What would you do with an entire year off work?

No Slack notifications.
No Zoom calls.
No quarterly goals.

Just complete freedom to explore life on your terms.

At 31, I stepped away from Jasper—the startup I helped scale from zero to a $1.5B AI marketing platform, hitting milestones like 100,000 subscribers and $80M ARR. Truth is, I'm a zero-to-one entrepreneur at heart. 

I love small teams, early-stage hustle, moving fast (sometimes breaking things), building communities, and creating brands from scratch.

Even my mentor and Jasper’s CEO, Dave Rogenmoser, knew when it was time to pass the baton. In his words, going from a "hot startup to an enduring enterprise-grade scale-up" requires new leadership. So in 2023, Dave transitioned to Chairman, bringing in Tim Young—a seasoned exec from VMware and Dropbox—to scale Jasper into the enterprise, (which worked!) and now powers over 20% of Fortune 500 companies.

With this shift, I saw my opportunity for a mini-retirement—or as I playfully call it, my year of 're-wirement.'

Throughout this intentional pause, I journaled constantly, capturing deep reflections, tactical insights, and meaningful epiphanies about life beyond work. Below, I’m openly sharing 12 valuable lessons learned during my mini-retirement. My hope is to inspire and equip you, or any entrepreneur considering a sabbatical, to maximize your own journey when your moment comes.

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Why a Mini-Retirement?

Ever read Tim Ferriss’s classic The 4-Hour Workweek?

One idea really stuck with me:

Don’t wait until you’re older to start ticking off your bucket list. Instead, take intentional breaks—what Tim calls “mini-retirements”—throughout your life, not just at the end.

I first read that book at 21, and honestly, it's lived in my head rent-free ever since.

For years, I’ve been a quiet reader in the r/fatFIRE Reddit community… always reading posts about how people became financially independent & retire early.

Stepping away from Jasper was my chance to finally live out the mini-retirement dream I’d had for years. I didn’t want to wait until 65 to travel the world, learn new skills, and collect unforgettable adventures. No better time than the present!

Plus, at the start of my sabbatical, Paige and I were engaged and preparing for our wedding. I wanted to fully savor that season—wedding planning, honeymooning, and building a life together—without any distractions or deadlines.

Over the course of that year, I committed to getting into the best shape of my life, exploring new hobbies, traveling extensively (solo and with Paige), and eventually finding our forever home in Austin’s scenic hill country. It became the perfect year to slow down, put down roots, and create lasting memories.

Inspired by others who've taken similar leaps, like Sam Altman—who famously took a year off before leading Y Combinator and launching OpenAI—I knew this was more than just a pause. Sam spent his break learning deeply, exploring new ideas, and planting seeds that eventually grew into massive breakthroughs. I intended to follow a similar path, investing in myself and my future.

My 1-Year Mini-Retirement Highlights Month-by-Month

• January: Cooking classes, fitness training, snowboarding trips.
• February: Luxurious father-son trip to Mexico for my bachelor party.
• March: Married my dream girl and had an epic Lake Como-style wedding.
• April: Month-long honeymoon in Bali mixing romance & adventure.
• May: Guided psychedelic mushroom journey for deep reflection.
• June: Built our dream home in the Austin, Texas hill country.
• July: Sold our downtown home, which was kind of stressful tbh.
• August: Took business acquisition courses and signed my first deal.
• September: Officiated a friend's wedding & hiked Banff National Park.
• October: Took my mom to a 3-day music festival.
• November: Solo spontaneous adventure—walked into the airport, bought a random flight, and landed in the jungle of Panama.
• December: Fully supported my wife through surgery recovery, capped with a surprise Christmas trip to Paris.

Using Jesse Itzler's Big A## Calendar kept me intentional—turning dreams into reality rather than drifting aimlessly. Not sponsored, just a cool product especially for planning a 1 year mini-retirement.

12 Lessons from a Year Off

Quick side note before I dive into these lessons:

I realize sharing details about my mini-retirement might stir mixed feelings—maybe admiration, skepticism, or even envy. My intent isn’t to boast or prescribe this path. Instead, I’m openly documenting my journey—mistakes included—to inspire and support anyone contemplating a similar sabbatical, whether it’s a month or a full year.

