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How to Be Successful on Your Own Terms

How do you define success? This isn’t an easy question to answer. But it’s likely your current definition of success wasn’t a deliberate choice. For most people, our definition of success is handed to us from the world around us. That makes it difficult to be successful on your own terms.

How You Lose Sight of Success on Your Own Terms

Peers, Parents, and Society

We believe that we can’t be successful until we cross off all the checkboxes of society’s life plan.

When I was younger, my definition of success was pedigree and money: the most impressive jobs, a prestigious degree, and the highest salary. The world encourages us to pursue this definition. Saying “I’m going to Harvard Medical School” sounds more impressive than “I’m trying to write books for a living.” (especially if you’re talking to Indians or Asians).

My friends in high school were brilliant. Those of us who went to Berkeley were the dumb ones. My culture planted the seed for this narrative; my peers watered it; and the world around me reinforced it.

Internet, Media, and Culture

Fast forward to the early 2000s, Tim Ferriss published The 4-Hour Workweek. After that, a whole subculture of digital nomads preaching and selling “success on your own terms” was born.

Chris Guillebeau spread the message of non-conformity, while hundreds of thousands of people paradoxically conformed to those ideals. They aspired to travel hack their way out of the monotony of life in suburbia.

What followed was a mimicry epidemic of lifestyle design bloggers, life coaches, and other jobs that didn’t exist. Bloggers got book deals; YouTubers became stars; and the birth of the influencer led to the death of hobbies.

Yet, somehow we overlooked that all we did was trade in society’s definition of success for some Internet celebrity’s definition. And like most people, I bought into the delusion that this was what it meant to be successful on your own terms.

Unlike the previous game I was playing, I started to win at this one. I built an audience; became a Wall Street Journal best-selling author, and got a two-book deal with the biggest publisher in the world. I was “successful” according to strangers on the Internet and my status.

But at the height of my professional career, I was at an emotional rock bottom.

The Hidden Danger of Other People’s Expectations

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Community and Culture

The most well known Indian spiritual text is the Bhagavad Gita. One of its primary messages is that we’re not entitled to the fruits of our labor. But as a culture, our primary metric for success is the fruit of someone’s labor.

  • What degrees do they have?
  • How much money do they make?

We attempt to live up to other people’s expectations and their definitions of success. And we forget that they won’t be the ones to live with the consequences of our choices and circumstances. Whose life is this anyway?

By the standards of the Indian community, especially when it comes to marriage prospects, I’m a flight risk. I’ve chosen a path in life where nothing is guaranteed and anything is possible. I don’t want what most of them want. This isn’t exactly what most Indian families want for their daughters.

But this isn’t isolated to Indians. It’s universal.

The Crossroads of Should and Must

When we arrive at what Elle Luna calls The Crossroads of Should and Must, we choose “should” over “must.” Then, we wake up and wonder why we’re so dissatisfied with our lives. Success on your own terms is about choosing “must.”

It’s easier said than done because there are so many “shoulds” that society imposes on us. You should:

  • Work at a stable job with a steady paycheck.
  • Pursue a prestigious degree or job.
  • Stay at a job after working so hard to find one.
  • Stay in a relationship even if it doesn’t feed your soul.

But none of these things might be right for you.

Choosing Must

Six months after I graduated from business school, I finally found a job. Within 6 days of working there, I had a familiar feeling. My stomach was hurting, and I was smoking cigarettes at lunch. Nobody in their right mind would leave a job after a grueling job search in the midst of the worst economic recession in history.

I’d arrived at my very first crossroads of should and must. In The Matrix, Trinity picks Neo up to drive him to Morpheus. When he threatens to get out of the car, she says, “You know where that road ends.”

The whole point of my MBA was to never work the exact job I was working in. If I stayed there for another day, I knew where the road would end.

I didn’t give a two-week notice. I just walked out the door, and never looked back. If I hadn’t, there might not be an Unmistakable Creative Podcast. I might not be doing work I look forward to every day.

A Goal is Empty Unless you Know Why it Matters

When it comes to money, we set money goals like earning a six-figure salary, becoming a millionaire or having “fuck you money.”

The purpose of wealth is freedom. It’s nothing more than that. It’s not to buy fur coats, or drive Ferraris, or sail yachts, or jet around the world in your Gulfstream. That stuff gets really boring and really stupid, really fast. It’s really so that you are your own sovereign individual. — Naval Ravikant

When it comes to money, we never bother to ask why we want this goal? When we do this, we overlook the purpose of wealth and the illusion of the next level.

Base Your Goals on Experience

Most of us base our goals on the advice and approval of peers, parents and society. We don’t base them on our lived experience.

