Getting Back To Play, From Net Worth To Net Life, Normalizing The Life You Want | FRLN 147

I recently went back to Stanford for my 20th reunion.

And in several conversations, I shared something that surprised people:

I've been early retired and work optional for the last two and a half years.

My classmates were happy for me. Impressed. Curious. A few were familiar with the FIRE movement, but told me I was the first person they'd met in real life who was actually doing it.

I felt proud. And a little like an anomaly.

Then again, my path has never been a straight line. I didn't get into Stanford on my first try. After being waitlisted and not getting in, I took a gap year, reapplied, and got accepted.

Once there, I tried investment banking internships — a common career track among my classmates — and realized that world wasn't for me. I left Stanford with two quarters remaining and ended up spending about eight years in the Hollywood nightclub business.

I eventually returned at the end of 2013 and received my degree in September 2014 — eight years after my original class of 2006 had graduated.

Then came a decade in tech sales. Financial independence. And now this chapter.

So being a little different at the reunion felt pretty familiar.

I loved reconnecting with my classmates and hearing about the incredible things they’re doing in their careers. I admire their brilliant minds, ambition, and good hearts. But hearing their stories didn’t make me want to return to tech. It reminded me how much I value the work I do now — writing, podcasting, and helping others — and the deep sense of purpose, meaning, and joy it brings me.

I did notice a familiar expectation, though: shouldn't I be up to something big? Starting a company? Working at an impressive tech company? Building the next thing?

And I could feel that expectation without wanting to follow it.

Writing. Podcasting. Playing pickleball. Strength training. Spending time with Carly, my friends, and the people I love.

That's what I want this season of my life to look like.

The definition of success that helped me build financial independence isn't the definition I want to live by forever.

Maybe yours is changing, too.

FIT — Getting Back To Play

Last Monday, I finally had the thought I'd been waiting more than three weeks to have:

Holy shit. I'm starting to feel like myself again.

After getting sick on September 27, my normal energy had felt frustratingly out of reach. Heading into this weekend, I still had some pressure in my head, but most of the fatigue was gone, and my vitality was improving.

I started back with about 45 minutes of pickleball Monday, an hour Tuesday, and an hour and fifteen minutes Wednesday. Thursday, I had a good strength training session, although seeing how much strength I'd lost after barely training for three and a half weeks was a little disheartening.

I've been through interruptions before. I know I can rebuild.

The first few days on the pickleball court were humbling, too. Shots that had felt reliable before I got sick suddenly weren't so reliable. Friday morning, I drilled with a friend and started dialing some of them back in.

Then I played really well. And had so much fun that I ended up playing 3.5 hours. Saturday, I played another 2.5 hours and felt good, though I could feel some tiredness from Friday.

By Sunday, I felt even better and got in a great workout at the gym. My strength was still down, but my energy was good. I've been through this before, and I'm confident that with a few weeks of consistent training, I'll be back where I was strength-wise. With all the rest and recovery I've given my body, I'm hopeful I'll eventually come back even stronger.

The weights aren't back to normal yet, but the energy and excitement are coming back. And that feels really good.

What I've been most grateful to get back is the play itself.

As a kid, I was constantly moving. Trampoline. Soccer. Gymnastics. BMX biking. Mountain biking. Rollerblading. Pretending to be a ninja.

Being outside and doing physical things was a huge part of what made life fun.

Later, strength training and bodybuilding became a much bigger focus. For close to two decades, I spent far more time working out than physically playing. I still rollerbladed, but usually only a few times a week at most.

Pickleball has brought that childhood joy back into my everyday life. When I'm healthy, I often play five, six, or even seven days a week. I'm outside, laughing, learning, competing, making friends, and getting better at something I love.

If my younger self could see how much of my life now revolves around playing outside, I think he'd be pretty damn happy.

He'd probably love that I still make things, too. The kid who enjoyed drawing and art grew into an adult who writes and creates podcasts.

