How to Guarantee Success Without Ever Doubting Yourself

It all comes down to your definition

Kunal Walia
Age of Awareness
8 min readAug 6, 2020

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In the hustle and bustle that is life, in the daily grind that keeps us going, have you ever once stopped to ask yourself, “what does success really mean to me”?

What if you got this fundamental question so drastically wrong? What if, after all these years, or even decades, you’ve been pursuing the wrong definition of success?

Perhaps you’ve been seeking fame, but when you come to think of it, you don’t really want to be famous…

Maybe that’s why you’re not seeing the results you desire. Maybe that’s why you never feel happy with the progress you’re making. Maybe that’s why everyone around you is so impressed with your accomplishments, but to you, “it’s no biggie”.

In every ambition you hold that is predicated on your desire to become successful, 50% of the battle is knowing what success truly means to you.

Failing to address this question truthfully almost always leads to a state of confusion. And according to our friends at Psychology Today, such confusion is more prevalent than you might think:

“…[Young people] take for granted one particular definition of ‘success’ given in the dictionary: namely… ‘the gaining of wealth, fame, rank, etc.’…”

The first step, therefore, is to determine what success really means to you. Only then can you think about how to use this to your advantage.

‘Success’ Is a Puzzle With Too Many Pieces

There are countless variables that influence how successful you feel at any given point in time. And when you combine these pieces of the puzzle and attach varying degrees of importance to them, you’ll end up with a definition of success that is well, entirely unique to you.

Examples of these components that make up the DNA to your “successful being” include your:

With so much to consider, in reality, no two people are likely to share the puzzle, even if the pieces look similar.

In her recent podcast, Michelle Obama discussed how she quit her corporate law job to take up a role at a non-profit. She was desperate to reach out to the broader community of Chicago. She felt lonely reviewing stacks of legal documents in a high-rise building.

Giving back to the city that gave her so much as a child, was what success meant to her. But that doesn’t mean that’s what success should mean to you too.

At the end of the day, there are lots of ways to skin a cat. But not all of them will best suit you as a person.

So the question really becomes, is your current definition of success most suitable to you and your personality?

But What If Your Visibility Is Being Blurred by Your Surroundings…

So where do you begin? How do you figure out what matters most to you, and you alone?

It’s hard to pinpoint this exactly. Often, we tend to absorb the definitions of success that matter most to the people around us. We take on board what our parents aspire us to achieve. We relate to the dreams our classmates once narrated to us during recess.

Eventually, we end up defining success in terms of other people’s definitions because that’s what’s most visible to us, there and then.

You bump into a childhood friend who you haven’t spoken to in years, and they tell you how they’ve just landed their fifth book deal. Is that what success looks like these days?

You switch to CNBC and suddenly see a former colleague giving an interview on on why the stock market keeps going up. Maybe success actually looks like this…

With exposure to so much, it’s genuinely hard to tap into your inner self and determine what your own version of success looks like.

And so, your version of success will always be at risk of falling into the lap of how other people define this concept, if you allow it to, that is.

There’s an Element of “Trial And Error”

If you’re struggling to determine what success means to you, my advice would be to try your hand at everything.

For the next couple of years, say “yes” to every opportunity that comes your way. The aim is to see what you like, what you don’t, and to find what feels natural.

Gary Vee phrases this nicely when he says “close your eyes until you’re 29”. In other words, if you’re currently in your twenties, don’t get caught up in the desperation to find immediate success. Instead, figure out what matters to you and what doesn’t.

And while this advice sounds most appropriate for most 20-somethings, it’s still equally important to try as much as you can until you figure out what it is you want.

Six years ago, when I earned my first paycheque, money was my definition of success. Seeing a few numbers hit my bank account every month felt like I was progressing in life. And so I went on to define success as my desire to reach a certain salary by a certain age.

Fast-forward a few years, and I’ll tell you that it’s not the money itself that matters, it’s what I do with that money. It’s how I invest my earnings, the feeling I get when I decide what to buy, and what to save.

Does splashing out on a fancy meal or high-end clothes make me feel successful? Nope. I’ve tried that, and I don’t find it as glamorous or rewarding as others might. But I wouldn’t have known that unless I tried it out.

