How to Learn to Feel Like You’re Enough

“Really, you’re that shallow? Wow.”

I thought this to myself the other day as I was getting dressed to go out and see some friends.

See, 2020 has been the most successful professional period in my life. Last year, I was working on ‘cracking the wall of success.’

Back then, I went to the coffee shop every day to write with a similar outfit on — a plain shirt, some basic pants/shorts, and one of the half-dozen or so shoes I owned.

Fast forward a year, and…I have a few more pairs of shoes. My apartment is a little nicer. I’ve saved the vast majority of my money, but I’ve upgraded a little bit in some areas. And I have to fight the urge to keep upgrading.

I looked through my whole closest and none of my clothes seemed good enough. Those same $5 H&M t-shirts I wore every day, without thinking twice, all a sudden didn’t seem up to par. I needed new shirts and pants to match the news shoes, and the new apartment, and the new lifestyle.

Why? I suppose because, like every other human being on planet earth, I’m driven by the desire to have more. Why? Because I must not feel like I’m good enough as is.

The answer to this riddle, however, isn’t to move to a cave and wear white linens. It’s not to abandon ambition altogether.

It’s simply to check yourself when you’re falling prey to those feelings of ‘needing to upgrade’ and ‘not feeling enough’ a little bit too much.

Success in life is this paradox where you do try to improve aspects of your life that are important. Resources create freedom and you need them. Earned accomplishments create confidence. Presenting yourself well does matter. But then you can also do too much of all the above and create a new inferiority complex based on desire.

The answer? Continue to learn how, when, and where to start and stop.

The Paradox of Desire, Contentment, and Self-Confidence

This is no easy mess to untangle.

On the one hand, if you feel like you’re enough, if you feel like a worthy person, that means you’ll feel entitled to be, do, and have certain things. After all, if you’re a good person with a solid work ethic who believes in the value you provide to the world, you do deserve success.

On the other hand, if you really feel like you’re enough just the way you are, maybe you shouldn’t want to achieve anything. You could make the argument that complete contentment leads to total inaction.

The answer is somewhere in the middle, right? That’s where the answer always seems to be.

Take something like money. Sure, you’re an inherently worthy human being with or without money. But money can buy you the freedom to do what you want. So the goal is to make money to use toward the right ends without having money define who you are.

That’s the crux of all this. It’s never the items or the stimuli themselves that determine whether or not you feel good enough, it’s you.

Some people like to dress nicely just because they like it, not because they’re trying to fill a void. Some people are natural explorers and travel the world while others do it for photo-ops.

Some people feign inherent worth because they don’t feel worthy, e.g., people who claim contentment but just lack confidence in their ability to achieve anything because they have low self-esteem.

Is there even such a thing as a totally whole, content, self-assured human being? Doesn’t aiming for those qualities themselves make you goal-oriented, thus trying to fill a void by not filling a void?

So far I’ve answered nothing because I don’t need to. The point is to paint a picture of the problem, let you try to solve it, and fail while getting closer to that sweet spot along the way. There’s no guaranteed way to do this, but here are some of my favorite strategies.

Attack Self-Doubt From Both Angles

I make it a point to talk to myself, sometimes out loud like a crazy person. I tell myself I’m good enough. I’m good. If I never write another book, I’m good. If I don’t make any more money, I’m good. If the outcomes I want don’t happen even if I work hard for them, I’m good.

I do this to counteract myself doubt that always tells me I’m not good enough. That I need to make seven-figures to be happy. That I need 10 million views a month. The voice that tells me I need to be in perfect shape, impeccably dressed, and impressive to everyone I meet.

You have to convince yourself to somehow go for what you want in life while simultaneously reminding yourself that none of your accomplishments matter at all and that you don’t have to accomplish anything to feel good enough.

This doesn’t work by itself, though, because confidence comes from competence. You need the fight the battle on two-flanks because the negative energy of your mind is too powerful. Sometimes you’ll try to convince your brain that you’re good enough, but it’ll say “Nah, look at your life.”

If you’re broke, out of shape, have terrible habits, don’t spend time learning, keep toxic people around, obsess and outrage over news and media, etc, it’s going to be hard to look in the mirror and think you’re good enough. So self-improvement, grounded by trying to remember you’re good enough in the first place, helps you feel good enough.

