9 Life Lessons After Leaving My $100,000+ 9–5 Job to Live My Dreams

Is the laptop lifestyle actually possible?

Michael Leonard
Jul 5, 2018 · 9 min read

I know you’ve thought about what it would be like to quit your job and start living life on your terms.

I know because worldwide, 8 out of 10 people hate or dislike their jobs.

I used to sit at work and dream about what I’d be doing if I didn’t have to sit in pointless meetings working on someone else’s dream.

The golden handcuffs were tight in my 20’s.

Each year, I got promoted, got more stock options, a raise, or a combination.

I realize this sounds like a good problem but here’s the thing…

I was miserable.

I was unfulfilled.

I felt like I was going through the motions of life without really living it.

I felt like I was doing what society told me to do but not what I actually wanted to do.

Each week brought the same thing — “Sunday scaries”, Wednesday slump, and Friday anticipation.

But I didn’t just sit around, I made a plan and executed on it.

On May 11th, 2017, I engineered my escape from the real world. I saved up 12 months of my working budget and quit my six-figure job.

At the time, I had no money coming in, just savings.

I had a blog that had made $200 and a dream to make it as a side hustle guru, writer, and pursue my dream of professional golf.

In May of 2018, I hit my one-year solopreneur anniversary. 12 months of no boss, no meetings, and doing what I wanted each day.

I’ve never made less money but never had as much happiness since I was a kid.

If you’re sitting a job that you hate and thinking about what it’s like to leave, let me help you kill time on your employer’s clock with these nine valuable lessons.

1. Success Is NEVER Overnight

“It doesn’t matter how many times you fail. You only have to be right one time and then people can call you an overnight success.” — Marc Cuban

I want this post to be realistic and not another promise to earn millions of dollars overnight in some “passive income” dream.

I’m not here to tell you I quit a $100,000+ job and replaced my salary instantly.

But that’s ok… for now.

I used to think entrepreneurship was like every Instagram ad I saw on my feed— Laptop, beach, a briefcase of money, and lavish life.

What I’ve learned is that this life is 100% possible but it’s NOT overnight.

Making money from nothing is MUCH HARDER than working for an employer.

But it’s also 100X more rewarding.

The first $60 I made from a golf blog post was the most rewarding money I’ve ever earned in my entire life. It showed me it was possible to actually make money online as a writer.

So, if you think making money from your laptop will be easy and you’ll replace your income immediately, you’re wrong.

But, if you want a challenge and love what you’re doing, there is no greater satisfaction than being your own boss.

2. Freedom is Better Than Money

“Success is doing what you want, when you want, where you want, with whom you want, as much as you want.” — Tony Robbins

I used to base my success my annual income. Now, I base my success off my freedom and how much I’m learning.

Of course, I still want to earn millions but since I’ve learned that success isn’t overnight, I’m more focused on the process of learning to BE a millionaire.

Instead of chasing the next $1,000, I’m putting in work to build my online business — Inspire Your Success.

I am fully committed to making this life work.

Honestly, it’s like being free after serving a prison sentence.

I never want to go back to cubicles, meetings, and a schedule of when I’m supposed to complete my work.

The short-term money sacrifice is WELL worth the freedom of being able to do whatever, whenever.

3. You Can Live on WAY Less Than You Think

“The best things in life are free. And it is important never to lose sight of that, so look around you. Wherever you see friendship, loyalty, laughter, and love. there is your treasure.” — Neale Donald Walsch

I was a great money manager when I was in the 9–5 world but I still wasted money all the time.

I was trying to fill the void of un-fulfillment from my job by buying random stuff on Amazon and getting drunk.

When I went from making 8–10K per month to making $0, I quickly realized how much money I actually wasted.

But, at the same time, even though I made WAY less money in the last year, I am 100X happier.

Yes, money doesn’t equal happiness.

Of course, there were some tough months with hardly any income but that’s why I saved so much before burning the boats.

Now that I’m making more than any time in my entrepreneurial career, I know that I can live on hardly anything.

How much money are you wasting to fill the void of unhappiness in your life?

4. People Won’t Understand What You’re Doing

“You are only going to be as good as the people you surround yourself with, so be brave enough to let go of those who keep weighing you down.” — Unknown

I worked at a cool, young start up company with many like-minded people who became friends and some of them even best friends.

While I still talk to some people, a lot of them were more coworkers than friends.

Now that I’ve been out of the 9–5 grind and see old friends and coworkers, they still have NO CLUE what I’m doing or how I actually make money.

Even if they do understand, they won’t get my WHY behind it. It’s resulted in some lost friends but also made room for new friends in my life.

That’s part of life…sometimes you need to get rid of the old to welcome the new.

On the way to a billionaire’s house (seriously) in Beverly Hills… Passion DOES Pay!

