic, but these things are absolutely essential if you want to live a happy, successful life.


Have you ever noticed how often we equate success with more? Whether that’s more products, more profits, more activities or more accomplishments, we buy into the belief that we have to do more to have more to be more. And that will sum up to success. And then along comes The Great Resignation. Where employees are signaling that the “more” that’s being offered — even more pay, more perks, and more PTO — isn’t summing up to success for them. We visited with leaders who are redefining what success means now. Their answers might surprise you.

As a part of this series I had the distinct pleasure of interviewing Alex Tiffany.

Alex is a former corporate lawyer and lifelong travel enthusiast on a mission to make adventurous independent travel accessible to all. Alex climbed the ladder at a major U.S. law firm for five years before realizing that he needed a total change of direction. In January of this year, Alex quit his job and founded Just Go Exploring, a travel website offering free and detailed guides and itineraries for off-the-beaten-track destinations around the world.


Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

My most formative life experience without a doubt was spending a year solo backpacking around the world when I was 18.

I’d just left school and had virtually no money, but wanted to see as much of the world as possible. I travelled on an extremely tight budget, sleeping in a tent and eating street food wherever I could. I couch-surfed, hitch-hiked, met some incredible people, witnessed and received countless acts of kindness and hospitality from total strangers.

During that year, I grew up very quickly. The experience taught me so much about the world, and about myself. It taught me how to look after myself, how to be resourceful and self-sufficient, and how to live on a tiny budget.

It also increased my self-confidence hugely. I was a fairly shy kid. But when you’re travelling by yourself, if you can’t strike up a conversation with a stranger, you get very lonely very quickly.

We all have myths and misconceptions about success. What are some myths or misconceptions that you used to believe?

I used to have a classic, clichéd view of success, and it largely revolved around wealth and career status. Rich people are probably successful, right? Successful people live in big houses and drive fancy cars, right?

During my career as a lawyer, success meant pleasing senior colleagues, receiving positive performance reviews, and getting promoted up the formal ladder, with the ultimate goal of being invited to join the partnership.

One of the key metrics that lawyers are assessed on in most firms is billable hours. To succeed in a top law firm, you need to meet very high (and punishing) billable hours targets. Lawyers at all levels of seniority are judged by their ability to “bill, bill, bill”. Everyone’s competing with each other all the time to clock the highest numbers, on a monthly and yearly basis.

This is unfortunate, not merely because it incentivizes lawyers to work themselves to the point of burnout.

Perversely, the culture of rewarding lawyers who bill the most hours actually disincentivizes them from working efficiently. If I can get a job done in 10 hours, but am under constant pressure to bill as many hours as I physically can, where’s the incentive for me to work efficiently? At best, this is stupid. At worst, it’s a conflict of interest.

This is also why I reject what many people have described as “the cult of busyness” which is so common in our society. In truth, you really don’t need to be busy to be successful. You need to work hard and work smart, sure. But that doesn’t mean you need to be busy all of the time.

Funnily enough, now I get some of my best work done when I’m NOT busy. Having some mental space can be crucial for clarity of thought and many creative tasks. Sometimes it really does pay to take a break and chill out.

How has your definition of success changed?

My definition of success has come to be tied — at least partly — to happiness and self-satisfaction. Consider a partner at a “BigLaw” firm who makes millions every year. Some would say that person must be successful by the nature of what they have achieved in their career.

But what if that partner is constantly over-stressed, never spends time with friends or family, is lonely, always one step away from a breakdown, and generally hates their life. (The legal profession is full of people like this). Is that person really successful? I don’t think so.

Money is important, but I have come to see it more as a facilitator. It’s a means to being able to do the things that actually make you happy.

Now I place an even higher priority on my quality of life than on my annual income. I’d much rather earn less doing something that makes me happy than do a job that pays highly but makes me miserable. That’s why I’ll never go back to corporate law.

Now I work for myself, success means making a good living doing something that I truly enjoy, on my terms, and at the pace that I choose. It means being able to fit my work around my life and the things I want to do, not the other way around.

One of the most powerful quotes I’ve heard recently is from Maya Angelou, who said that “success is liking yourself, liking what you do, and liking how you do it.” I love this, and it really resonates with what I now view success to mean.

The pandemic, in many ways, was a time of collective self-reflection. What changes do you believe we need to make as a society to access success post pandemic?

So many people go through their lives making decisions on auto-pilot. They make default choices, either because it’s the path of least resistance or because it’s what other people expect of them.

