8 Signs You’re Doing Well In Life

8 Signs You're Doing Well In Life

It’s not easy to feel ‘successful’ these days. 

We’re expected to do more, be more and have more than ever, and this obsession with ‘more’ can often seem to have no limits.

In Singapore (which I live next door to and visit pretty often), success has, for decades meant achieving the 5 Cs — the cash, car, credit card, condo and country club membership.

These have since started making way for a new line-up of Cs, but either way, I wouldn’t say they’re unique to Singapore and are basically the Asian equivalent of keeping up with the Joneses in the West.

Do most people actually accumulate enough cash to acquire these societal milestones without going heavily into debt?

Sadly, no — certainly not in Singapore and not in the U.S either.

And are these markers of success realistic? Not for the majority of people grinding it out to make ends meet as the cost of living keeps rising.

So how do you ‘feel’ successful without defining your worth in terms of dollar signs, the things you own or what you do for a living?

This is something I’ve been grappling with since I started taking a series of sabbaticals that’ve lasted anything from a couple of months to two years in-between full-time gigs.

When I’m not ensconced in the ‘busy-ness’ of a full-time job, where do I look for the signs that I’m doing well in life?

When I am working, when do I get to take a step back and say “I’m doing good”?


Your markers of success will inevitably be tinted by comparisons that we tend to make between ourselves and everyone else, as well as unsolicited comparisons that come our way.

While there’s nothing wrong with stacking yourself up against the traditional standards of personal and professional accomplishments, what you truly want may not be what everyone else wants, and guess what? That’s completely OK.

Personally, I’m beginning to find the unnecessary stresses that come with trying to fit into a rigid cookie-cutter mold unbearable as I get older.

And whenever I manage to talk myself into believing that aspiring to check the standard boxes will automatically set me up to win, I end up realizing that:

  • Having more money will make me happier than not having enough of it (just ask anyone who’s barely able to make ends meet), but up to a certain point and not for long. It also won’t solve all my problems. In some instances, it can create new ones.
  • I’ll be allowing someone else to dictate how I spend my money just to keep up, and I’ll be spending it on stuff that I don’t care about.
  • And let’s be real: I can love my job, but it’s not going to love me back — anyone with a job can be replaced in the blink of an eye. Anyone. Even the CEO.

If I’m able to check all the boxes but aren’t happy, am I really successful?

And how do you tell if you are doing well in life once all these typical markers of success are stripped away?


If you’ve been wondering the same thing, here are 8 healthier and much saner ways to consider measuring your success as a human being:

1. You have a healthy relationship with money.

You work hard for your money, but you also recognize that it’s not the only thing you work for. You see money as a means to an end, not the end goal.

When you spend your money, you do it with intention and purpose instead of mindlessly.

And you most definitely don’t spend your money to keep up with anyone who seems to have more than you.

As a result, you’re still able to save and invest for your future while also making the most of your present even if you’re not pulling in a substantial income.

2. You’re doing work that you find purposeful.

Not everyone is lucky enough to have a high-paying job that brings them joy and makes them feel like they’re fulfilling their purpose in life, so if you’re one of the fortunate few, you’ve hit the work-life jackpot.

But even if you’re not working at your dream job, you find a way to bring meaning into your day by being of service to others during your 9-5 or outside of it.

3. You have healthy, meaningful relationships.

You don’t necessarily have a ton of friends, but you do have relationships in your life that are built on mutual trust, a deep emotional connection, respect and honesty.

You have boundaries in place that clearly let the people in your life know what the personal and professional rules you live by are, and aren’t afraid to communicate how you feel when a boundary has been crossed.

These relationships serve as a foundation that keeps you grounded, humble and purposeful as you go about living your life.

4. You’re taking care of your body and mind.

“Put your own oxygen mask on first” is anything but a cliche to you because you know that it’s truth, and do your best to live by it.

If you can’t breathe, you can’t help others who rely on you to get the air they need, so you’ve made it a principle to put yourself first whenever you can.

You take care of yourself by eating the foods your body needs, mindfully and intuitively.

