Welcome back. Today, I’m going to discuss the not-so-secret secret sauce that everybody needs, but very few can explain how to get:
Self confidence.
It opens doors.
It makes you respectable and attractive.
It picks you back up when you hit the ground.
It gives you a forcefield against negative emotions.
I can remember when I didn’t have it, and all the ways I tried to compensate for that (they didn’t work).
I can remember what had to change before I could truly acquire it,
And I can see and appreciate all the ways in which I now live in a different world, living a different life, on account of finally having it.
The reason the confident and the unconfident person live in different worlds is because each sees the world differently:
Different perspectives cause different observations,
Different observations cause different conclusions,
Different conclusions cause different actions,
And different actions cause different results.
This is why I’m here to lay out the 3 distinctions that separate confident people from unconfident people:
It really is mental. Well, it begins that way. When you start enacting the new understanding I’m about to lay out, you’ll soon find everything changes, not just your thoughts.

Distinction One: preparation, not faith
Oxford Languages defines “confidence” as “the feeling of belief that one can rely on someone or something; firm trust.”
To be self confident, then, is to be convinced of oneself.
If you were going to make a significant purchase, what would convince you of your ability to do so, checking your account balance and reviewing other upcoming expenses, or quietly affirming to yourself “I am abundant, prosperous, and wealthy?”
The numbers adding up is what convinces you. This is why companies have finance and accounting departments: confidence comes from evidence, not faith.
When I lacked confidence, I would try to pantomime the behaviors of a more confident person. Sooner or later, however, I always self sabotaged. I self sabotaged because, deep down, I knew that I didn’t know what I was doing.
I was unprepared!
How did I remedy this?
There’s no shortcut for this, and that’s why it separates the committed from the merely wishful: I started putting in the time.
Let me give you some examples:
With respect to my musicianship, I began actually practicing my guitar to a metronome for a minimum of 30 minutes every day. I began reading through the sheet of music of, say, Mozart’s piano sonatas and John Coltrane’s saxophone solos.
In other words, I began to systematically learn new musical ideas, practice them to an unforgiving click that would reveal, rather than flatter, my technique, and, as a result, I began walking into my rehearsals feeling excited and intentional about getting into the material and applying what I was learning.
I wasn’t afraid to make mistakes, because I had clear targets for what I was trying to implement, and I was willing to make as many mistakes as it took before I could demonstrate a command of the material.
As a result, I take more risks, try things that push my limits, and feel pretty uninhibited about floating ideas about how my band might realize a particular song or evolve in general terms.
I don’t just have faith in myself: I have repeatedly gone through the process of introducing, developing, and mastering new ideas. Some of them work, some don’t, and I know how much practice it takes before you can really tell the difference.
I have the confidence to assert my ideas, even in an inchoate form, because I have the evidence of my previous successes and failures to lean on: I know I can do this.
It is the same with writing. Once I found templates and guidelines from credible sources, I just began implementing them, publishing short form content to X every day, and, eventually, newsletters like this one every week. Every time I hit “publish,” I’ve created more evidence that I can do this. This thing I’m doing now is a thing I have done before, and with each successive word that I write, each new word that I have to write becomes smaller and smaller in comparison to the total lifetime volume.
In the beginning, it was hard. But one article is evidence I can do it. Twenty articles is proof that I am doing it.
The same applies to weightlifting, or discussing a sensitive topic with my girlfriend: I’ve done this before, and the evidence of my past efforts both gives me the confidence to try now and the experience to avoid error. I have faith, yes, but it is faith informed by evidence.
How to generalize this and apply to your life:
Take some quiet time for yourself and write down in a doc or in a notebook about the areas where you don’t feel solid. There might be a couple, there might be several. Just pick one for now.
Write down all the “wins” you can think of for this topic. Let’s say you want to get your finances together, or feel together about them. Create a checklist of everything someone who feels confident about money would be able to say.
For example: how often do you check your balances? Do you have a place where all your recurring expenses are written down? Do you track your one-off spending? Are you saving money? Do you have a notice or a spreadsheet that’s set aside for this? Do you have a time set aside once a week for this?
When you are happy to answer all those questions, and this holds for six months, you have established some evidence that you have your finances together, and what you get in exchange for this is confidence. What you lose is anxiety.

