The 5-Step Strategy I Used to Quit My 9–5

Michael Leonard

April 29th, 2017, was the day my life changed.

I told my boss I was retiring (at 29 years old), going to build an online business that inspires the world and pursue professional golf.At the time, I was making $100,000+ at my job, and I had only made $200 from my blog… ever.

When I told him, he thought I was kidding, but I had been preparing for this day for nearly a year. I knew it was time to go 100% on my goals.Most people thought I was insane.

My old job was the definition of cushy; free insurance, six-figure pay, no dress code, ping pong tables, kegs, and kitchens.But ultimately, the perks weren’t worth 40 hours of my week. I knew there was more to life than working on someone else’s dream.

I didn’t want to grow old and end up with regrets, so I took the leap.

But I didn’t just quit on a whim. I made a plan for about 15 months and made it happen. Here is the five-step process that I used to quit my six-figure job to blog.

1. Got Clear on the Outcome

A study from Gallup shows that 8 out of 10 people dislike or hate their job.I get it. I was right there myself not too long ago.From late 2015 until the day I “retired early,” I always imagined what it would be like to make money online. But I didn’t just dream about it; I got wildly clear on what I wanted my life to look like.I knew I wanted to:

  • Work from home
  • Make money writing/blogging
  • Build online products and start a brand
  • Create my own schedule so I could play golf any day of the week

I would routinely imagine what I would be doing each day. I even wrote down dream plans for what I would do each hour, day, and week.I made it happen first in my mind.Nearly three years later, it’s crazy how similar my life is to what I planned. Now, I run Inspire Your Success, make a full-time income writing, and play golf whenever I want.But none of this would’ve happened if I didn’t first get clear about what I wanted.Don’t get me wrong; it’s not like this happened overnight.All of 2015 and 2016, I did a lot of experimenting to figure out what I wanted. I joined an acting class, tried photography, attempted an e-commerce brand, started writing a book, and all sorts of random passion projects.Eventually, I realized that I loved the thrill of building online businesses and helping people, which led me to start my first blog.

Escape Plan Tip #1

Make a plan before leaving your safe, secure job. Don’t quit because you’re having a bad day or hate your boss.I find that most people don’t know what they want to do; they just know they don’t like what they’re doing.But if you quit without having a clear goal or vision of your future, you’re making things harder on yourself. In my case, I knew I wanted to blog, publish more books, start freelance writing, and have no schedule so that I could pursue golf full-time.Everyone will have a different vision, but what’s important is that you craft it around doing what you love. Unfortunately, doing what you love doesn’t always create instant income, so it’s crucial to have a sound financial plan, so you don’t have to go back to a 9–5 job.

“Always begin with the end in mind.” — Stephen Covey

2. Mastered My Money

As an ex-personal finance blogger, I’ve always been obsessed with financial freedom and making good financial choices.Here’s how I prepared financially for my millennial life crisis.

Opened a New Savings Account

More than a year before I quit my 9–5, I opened an Ally savings account to prepare for my new life. I went into extreme savings mode by stashing at least 20% of my paycheck after tax and 80% of all commissions or bonuses.I told myself that I couldn’t retire until I had 12 months of my new budget saved. This account was completely separate from my 401K, Roth IRA, and emergency fund.

Started a Budget

The next step was to start a budget and cut unnecessary expenses (i.e., Pointless bar tabs, Amazon, etc.).Luckily our mortgage doesn’t cost much, and all of my overhead was less than $2,500 per month.

0% Credit Card

I had a feeling this whole “making money online” adventure wasn’t going to be easy, so I got a new credit card with 0% interest for 21 months.Looking back, this one really helped keep me afloat during the first 6–7 months.

Stocked Up

To help keep costs low, I also bought as much as I could to keep spending to a minimum in the future. Some of these items included:

  • Food: I probably spent $500 on protein, pantry stuff, and anything else I figured wouldn’t go bad.
  • Office: Before quitting, I converted my second bedroom into an office and bought an iMac, desk, and bookshelf.
  • Golf Membership: Because you can’t pursue professional golf without a golf course to practice on, right? I found a club that let me pay in advance, so I didn’t have to worry about monthly payments.

My house looked like I was prepared for a zombie apocalypse with all the extra food and house supplies. But it was what set me up for success on the first steps of my journey as an entrepreneur.

Escape Plan Tip #2

If you plan to leave your job, minimize your overhead costs to help you feel less stressed. Starting an online business is hard enough, but having a $3,000 mortgage isn’t going to make it any easier.Remember, despite what some gurus say, starting a business isn’t free.Cash is oxygen.You need money for website hosting, online platforms, VA’s, advertising, and more. Trying to do this when you’re dead broke is setting yourself up to fail.“Wealth is the ability to fully experience life.” — Henry David Thoreau

3. Invested in Me

Not only did I buy a ton of physical items, but I also spent a ton of money investing in myself.As Warren Buffett said, “The greatest investment you can make is an investment in yourself.”I took that quote to heart in 2017 and spared no expense when it came to learning new skills and investing in myself. Before I left the corporate world, I purchased some big-ticket items to help take my online career and life to the next level:

Online Courses

I spent over $4,000 on more than five different online courses. Some of the topics included blogging, website development, selling online products, and freelance writing.


