Do Over

What would it feel like to wake up on a Monday genuinely excited for work? To know that even if your company disappeared tomorrow, your career wouldn’t collapse with it? In Do Over, Jon Acuff argues that true career security—and joy—comes not from a single job, company, or title, but from the investments you make in yourself. His concept of a Career Savings Account (CSA) is the cornerstone of reinventing your work and protecting your future: a personal vault made up of relationships, skills, character, and hustle.

Acuff contends that anyone, at any stage of life, can have what he calls a “Do Over”: a chance to hit reset on your career before you hit a crisis. By strategically building your Career Savings Account, you’ll be ready for any of the four major career transitions every professional faces—Ceilings, Bumps, Jumps, and Opportunities. With humor, honesty, and practicality, Acuff dismantles the fear that surrounds career change and replaces it with a toolkit for long-term resilience.

The Four Career Transitions

Acuff’s chart of the four career transitions is deceptively simple but profoundly helpful:

• Career Ceilings: When you reach the limit of what your current role offers, skills will be the hammer that breaks through the ceiling.
• Career Jumps: Voluntary, positive transitions—like starting a business or changing industries—require rock-solid character to handle chaos and risk.
• Career Opportunities: Unexpected good surprises that fall into your lap—those depend on hustle, your ability to act quickly and make the most of luck.
• Career Bumps: Layoffs, failures, or setbacks that happen to you; in those moments, relationships become your safety net.

You can’t control which transition will hit next, but your CSA ensures you’re prepared for all four. In Acuff’s view, careers aren’t built—they’re continuously rebuilt.

The Four Investments that Build a Strong CSA

The formula Acuff presents—(Relationships + Skills + Character) × Hustle = Career Savings Account—is the foundation of his guidance. He devotes much of the book to explaining how each investment reinforces the others:

• Relationships get you the first gig. They’re the “who you know.” Connection, rather than networking sleaze, drives real opportunity.
• Skills get you the second gig. They’re the “what you do.” Developing new skills and sharpening old ones keeps you employable.
• Character is the “who you are.” It maintains your reputation and helps you handle success without arrogance or greed.
• Hustle multiplies everything else. Without hard work, none of the other three matter—your potential stays theoretical.

These aren’t theoretical qualities; Acuff infuses them with humor and realism. Relationships aren’t about “networking events and business cards” but about staying in touch with people who trust and respect you. Skills aren’t degrees—they’re learnable abilities like communication, adaptability, and even time management. Character requires long-term care, like tending an orchard. And hustle, while critical, must be practiced with balance and awareness to avoid burnout.

Why This Matters Now

In an economy where layoffs, automation, and job-hopping are the norm, Acuff’s framework hits home. “People were taught to work jobs, not build careers,” he writes—a provocative reminder that we often plan for college and retirement but not for the 40 years in between. A CSA is a lifelong safety net that lets you adapt when the unexpected happens. If you’re stuck, disengaged, or afraid to change, this book argues that the solution isn’t a miraculous job post—it’s building a stronger you.

“Good job, bad job, dream job, no job—this is true: you control more than you think.”

Acuff combines research, storytelling, and wit—mixing neuroscience about resilience with anecdotes about burnt popcorn coworkers and balloon artists—to make serious career advice fun and readable. His message is clear: no career is permanent, but with the right mix of relationships, skills, character, and hustle, you can thrive regardless of what happens next. It’s never too late to call a Do Over.

Acuff opens his first major investment—relationships—by redefining what true connection looks like in a professional context. He argues we don’t need more “networking events” or LinkedIn spam; we need genuine relationships built on authenticity and service. Relationships are what get you the first gig and sustain you through the tough seasons.

Foes, Friends, and Advocates

Acuff breaks career relationships into three groups: foes, friends, and advocates. Most of your relationships will be friends—friendly, everyday colleagues who might one day open doors. Advocates, on the other hand, are rare and powerful: people invested in your growth who tell you the truth, even when it’s uncomfortable. “A friend shares your day. An advocate shapes your career,” he writes.

Foes, meanwhile, should be given distance—not drama. Acuff satirizes our obsession with “haters” and recounts lessons from a cab driver who survived real enemies in Iraq to remind readers most workplace foes are harmless. Don’t waste energy fighting people who don’t control your future. Instead, focus on allies who do.

