Retiring early might sound like a far-fetched dream, but for the FIRE (Financial Independence, Retire Early) community, it’s a path filled with trial, error, resilience, and a lot of learning.

In a recent episode of the Get Rich Slow Club, Tash chats with three fascinating FIRE-aligned guests – David, Keith and Rob – about their unique journeys toward financial freedom.

Whether you're curious about property investing, managing money mistakes, or navigating early retirement emotionally, this episode is packed with insights.

Redefining the retirement goal

The episode opens with David challenging a common mindset: settling for a job that’s just “okay.” He says, “The baseline should be: I love my job. I get excited to wake up in the morning and go do what I’m doing. If I would do the job for free, okay, that’s a good gauge.”

For David, early retirement isn’t necessarily about never working again – it’s about having the freedom to choose what to do with his time . While he’s currently not working, he admits: “We’re not done making money yet, but we’re really enjoying life right now and drawing down on savings.”

Keith, meanwhile, is fully retired and travelling the world – living proof that Financial Independence opens doors to adventure and lifestyle freedom.

Rob recently bought a car and is road-tripping across Australia, showing how even transitional moments can lead to both practical and joyful experiences.

Property investing: wins, losses and everything in between

All three guests have dipped into real estate investing , with varying results. Keith is all-in on property, owning 40 houses, mostly in a small town in Illinois.

“I buy the worst house on the nicest block,” he says, explaining his strategy of fixing up cheap properties to build equity and snowball into the next deal.

His properties are modest – one was bought for just $5,000 – yet they’ve built him a lifestyle of financial freedom.

David’s property story, however, hasn’t been as smooth. He once purchased six turnkey rental properties via a third party, hoping for easy cash flow. Instead, he faced underestimated expenses, misrepresented projections, and poor property management.

“Nobody is going to care about your property as much as you do,” he warns.

One example involved a house in Indiana that was meant to cash flow $650/month, but utility bills he hadn't anticipated wiped out the returns. Another sat vacant for three months and eventually rented for far less than projected.

“It mentally scarred me,” he admits, adding that at one point, he considered giving up on real estate altogether. But after learning from the experience and leaning on FIRE friends like Keith, he's now open to giving it another go – with a lot more due diligence.

Why emotional resilience matters

One of the most striking parts of the conversation is how openly David speaks about the emotional rollercoaster of reaching Financial Independence.

At one point, he had to use joint savings with his new wife to cover $10,000 in damage to a rental property – an emotionally tough experience.

“Even though it was both our money… it was really emotionally difficult for me to have to pull out money from our combined savings account,” he says.

He also opens up about how the FIRE mindset can become all-consuming.

“I would stress out any time I spent any extra money because I would think: ‘Oh, I've got to get to this FIRE goal.’” That pressure, he now realises, isn't healthy.

“Take a sabbatical, take six months off, take a year off to decompress and discover yourself," he says. "If there's something else you could be doing, take that opportunity right now.”

Keith echoes this with a big lesson from his former boss: incremental improvement.

“You don't have to go from trash to the best house in the neighbourhood. Just make it better than it was.”

Whether it’s money, health, relationships or personal development, slow progress is still progress.

The community that fuels the journey

If there’s one recurring theme throughout the episode, it’s the power of community. The trio met through FIRE events like CampFI and EconoMe in the US and have continued to support each other through cross-country road trips, global retreats, and ongoing friendships.

Keith puts it simply: “That’s probably been one of the best parts of the FIRE community. I travel and visit people wherever I’m going.”

It’s through this community that David also found love – literally. He met his wife on a FIRE-themed dating site.

“I remember we talked for more than two hours, because I got charged for parking,” he laughs.

That connection grew into a meaningful relationship with someone who shares his values around money and lifestyle.

From burnout to business: creating value post-retirement

David now runs a financial coaching business called Dream Financial Coaching, where he helps people work through money shame and build practical strategies for financial stability. But it didn’t come easy. He admits he struggled with Imposter Syndrome and hesitated to take his business seriously.

“My excuse was: ‘Oh, we don’t really need the money.’ But the truth is, I was afraid of putting myself out there,” he says. With encouragement from his friends, he’s now leaning into the work.

“I like digging into people’s money situations and helping them go from feeling ashamed to getting them to a place of optimism, confidence, and stability."

David also volunteers with a US-based nonprofit called 3rd Decade, offering free financial coaching to young adults. It’s part of his mission to make quality financial guidance more accessible – something the whole group agrees is sorely needed, especially in Australia.

Final takeaways for aspiring early retirees

The episode wraps with each guest sharing their key advice:

• Keith: Focus on “incremental improvement” in every area of life. “Keep trying to do a little better than you did before. If you keep doing better, then eventually you're going to be doing amazing things.
• Rob: Don’t wait for perfection – just start. “If you’ve got a dream, follow it. if you give it a go, you'll get feedback. And you can use that feedback to make yourself better for next time."
• David: Don’t be discouraged by other people’s flashy success. “Do what you can with what you can or with what you have. It might take you longer to achieve what you're trying to achieve, but you will get there."

And perhaps the most powerful reminder of all? FIRE isn’t about avoiding work – it’s about creating a life you don’t need to escape from. “If your baseline is, ‘well, it’s okay,’ that should not be the baseline,” David insists.

Instead, aim for a life filled with purpose, flexibility and joy. That could look like managing your own rental properties, building a business, or road-tripping across continents with FIRE friends.

As the episode proves, Financial Independence is as much about mindset and meaning as it is about money.

If this episode sparked something in you, give it a five-star rating, drop a review, or better yet, share it with a friend. And if you're just starting out, the first ten episodes will get the financial gears turning. Follow us at @getrichslowclub and catch our personal updates at @tashinvest or @anakresina.

Happy investing!