Distinction Two: rules, not exceptions
Confidence is all about feeling solid, and that includes solid boundaries. Yes means yes, and no means no.
Do things you know you shouldn’t do,
Say things you know you don’t mean,
Get involved in situations you feel uneasy about,
And stifle the impulse to say or do something,
And you have only confused yourself.
On the one hand, it’s your life.
On the other, it doesn’t seem like you realize that.
Owning your life, really taking charge of things, is about defining the rules and sticking by them. Enforcing them.
Have you really quit, or just cut back?
Have you cut back, or are you just saying that?
Did you break up, but keep answering late night texts?
Did you say you wouldn’t eat that, and yet you are?
Are you uncomfortable with how much you’re on social media, but don’t really make changes?
All these situations undermine your sense of self confidence for two reasons:
You’re shutting out your intuitions.
You’re not abiding by your decisions.
Your intuitions should be the source of your rules.
Your decisions enforce them.
When I say that I live by my own rules, and I do, I don’t mean I break the rules of society, or that I care less about the consequences of my actions than others –
I mean what Socrates meant when he said he has an inner dæmon that calls bullshit when he says or does or is about to say or do something that he knows to be not quite correct and forthright but merely expedient. When you don’t know better, then you don’t know. You can’t act consistently with knowledge you don’t have. But if you do know, and here I’ll sound a bit authoritarian, you must obey. Not because someone else said so, but because you said so!
I cannot overstate how much self-confidence has followed as a result of knowing myself to be free from as many contradictions as possible. When I know I’m wrong, I admit it and correct course. When I think I might be right, I dare to speak up, find out, and abide by the results with dignity. When I know I’ve said or done something I find morally offensive, I apologize. Even more importantly, I do not apologize simply because someone else is offended: perhaps they are unreasonable, or have incomplete information. Sometimes, an explanation is needed, even if an apology is what is expected.
When I know I’ve done nothing wrong, I offer only information, courteously, but never an apology. One person’s indignance does not inspire my contrition, but my sense of right and wrong does.
This is called having some respect for yourself, having some boundaries, and having an internal locus of self worth.
I know right from wrong.
I know I have impulses that fly in the face of my moral judgments, and I know that I am the best person to police my impulses in the name of my moral judgments.
Kant said that only that action that runs contrary to inclination has moral worth, and this is what he meant: an adult is a responsible parent to the eternal child within. You do not capitulate to children, but you do negotiate with them: you set clear expectations and boundaries, and you make proper behavior as appealing and richly rewarded as possible. You overcome destructive impulses with sustained corrective pressure. You do this as an investment in the realization of their potential. This is love.
And, when you do this, you are a person with moral worth, and a deep wellspring of self confidence. A child without boundaries is anxious, not comfortable, not confident.
How to adapt this to your own life:
Make a list of the promises you keep breaking for yourself. Come up with concrete strategies for finally keeping them.
If you promised yourself less screen time, buy an exciting book, and set down the phone in another room until the next day.
Buy an actual alarm clock, instead of using your phone.
Purchase your next book when you’re within 100 pages of finishing the book you’re in now.
Treat the promises you make to yourself like contracts that would incur steep fines and reputational damage were they to be broken.

Distinction Three: inner, not outer.
Confident people are confident because they address underlying issues, rather than cover them up. Let me make one caveat here, worded as an additional distinction: not necessarily permanently resolved, but resolved into a plan. Resolved into a system where the problem is managed.
Some things can be overcome with a little planning and effort: go and overcome them (this is what distinction two is all about: “I solve all the problems I possibly can” is a rule everyone should follow).
Some things, however, need ongoing management. You can manage them from one of two places: the inside or the outside.
Eating right, drinking plenty of water, and getting plenty of rest and vigorous exercise would be managing your appearance from the inside. You look good because you are healthy. The exterior is an expression of the interior.
Managing it from the outside means covering up imperfections. Outer presentation is necessary and important, but you know exactly what I mean: can you say you show care and respect to your body and its needs?
Finances are the same way: are you working to increase your productive capacity, finding ways to offer more valuable skills to the marketplace, becoming more efficient and reliable, and adventurously expanding your horizons,
Or is your courageous plan to settle for second best so you can afford to retire?
You resolve money issues by inwardly transforming your capacity to generate it. For example, I write, and invest in every opportunity to become a better writer, so that writing can one day replace my day job. That’s an example of managing it from the inside. As a result, I don’t quite feel so self conscious about where I am in those terms, and I don’t unfavorably compare myself to others: I have a plan, a goal, and a system for getting me there. It will take time, but, here I am, putting in the time.
That’s inner work. And, here’s how it’s distinct from our first distinction (evidence, not faith):
Yes, all work creates persuasive evidence, but the confidence that comes from working to resolve rather than working to conceal comes from reducing the number of loose ends, rather than adding to a pile of wins.
You don’t win the game of fitness, or career, or relationships, or creative, artistic pursuits. You don’t win the game of learning. What you do is stay in the game. And you stay in the game by accounting for and managing the entropic forces that could eventually take you out of the game:
Hubris, apathy, futility, atrophy, boredom, cowardice.
Essentially, you stop trying, and one day you realize you’re no longer in the game of life. You’re replaying it in your head. Activity lives in memory.
The answer to this is to envelope whatever cannot be truly defeated into a system that can be run in perpetuity.
Some examples you can use?
Date night every week is a system.
Reading books and studying new things is a system.
Staying physically active is a system.
Calling and texting to check up on people is a system.
Having ongoing projects, the more difficult the better, is a system.
Always having something in your life that you’re taking to the next level is a system.
A newsletter every week, a handful of pithy tweets a day, is also a system.
I was born a mass of weakness, ignorance, incompetence, and selfishness: converting as much of that coal as possible into the diamonds of strength, knowledge, skill, and caring with the time I have available to me
Is a system.
And what confidence does that give me? The confidence that this will not be a wasted life.
Thank you for reading, talk to you soon.
Jas