7 Stages to Level Up Your Life into Financial Freedom

When I first made the leap into entrepreneurialism, I wanted it all.

I wanted everything at once. I wanted to build my dream business overnight and have an enormous community of fans and friends and make millions of dollars creating products I loved.  

Having zero experience and a small network, those ambitions soon sputtered out. I adopted a new mindset, a new operating principle.

I figured out how to “level up.”

Doing work you’re passionate about is important. But even the word “passion” has become trendy these days. Everything in the entrepreneur space is positioned towards making money doing what you love.

You SHOULD work towards doing what you love. But sometimes you’ll have to go through several iterations of this process, gradually “leveling up” every time in order to get closer to what you want and who you want to be.

How I Leveled Up My Life into Financial Freedom

Level 1

I graduated college in 2009 and had absolutely no idea what I wanted to do. I figured I had two choices:

  1. Go back to school
  2. Join the corporate rat race

The only problem was that I didn’t want to be a doctor, lawyer or engineer. So more school didn’t make sense to me. And I didn’t want to do the corporate thing. Hell no.

In fact, the very thought of working in a cubicle made me want to throw myself head first into a boiling vat of tar. Not very inspiring.

Since I refused to take the next “logical” step, I was stuck at low-paying jobs waiting tables and answering phones. I started officially working at Longhorn Steakhouse to make ends meet and, as you’d expect, it sucked. I wasn’t happy and I wasn’t making any money. I was fed up and frustrated. So I decided to take things into my own hands.

Level 2:

I left Longhorn Steakhouse in 2012 and immediately started doing SAT test prep for Kaplan. Was test prep my #1 passion? HELL NO. But it was a level up from serving steak.

My hourly rate was $18. I thought this was fantastic at the time. Then I found that they were charging the families I was helping over $100/hour for me to come to the house and teach little Timmy quadratic equations. In other words, I was doing $100 worth of work, and Kaplan was taking $82 out of my pocket for MY time.

Not cool.

Level 3:

At that point, I realized that I had a viable skill that people had proven they would pay me for, and I decided to level up. I launched my own test prep company–effectively cutting out the middleman and reaping all the benefits.

I learned that I didn’t have to start from scratch. Rather than scouring Craigslist for clients, I cut the line and made deals with l private admissions coaches who prep high school students for their college essays, interviews and how to package themselves.

I sold myself well and became their in-house test prep instructor, and everyone won. Instantly, I went from having no clients to a treasure trove of them overnight.

Level 4:  

From there, I decided to level up again. I got bored of test prep, but realized how much I loved business and marketing.

I started freelancing online and got crafty about how to make money using skills I already had. Along the way, I learned how position myself in a saturated marketplace, write amazing copy, and close sales. I eventually bootstrapped a web development firm that started pulling 6-figures in a year.

Game on.

Level 5:

At that point, I realized there was something to this whole “online business thing.” I started devouring whatever I could find regarding subjects like entrepreneurialism, startups, email marketing, copywriting, sales funnels, building an audience, and whatever else.

Then, I made the best decision of my life and started my blog, writing about my experience as a frustrated 20-something who knew there had to be more to life than the nine-to-five. I found an audience who resonated with my message — or rather, they found me.  

Soon after, I began working with really awesome startups like Art of Charm and Pavlok, as an employee in some cases and a consultant in others. I was brought on to develop deep marketing strategies and funnel positioning to help them separate from the pack — and I wrote world-class copy.
I got an inside scoop what it takes to dominate an online business and then knew I was ready.

Level 6:

In 2014, I leveled up and took the leap–going full time with Rich20Something and managing it completely by myself.
There was no turning back. I wrote and wrote and wrote and created a huge following by giving all of my content away for free. I made money by teaching young people how to start their own freelance businesses.

Level 7:

Nowadays, I’ve got a full TEAM with me, in the trenches, every day. Hustler city over here in Rich20 HQ, Santa Monica. There are 3 full-time employees, a few part-timers, and dozens of service providers whom I depend on every week for various tasks.

I’ve made a career for myself that didn’t exist. The ultimate win.

The Take-Away

Each time I took on a new project, it got a bit closer to what my ideal vision looked like. That’s leveling up.

Even now, I know Rich20 isn’t my final stop. Each project has taught me new, valuable skills that I carry with me from one business to the next.

You don’t need to build your dream business overnight. Feel free to go through the process of “becoming” and actively try many new things. Your goal should be to find something that feels more and more like “you” every time.

Focus on growing and constantly leveling up.

Try not to get frustrated with this process, especially the amount of time it’s taking…because the growth you’re going through is crucial.

You probably aren’t ready to run your dream business right out of the gate anyway — and that’s ok. Believe me, I speak from experience. One step at a time.



If you enjoyed today’s article, I recommend you check out my debut book, Rich20Something.

It’s not some boring spiel on “paying your dues”…it’s about hustle. Instead of inching your way up the traditional career ladder, I teach you how to hack it, sharing hard-earned advice, anecdotes from other entrepreneurial badasses, and step-by-step techniques for turning your best skills into a business you’re passionate about (that pays well to boot).


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