Career Choices

We think we want to be doctors, lawyers, and engineers or work at Google, Goldman or Mckinsey. All of these are fine career choices and great companies. But you can’t base your calling solely on assumptions and advice from other people. As Tina Seelig says, “Passion follows engagement.”

What You Find Engaging

If you’ve never worked at a hospital, how can you possibly know you’re passionate about medicine? Like most Indian kids, my parents thought to become a doctor was a good life path. But it wasn’t for me. When I told my parents I get sick all the time and I hate hospitals, they said, “You’ll develop immunity.” Fortunately, my sister satisfied every Indian family’s need to have at least one doctor.

Undergrads at elite schools across America believe that investment banking is their golden ticket. Yet most of them have never worked at a bank. When I found out what they actually did all day, it sounded mind-numbing.

One of my professors said I was a “hell of a salesman.” I didn’t have the GPA for consulting firms and investment banks, so I pursued a career in sales. It was the only way I could make just as much money as my friends.

It took me years to come to terms with the fact that I HATED working in sales. I couldn’t stand sitting at a desk making cold calls. What my professor spotted was an ability to give great presentations. So it’s no surprise I’m a public speaker.

Envying people on the Internet who are “living the dream, crushing it, etc.” is just a different version of the same. Someone else is still defining success for you.

Don’t blindly follow something you think you’re passionate about. Pay attention to what you find engaging.

Treat Other People’s Advice as Ingredients. Create your Own Recipes.

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When it comes to success, we have a cognitive bias. You won’t necessarily become a millionaire by doing the 10 things Ben Hardy says you should.

X does Y and Z happens. So we think it will happen to us. But nothing in life is a one-size-fits-all solution.

For example, If I followed Lebron’s work out to the letter, I’m not going to make it to the NBA. Or let’s consider a more common example. Some person with a massive email list (x) starts a podcast (y) and It skyrockets to the top of the iTunes charts (z).

Assuming the same will happen for you is a cognitive bias at work. There so many other factors at work. Maybe people hate the sound of your voice or you hate the process of recording a show.

The worst possible career advice I could give someone is to follow in my footsteps:

  • Get fired.
  • Get lucky and have an editor at a publisher find your article on Medium.
  • Live at your parents’ home way too long into your adult life.

Following that advice would be idiotic. We like the idea of reverse engineering success. It’s easy to package and sell. It makes for great copywriting. And yet we fail to see that we are the variable that throws off every formula.

Frameworks vs Formulas

The wisest thing anyone ever said to me about this was Michael Roderick. You want to think in frameworks, not formulas. Looking through the lens of a framework mitigates your cognitive biases.

James Clear shared the writing process with me behind his wildly popular blog in an episode of the Unmistakable Creative. Initially, I tried to look at one of his blog posts, and match the steps. It didn’t work. But when I applied the PROCESS to one of my own pieces of writing, I was amazed by how effective it was.

  • Organizations depend on best practices because it lets them off the hook.
  • Individuals depend on formulas because they think it will give them some sort of shortcut.

But both of these things lead to mimicry instead of innovation and creativity.

It’s impossible to be successful on your own terms when you’re always following other people’s advice. Yes, they might approve of your choices and sing your praises. But you’re the only one who is going to live with the consequences of your decisions. You’re the one who has to show up at the job you hate, regardless of how impressive it looks on your resume.

Advice isn’t a One-Size-Fits-All Solution

If you have kids, you know that you can give both the same advice and end up with wildly different outcomes. My parents did their best with both me and my sister. And their perspective made complete sense. In their generation, life was binary. It was security or poverty. So they based their advice on that experience.

Me and My Sister

My sister graduated from Berkeley with a high GPA and got a master’s degree in Anatomy. She became one of the top students at her medical school and the chief anesthesiology resident at Yale. I couldn’t be more proud of her. And I joke with my friends that if you’re in a room with her, she’s probably the smartest one in it. My brother-in-law is a close second.

The same life plan helped me get into Berkeley. But it was all downhill from there. I ended up with a piss poor GPA and a resume of failures that looked more like a rap sheet. And I was rejected from every business school where I applied.

Did my parents do something wrong?

Not at all. Even though they weren’t rich, I grew up in privileged circumstances. There was never a question about whether or not I was going to college. They invested whatever they could afford in the future of my education with SAT classes, flights to colleges and more.

But, I was a creative person who never had a creative job. And when you mismatch talent and environment, you get poor job performance.

You have to define success for yourself. You can’t let Dave Ramsey, Tony Robbins, or any other person define it for you. Dave would certainly disagree with the way I’ve handled my student loan debt. But I’m sure the people who listen to Unmistakable Creative could give two shits what he thinks.

