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How I Went From Broke and Stuck to Earning a Living Doing What I Love

You know why I write these types of posts?

Because I have a feeling I know just where you’re at right now. You’re probably like I was a few years ago

You want more for your life. Specifically, you want to make some sort of bold move.

Maybe you want to start a side business, become a writer, switch jobs, start networking more, create something, anything, do something, anything.

Today, I want to talk about how you get to that something. And I’m going to talk about it from the perspective I have right now.


I’ve figured out how to do a lot of different things to get where I’m at today. I learned how to write, how to market myself, how to get site visitors, how to outline a book, how to write a draft, how to publish the thing, how to market it, etc.

The truth? The technical ‘how to’ steps of accomplishing something aren’t difficult at all. In fact, all of the business courses you see available…actually work. I’ve taken them and made money from them. I took the advice from the blog gurus and it worked…really well.

So if all of the ‘how’ information is readily available, why isn’t everyone doing what they love?

If I could attribute it to one word it’s this — confidence.

The problem is bringing yourself to take the steps, not the steps themselves.

You know this because I’m sure you’ve tried something before only to find yourself procrastinating or giving up.

And Why Do You Do This?

It’s not because you’re lazy. You’re not lazy. Every person has that motivated gear in them. It’s just a matter of tapping into it through interests (passion) and habits (people fail to build habits out of fear.)

It’s not because you’re a ‘chronic procrastinator.’ It’s because you’re afraid — of the feeling of failure, of getting rejected, of embarrassment and ridicule, of the true vulnerability that comes with really putting yourself out into the world

It’s definitely not because you’re ‘trying to get all your ducks in a row.’ Those goddamned ducks. People who say they need to get their ducks in a row are really saying ‘I don’t trust myself to get this done and do it well. I’m afraid I’m going to fall flat on my face, so I’ll pretend like I’m planning.’

I don’t need to know you to know that if you’re not where you want to be, it’s because you need to improve your self-esteem and confidence.

It’s no easy task either. You have to deal with mountains of evidence against your case for confidence — past failures, that voice in your head, the little cues society gives you to stay in your box.

So what do you do when you feel like time is slipping away? How do you get out of the loop of self-doubt and procrastination?

How do you become the confident person you envision yourself being? You know, the one you daydream about becoming — being productive, advancing in your career, starting projects you love, crossing bucket list items off left and right?

This is a layered topic, which I’ll be covering quite a bit in the near future, but here are some useful nuggets for you…. here are some of the things I did myself to 10x my confidence since my doubt-ridden, broke, and frustrated days…

How I 10X’d My Own Confidence

First, I took a hard look at my past. I literally sat in a room alone and asked myself how I got to the point I was at and why I felt the way I felt. In my case — to make a long story short — I got to the root cause which was the fact I took my actions as a definition of who I was as a person. I screwed-up so much, I thought of myself as a screw up.

I also, however, looked at everything good I’d done — my potential, the things I’d been praised for and the situations I did excel in. We all have those. You have those. If you focus on them, you’ll have once piece of the puzzle of rebuilding your self-image and growing your confidence.

If you can get to the point where you’ve internalized that you, in fact, have been successful in some capacity before, you realize you can be successful in this next path you want to travel.

Next, I made a small commitment and heavily congratulated myself for it. I bought a self-improvement course, watched the first lesson, and called it a win. The next day, I watched the second lesson — meaning I spent only 15 minutes of my entire day being productive — and I congratulated myself again.

I made the tiniest commitments to a better life each day. And gave myself way too much credit each time. At one point I discovered mindfulness and meditation. I genuinely committed to not thinking about the next day and doing everything I could to have one good day.

I finished the course. My circumstances hadn’t changed, but my attitude did.

After finishing the course, I started writing. One post here, another there, and another. All tiny commitments. And to be honest, once I was self-adjusted, doing something I enjoyed doing wasn’t hard.

I could detail the step by step process from being broke and sad to tripling my income (maybe I will someday if you want me to), but the steps themselves don’t matter much. The fact that I took them did. I repeat myself and my insights often because the core of personal development is a short list.

The Recipe

That’s the combination for you. Get mentally adjusted through practice, habits, and tiny commitments. Combine it with something you enjoy and make tiny commitments in that arena, and build on it. As far as finding something you can enjoy, you know I wrote two books about that subject. I won’t link to it here today. But it’s just a matter of reminiscing and exploring. The equation is childhood experience + current interests + currents skills X experimentation.

Let’s put this into action. Together, we are going to grow into more confident people.

Today, I want you to do two teeny tiny things. One, think of ONE TIME you’ve been successful or someone has praised you (even if you don’t fully believe it, but you know they did.) Two, pick ONE LITTLE THING you are going to do today to build one brick of confidence — it can be something as simple as reading a blog post about something you want to try. Give yourself credit for it.