I still care about being strong and keeping my physique in great shape. I also love having something physical in my life that I look forward to simply because it's so much fun.

And I'm still figuring out how to give that enthusiasm room while making room for rest. Getting my energy back doesn't mean I've finished learning that lesson.

What did you love doing physically before you ever thought about calories, body fat, or workout programs? Is there a version of it you'd enjoy making room for now?

RICH — From Net Worth To Net Life

During my tech sales years, success had a very clear definition:

Earn more. Invest more. Grow my net worth. Buy back control of my time.

There was a deeply personal reason for that drive. I grew up with financial insecurity. I felt shame about how little money we had. I witnessed my parents fight about money and, after they separated, watched my mom struggle as a single mother.

Then I created my own financial mess as an adult.

Building wealth meant creating security I desperately wanted. I never wanted to feel that financially vulnerable again.

I also loved being a top performer. That part of me showed up in school, sports, and eventually sales. Achievement has been a consistent value throughout my life, and the reunion reminded me how much I share that with my classmates.

There is a lot to appreciate about ambition. It can inspire us to learn, grow, contribute, and accomplish things we're proud of.

The question I'm asking now is: What's fueling my desire to achieve?

Fear and insecurity were powerful motivators. Going forward, I want more of that drive to come from inspiration, love, and the joy of discovering what I'm capable of.

That shift has taken time.

My original financial independence target was $1.5 million. When I reached it, I raised it to $2 million. Then $3 million. Growing the number was the game I knew how to play.

When I was laid off in March 2024, I decided to try early retirement instead of pursuing another sales job. Then I immediately poured my achievement energy into building a highly profitable online business.

For about nine months, I pushed without giving myself much of a break. Eventually, I had to acknowledge something:

I didn't need to make a ton of money anymore.

I could still earn money. I could still build things. But sacrificing the quality of my life to reach another income target no longer made sense.

My net life needed to become the priority. Additional income was optional.

For the last year and a half, I've been exploring what that means in practice.

I love writing and podcasting because I'm creating a body of work that can help someone else. Sharing what worked, what didn't, and what I wish I'd understood sooner might make another person's journey easier, faster, or more fulfilling.

That feels worthwhile to me. Writing a book is one project I could imagine choosing to devote more of my time to.

Another corporate career doesn't have that same pull. I loved the people I worked with, and I'm grateful for that chapter. It served its purpose. There are other things I want to do now.

Your answer might be different. You might love your career and want to keep doing it for decades. I can't know what my classmates want from their lives based on a reunion conversation, and financial freedom doesn't require everyone to make the same choices.

But I think it's worth asking what all the earning and achieving is meant to make possible.

Start with an ordinary Tuesday.

If money weren't an issue, what would a Tuesday you absolutely loved look like? No exotic vacation. Your actual day-to-day life.

Mine starts with meditation, followed by a slow morning of creative work, foam rolling, some Theragun time, and a protein-packed breakfast. Then a 1-2 hour strength training session and a couple hours of pickleball. Home for a nap that might last 30 minutes or two hours. An early dinner and an evening with Carly, followed by reading a fun fantasy or sci-fi book before bed.

That's a day I feel lucky to live.

Yours might involve a completely different mix of family, work, creativity, adventure, or quiet. Get specific about it. Then imagine the rest of that ordinary week.

It's easier to know what “enough” is when you know the life you want it to support.

LIFE — Normalizing The Life You Want

When I lived in Menlo Park, I didn't realize how much pressure I felt to keep advancing my career.

I was immersed in it. It was normal.

People were building innovative things, moving up in their companies, switching to more exciting companies, and pursuing bigger paychecks. What you did and where you worked carried a lot of weight in the conversations around me.

There was a career version of keeping up with the Joneses (I call it Career Maxxing), and I didn't fully recognize how much I participated in it until I stepped outside that world.

That environment helped me. I enjoyed it. Its intensity supported a season when earning and building wealth were major priorities.