This isn’t a “how-to-make-money” post, but an open and honest documentation of my experience as an entrepreneur. If this journey inspires you, even just a bit, I’m thrilled. I truly believe that something similar can be possible for you too—whether your mini-retirement is a month away or a decade out. So please, take inspiration from this, make your bold life plans, and when your moment comes, embrace it fully.

12. Shed vanity labels and redefine who you really are:

As entrepreneurs, it’s easy to wrap our identity up in our professional titles—Head of Marketing, Team Leader, Entrepreneur. Especially in America, when you meet people the first question people ask is, "So what do you do for a living?". You work on your business from sunup to sundown and then all of a sudden, poof, the thing you put your whole identity into is no longer there when you exit your business. But during one of my guided mushroom journeys with close entrepreneurial friends, I experienced something known as an “ego death,” realizing how much we tie our self-worth to labels. During one visualization, I pictured a whiteboard covered in labels describing me: CMO of Jasper, Employer, The AI Guy, etc... One by one, I erased these superficial "ego" titles and replaced them with deeper, more authentic "soul" descriptors: Creative Problem Solver, Community Builder, Advisor. Along with who I am to the world: Husband, Friend, Son. I realized those career labels had actually been limiting my potential. By stepping beyond the confines of a single company, I expanded the vision of my impact to multiple businesses, broader community initiatives, and even meaningful personal experiences—like officiating a friend’s wedding. This reframing not only relieved the fear of losing relevance or becoming rusty but also allowed me to redirect my energy and leadership toward family, community, and experiences with deeper, lasting value.

11. Slow down, settle in, and listen deeply:

‍Life as a startup founder often felt like waking up in chaos—constantly putting out fires, racing from one task to the next, and rarely pausing to breathe. During my mini-retirement, I intentionally chose the opposite: slow mornings, daily meditation, grounding my feet in the yard, and lingering over quiet moments without rushing. I spent significant time journaling, exploring deep soul-searching topics, and untangling limiting beliefs. Instead of sprinting through life, I embraced slow travel, relaxed lunches with friends, and regular practices of prayer and gratitude. This intentional slowdown revealed insights that can only surface in stillness. Whether or not you take a full year off, creating space in your days to quiet both external noise and internal chatter—so you can sit, journal, reflect, and truly listen—is a transformative practice worth cultivating.

10. Redefine success beyond business:

As an entrepreneur, many of my goals have been business-related, whether it’s a product launch or a sales target. This year off work, I set annual and monthly goals with my wife, for travel and experiences, for learning new things, and for diving deeper into friendships. I guess I’m finally a “well-rounded person”.‍

9. Pay yourself a salary:

‍I set up automatic transfers from my savings, matching my previous salary at Jasper. Selling monthly portions of my S&P 500 index and Airbnb income provided predictable cash flow, keeping me within a comfortable budget. This structured approach helped me manage my spending without guilt, allowed consistent bill payments, and clearly defined my sabbatical's timeline and burn rate—giving me space to thoughtfully plan my next move.‍

8. Map your runway:‍

"Net worth doesn’t pay bills—cash flow does." While common FIRE wisdom suggests withdrawing 3%-8% of your savings annually, you can responsibly budget a bit more if you’re planning to return to work eventually. Just keep in mind, things often take twice as long and cost twice as much as you expect, so plan accordingly.‍

7. Go on a spontaneous solo trip:‍

I was craving some danger and adventure, for my birthday I packed a backpack and went straight to the airport. I looked on the screen of flights departing and chose a random international destination. Randomly, I ended up on a flight to Panama with zero plans—I booked a $40/night hostel on the flight, followed my gut, and a day later ended up in the jungle with an off-grid tribe. I wandered down roads that looked interesting. Lingered in museums reading the history of the Panama Canal. Normally, Paige and I like luxury resorts and do things like go to The Four Seasons spa, but my solo travel trip was for the thrill of the adventure and find the edge of my comfort zone. Traveling alone lets you genuinely follow your curiosity without worrying about entertaining other's interests. Add in the fact that I don't even speak Spanish, so I had a lot of time to think by myself. The journal reflections that came from that week were profound and I highly recommend taking a spontanious solo travel trip.‍

‍6. Embrace restlessness as growth:‍

Midway through my sabbatical, I felt restless—there’s only so much pickleball you can play. I started exploring new AI tools, content creation, and investing, all without cutting my year off short. I dove into books on investing, enrolled in a $10,000 business acquisitions course, attended conferences, and networked purely out of curiosity, with no specific outcome in mind. Inspired by Codie Sanchez, I reviewed over 120 businesses for sale during the summer, made a few small investments, and essentially squeezed in a crash course in finance and M&A. More on my first acquisition soon!