You move your body as much as you can, make it a point to get at least 7 hours of restful sleep daily and practice good mental hygiene by learning how to master your thoughts so they don’t master you.

You’re not perfect and slip up from time to time, but you don’t beat yourself up over them because you know that expecting perfection isn’t realistic or sustainable.

After all, you’re human, not a robot.

In fact, recognizing that you’re inherently flawed and being patient with yourself as a result of this is part of your self-care practice.

5. You live with integrity.

You’re not a fan of lip service — paying or receiving, so you say what you mean and mean what you say.

By being honest with yourself and others, you make it easier to live by your truth, not someone else’s.

You’ve been through a lot — to the highest of highs and lowest of lows, so you know what exactly what it feels like to be done wrong and right by.

Because of this, you’ve learned a lot about how you want to be treated, and have made it a personal rule to treat everyone who crosses your path, the same way.

6. You’re not afraid to be vulnerable.

It’s easy to feel alone even when you’re in a roomful of people, especially when everyone’s got that ‘I’m-popular-confident-and-have-my-shit-together’ game face on.

You know that pretending to be perfect doesn’t help you or anyone else connect authentically, so you make it a point to let your guard down by being honest about how you feel, even if it puts you at risk of looking ‘weak’.

This is why you’re not afraid to be upfront about who you are, what your weaknesses are and all the hard work you need to put into growing as a human being.

7. You’re kind.

Everyone is busy, everyone has an ego and everyone deals with hardships in life.

And let’s face it: Life can make us brasher, more guarded and less sensitive with every passing day.

The harder the things we face, the harder our hearts can become.

You’re well aware of the potential effects that dealing with pain over and over can have on you, so you always remind yourself that you’re not the only one who’s experiencing it.

Rather than react without thought when someone hurts you, you put yourself in the other person’s shoes because you know that being kind can make someone else’s day and yours better, but being hateful won’t.

8. You’re down, but you don’t plan to stay there.

Life hasn’t been kind to you lately.

Your spirit’s feeling so broken, beaten and bruised that you’re not sure if you’ll ever heal from the pain that’s weighing you down.

But even though you’re feeling low, you know that giving up whenever the universe throws you a curveball isn’t how you want to go through life.

So you keep showing up every single day, open and willing to give things another go at 110%.

Little by little, you find ways to invite joy into your life, rebuild your confidence, nourish your soul and strengthen your spirit.

You may be down, but back on your feet and on top of your game is where you plan to be, because to you, that’s what being successful in life truly means.

You get to say “I’m doing good” and feel good saying it, and that’s what truly matters.

Resources that you might find helpful:

(*note: Some of the links below are affiliate links, which means that should you choose to use them, this blog will earn a small commission at no extra cost to you. If you do, thank you!)

Lose 4 Pounds in 4 Weeks Without Going On A Diet Struggling with constant overeating and uncontrolled weight gain? In this email course, I show you how to get started with the exact steps I took to stop feeling like a slave to the food around me, lose over 22 pounds of fat and keep them off for almost a decade now.

The Good Morning Guide If your mornings are typically rushed, chaotic and stressful, I made this guide to help you start your day calm, sane and strong.

The Simple Living Guide When life feels overwhelming, this guide-and-workbook-in-one will help you gain clarity with your values, well-being, career, relationships and money.

Simplify Your Life: 100 Ways To Slow Down And Enjoy The Things That Really Matter by Elaine St. James I got my hands on this treasure over 15 years ago, way before simple living and minimalism became popular, and it was the first resource that introduced me to practical, everyday steps I could take to ‘un-complicate’ my life. I didn’t have enough life experience then to ‘get’ everything that St. James presents in this book, but when I revisit the pages of Simplify Your Life now, they make perfect sense. If you’re just starting out in your simple living journey and are exploring your possibilities, I highly recommend giving this a read first.

The Life-Changing Magic of Tidying: A Simple, Effective Way To Banish Clutter Forever by Marie Kondo Being able to pay attention to the little things in your life starts with decluttering — not the easiest thing to do if your living (or even work) space is disorganised and drowning in stuff. This is my bible as far as tidying up my space and keeping it that way goes.