We need to encourage people to ask themselves what they really want to achieve in life. What do they want to do, how do they want to live, and who do they want to be. We should also encourage people to actually listen to, and act on, those ideas, desires and feelings.

Being a free thinker doesn’t mean always having to choose the harder path. But it does require people to make mindful, conscious choices. Not simply to default to what everybody else seems to be doing.

Another thing that our society gets really wrong is putting so much pressure on children to make important decisions so early on in their lives. How on earth is a 15-year-old supposed to know what they want to be doing when they’re 30?

Yet, there’s this overwhelming pressure that forces kids to make decisions that can have a huge impact on their futures. Should I go to university or get a job after leaving school? What career should I pursue? What subjects should I study? What work experience/internships should I apply for? These questions are all “should” questions. The problem is, we don’t give young people enough time, space and opportunity to ask themselves, and to learn about, what they actually want to do.

I’m not saying that everybody needs to do a year of solo backpacking as a young adult (although this would be valuable and transformative for many). But at a minimum, I think we should encourage young people to get some sort of life experience — whether through travel, volunteering, doing a ski season… whatever — and get to know themselves a bit better as people before requiring them to make such important decisions about their future.

Another key thing that we need to improve on as a society is to normalize discussions surrounding mental health. For countless millions of people, month after month of rolling lockdowns and living in fear had an extremely negative effect on their mental wellbeing. Even for those who found the pandemic easier to live with, this period highlighted how important it is to look after our mental — as well as our physical — health.

While some progress has been made in recent years, many people still find the topic of their mental health either too difficult to talk about or downright taboo. This is a problem and one that our society needs to overcome. Unless we can be honest with ourselves and others about the help that we might need at various times, this will hold so many people back from achieving true happiness and success in their lives.

What do you see as the unexpected positives in the pandemic? We would love to hear a few of your stories or examples.

One of the most positive things for me was having to spend a large amount of time by myself, with my own thoughts, away from a hectic schedule and a busy life. This time was obviously very difficult in many ways. But it also gave us all time to get to know ourselves a little better and to be honest with ourselves about what lives we actually want to lead. For me, it helped to cement the idea that I needed a change of direction in my career and to try something new.

This is tied with an increase in gratitude. It’s so true that we often don’t appreciate what we have until it’s either under threat or taken away. This was the case with many things during the pandemic. Our friends, family, hobbies, freedom, even our health. I think most people now have a new-found sense of gratitude for things that they used to take for granted. I certainly do.

The increasing popularity (and acceptance) of remote work is another huge positive. For people fortunate enough to have jobs that can now be performed from anywhere in the world, this is hugely liberating and a total game-changer.

For many people, the months spent under lockdown were also an opportunity for personal development. Personally, I read a ton of books, taught myself how to cook new dishes, and dedicated a good amount of time to working on my fitness and mental health with a combination of running, yoga and strength training. (I also played a LOT of PlayStation!)

For working parents, having to juggle parenting with a stressful job must have been incredibly difficult, and I have huge respect for those who were able to do this. But for those parents whose pre-pandemic jobs meant they hardly got to spend any time with their families, the pandemic gave them an opportunity to spend far more time with their loved ones. I don’t have kids, but being able to be with my partner every evening — not having to work late at the office — was a definite positive.

We’re all looking for answers about how to be successful now. Could you please share “5 Ways To Redefine Success Now?” (Please share a story or example for each.)

1. Try to be less materialistic

We really need to move away from the idea that material wealth equals success. In my legal career, I came across countless people who had all of the material possessions they could ever dream of, but were still incredibly unhappy.

Instead, focus on what actually makes you happy; what makes you feel good inside at a deep level. These things are far more likely to be experiences, rather than material objects.

2. Look after yourself

Make sure you get enough sleep, do regular exercise and eat healthily. It sounds basic, but these things are absolutely essential if you want to live a happy, successful life.

Also, don’t try to optimize every hour of the day with “productive” tasks. However long your to-do list, it’s important to take some time every day to do things that make you feel good. Make a point of allowing yourself some me-time every day. Listen to your favorite music, go for a walk, get lost in a good book, have a candlelit bath, get a massage, cuddle a puppy, whatever.

3. Meditate daily

When I first started hearing people talking about the benefits of meditation, I was skeptical. It sounded like hippie-dippy nonsense. Trust me, it’s not.

Start small — 5 minutes per day is totally fine. Just give yourself the chance every day to sit in silence with yourself, no distractions. Try to clear your mind of any worrying thoughts or feelings. If you struggle to do this, focus instead on all of the things that you are grateful for in your life. All the while your mind is on the things you are grateful for having, it’s virtually impossible to feel anxious or stressed about the things you don’t have.