But career growth competes for time and energy with everything else we care about: our partners, families, health, friendships, spirituality, and the things we do purely for joy.

When almost everyone around you is focused on the next professional milestone, it can be hard to notice what else you'd like to give more attention to.

An environment can serve one season of your life beautifully and be less suited to the next.

In my Santa Cruz circles, I encounter more people who organize their lives around enjoying where we live. Surfing. Mountain biking. Cycling. Running. Pickleball. Spending time outside matters here, and I fucking love that.

It supports something I've loved since I was a kid.

Would I have found my way to this version of early retirement if I'd stayed in the epicenter of SF Bay Area tech? Maybe. I can't know. But I believe moving made it easier to explore what I wanted beyond my career.

I've seen the influence of environment in very different chapters of my life. Before Hollywood, I didn't do drugs. Within about two years of working in the nightclub business, I was drinking seven days a week and using drugs every day. In that world, it had become normal.

I think about that when I hear people talk as if discipline alone makes us immune to our surroundings. My experience taught me to take those surroundings seriously.

And your environment includes what you consume online.

When I first became work optional, I was following online entrepreneurs focused on making a million dollars or more a year. Of course I started working toward that, too. I had left my sales job, but I was still filling my attention with people whose central goal was growing income.

Earlier in my FI journey, I'd intentionally created a different kind of influence: I started a financial independence meetup group. I wanted real-life friendships with people pursuing freedom or already living it.

Reconnecting with my FI community through FinCon, EconoMe, and friendships helped me remember why I had pursued this in the first place. I also shifted away from so much business-growth content and toward conversations about enjoying life after FI.

My friend Doug's podcast, Mile High FI, has been part of that. Hearing people discuss the opportunities and challenges of this stage helped me embrace my own.

Interviewing people in early retirement about their experience on my podcast has also been incredibly helpful. Listeners will notice a lot of the recent podcast episodes delve into early retirement — not just getting there, but the challenges and blessings of living it. A big part of my own growth is externally processing what I'm going through in conversation with others.

Moving alone didn't build my new life. I still had to find community, explore what I enjoyed, and choose what I gave my attention to.

Spend time with people who make the life you want feel possible — and normal.

You don't need to replace all your friends or move to Santa Cruz. You can join a community, start a meetup, make one new friend, or change what you regularly listen to and read.

Give the values you want to live more company.

ACTION — Define Success For This Season

What does success look like in your life right now?

Give yourself permission to answer differently than you would have 5-10 years ago. Then pick one of these to act on this week:

• FIT: Make time for a physical activity you enjoy for its own sake. Revisit something you loved as a kid or try something you've been curious about.

• RICH: Write out your ideal ordinary Tuesday, then sketch your ideal week. Identify one part you can bring into your life now, while you're still building toward financial independence.

• LIFE: Look at the people and content shaping your sense of success. Add one influence that supports the season you want to live. If an old influence keeps pulling you toward a goal you no longer want, give it less of your attention.

When I was still working in tech, I made room for my creative work, training, reading, and spiritual practices before my nine-to-five. I'm naturally an early riser, so that 5 a.m.- 9 a.m. window worked for me.

Your window may look different. The point is to start making room for the things you want your life to contain. Financial independence has given me much more time for things I was already enjoying.

At my reunion, I could appreciate the lives my classmates were building and feel happy about the one I'm building, too.

I want to keep achieving. Today, that includes becoming a better writer, creating useful conversations, improving at pickleball, and being present with the people I love.

That's success in this season of my life.

What would it look like in yours?

To your health, wealth, and happiness,

— Justin David Carl

P.S. I created my flagship course Investing Mastery: Your Path To Millionaire to teach you how to manage and grow your money so you can get to the point where all work is optional. Imagine choosing how you spend your days because you want to, not because you need a paycheck. That’s the freedom I want to help you build — so you can spend more of your life actually living it. [Explore Investing Mastery here.]