5. Spend fearlessly on meaningful experiences:‍

Weddings are once-in-a-lifetime moments, and I approached ours fearlessly, investing in memories we’d cherish forever. For my bachelor party, I flew my dad down to Mexico for golf, jet skis, and Caronas on the beach. I was also travel savvy, leveraging over 2 million accumulated travel points (which my Travel Points Consultant shared on Instagram), allowing us to spend a month in Bali for our honeymoon, enjoying slow travel and even flying first class without breaking the bank. 

4. Show up deeply for loved ones:‍

Caring for my wife through her difficult surgery, being fully present to help her through pain, emotions, stress, and healing, made all the difference. If I had a 40-60hr work week, I wouldn’t be able to show up as a husband to the level I did for her during that hard time. So I’m grateful for the space to be there by her side.‍

3. Deepen friendships and show up in big ways:‍

Beyond my business, I started asking myself: “What else am I providing?” The answer became clear—deep, authentic friendships. So with that intention, I crafted a unique experience at my bachelor party. I flew in a professional shaman to host a guided psychedelic ceremony that created space for men to be vulnerable and connect deeply. One friend later shared, “I said things last night I’ve never spoken about before.” Another added, “Most bachelor parties leave you with more shame or guilt, but here we left with less.” That meant a lot to me, highlighting how many men quietly carry heavy burdens and struggle to open up. Throughout the year, I hosted several experiences designed to deepen connections in a safe space, encouraging vulnerability, openness, and unconditional friendship. I also had the honor of officiating two close friends’ weddings, interviewing them about their relationships, crafting personalized wedding addresses that told their love stories, and ultimately pronouncing them husband and wife. Slowing down during this year off taught me the power of being fully present and building deeper, meaningful connections—especially in life’s big moments.

2. Prepare for the slingshot:‍

I think of my career like a slingshot—pulling back intentionally to build tension, strength, and aim. This past year, I paused to study emerging trends like “Buying Boring Businesses” and experimented with new tech like AI coding models, even hosting a few hackathons to “vibe code” apps in a weekend. This intentional pause created a powerful tension that’s helping me zero in on my next exciting opportunities.‍

1. You’re not starting from scratch:‍

During my mini-retirement, I often wrestled with thoughts like, “Will I lose my edge?” or “Will I become irrelevant if I step away?” Here’s what I learned: Life moves forward, but the core opportunities remain. Sure, I missed some moments in the rapidly evolving AI world, but there’s always another “opportunity of a lifetime” waiting around the corner. The beauty is, you’re never truly starting from zero. Your skills, connections, and experiences don’t vanish—they provide fresh perspective and a unique advantage for your next chapter. Letting go of FOMO is easier said than done, but once you do, it allows you to be genuinely present and enjoy the journey, and that’s a trade worth making.

Final Reflections & Advice for Fellow Mini-Retirement Seekers

Life is bigger than business, yet business remains part of the adventure. Business bought freedom—but relationships, unforgettable experiences, and personal growth made me genuinely wealthy.

Taking a year off was the greatest investment I could ever have made—financially, emotionally, and spiritually. If your opportunity arises, embrace it fully and intentionally. This is my guide from the year I chose to live boldly. Ultimately, a mini-retirement isn't about stepping away from life—it's about stepping deeper into it. It's about clarity, intention, and defining success by your own standards. The greatest opportunities often arise when you give yourself permission to pause and reflect. Whether it's a year, a month, or even just a weekend—invest boldly in yourself. You’ll never regret choosing adventure and meaning over routine and comfort. 

Don’t just chase success; define it on your own terms. Step away, recharge, and come back with clarity and intention. Life's too short for anything less than extraordinary.

If you’re considering a mini-retirement or something I said spoke to you, I’d love to connect. Message me and follow along—I’ll continue sharing everything openly.

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