There are loads of excellent resources online that can teach you how to meditate. Give it a try.

4. Adjust your role models

Think about who are your role models. Then ask yourself, why those people? What is it about their lives that makes them successful?

Several of the people I encountered in my early career, who I used to look up to and thought had really made it, turned out to be deeply unhappy. From a distance these people seemed to be the epitome of successful professionals. But they’d had to sacrifice so much of themselves to their careers that under the surface they were hollowed out and their lives lacked real meaning. People like that don’t make great role models, unless you want to end up exactly like them.

5. Ditch social media

I hate social media. Yes, I know there can be benefits to using it. But for many people, social media has a negative overall effect on their mental wellbeing. I’m not a psychologist, but it seems obvious that constantly being bombarded with airbrushed versions of the lives of others can’t be good for our mental state or self-esteem.

Social media makes people (consciously or unconsciously) compare themselves to a version of reality that’s not realistic. It also takes people out of enjoying the present moment, seeing every experience as an opportunity for an Instagram post. And for what? “Likes”? Do we really need that kind of validation?

I’ve been infinitely happier, more present, and less envious of others ever since I stopped using social media. I don’t really care whether that’s correlation or causation, I just know that I have no desire to get sucked back into it.

If you don’t think you could live without social media, here’s a challenge for you. Try removing the apps from your phone for a week. After that week is done, notice how you feel. If you honestly think your life would be better by reinstalling those apps, by all means go for it. But give yourself the chance to feel what it’s like without them.

(Sorry, rant over.)

How would our lives improve if we changed our definition of success?

To start with, we’d probably be a lot happier. More people would do more things that they enjoy, and would spend more time focusing on things that make them feel good.

We’d be more fulfilled, appreciating what we actually have now, rather than constantly chasing the next thing, be it a promotion, salary increase, fancier clothes, flashier car, bigger house, etc. We’d also give ourselves more opportunities to be healthy, both physically and mentally, and have more time for personal development.

We’d be better off in so many ways.

What’s the biggest obstacle that stands in the way of our redefined success? And what advice would you offer about overcoming those obstacles?

I think for many people the biggest obstacle is having to deal with the judgment of others. Especially close friends and family.

When I told people that I was planning to quit law and start up my own business, many people were skeptical. Why would you want to trade in a prestigious, highly-paying career for uncertainty, risking your future on a venture that might fail, they asked. You’ve trained for so long and invested so much in your career, they said.

Even when I told them that I hated being a lawyer, and that it was making me seriously unhappy, some people just didn’t get it. It’s hard to stand up to people who voice fears that you yourself feel. All the more so when they are people whose opinions you usually value.

To overcome these doubts in your own head, you need to focus on the reasons why you want to make the change. What is it you want to achieve? What was it about your previous idea of success that made you unhappy? How will your life be better once you start following your new idea of success instead?

Where do you go to look for inspiration and information about how to redefine success?

One of the books I regularly turn to is Tools of Titans by Tim Ferriss. This easy-to-read, engaging book is packed full of advice, useful habits and routines recommended by leading experts in their various fields. You don’t need to read it cover to cover, it’s intended more as a pick-’n-mix; something you can dip into and out of whenever you’re in the mood for information and a little inspiration.

I’m also a big fan of TED Talks. These are great ways to get an insight into the thoughts and lives of influential people who are enjoying professional success in a huge range of different fields.

For meditation and mindfulness, I love the Insight Timer app. This has an enormous library of guided meditations, personal insights and relaxing soundscapes. It’s one of the best and easiest ways to bring a few minutes of calm and clarity to your day. I use it every day and leave every session feeling more positive and inspired than I was before I started. I’d recommend it to everyone.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she or they might just see this if we tag them.

Probably Arnold Schwarzenegger. He’s a self-made millionaire entrepreneur who came from a very humble background and went on to achieve success in several different fields.

From a cash-strapped immigrant competing in a niche fringe sport, Schwarzenegger overcame the doubts of others to become incredibly influential, wealthy and well-respected. He built a property portfolio before becoming famous as an actor as he knew that this would help to ensure he only had to take on the acting jobs that he actually wanted to do. Achieving financial independence helped him to also achieve career independence.

I find his story and his foresight both impressive and very inspiring.

How can our readers further follow your work online?

Check out my travel website www.justgoexploring.com. Here you’ll find materials and resources to inspire, encourage and enable you to explore as much of our beautiful planet as possible.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.

Thank you for having me!

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