Boundaries: When To Say Yes, How To Say No To Take Control of Your Life by Dr. Henry Cloud and Dr. John Townsend If you have trouble saying “No” to the people in your life, you’re probably biting off more than you can chew, and constantly struggling with feelings of guilt and resentment, or even clinical psychological symptoms like anxiety, addictions and depression. This book is just as much about learning how to define intangible boundaries as it is about saving your life from a lack of them.

Your Inner Awakening: The Work Of Byron Katie – Four Questions That Will Transform Your Life by Byron Katie When you’re drowning in stressful, painful thoughts and beliefs, you’re anything but rational. In this guide, Katie teaches you, through personal stories and real-life scenarios from her live events, how to use what she calls The Work (which comprises 4 questions and a turnaround) on each painful thought so you can objectively see the cause and effect of it, breaking down its hold on you and freeing you from it.

The Millionaire Next Door: The Surprising Secrets Of America’s Wealthy by Thomas J. Stanley, Ph.D and William D. Danko Ph.D This was one of the first books I dove into as soon as I started earning an income, and the lessons I’ve learned from it are always the ones I turn back to when I feel like I’m losing control or focus with my money goals. If you need to have your priorities around money reset, this book is what you need.

Secrets Of The Millionaire Mind: Mastering The Inner Game Of Wealth by T. Harv Eker A valuable read that helped me tremendously when I was struggling with fear and a scarcity mindset around money. Eker delivers bite-sized lessons that take the reader inside the attitudes, thoughts and actions that allow the wealthy to make, grow and keep their money.

Think And Grow Rich by Napoleon Hill In this self-development classic, Hill outlines the 13 steps that America’s most affluent have taken to earn riches beyond their wildest dreams, and how you can use these same principles to sculpt your own path to wealth and success. This book stays on my nightstand for constant re-reading.

Money Master The Game: 7 Simple Steps To Financial Freedom by Tony Robbins This massive, 600-plus page tome will seem intimidating at first glance, but as you dive into it, it begins to feel like a journey into one of Robbins’ intense, 13-hour day seminars, but on paper. In his signature conversational style of coaching, Robbins takes you through the basics of how to make money work for you, and how you can use the same investing principles that the ultra-wealthy live by to achieve financial peace of mind.

What Color Is Your Parachute? A Practical Guide For Job Hunters And Career-Changers by Richard Bolles I’ve been relying on this classic throughout my 15+ year career, and for good reason: It’s the the ultimate guide to  figuring out who you are as a person, what you want to do in life and how to successfully pursue work that brings you meaning. For the entrepreneurially-inclined, it also includes a guide on how to start your own business.

The 4-Hour Workweek: Escape 9-5, Live Anywhere, And Join The New Rich by Timothy Ferriss Not a resource on achieving financial independence in the traditional sense, but it introduces you to a new way to think about work, earning an income and retirement. You’ll find this read to be a much-needed breath of fresh air if your 9-5 is killing, not inspiring you.

Tribe Of Mentors: Short Life Advice From The Best In The World by Timothy Ferriss Nothing beats having a mentor in your life who can personally guide you from day one. But not everyone does, and if (like me), you don’t, it doesn’t mean that you can’t learn from the best virtually or through books. Take what you need from the likes of Ray Dalio, Ben Stiller, Bear Grylls and more in this varied but comprehensive compilation of bite-sized advice on life, work and purpose from some of the best minds in the world.


Trying to win at life from day to day is hard. It gets even harder when you’re struggling with thoughts that leave you feeling reactive to the world and heavy with painful emotions that hold you back from living your best life. Start re-framing your thoughts to calm your mind, feel good about life and create the mental space that’s a must to reach your highest potential with my FREE, 7-Day Calm Mind Challenge. You’ll also receive my best calm-living tips & trainings delivered to your inbox every week. Sign up for your dose of calm now.

Photo by Joshua EarleUnsplash

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