It’s easy to scroll through your news feed, read sites like Medium, listen to podcasts and read self-help books. But basing your definition of success on that is a recipe for dissatisfaction. Treat other people’s advice like ingredients but come up with your own recipes.

Don’t Use Outliers as Your Role Models

Outliers write books, make headlines, build empires and end up on magazine covers. But they are unrealistic role models if you want to be successful on your own terms.

Consider the following advice I got from my old mentor, Greg:

They were born in a way that they are just going to win no matter what and so those people are not good models to follow for the rest of us. What we should be doing is we should be creating a safe environment in which we can be as vulnerable as we need to be to not only hold on to the possible, but you actually increase our chances of the probable.

And we don’t create those environments for ourselves as a society as a government as businesses as a culture in America. We tend not to create vulnerable environments that allow us to be safe enough to be exposed enough to actually increase our probabilities. So what we do is we look at all these examples of people that don’t need that, and we try to live like them.

And then we fail, and then we experience unnecessary suffering. We hold on we can’t find the safe places to explore our vulnerabilities and our flaws and the fact that it’s not probable for us to be like them. So what we do is we go to the safe places.

It’s the safe places are the motivational events. The safe places are the places where everyone else is pretending to be happy. The safe places are the Internet and the television and the happy commercials and all the things that allow us to avoid looking at the things that are not increasing our probabilities of success.

When we use outliers as our role models, we develop delusional optimism. We start to believe we’re going to end up on Oprah or sell our unicorn for a billion dollars. The gap between expectations and reality widens. Along with it, our misery increases. We continue to chase unrealistic dreams that just seem out of reach. Where has this gotten you so far?

Pursue Significance Over Status

The most celebrated people in American public life today – athletes, business leaders, Hollywood Stars, politicians – are generally known for their resume virtues, not their eulogy virtues. They’re admired for their physical attractiveness, charisma and professional success, not for their kindness, decency and generosity. — Sarah Hurwitz, Here All Along

As individuals, we optimize our lives for what society celebrates. And we live our lives chasing the false horizon of the “I’ve made it” moment.

  • Kids stress out over grades, activities, and accolades.
  • Aspiring artists don’t see the value of creating for An Audience of One.
  • Businessmen/founders work their fingers to the bone, even if it means leaving complete destruction in their wake. Who cares? You can fix all these things when you have “fuck you money.”

If society doesn’t celebrate kindness, decency and generosity, eventually we’ll have less of it. For all the good that social media has brought to our lives, it’s also turned all of us (myself included) into self-obsessed narcissists. This message is reinforced by book titles like Choose Yourself, The Life-Changing Magic of Not Giving a Fuck, etc. etc.

The media we consume, and our use of social media fuels a toxic internal narrative. It convinces you that your life is worthless unless you’re the next Steve Jobs, Oprah or Beyonce.

Eulogy Virtues vs Resume Virtues

We are deluded into thinking we are chasing success on our own terms. By definition, the “I’ve made it” moment is not success on your own terms. It’s determined entirely by external metrics. This kind of success is all about resume virtues instead of eulogy virtues.

With age, your definition of success will change. You’ll come to the realization that no matter how much you acquire, you go to your grave empty-handed. All that will matter is what kind of person you were.

You Will Never Feel Like You’ve “Made It”

For about 3 weeks after I self-published a Wall Street Journal best-seller, I felt like I had made it. It was the same when I got a book deal, and raised a round of venture funding.

Once these things became normal, I found that I still had the same insecurities and doubts. Or as I like to say, I’m still the same screwed up person I was before.

I don’t, by any stretch of the imagination, feel like “I’ve made it.” I still wake up and do the same thing I’ve been doing for 10 years: read and write.

One of our podcast listeners made an interesting observation about me:

I wouldn’t have thought that Srinivas Rao would have many insecurities given the success of being an author and building a community.

Achievement is nothing more than a Band-Aid for your insecurities.

And family is a good way of keeping that in check. My parents are proud of my accomplishments, but I wouldn’t say they’re impressed.

  • My dad still yells at me for leaving the lights on and explains, “It’s not Diwali so turn them off.”
  • My mom still gets on my case when I leave the cap off the toothpaste.

Even if I took a company public, these things would still be true. Regardless of who it is, if you’re trying to impress people with your achievements, you’re only going to succeed on their terms.

Want Less and Have Enough

Throughout our lives, we are taught that more is better. Bigger is more impressive. This constant desire for more ensures that we are never satisfied—always on the hedonic treadmill chasing false horizons. But as my friend, Paul Jarvis, once said, “In any field other than business, infinite growth is called cancer.”

