Michael Leonard (Submitted Photo)

On May 11th, 2017, I walked away from a six-figure career at Yelp.com to pursue two audacious goals: pro golf and entrepreneurship.

At the time, I was 29 years old, had only earned $200 from my blog and was hovering around a 3-handicap. When I handed in my resignation, my boss asked, "What’s your plan?"

Without hesitation, I replied, "I’m going to pursue professional golf and build an online business that inspires the world—or maybe both." 

Professional golf had been a childhood dream I’d set aside, but in 2016, I rediscovered my passion for the game. The thought of living with regrets, always wondering "what if," became unbearable. The same went for building a business—I’d always envisioned working for myself, and I realized it was time to break free from the golden handcuffs and chase that vision.

It’s been a whirlwind journey, but much of that dream has become a reality. Keep reading to discover how I’ve played over 300 days of tournament golf, written millions of words about the sport, experienced Q-School as an amateur, and turned golf into a thriving business.

Why I Left My Corporate Career for Golf  

I vividly remember sitting at my desk in 2015, Googling “how to retire early.” I had a fantastic career at a cool, young startup with all the perks. But there I was, trying to figure out how to escape and chase my dreams—though, at the time, I wasn’t entirely sure what they were. But I knew I had the potential to achieve more. 

I had developed an interest in personal finance that year and decided 2016 was the year I would figure out what my true goal was. I called it the year of finding my passion in life—which included enrolling in acting classes (despite having zero theater background, just a love for movies), buying a camera to attempt photography, starting a personal finance blog, trying out various side hustles, and getting back into golf.

As a kid I was obsessed with the game, dropped 50 shots in high school, and played a few years of college golf (though very unsuccessfully). I played some in my 20s, but not much as I climbed the corporate ladder. 

Pretty quickly, I remembered why I loved the game so much. For my birthday that year, we booked a tee time at Pebble Beach seven months out, so I knew I had to practice hard to play well at such an iconic course.

For the next six months, I was obsessed with golf. I’d chip and putt before work, practice putting at lunch, and race to the golf course like Dominic Toretto in Fast and the Furious when the clock hit 4 pm. Hard work paid off, and shot a 79 at Pebble and a 73 at Spyglass Hill—the golf bug had officially bitten me again.

During that trip, I had an epiphany—it was time to go all in. I had always wanted to pursue entrepreneurship, and figured I might as well see how far I could take my golf game, too. Over the next nine months, I prepared to hand in my notice and embrace Life 2.0.

Turning Doubts Into Determination

If I wasn’t golfing or working, I was focused on my side hustles, trying to figure out how to make money online. While my game was improving, I still had no clue how to build an online business. But I figured without enough time and my work ethic, I could figure it out.

After saving enough money to live for a year on a reduced lifestyle with little income, I figured it was worth a shot.  When I quit, everyone thought I was nuts—even I had my doubts at times. But I always kept the Tony Robbins quote in my head: “If you want to take the island, burn your boats. With absolute commitment comes the insight that creates real victory.”

Once I quit, the boats were burned and it was time to figure it out. I’ll never forget the first Monday after I quit—my girlfriend went to work, and suddenly, I had no boss telling me what to do. It was all on me.

For the next 24 months, all I did was golf and work. It sounds cool, but it was 100x more stressful than anything I’d ever experienced.

Early mornings, late nights, no social life, financial woes, and more often than not, crippling self-doubt. I often felt lost in my business, unsure if I’d make it or if I had what it took to run my own business. My golf game was up and down too—some days I felt like I could compete with anyone, while others, I could barely break 80.

But I kept telling myself to stay in the fight—both with golf and business. I celebrated the small wins, like landing a new freelance client or playing well in a big tournament. Eventually, I found success as a freelance writer and work on a schedule that allowed me to practice relentlessly. 

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The Q-School Dream

In 2019, I took a leap and signed up for Q-School as an amateur, determined to test my game on one of golf’s biggest stages. After competing in countless tournaments over the past few years (full schedule below), I decided it was time to see just how close—or far—I was from making the jump to professional golf.

I browsed the Q-School sites, signed up for Wilderness Ridge in Nebraska (never been, but the course looked great), and made a plan. With only about 35 days to prepare, I focused on getting ready—this included playing in a few tournaments, a lot of practice, and working with a sports psychologist.

My mindset was that going to Q-School was a win, regardless of the results. It was a childhood dream, and I felt it would create lasting memories above all else.

Once I landed, I headed straight to the course to check it out, and I was impressed with the layout. After 18 holes on the first day and 9 the next, I felt as ready as I could be. I was hitting the ball decently, but the weather was rough—90 degrees with 90% humidity. 

I didn’t have a caddy, so I knew it would be a long few days, but the adrenaline was stronger than ever. Sitting in my hotel room the night before, I chuckled thinking barely two years ago I was stuck in a 9-to-5 job I hated—now, I was competing in Q-school as an amateur. 

The Most Nerve-Racking Day of My Golf Journey

The night before the first round, I barely slept—my mind racing with a mix of nerves and excitement. By the time morning came, the anticipation had my stomach in knots. My warm-up was rough (to be honest, I felt like I might throw up the entire time), but before I knew it, it was time to step up to the first tee.

First tee jitters were real, and I started with a thin 3-wood, an ugly approach, an awful chip, and had to bury a 10-footer to save bogey. Two holes later, I made my first birdie and started to get comfortable on the course. 

Despite the nerves, I played great on the first day and made a birdie on the final hole for a clutch, even-par 71. Walking off the green was a surreal moment, and all the struggles of the past few years suddenly felt worth it. 