Before I quit my job, I bought several tickets to seminars that I wanted to attend. These included a 4 day Tony Robbins event, FINCON (financial blogger conference), and several one-day events.


In the pursuit to change my life in 2017, I knew I needed to be reading more. It’s one of the most common habits of successful people. I bought over 50 books on a wide variety of topics, including entrepreneurship, personal development, biographies, and psychology.

Escape Tip #3

Invest in yourself.Running an online business is nothing like working at a 9–5 job.It’s so important to learn from people doing what you want to do. By joining online masterminds and buying courses or coaching, you are fast-tracking your success.Don’t try to reinvent the wheel.I can almost guarantee that no matter what you want to do online, someone else has done or is already doing it. Find a mentor, listen to their advice, and take action on your dreams.

“Success always leaves clues.” — Tony Robbins

4. Created Multiple Income Streams

Ultimately, if I could do this all over again, I would have increased the amount of recurring revenue I had before I quit.When I gave notice, my blog had made $200, and I hadn’t really side hustled before leaving.My plan was to save a ton of money and force myself to learn new ways to make money hustling.Within the last two weeks of working, I was able to start a few side hustles for some income each month:

  • Started dog walking
  • Self-published my first book
  • Attempted freelance writing
  • Monetized my blog with affiliates

Escape Plan Tip #4

Don’t put all your eggs in one basket.Which, ironically, is what most people do at a 9–5. If most people get fired tomorrow, they have to find a new job to pay the bills.It’s never a bad idea to have more than one stream of income.That’s why I always have more than one freelance writing client, bloggers make money in tons of different ways, and the average millionaire has seven income streams (or so they say).But you should also prove that your online business works before quitting. This was definitely a huge error on my end, but luckily I had a good amount of money saved up.“In today’s uncertain economy, the safest solution to be wealthy, be in total control, and enjoy freedom for you and your family is to have multiple streams of income.” — Robert Allen

5. Had “The Talk” With Those Closest to Me

Do you remember when your parents (or one of them) had the awkward, “birds and bees” talk with you as a teenager?That’s about how awkward and uncomfortable it was telling my parents, (who I’m extremely close with) that I was leaving my safe, secure 9–5 career to build an online business from scratch. It was arguably the hardest part of the entire planning process.They couldn’t believe I wanted to leave a very lucrative sales job for the unknown of online income. Not to mention, I hadn’t made the concept work (yet), so they were extremely skeptical.But I explained that I had thought this through, planned ahead, and had to make a move before I turned 30 or I never would. Eventually, they understood and admired me for going after my passions.My girlfriend saw my misery every day after work and knew I had a good plan in place, so she was always incredibly supportive.Needless to say, please don’t quit without telling people closest to you.

Escape Tip #5

Have the talk (even if it’s wildly uncomfortable)Let those closest to you know what you’re doing, but don’t let them sway your decision.At the end of the day, it’s your life; always go with your gut.If not, you might resent them later in life and waste so much time before creating the life that you deserve.

“The number one regret of the dying is not living a life true to yourself.” — Bronnie Ware

Final Thoughts

As I wrote this post, I actually laughed out loud at myself.Who leaves a six-figure job to blog after making $200? Such a millennial move.While I did a lot of things right, I should have done the biggest thing to prove my concept works before quitting. But hindsight is always 20/20, and I did the best I could with the knowledge I had.I wouldn’t advise most people to take the route I did.Instead, I would suggest that you prove your idea (blogging, writing, e-commerce, podcasting, online coaching, etc.) works as a side hustle, and then, with the steps outlined above, quit your job if you want.Regardless, I can say that quitting my job to bet on myself changed my life in more ways than I ever could have imagined. Had I not ever made the leap and burned the boats, I wouldn’t have:

  • Published three books
  • Pursued professional golf (and still am)
  • Created a viral video with nearly two million views
  • Joined a mastermind with high-level entrepreneurs
  • Started a brand that inspires others to make money writing
  • Started a podcast and interviewed world-class entrepreneurs
  • Earned over $100,000 freelance writing (working part-time, at home)
  • Learned more about the subconscious mind, mindset, habits, and personal development in two years than most will in five lifetimes

I say none of this to brag; I just want to share what can happen if you bet on yourself and take on entrepreneurship.While the journey has been far from easy, I wouldn’t change it for a million dollars.Each day, I get to wake up and control my destiny. To me, that is the greatest gift you can give yourself.If I can do it, so can you.Use these steps to start creating the life you have always wanted for yourself.There has never been a better time in the history of the world to build an online business.Go out there and make it happen.

“Decide what it is you want, write it down, review it constantly, and each day do something that moves you toward those goals.” — Jack Canfield
Photo: GaudiLab/Deposit Photos

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My name is Michael Leonard and I am the creator of Inspire Your Success. I'm on a mission to help readers build online writing businesses and quit their jobs to live a life of freedom!

Scottsdale, AZ

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