The progress of humanity depends on your desire for more.

  • You need to buy more shit to keep companies in business.
  • You need to pursue more ambitious goals for progress and innovation.

But if you want to be successful on your own terms, you have to see this for the illusion that it is.

If you want to live a life of abundance, the fastest path to getting there is to want less and have enough.

There’s No Better Version of You in the Future

There is no better version of you waiting in the future. The best version of you is who you are right here, right now, in this fucked up, impatient, imperfect sublime moment. Shut out the noise and enjoy exactly who you are and what you have right here, right now. — Heather Havrilesky

We are always thinking about whatever is next. In doing so, we forget to celebrate and appreciate today. We take it for granted that we are even alive.

We buy into the delusion that our accomplishments will alter our self-image and increase our confidence.

  • Sell more books.
  • Make more money.
  • Date a hotter girl.
  • Drive a nicer car.

The checkboxes of society’s life plan and our never-ending pursuit of accomplishment cause us to seek more and chase false horizons.

A million dollars isn’t cool. You know what’s cool. A billion dollars.

What’s the point of having fuck you money if you can’t say fuck you.

The goal post for success keeps moving. We keep chasing it. All because we believe there’s some better version of ourselves in the future.

Ryan Holiday’s new book, Stillness is the Key reached number one on The New York Times Best Sellers list. On his Instagram post, he said: “If at first you don’t succeed, try 8 more times.”

Other authors said things like “You give us hope.” But what he said to me in our interview is more likely to make you a happier person.

I don’t feel good because I haven’t broken into that next level. So I just have to keep going. I’m almost there. But if I:

  • Sell another book.
  • Get a book that sells a million copies.

Then, I’ll finally have:

  • All the money that I want.
  • All the audience that I want.
  • More influence than I know what to do with.

Then, I’ll feel good. My parents will be proud of me, and all will be well, and that’s what a lot of people do.

They make it to first base. They hit single, and they say,Oh, that was great.” But like hitting a home run. That’s what it is. Then they hit a home run, and then you go, “Ah, it’s a grand slam.” That’s what it is. No, it’s hitting a grand slam in a World Series, right? Oh, it’s citing the biggest contract in baseball.

You can see how that belief drives a lot of accomplishment, right?

It is good in the aggregate, but on the individual level, the truth is, that it’s a lie.

My personal addiction to achievement sent me into one of the darkest periods of the last 10 years. Instead of being grateful that I got to write a second book with a publisher, I was miserable because it wasn’t selling more copies.

My sister made a wise observation. “That means you don’t even believe what you wrote in your own book. Why would anybody buy that?”

I put on my game face for my conversation with Chase Jarvis and promoted the virtues of creating for An Audience of One.

Yet, deep down, all I could think about was the next book, and the next mountain to climb. I forgot one of the fundamental lessons of creative success. It’s a lesson that Neil Gaiman forgot at the height of his career too: enjoy this.

When you always believe there’s some better version of you waiting in the future, you suck the joy out of the present. The paradox of becoming the next best version of yourself is that you have to accept and love the current version of yourself.

The Illusion of Eternal Happiness and the Hedonic Treadmill

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Nothing you accomplish will permanently alter your self-image or lead to everlasting happiness. The “high” of getting a book deal wore off after about a month. And a year later, I was still unhappy about certain aspects of my life. It’s easy to forget you still have to deal with the person in the mirror when you accomplish a goal.

As you fool yourself into thinking we’re climbing the ladder for success, the goal post keeps moving. Every distant dream becomes your new normal. You:

  • Become a published author and success is a best-seller list.
  • Win a silver medal and success is a gold.
  • Become a millionaire, but your neighbor has more, so success is a billion dollars.

And instead, you find yourself on a hedonic treadmill. You keep trading in your current definition of success for a more impressive one.

Throughout our lives, the goal post for success will keep moving. That’s human nature. We have to be careful about this. Or we’ll get caught up in the ego-driven pursuit of a life that looks good on paper, instead of pursuing one that is.

It’s not easy to be successful on your own terms. It’s far easier to write an article like this one than it is to live and breathe the principles in it.

I still struggle with my desire for validation, particularly from my parents. After all, I’m not saving any lives or showing up at a hospital to do God’s work. I haven’t planned a wedding or given my parents grandkids. Layer social media, Medium headlines about success, IPOs and six-pack abs on top of that, and no wonder people are completely self-obsessed, anxious, insecure and depressed.

You’re not going to be successful on your own terms by reading self-help books and hiring life coaches. It doesn’t matter if you’re listening to podcasts or finding the perfect mentor. This is an inner job. Somebody might be able to guide you, but at the end of the day, nobody can do that work but you.

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