Boomerangs and Casual Relationships

While many career guides glorify tight-knit mentorships, Acuff insists that “casual counts.” The people who open key doors are often acquaintances rather than close friends—like an old coworker or Twitter connection you haven’t talked to in years. These “boomerang relationships,” he says, circle back unexpectedly when you least expect it. The key is to throw as many as possible by being generous, kind, and staying in touch.

He uses vivid examples—from Shauna Callaghan, who built his blog after years of silence, to a lifeguard who landed a Grammy-winning songwriting partner—to show that serendipity favors those who’ve invested relationally. The takeaway: every email, thank-you note, or kind act is a deposit into your CSA. Don’t underestimate the power of small gestures.

Building Advocates

Great advocates, like mentors, share three traits: bravery, respectability, and trustworthiness. They also hold the “cheat codes” to success—the insider wisdom that shortcuts your learning curve. Acuff compares them to video game experts who’ve already played the level you’re on. As rapper André 3000 once said about mentors, they “tell you where the traps are.”

Finding such people requires humility and proactive effort. You must give them access—not just superficial updates, but the real story. When Acuff let a mentor grill him with hard questions (“Is that the story you want to tell your kids?”), he realized that uncomfortable truth is the tuition fee for authentic growth.

The Bridge You Don’t Burn

In Chapter 7, “Don’t Burn Many Bridges,” Acuff reminds readers that every industry is smaller than it seems. Even “Brenda,” your office nemesis, could be your boss someday. His advice: leave every job with one finger raised high—your thumb. Ending relationships with grace preserves your professional reputation and keeps old bridges intact for the future.

“Don’t be an idiot online. Digital bridges burn forever.”

From the humility of apologizing for past mistakes to the warmth of sending a handwritten note, Acuff’s relationship advice boils down to this: be kind now, because you’ll meet everyone again. In careers, as in life, generosity compounds—and no one succeeds alone.

If relationships get you in the door, skills keep you in the room. Acuff’s second career investment emphasizes that skills—not luck or personality—turn opportunities into long-term success. His message is encouraging: you have more skills than you think, and you can always learn more.

Reevaluating What Counts as a Skill

Acuff redefines skills as everything you do to add value, not just the technical abilities on your résumé. Even soft skills like gratitude, punctuality, and communication are career rocket fuel. As he jokingly says, “Everything is a skill—even not microwaving seafood in the break room.”

He also teaches readers to catalog their hidden skills using “note cards.” This analog exercise helps uncover patterns—connecting past wins, natural strengths, and even fears that may point toward untapped potential. (A nod to psychologist Roy H. Williams’s quote, “It’s hard to read the label when you’re inside the bottle.”)

Learning and Keeping Skills Alive

Developing new skills is equal parts curiosity and necessity. Acuff argues that the smartest way to start is with a “could” skill—something fun and interesting that builds confidence—before tackling the “should” skills your job demands. For example, learning pottery might lead to creative momentum that later fuels a marketing certification. Progress, he says, is contagious.

However, skills dull quickly if ignored. Acuff compares unused abilities to saplings of fear taking root in your brain. The longer you avoid practice, the larger those roots grow until you’re paralyzed by doubt. His remedy: practice regularly, create repeatable systems, and build routines that keep your saw sharp—what he calls “career autopilot.”

Avoiding Career Extinction

In “Never Become a Dinosaur,” Acuff captures the urgency of lifelong learning. He recounts conversations with a pharmaceutical rep, a designer, and a network engineer—all realizing that ignoring change for even a month puts them behind. The difference between extinction and evolution, he insists, is curiosity. “Learning something new always leads somewhere new,” he writes, echoing the growth mindset of Carol Dweck.

He assures readers that being a beginner isn’t failure—it’s proof you’re still growing. “Be a tourist,” he jokes. Tourists ask questions, take photos, make mistakes, and have fun. That humility keeps your career alive while others cling to outdated “perfect plans.”

“Your career will become extinct unless you learn new skills.”

Skills are the bridge between dreams and doing. By writing them down, maintaining them, and daring to learn new ones—whether through note cards, night classes, or YouTube tutorials—you keep yourself future-ready. In Acuff’s world, every new skill is a hammer, and every hammer can break through the next ceiling.

Acuff calls character “the mortar that holds your entire Career Savings Account together.” Without it, even the best skills and relationships crumble. He likens character to an orchard: full of trees that take time to grow, weeds that must be pulled, and a patient farmer—you.