5. Busy Doesn’t Equal Work

“Beware the barrenness of a busy life.” — Socrates

How many times have you been at your 9–5, had 20 things on a to-do list, and spent the whole day putting out fires?

Then, when you look up, you realize you didn’t do much that actually moved the needle that day

The blogger/writer/entrepreneur life is 10X that.

Looking back, I’m not even sure what I was doing the first few months. I still had the employee mindset.

When I was in a 9–5, I felt “proud” if I was busy. This created a TERRIBLE habit that I’ve finally broken.

Switching from employee to owner made me realize that doing 2–3 IMPORTANT things are way better than 15 meaningless tasks.

As Tim Ferris said, “Focus on being productive instead of busy.

6. You Can’t Connect The Dots

“You can’t connect the dots looking forward. You can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me know and it has made all the difference in my life.” — Steve Jobs

Sometimes you just have to take the first step.

The leap of faith.

The calculated risk.

No plan works 100% perfectly when you start an entrepreneurial journey. But that’s part of the epic journey.

I had tons of plans before I left and most of them have failed.

And that’s okay. Failing is part of the process.

I’ve learned, adapted, and made new plans.

I hadn’t written a single article about personal development before I quit, then I attended a few seminars. Then, I got hooked on studying the subconscious and learning what it takes to make real change in your life.

Now I’m a top writer for Goalcast, Fearless Motivation and other top motivational sites. Not to mention, I just had a voice over video that I did reach 1,000,000+ views in only three months on Youtube.

Sometimes you have to take the first step, like quitting a job, to understand there are endless opportunities outside the corporate world.

Success starts by betting on yourself!

7. Social Media is a Drug

“Social media has created jealous behavior over illusions. Sadly, some are envious of things, relationships & lifestyles that don’t even exist.” — Unknown

I used to waste SO much time on social media while sitting at my desk. Now, I can barely get myself to log on for my business accounts.

Social media is dangerously addictive.

Millennials anxiously checking their phones 150X per day is the 2018 version of smoking.

So I do my best (I’m far from perfect) to limit my social media intake.

I’ve learned to quit caring about likes and notifications. It just doesn’t matter.

Plus, social media robs people of human interaction.

Now, I don’t even have mine out on the table during a meal after learning subconsciously this signals to others they are less important than your phone. Even if it’s face down.

The less I use social media the happier I am.

8. Happiness is a Choice

“Happiness is not by chance, but by choice.” — Jim Rohn

Again, my success (and happiness) used to be tied to my income.

Sound familiar?

After six months of only making a few thousand dollars (or less) each month, I was bummed.

I felt stuck.

I had no idea what I was doing.

I was working harder than ever and making less than ever.

Then, I listened to a podcast from the Quest co-founder Tom Bilyeu, about how you should be careful how you define happiness.

This idea clicked.

Instantly, I started being happy because I chose to associate learning with my success, not income.

Unsurprisingly, I’m learning and earning more than ever.

How do you associate success? Money, freedom, working on your passion?

9. Health is Wealth

“So many people spend their health gaining wealth, and then have to spend their wealth to regain their health.” — A.J. Reb Materi

The 9–5 life crushed my health.

My posture became hunched, I ate all the carb-loaded, free food in the kitchen, and blamed work for my lack of exercise. I developed neurological issues from stress and even got diagnosed with a small liason on my pitutary gland.

Everything manifested from being stressed 24/7/365…despite making six figures.

Since leaving the cub, I’ve made health a top priority.

Besides..what’s the point of working to make tons of money only to feel terrible all the time?

The World Keeps on Going

“To some extent, being an entrepreneur is a lonely journey.” — Chad Hurley

The world is a busy place and it doesn’t slow down for you.

The world still turns when you’re not in corporate America.

If you’re fed up with the 9–5 slog and want to take the leap to work for yourself, understand it won’t be easy.

But it will be SO worth it.

It’s been the most rewarding journey of my entire life.

In October of 2019, I just updated this as I’ve been at it 2.5 years.

I’m still working on my professional golf dream and just earned $20,000+ in one month as a freelance writer.

Over double what I ever made from the 9–5.

While it wasn’t easy, it’s been the most amazing journey of my life.

You have no idea how much you can change in a few years if you put in the work.

Don’t settle, keep striving for greatness.

If I can do it, so can YOU!


If you liked this story, feel free to 👏👏👏 a few times (Up to 50 times — thanks!)


Call to Action

Do you want to learn how to build an online business and maybe leave your 9–5? Check out these 10 proven business models to help you get started.

→10 Online Businesses to Earn Your First $1,000 (and beyond)

The Post-Grad Survival Guide

Medium’s Millennial Career and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Michael Leonard

Written by

Inspirational Writer, Coach, & Creator of Inspire Your Success Podcast. Earn your first $1K as a writer —> https://lynxinbio.com/michaelleonard

The Post-Grad Survival Guide

Medium’s Millennial Career and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade