Are you stuck in a monotonous job while dreaming of doing something more fulfilling? Are you ready to bridge the gap between your day job and your dream job? Have you ever wondered how you could balance a day job with pursuing your passion? Discover how to hustle smartly, recognize your 'hinge moments', and learn from the journeys of successful personalities like Malcolm Gladwell, Leonardo da Vinci, and Robert Downey Jr.

Quitter: Closing the Gap Between Your Day Job and Your Dream Job

Imagine taking off your clothes in a bathroom stall. You would probably start with your shirt. Then check the strength of the door hook before hanging anything up. These nuggets of wisdom come from Jon's days of doing the reverse Superman—changing from conference speaker back to office drone in a bathroom stall.

For years, Jon flew across the country saving lives on weekends, only to return to a cubicle on Monday mornings. He loved his weekend gig but despised the monotony of his day job. So, like many, he thought it was quitting time.

Jon has gotten really good at quitting jobs—he's held eight jobs in eight years. But quitting isn’t always the answer. In fact, a recent survey showed that 84% of employees plan to look for a new job this year, and job tenures are getting shorter across generations. People used to get gold watches for decades of service; now, they just want to escape the grind.

Enter Donnie, Jon's worst boss ever. Chewing tobacco in the office, berating Jon constantly—he made Jon physically ill. Jon dreamed of quitting, but the truth is, quitting doesn’t eliminate bad bosses; it just trades them for new ones: bills, mortgage, and family expectations.

When Jon got his first publishing offer, he was ecstatic. But the deal was terrible. Because he had a day job, he could afford to say no. Quitting your job limits your ability to say no and forces you to compromise. It also makes you less dangerous and more likely to play it safe.

Discipline begets discipline. When Jon started eating healthier, he got more productive at work and at home. Men, especially, need work for a sense of purpose. Quitting without a plan can unravel your life and relationships.

So, Jon advises you to keep your day job while you chase your dream. It gives you stability, the power to say no, and the freedom to stay dangerous. Eventually, you might quit, but do it wisely, and only after dispelling the myths about quitting.

This chapter isn’t just about bathroom stalls and bad bosses—it's about making smart decisions for your dreams. Keep your day job for now, and let's tackle those dreams together.

Is Quitting Your Job the Key to Happiness or a Path to New Nightmares?

We live in a culture that celebrates leaving jobs rather than staying put. Jon remembers attending a going-away party for a colleague who quit her high-paying job with no clear plan. Everyone lauded her courage, ignoring the reality of her impulsiveness. This celebration of quitting has turned us into the “I’m, but” Generation. We often say, “I’m a teacher, but I want to be an artist,” or “I’m an accountant, but I want to be a therapist.” Many of us know what we want to do if given the chance. 

Personality tests like Myers-Briggs or DISC can give insights into our preferences, but they aren't definitive in finding our dream jobs. Discovering what we love often involves recovering old passions rather than finding something new. For instance, Jon recalls how a teacher laminated his poetry book in third grade, making him feel like a published author. Another pivotal moment was when his dad handed him a packet on how to publish a book, showing belief in his writing potential.

Hinge moments, like Mercedes-Benz adding a hinge to their ignition button to evoke the feeling of launching a missile, can pivot our lives. These small but significant details can guide us towards our true passions. Jon experienced both positive and challenging hinge moments, like a discouraging meeting at an advertising agency that clarified he didn't want to pursue advertising but loved writing and insight.

Questions like, “What do I love enough to do for free?” or “What do I do that causes time to feel different?” can help identify these hinge moments. Recognizing these moments, whether happy or discouraging, can guide us towards our true calling. It’s about recovering what we’ve always loved doing, not discovering something entirely new.

Embracing Passion Over Paychecks

Jon and his wife were excited about buying a charming house in Tennessee, complete with holiday block parties and friendly neighbors. But the more they looked, the more problems they found—a leaky roof, water in the crawl space, and a ninety-eight-point home inspection list. Jon and his wife, both with backgrounds in construction, knew they should walk away, but fear of losing a loan opportunity made them hesitate.

Every dream comes with risks, but how one perceives those risks can make all the difference. One might see risks through a magnifying glass, making them seem larger than life, or through a kaleidoscope, connecting them to every part of life and blowing them out of proportion. The best approach is the telescope method, where one acknowledges risks but keeps them at a distance, planning for them without letting them dominate decisions.

Perfectionism can also be a huge obstacle. Jon used to spend hours trying to make his blog posts perfect, but he learned that 90 percent perfect and shared with the world is better than 100 percent perfect and stuck in one's head. The same goes for pursuing a dream—it's better to start and make progress than to wait for the perfect moment, which might never come.

Another major hurdle is the constant internal discussion that can paralyze one. Deciding once and sticking to that decision can help to avoid the endless back-and-forth that saps energy and momentum.

Fear of failure can also hold one back. The odds of one's worst fears coming true are slim, but the odds of a dream not coming to fruition if one never tries are 100 percent. It's better to risk failure than to guarantee it by not trying at all.

Time is another common excuse. Everyone has busy lives, but everyone has the perfect amount of time for the things that matter most. It's about prioritizing and making the most of the time one has.

Money, too, can seem like an insurmountable barrier. Financial foolishness isn't a sign of commitment to a dream; it's a sign of poor planning. Getting control of one's finances can turn money from an obstacle into a resource that fuels a dream.

Lastly, one shouldn't let the phrase "by now" convince them it's too late to start. Whether one is 25 or 55, it's never too late to pursue a dream. Every path one has taken has given them the resources and experiences needed to succeed.

Chasing a dream will always come with risks, but with the right mindset and preparation, one can mitigate those risks and move closer to making their dream a reality.

Is Fear of Failure Keeping You From Your Dream Home?

For the first decade of Jon's day job, he fantasized about quitting weekly. At every annual team meeting, he convinced himself it would be his last. His dream of becoming a successful author started gaining traction in 2008 when he signed a book contract and his blog gained popularity. 

People began urging him to quit his job at AutoTrader.com, assuming his dream was more lucrative than it was. Contrary to popular belief, being an author doesn't always equate to wealth; the $30,000 advance Jon received for his first book shrank significantly after taxes, agent fees, and tithing, leaving him with about $13,000.

To make ends meet and incubate his dream, Jon stayed at his day job. Dreams take time to mature, and quitting too soon could kill them. Even Leonardo da Vinci had a day job, planning pageants and balls for his patrons between painting masterpieces. It's essential to view your day job as a platform rather than a prison.

In 2008, Jon spoke at Dave Ramsey’s organization and was later offered a job there. He initially declined, choosing to develop his dream further. By 2010, after much growth, he finally accepted a position as a full-time speaker and author, a role that perfectly aligned with his aspirations.

Balancing his day job and dream job required strategic planning. Jon found parallels between the two, like writing technical copy at work, which honed his brevity and clarity for his blog. Even in seemingly unrelated fields, there are always lessons to be learned and skills to be applied.

Ultimately, it's crucial to remember why we work. For Jon, it was to support his family and maintain financial stability. Embracing this mindset helped him find purpose and motivation in his day job, even as he pursued his dream. By treating his employer as a patron rather than an adversary and recognizing the value of hard work, Jon managed to nurture his dream without sabotaging his day job.

From AutoTrader to Author: Navigating Dreams with Dave Ramsey's Wisdom

When a leadership group called Catalyst invited Jon to speak at their events, his friend exclaimed, "We’ve got to get you on the main stage." Catalyst is a massive leadership conference with over 13,000 attendees, split into main stage and lab sessions. Speaking on the main stage is prestigious, unlike the smaller lab sessions.

Despite Jon's friends’ encouragement, the path to the main stage is slow and requires patience. We often get caught up in the Plan Myth, believing we need a perfect plan before starting. However, passion and practice are more crucial initially. Malcolm Gladwell, for example, didn't predict the success of his book "The Tipping Point." Passion led him, not an elaborate plan.

The story of David and Goliath, often confused with Cinderella's fairy tale, illustrates that real success takes time. David, anointed as king, returned to shepherding before facing Goliath years later. Cinderella’s transformation was instant, but David's journey was about doing small, consistent tasks—delivering lunch, not attending royal balls.

We should cherish invisibility, as it allows for growth and mistakes without the pressure of an audience. Eminem, despite his fame, reminisces about simpler times. My blog, Prodigal Jon, had few readers initially, but it was a crucial period of practice and development.

Starting small is essential. Jon's friend Rachel, embarking on her speaking career, had to accept speaking to thirty people in Nebraska, far from the grandeur of her father Dave Ramsey’s events. These are the Nebraska years, where the struggle is real but necessary for growth.

Embrace the small beginnings. Focus on passion, practice consistently, and see invisibility as a gift, not a punishment. Your dream will grow, and you’ll be prepared for the main stage when the time comes.

Can Malcolm Gladwell and Eminem Teach Us the Power of Passion Over Perfect Plans?

For two years, people assumed Jon's life was all about blogging and fun gigs. In reality, he juggled an IT day job and his passion, squeezing in radio interviews during lunch and speaking gigs using vacation days. His secret? Hustle. It's not glamorous, and the road is paved with stories like those of his cousin Charlie, a firefighter who works double shifts to afford a ski trip, asking his wife, "Do you really want to go to Colorado?" before heading out for another long day.

Hustle is about doing the unglamorous work—like Jon carrying boxes of his books through airports—to afford the chance to do what he loves. It's about waking up early to work on his dreams before excuses wake up. He learned from his wife's cousin, Charlie, and his persistent hairstylist, who works two jobs, that hustle doesn’t have to be complicated. It’s the simple equation: “Do I want ABC? Then I have to XYZ.”

In the early morning, Jon's excuses and doubts are asleep. That’s the best time to work on his dreams, uninterrupted by the chaos of the day. Morning hustle gives him a sense of accomplishment that can fuel his whole day, unlike working at night, where sleep resets his progress.

Hustle also means making choices for Jon. He has to prioritize what he loves over what he merely likes. He stopped watching marathon sessions of "The Real World" when he got married and had kids. His time became precious—he wanted to spend it writing or doing something meaningful. This focus on love over like is crucial in balancing a full-time job and a dream job for him.

To achieve quality, Jon must embrace quantity—practice his dream relentlessly. He wrote a million words on his blog before publishing a 50,000-word book. The hard truth is, dreams require practice, quantity before quality. Even Jerry Seinfeld performed thousands of unpaid shows to hone his craft.

Giving away his work for free can also pay dividends for Jon. He didn't charge Dave Ramsey for his early speaking gigs, which ultimately led to his dream job. Free work can lead to practice, exposure, and audience, which are invaluable.

Competition can motivate Jon but shouldn't be a measure of his success. He learned not to compare himself to others like Michael Hyatt, who has a different dream. Instead, he focuses on measuring his hustle—the efforts he controls, like how many days he wakes up early to work on his dream. Success comes from relentless hustle, not just hits. For Jon, it's about hustle first, and the hits will follow.

Unleashing the Power of Hustle: Lessons from Jerry Seinfeld and Dave Ramsey

Robert Downey Jr. and Jodie Foster unknowingly shattered Jon's childhood dream of becoming a wealthy, successful author. Jon once believed that writing a book meant instant riches and fame. That illusion was destroyed when he met Chris Radant, who had her book turned into a movie by Foster, yet still worked a regular job at Bose like Jon. It was a rude awakening that success doesn't always equate to piles of money or fame.

Success can be more perilous than failure, often leading to arrogance and a lack of preparedness for its challenges. Malcolm Gladwell highlighted this, noting that overconfidence in successful leaders can lead to disaster. To avoid this trap, it's essential to define what "enough" means to you. For example, when Jon's blog gained popularity, he sent a future email to remind himself not to chase more at the expense of his current happiness and relationships.

Burnout is another enemy of success. Pursuing dreams can consume our time and energy, often leading to neglected relationships and personal well-being. Jon realized this too late when his blog took off, and his friendships suffered. It's crucial to avoid burnout by balancing hustle with rest and prioritizing meaningful relationships.

Success can also trap you in a platform of your own making, turning it into a prison if you're not willing to share it. By involving others and not hoarding the spotlight, you can create a legacy that goes beyond personal achievements.

Lastly, saying yes to every opportunity can lead you away from your true dream. It's important to evaluate new opportunities and ensure they align with your core goals. Success should be defined on your terms, not by external standards or temptations.

Ken Bradshaw, a big-wave surfer, exemplifies this by choosing passion over industry. He defined his success by his own standards, not by fame or wealth. Embrace your faults as choices made for passion, not regrets of missed conventional success. Defining your enough and staying true to your dream will lead to a fulfilling and authentic life.

Did Robert Downey Jr. and Jodie Foster Unintentionally Destroy Your Dream of Literary Fame?

Jon eventually quit his day job. Despite appreciating many aspects of it, he knew it was time to move on. His boss wasn’t surprised when Jon scheduled a suspiciously vague meeting. Jon had been smart and deliberate about his exit plan, transitioning from tolerating his job to starting small on his dream.

How do you know if you’re ready to quit? Here’s a quick scorecard to help:

- Plan and hone your dream: If you’ve worked on it for over a year, give yourself 3 points. If you’ve only thought about it for an hour, deduct 10 points.

- Use your free time: If you’ve pursued your dream during nights and weekends, add 2 points. If you wait for the mood to strike, subtract 10 points.

- Financial preparedness: Having an emergency fund for six months adds 2 points. Depending on your car never breaking down deducts 1 point.

- Support: If your spouse supports you, add 5 points. If they throw up a little in their mouth every time you mention quitting, subtract 3 points.

Tallies range from “Job Lover or Serial Quitter” if you score negatively, to “It’s Go Time” if you score over 50 points. Jon scored high when he left AutoTrader.com for an opportunity with Dave Ramsey. Here’s why he knew it was time:

1. Jon had a solid landing place: After years of talking about quitting, he finally found an opportunity that aligned with his long-term goals as an author and speaker.

2. The opportunity fit their criteria: Jon and his wife had discussed what his dream job would look like and this opportunity met all those criteria.

3. Jon tested the waters: He’d been interacting with Dave Ramsey’s team for two years, speaking at their events and getting a feel for the culture.

4. They had a support network: From their parents to Jon's blog readers, they had a community that backed them.

5. They were financially prepared: They hustled to pay off debts and saved enough to make the move feasible.

6. They felt God’s backing: Through prayer and reflection, they felt this was where they were being called.

However, Jon wishes they had discussed some ground rules before he started, especially regarding travel, as it created tension at home.

If you’re considering quitting your day job, create a risk list. Identify potential challenges and plan for them. And remember, work doesn’t have to be miserable. Your job can fund your dreams, and with deliberate effort, you can close the gap between your day job and your dream job.

Start where you are, use what you have, and begin today. If Jon can do it, so can you. It’s time to be a Quitter.

From AutoTrader to Dave Ramsey: Jon's Journey to Dream Job Success

Quitting a job isn't always the solution to dissatisfaction. It's about finding balance and making informed decisions. While many people dream of leaving their mundane jobs to pursue their passions, it's essential to maintain a stable income to avoid compromising on crucial aspects of life. Keeping a day job provides financial security and the freedom to say no to bad opportunities, allowing one to chase dreams without undue pressure. 

Discipline in various aspects of life, such as health, can enhance productivity and help maintain purpose. Strategic planning and hustle are key to nurturing dreams. Small beginnings are valuable, offering the chance to grow and make mistakes without the pressure of immediate success. Embracing invisibility and starting small can lead to substantial progress.

Perfectionism and fear of failure can hinder progress, but prioritizing and making the most of available time can help overcome these obstacles. Financial management is crucial, as poor planning can turn money into a barrier rather than a resource. It's never too late to pursue a dream, and each path taken provides valuable experiences.

Success should be defined personally, not by external standards. It's vital to avoid burnout and balance hustle with rest, involving others to create a broader impact. Evaluating new opportunities ensures alignment with core goals, and defining "enough" can lead to a fulfilling life.

Strategic quitting involves preparation and a solid plan, ensuring readiness for transition. Maintaining support networks and financial readiness are critical steps. Work can be a platform for dreams, and with deliberate effort, one can bridge the gap between a day job and a dream job.

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Quitter: Closing the Gap Between Your Day Job and Your Dream Job

Jon Acuff

9 Key ideas

21 MINS

4.5 (710)

Are you stuck in a monotonous job while dreaming of doing something more fulfilling?

Are you ready to bridge the gap between your day job and your dream job?

Have you ever wondered how you could balance a day job with pursuing your passion?

Discover how to hustle smartly, recognize your 'hinge moments', and learn from the journeys of successful personalities like Malcolm Gladwell, Leonardo da Vinci, and Robert Downey Jr.

Key Ideas

#1