Planting and Pruning Your Character

Character isn’t built overnight; it’s cultivated through steady habits. Acuff invites you to plant one tree—a single character trait to strengthen. Whether it’s patience, humility, or accountability, you grow it by showing up. He also encourages taking a “flyover view” of your career orchard to spot recurring personal patterns—like his own addiction to chaos and overwork.

Weeds—narcissism, dishonesty, pessimism, and apathy—are character’s enemies. They suffocate growth and quickly poison workplaces. Acuff’s self-deprecating humor (“I might press my own elevator buttons but sometimes feel too important to”) underlines that no one is immune. The challenge is recognizing and pulling those weeds before they overtake your orchard.

Generosity, Empathy, and Presence

Once the weeds are gone, Acuff focuses on three character “trees” to cultivate. Generosity builds loyalty, proving that kindness is the most profitable business model. Empathy transforms coworkers into collaborators by understanding others’ needs and acting on them. He tells vivid stories of a dentist who waived a bill after Acuff’s job loss, and a chimney sweep who sent photos of customers’ dogs as thank-you postcards—because he cared about what mattered to them. Finally, presence—putting your phone down, showing up for meetings, and listening—sets you apart in a distracted world.

The evidence is clear: character leads to sustainable success. It steadies your moral compass when chaos hits, especially during Career Jumps, where temptation and anxiety run high. In Mary Caroline Richards’s metaphor that Acuff cites, a dancer never loses balance mid-leap because she shifts her center. Character is that center.

“You might leave a company, but your character always jumps with you.”

For Acuff, great careers depend less on raw ambition and more on consistent decency. When you plant generosity, empathy, and presence, the harvest lasts a lifetime—and the storms of change can’t uproot what’s deeply rooted in who you are.

Acuff begins his final investment with a simple declaration: “Hustle is not about busyness; it’s about focus.” It’s the fuel that multiplies everything else—relationships, skills, and character—turning potential into momentum. But unlike the empty grind culture that glorifies burnout, Acuff reframes hustle as purposeful, aware, and sustainable.

Grit Is a Choice, Not a Feeling

In one of the book’s most memorable chapters, Acuff dismantles Hollywood myths about grit. “It never feels like bravery,” he confesses. “It feels like throwing up.” Grit isn’t glamorous—it’s the decision to try again when you fail. He quotes Steven Pressfield’s The War of Art: fear never disappears; professionals simply work anyway. His lesson: hustle doesn’t require fearlessness—just stubbornness in the face of fear.

He also contrasts fear and regret: fear is temporary, regret is permanent. When you avoid risk, you choose lifelong regret over short-term discomfort. Hustle, then, is how you choose courage daily.

Awareness and Seasons of Hustle

In “Hustle Has Seasons,” Acuff introduces the concept of hustle awareness: knowing when to sprint and when to rest. “Maybe right now you’re in med school season,” he writes. Intense hustle is warranted in some seasons but destructive in others—like parenthood or recovery. Awareness ensures your ambition doesn’t wreck your life. Hustle, he insists, should act like a scalpel—precise and intentional, not a chainsaw tearing through everything.

Flexibility and Fun

The final form of hustle, which Acuff calls “Career Yoga,” is flexibility. Purpose isn’t something you find before you start hustling—it’s something that emerges because you hustle. Your dreams evolve; success isn’t static. He urges readers to embrace fuzzy visions, not rigid plans, because much of what you’ll end up loving might not even exist yet. (Think of social media managers or remote creators—a decade ago, those jobs didn’t exist.)

Acuff also inserts an unexpected but essential ingredient: fun. “Have fun storming the castle,” he writes, reminding readers that joy fuels perseverance. His parable of Nashville’s weather tweeter, David Drobny—who volunteers predicting storms just because it’s fun—shows how hobby-level fun often leads to unexpected opportunities and protection from burnout.

“Purpose is often a by-product of hustle, not a prerequisite.”

When Acuff concludes with Misty’s story—the 42-year-old who moved to Spain for music—he fuses every part of the Career Savings Account in motion: relationships that dared her to leap, skills that lifted her ceiling, character that anchored her confidence, and hustle that carried her to the opportunity of a lifetime. The implication is inspiring: you already have what it takes to start where you are. As Acuff ends, “Do you think you can have a Do Over? Apparently, you can.”