After a considerable amount of trial and error, you’ll know what measure of success best suits your personality. You’ll know what’s worth chasing for and what isn’t. Often, it will exist in the state of what feels most natural to you.

Invest the time up front to figure this out, even if this means trying everything until you’ve understood what makes you tick and what doesn’t.

Flexibility Will Help You Achieve Great Things Forever

One clarification to stress: once you’ve determined what success means to you, it’s crucial that you don’t stay rigid on this definition.

Your mindset will evolve — just like it did for me and how I view money. Your goals will change, your circumstances will need adjusting. There will come a time when you need to tailor what success means to the current version of you.

If you’ve now got a family to feed, success probably means bringing food to the table, or balancing your career with time spent dearly with your kids. Gone are the days when it was all about seeing as many countries in as little time as possible.

This is where a 5-year plan comes in handy, or even more frequent checkmarks if you prefer. Noting down what your plan is for the next few years gives you a chance to reflect on how you’ve evolved as of late, and whether your existing definition of success is due for a software update too.

How to Let Go to Feel Comfortable Again

Let’s say you’ve done all this, and you’re now happy with your existing definition of success.

Now what?

Now the real test begins.

You see, it’s remarkably easy to be persuaded or allured by other people’s versions of success. Again, it goes back to what becomes visible to you.

Your old school pal, Bobby phones up to tell you how he just bought his second house. He asks what’s new with you. You tell him you’re still renting because you need to be closer to town in order to work on your latest start-up. But now you’re questioning yourself with thoughts like, “it sure would be nice to get on the property ladder.”

What I’m describing here is essentially a variant of FOMO (“fear of missing out”).

Going down this line of thought naturally leads to a whirlwind of self-doubt. In reality, such comparisons are meaningless — it’s simply a case that Bobby’s version of success is different from yours.

Nothing more, and nothing less.

And because your versions of success are so uniquely distinct, yet so visible to each other, you’re naturally exposed to the opportunity to compare, contrast, and eventually, fear what you’re missing out on.

Mark Manson described this wonderfully in a recent video:

“Actually what freedom really is, is knowing what to give up. It’s knowing what you’re committed to.”

In other words, you have to learn to let go of the idea that you must pursue everything. If you’ve defined success in the right way, this is an easy skill to implement.

Every Decision Comes With an Opportunity Cost

But if you find yourself at risk of constantly being swayed by how other people view success, then you have a choice to make.

Choice #1: Restart your journey and return to the “trial-and-error” phase. There’s nothing wrong with this, as you long you admit to yourself that you’re still unsure what success looks like to you and that you need to figure this out again.

Crucially, you must be 100% convinced that you’re not just being swayed for the sake of it. That’s the worst possible route to take.

Choice #2: Trust your gut, go from 2nd to 3rd gear, and continue cruising in your own lane. Forget about the traffic that’s passing by. They’re on their own journey, you’re on yours.

If you go for the second option, it’s often useful to think of your past and future decisions in terms of opportunity costs. Economists view this as follows: if you buy a bar of chocolate, you’ve incurred the cost of not buying a can of Pepsi.

If you buy a new car, you’ve incurred the cost of not saving your money to invest in the stock market.

The examples are endless, yet regularly overlooked.

And so when you begin to think of every major decision in terms of the opportunity cost it will incur, you begin to digest the consequences of switching away from your original path.

You begin to understand that the very act of pursuing somebody else’s definition of success because it looks more appealing, would mean incurring the cost of giving up on your own.

After all, chasing the wrong version of success is time spent away from chasing the right one.

A Final Thought

Take the time to figure out what you want, and what success means to you. Adopt a “trial-and-error” approach until you figure this out, and when you do, make sure to update it at regular intervals as you progress through life. Never stay rigid on an out-of-date definition of success.

And remember, your brain will always be tempted to switch lanes based on what it sees. But falling victim to other people’s aspirations will only incur the cost of giving up on your own. And you and I both know what a terrible outcome that would be.

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Kunal Walia
Age of Awareness

27. Finance nerd by day. Writer by night. Dreamer at all times. Finding new ways to learn. Sharing more ways to grow.