How to be Bold in Your Career With Less Than 500 Dollars in Cash and a $1,700 Mortgage.

I had 500 dollars in my bank account.

It was hovering at that amount for a long time no matter what I did. I bought fewer things and saved more money. I stopped going out on weekends. Somehow, someway, I always ended up with just 500 dollars in my account.

I was living paycheck to paycheck.

One day I attended a large conference. The keynote speaker said:

“Be bold. You have to take risks to advance. Be your own brand. You have to stand out.”

I’m sitting there, looking at this guy and thinking to myself, “Easy for you to say, Buddy. You want me to be bold and risky with $500 in my bank account? I’d rather be safe with $500 in the bank than be bold with no money in my account.”

Being bold wasn’t an option for me. He was inspirational but I still felt helpless.

The next person went up onto the stage and talked about how courageous the previous presenter had been for taking a huge leap and quitting their job.

“Give me a break,” is what I thought to myself. “That guy had money in the bank. If I had been in their shoes I’d have quit 3 years ago.”


I was bitter and jealous.

I had plenty of potential but I was tied down by my financials. It seemed like everyone was flying by me and I had a 4-ton anchor tied to my feet. I couldn’t take any risks.

That could have been me, but it wasn’t.

It got worse.

I had a manager that I didn’t quite get along with. Every day I went to work was worse than the previous day.

“Be bold,” is all I thought about. The thing is, that speaker was right. I needed to be bold but I just couldn’t afford it. This job meant everything to me. Let me rephrase that. The MONEY meant everything to me. I was living paycheck to paycheck. Even the slightest interruption in pay would cause a huge disruption.

I knew exactly when I was going to get paid. I would stay up late on Thursdays just to see if it would deposit early at midnight.

It never did.

I knew that quitting was my “be bold” moment, but instead of being bold I did the exact opposite.

I did everything my manager told me to do. I never asked why, I just did it. I never took any vacation days so I could prove how dedicated an employee I was. I did everything in my power to make my manager’s life as easy as possible while making mine as miserable as it could be. Instead of advancing my career, I could feel it plummeting right in front of my eyes.

I needed help.

Many years later I’m able to reflect and be thankful that I’ll never be in that situation again.

Here’s what I did:


STEP 1: I made difficult lifestyle decisions.

I tracked my finances like a mad man every single day. After 3 rejections from the bank, I figured out a way to refinance my mortgage. I cancelled services that I didn’t need. I disposed of a rental property that was losing money every month. I changed my payment plan for student loans to a way that aligned with my new financial goals.

I became as financially lean as I could be.

The only reason I hadn’t taken these steps before was that I didn’t think I could. I honestly thought I had no choices, when in reality I had plenty of them. They just weren’t clear to me.


STEP 2: I worked overtime… for myself

I had a great career, but again I knew I could do better.

I started working 40 hours a week for my employer and 20 hours a week for myself.

I taught myself how to code again. I started reading business books.

I created multiple businesses. Many of them failed in fantastic fashion.

I started investing in myself.


STEP 3: I learned how to be selfish.

I went from working 60 hours a week for my employer to just 40 hours a week.

I learned how to negotiate my salary after being screwed year after year.

I learned how to build a supportive community around me.

I learned to quit when something wasn’t working.


STEP 4: I learned that I could actually teach my brain things.

I know this one sounds stupid and obvious, but it was like I had an out-of-body epiphany when I realized that all I needed to do was to feed my brain information and I could learn anything. Kind of like The Matrix, but in real life.

I switched my mentality from “I can’t do that” to “How can I do that? Who could teach me this? Who is the best known person for this topic?”



Here’s my advice to you if you find yourself in a similar situation.


I don’t care if you have $20 or $100,000 in the bank. If you’re not educating yourself on how to manage your money, you’re doing it wrong.

Reddit has a great sub-Reddit called /r/personalfinance. Seriously, it’s an amazing community of people with great practical advice.

I bought the books, “I Will Teach You How to be Rich” by Ramit Sethi, and “Die Broke” by Mark Levine.

After doing this it became crystal clear why I was living paycheck to paycheck and what I could do about it.


Your best asset is your ability to make money. Even if you’re the best saver in the world, if you don’t make much money then you aren’t going to go anywhere fast.

There are books and conferences dedicated to this topic alone. Here’s one thing I’ll tell you that has put me far ahead of the crowd.

Read non-fiction books. Get recommendations from friends.

If I recommend just one thing for you to do, it would be to purchase the monthly1k course by Noah Kagan. He takes a practical approach to making $1,000/month profitable business.

The only reason I recommend this course over others is that it teaches you step-by-step how to turn your ideas into reality. I’ll also plug my free email course,Summer of Quitting, which teaches you how to build opportunities from nothing.


Meet new people and get new perspectives. I took 250 coffee meetings in 400 days to build my network. If I can do that, you can take a least one coffee meeting a week.

To this day, this was the best decision I’ve ever made.


I know, I know. I’m contradicting myself, but the speaker had a great point.

In my case, I became bold with my financial situation. I figured out ways to refinance my house, which reduced my payments significantly. I changed my lifestyle substantially to reduce the amount of money I spent on big-ticket items. I did a few other things that I couldn’t possibly write down for the world to see, all legal of course.

The point is that sometimes you have to do the unimaginable if you want to advance your career.

I would be negligent if I didn’t mention one of my favorite people, Brian Burkhart, whose motto just happens to be, “The fortune goes to the bold.”


I’m not going to tell you who the best is because everyone is in a different situation. What I will tell you is that you are most likely not the smartest person in the room.

Stop reading millions of articles a day online. Find someone you really like and find out everything you can about them. Learn from them. Never stop learning. Never think you’re the smartest in the room.

Never think that you will always have 500 dollars in your bank account. You can do better than that.

PS: Read the only resignation letter template you’ll ever need.