Unfortunately, after shooting 73 and 78, I fell three shots short of advancing to the first stage.

When I finished the round, a wave of emotions hit me—part sadness, but mostly pride that I had even entered, let alone played well. 

In that moment, I realized just how deeply I love the game—and how much I want others to experience that same joy. But I also came to a powerful understanding: pursuing professional golf wasn’t my dream anymore. While the idea had been a driving force behind starting Life 2.0, I knew it was time to shift my focus and redefine the bigger goal.

After playing alongside several pros, I saw firsthand how many of them had lost their passion for the game. For them, golf was about paying the bills to survive, not about the love of the sport.

I’d experienced burnout in college and quit golf before, and I wasn’t willing to go down that road again. Seeing it up close, I realized I didn’t need a professional career to find fulfillment.

Instead, I decided to channel my passion into golf writing and competing in amateur events—where I could truly enjoy the game without losing the joy that brought me back to the game in 2016. 

Wicked Smart Golf 

After writing millions of words for golf blogs, training aid companies, and various brands from 2019-2021, I launched Wicked Smart Golf, in 2022. The goal was simple—better golf without swing changes. 

I felt like 90% of golf content focused solely on swing instruction, overlooking the importance of thinking your way to lower scores. Don’t get me wrong, a good swing is important, but it’s not everything. 

I became a +2 handicap despite struggling with early extension and other swing issues. Which is why I wanted to share everything I had learned from my writing and tournament experiences—offering insights from a player’s perspective.

In 2022, I published Wicked Smart Golf and launched a podcast with the same name. In 2023, I added a YouTube channel and began offering mental golf coaching. And in 2024, I wrote the sequel, Wicked Smart Golf II, and continue to spend most of my time either playing golf, growing my business, or working on helping others reach their potential in the game.

What started as a leap into the unknown has evolved into a mission to change the way golfers think about their game. I love helping golfers play smarter and shoot lower scores without endless swing changes. 

My Tournament Golf Schedule 

As part of this ongoing journey, I’ve immersed myself in competitive golf, participating in over 300 tournament days since 2016. These experiences—ranging from one day local amateur tours, to state events, USGA qualifiers, and even professional events as an amateur—have been instrumental in shaping my approach to both golf and business. 

Below is a breakdown of how many tournament days I’ve played each year:

2016: 5 days.
2017: 14 days (played in my first mini tour event and first USGA qualifier). 
2018: 25 days.
2019: 24 days (including Q-school). 
2020: 41 days.
2021: 62 days.
2022: 62 days.
2023: 63 days (qualified for my first pro event, The AZ Open). 
2024: 45 days.

As you can see, it’s been a steady progression, and now I have a consistent tournament schedule in Arizona. I mostly play in Arizona Golf Association events and City Championships (like the Phoenix City and Chandler City tournaments). 

But I also make it a point to travel for a few others each year, such as the San Diego City Amateur at Torrey Pines and the SOGC in Oregon (where I’m from). Each year, I try to add at least one new tournament, typically during the summer, to escape the brutal Arizona heat. Needless to say, I’m obsessed with tournament golf and the lessons it teaches about both the game and life.

Key Takeaways

If you’re on AmateurGolf.com, chances are you either compete in tournaments or dream of doing so—and I’m here to help you get there. After testing my own game in competition and working with countless tournament golfers, I’ve put together seven essential tips to elevate your performance on the course:

Sign up for tournaments before you’re ready: Having an event to circle on the calendar gives you something to train for and will help speed up success. It keeps you motivated to practice, take lessons, and show up prepared. This website has been key in helping me find events and stay consistent each year, so plan ahead so you can work toward that goal. 

Practice like you play: Familiarize yourself with the rules and always putt everything out, as if you're in a tournament. Competition is mentally challenging, and it's even harder if you don’t practice with the same level of discipline and focus.

Play a practice round: If possible, play a round before the event to get comfortable with the course and venue. This will help you map out your strategy for each hole, learn the speed of the greens, and show up with as much confidence as possible. 

Trust your game: I’ve been paired with all types of players, and one of my early mistakes was trying to play like them. The key is to focus on your own strengths and strategies—don’t get distracted by how others are playing. Swing your swing and play your game. 

Have a go-to warm-up routine: Establish a pre-round routine that gets you both mentally and physically prepared for the round. A solid warm-up can help you settle into the right mindset and reduce nerves before you tee off.

Reflect on the round: After each round, take note of at least three positive shots, key mental takeaways, swing thoughts, and areas for improvement. This reflection will help you grow and progress as a player to avoid making the same mistakes. 

Don’t forget to have fun: Be grateful for the opportunity to play golf and compete. We’re not playing for our livelihood like the guys at Q-school—the more relaxed and focused you are, the better you’ll play. Remember, process > results.

Closing Thoughts

I hope my journey inspires you to chase the dream that’s been quietly calling your name. Whether it’s starting your own golf business, competing in tournaments again, or teeing it up in a USGA event, it’s never too late to pursue what truly excites you.

The path won’t always be smooth, but the effort you invest in yourself will pay off in ways you can’t imagine. Passion fuels progress, and the rewards of living your dream far outweigh the challenges you’ll face along the way.

So take the leap. Start now. Trust the journey, and give yourself the gift of a life without regrets.

About Michael Leonard

Michael is a golf writer, podcast host, and mental golf coach who is dedicated to helping golfers play better without swing changes. He uses his platform to help golfers play more consistently and lower their handicaps through his 5-pillar approach—focusing on mental strategies, practice routines, short game, putting, and course management lessons. If he’s not working on his business, Michael is probably fine-tuning his game or playing in a golf tournament.