It’s all about the place you’re coming from. Dr David Hawkins explains this well in his book Power vs. Force:

“Power serves others, whereas force is self-serving.”

Try to come from a place of power, where you’re living the way you want to live in a way that benefits others, not the way you think you need to live to impress others so you can use their validation to feel good about yourself. Counterintuitively, you’ll gain even more confidence by serving others doing what you naturally love anyway.

This next point can help you do just that.

Money: The Root of All Interpretations

I love that I started writing for fun, not for money. I did it for free, for years, and then made money from it, so I don’t feel guilty about making money from it.

There’s a saying, “How you make your money matters just as much, if not more than how much you make.” This is a metaphor that extends to all areas of life. It’s not what you do, but why you’re doing it.

Take someone like Steve Jobs or Elon Musk. I can’t read their minds, but it just seems like their ambitions are such that the byproduct of what they do has to be billions of dollars.

I’ve even seen interviews with Elon where he talks about how he doesn’t care much about money and it sure doesn’t seem like he does based on his actions — after selling his stake in PayPal for hundreds of millions of dollars, he reinvested all his money into new companies with no guarantees of success.  The dude just has a large mission. Large missions require money and the successful completion of them gives you money.

Success in writing doesn’t equate to billions, so I don’t want billions, I want to become a great writer and share impactful messages. As far as your mission goes, I suggest going for a happy medium.

Yes, be mission-oriented, but also choose a mission that helps you meet some of your goals. Some people get half the equation right, e.g., social workers who do love to help, but their finances are such that they themselves are in total stress. This doesn’t mean don’t be a social worker, it means to find the medium that works for you.

Remember, you’re wired to feel validation form intrinsic and extrinsic sources. It doesn’t help to pretend like you’re not. Just focus on the ratio.

You’ll feel good enough, at your best, when you’re doing something that makes you feel good across all areas — purpose, competence, and compensation.

Play Your Own Tailor Made Success Game

Resist the urge to play status games. Keeping up with the Joneses will not make you happy. Build wealth for your freedom. Do things you love and enjoy, but do it for you.

Consumerism is such a tricky beast, isn’t it?

I love my Nike gear. I’m a big fan of Nike and I wear it just to wear it. Or do I? Would I wear the same quality clothes, the same exact design, except without the swoosh? Nope. I’m paying $150 for a swoosh on a pair of shoes, which is ridiculous.

You’re going to have vices guided by societal status, but you can also enjoy your vices while staying away from keeping up with the Joneses crowd. I like Nikes. I’m a watch guy. I like art. But I’m not a car guy, so buying a sports car would be fake.

Jay Leno is a car guy, so as opulent as it seems, owning all them damn cars is congruent. I follow a guy on Twitter who is a millionaire, spends $2500 a month on expenses total, reinvents 90 percent of his money, but he owns two nice cars. He’s a car guy.

If you like shoes, buy shoes. If you’ve always dreamed of buying a nice house, buy a nice house. You like looking good naked in the mirror? Workout five times a week.

Nobody is completely devoid of status-seeking behavior. Impossible. You can’t live life without following some script and having some desires programmed into you.

Just keep it in check and understand your vices won’t make you happy. That, and don’t ‘clout chase’ which, for the non-hip folks out there, means you do, have, and be certain things strictly for the attention of other people.

Stack up your paper, live below your means, have a few trinkets and toys, don’t become a slave to them.

There’s No Perfect Answer

I decided on an outfit, hit the restaurant to visit my friend. We talked for hours. Not once did I think about the clothes I was wearing.

Balance is the key. Living within the paradox is the key.

Life’s best moments are usually spent enjoying time with others, engaging in crafts you love, experiencing moments from super-cool to banal that keep you in the present moment. But also, success facilitates your ability to do more of the above. Get stuck in the rat race and you have less time for those things.

And then there’s you. Inherently knowing you’re good enough logically, but having to wrestle over it emotionally. If you know me, you know I’m not the type to give you the perfect prescription.

Just know that you’re pretty much the shit already and you just need to figure that out.

Getting there is a combination of working on yourself in the worldly realm and working on your attitude at the same time, both of which have a symbiotic relationship with each other.

You do this your whole life, get some success and failures along the way, die, turn back into the matter of the earth, and disappear into the annals of time never to be heard from or thought about again.

This is life. Try to live it well.