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What Die With Zero Taught Me About Regret-Proof Living
Family Looking Across the HorizonI had been wanting to do an international family trip for years. But I kept waiting for some arbitrary “perfect date.” Finally, I bit the bullet and said, let’s fucking do this.
It turned out to be one of the greatest trips of my life – and ultimately one of my favorite memories with my family.
Money is a renewable resource. Time is not.
When you keep delaying, waiting for work to slow down, responsibilities to lighten, or life drama to magically resolve itself, you stay put. Your dreams stay put. And the truth is, most of the time, life never gets “easier.”
Same with my dogs. I already had multiple, but my dream dogs weren’t part of my pack yet. So what did I do? I bit the bullet and got them. Has it been easy? No. In fact, it’s created massive problems for my lifestyle. Has it been worth it? One hundred fucking percent. I wouldn’t trade them in for the world.
When I have to make tough decisions, I ask myself two questions:
What would my higher and future self do in this situation?
What happens if I don’t do this now and wait? How might it affect me?
A lot of decision-making is fear-based. A lot is scarcity-based. And yes, sometimes we find out we didn’t want something as much as we thought. But far more often, the opposite happens: we did want it, we did need it – and the only thing in the way was our own hesitation and drive to make it happen.
And here’s the part most people don’t think about: people will spend insane amounts of money to extend their life at the end – medical bills, treatments, assisted living – but spend nothing to make themselves comfortable and alive while they’re young.
They’ll happily burn through cash to buy themselves two extra years at 85, but won’t spend a dime to experience life fully at 25, 30, 40, 50, or 60.
Making yourself comfortable and alive now – without sabotaging your future – might be the smartest investment you ever make.
We don’t die with money. We die with memories.
Experiences > Money.
We’ve all heard it before, but it’s true. At the end of life, money might make things more comfortable – but what really matters is connection, people, love, and experiences.
So many people obsess over retirement balances, some “magical number” in their accounts, or hitting the next financial milestone. But here’s the real kicker: for the ones who do reach that number, it almost never ends there. They just set a bigger one.
Bill Perkins nails it in Die With Zero: “Whatever amount people say they need, the answer always seems to be more.”
It never ends. The appetite for money is nearly impossible to tame. But memories? Those you can savor forever.
I think about a young woman I knew who always wanted to go to France. She talked about it constantly in her 20s. Sometimes she had the money and freedom, and sometimes she didn’t, but she kept saying, “someday.” Someday when work slowed down. Someday when things lined up perfectly. Someday when my partner can go with me.
Someday never came. She died before she was 30 – without ever stepping foot in the country she dreamed about.
That’s the harshest truth: time doesn’t ask permission. You don’t get to schedule your expiration date. If there’s something you know you want to do, waiting for a perfect moment might mean missing the moment entirely.
And honestly, I hear it all the time: “I wish I could go here, I wish I could do that, but I can’t. I have responsibilities. I don’t have the money. I’m tied to this relationship, these kids, these animals, these obligations.” Excuse after excuse after excuse.
But here’s the reality: if you keep that mindset, you’ll look back on a life full of excuses instead of a life full of: “I fucking did that shit.”
Step outside of your container, your life, your responsibilities, your obligations, your excuses, your patterns, your habits, your mentality. And start exploring an expansion of possibilities.
Because at the end of the day, it’s not about the size of your bank account. It’s about the size of your life.
This content is for informational purposes only — not professional advice. Consult a qualified professional before making any major decisions.