You’ll Retire 3 Times in Your Life

And there is no reason to be 65 for any of them

Photo by Ethan on Unsplash

“Retirement starts when you stop sacrificing today for some imaginary tomorrow,” philosopher Naval says. That’s one way to look at it.

Another is that “retirement” is this vague, distant, supposedly rewarding thing meant to happen at the end of your life, and even though you actively plan for it, it feels too far away for you to grasp it.

You can see your pension contributions on your pay slip each month. You can check how much you’ve saved and how much it’s growing. Maybe your total projected payout even looks like an “I won the lottery” kind of jackpot that’ll unlock when you’re 65.

None of this, however, changes the fact that retirement is a long way down the road, and that’s why it feels strange, unfamiliar, and maybe even unimportant to think about it. Trust me, it is not.

As a self-employed writer, I think about it all the time — but I also make jokes. “What do you mean, ‘after graduating?’ I’ll retire, of course!” Lately, however, I started seeing a kernel of truth in all my early-retirement jokes.

I’ve only been an entrepreneur for six years, but looking back on my journey, I can see some clearly marked points after which I felt freer than ever before. Isn’t that what retirement is about? A sense of liberation?

Given the huge weight they lifted off my shoulders, I now consider these checkpoints my retirements. So far, there are three of them, and I think they mark my path to freedom and happiness much more clearly than any traditional definition of retirement ever could.

If you’re sick of the vague cloud of “retirement” hovering somewhere in the distance, here are three more hopeful, specific ways to look at it — none of which require you to be old, and all of which you can choose today.

1. The first time you’ll retire is when you stop living by society’s expectations.

For most of my life, I did what was expected of me — even though hardly anyone ever expressed any specific expectations. Isn’t that crazy? That’s how society works.

As you grow up, you look around you. You see what people do, you listen to what they say, and you begin to value what they value. Most of all, you think you’re the least qualified to come up with any answers, and so you start accepting the answers other people provide, even if they do so in silence — even if they are no more an expert at life than you are.

The only way to break this cycle is to start asking questions. Lots of them. And then, you must come up with your own answers.

I gave my first answer in 2012, and it was: “I will not be a consultant because being a consultant won’t make me happy. I want to be a writer instead.”

I was studying abroad in US. College was more structured; I had more time. That time gave me the space I needed to ask some important questions, like the one to which I gave the answer above: “How can I spend my working life doing something I enjoy?”

Since I wasn’t buried in work, I could finally think about what I actually want my work to look like. I woke up at 5 every day, watched the sunrise, and read. I read The Alchemist. I read James Altucher. I read everything I could get my hands on, and then I decided to be a writer.

Until that moment, I had mostly lived by expectations. I did my homework because my teachers wanted me to. I went to college because I thought my family wanted me to. I knew there were other paths out there, but I didn’t even consider them. That’s the power of social conditioning.

As soon as I decided to be a writer, I felt free. I knew hard conversations and difficult choices would follow, but I felt huge relief from knowing that, finally, I was on my own path — the path I was meant to be on rather than the one society had implicitly chosen for me.

In order to be happy, you must stop living by other people’s expectations. It doesn’t matter whether they tell you what they want you to do or whether you just imagine you know — neither will suffice.

Whatever you truly want to do in life, chances are, it’ll feel a little out there to someone who’s important to you, but you can’t let that stop you. It’ll definitely seem weird to a lot of strangers and friends, but what those think matters even less if your mission is one you know you were born to be on.

Don’t worry about your high school reunion, worry about your memories as a 90-year-old. Retire from society’s expectations.

2. The second time you’ll retire is when you start living below your means.

I decided to be a writer in 2012. I became a writer in 2014. I didn’t just quit everything and hoped for the best. That’s not how life works — at least most of the time — and so most of the time, it helps to have a plan.

After graduating, I gave myself a one-year window to test entrepreneurship. I lived cheaply, on 700 € per month. I only made $20,000 in my first year of freelancing, but it was enough to teach me a powerful lesson: As long as I make those 700 € per month and don’t overspend, I am free to do whatever I want.

Financial retirement happens when you spend less than you earn, not when someone hands you a big check for four decades of service.

The idea of retirement as a big pay day is the most ingrained in our society, but it’s also the easiest to overthrow: If you don’t have financial commitments that exceed your ability to pay them, you are free. Therefore, the easiest way to free yourself is to reduce your financial commitments.

Many of us start our careers this way — I know, some people have lots of college debt — but then we ramp up our spending before we’ve earned the right to do so, both literally and in a figurative sense. Pay off your debt, live in a flat, don’t order food every day, and feel your confidence grow. There is true peace in knowing you’ve got the bills covered for the next six months.

Basing our pensions on our current salary makes work and money look more entangled than they actually are. If you don’t need a lot of money every month, you don’t have to work a lot every month. How you make that money is another story, but that’s a problem you can solve all on its own once you live below your means.

So please, live below your means. Retire from the rat race.

3. The third time you’ll retire is when you focus on the work you truly love.

My first year of freelancing also showed me how easy it is to slip back into the “grind until you’re old” trap, even if you’re doing work you’re good at and aren’t at the mercy of a bad boss.

I extended my entrepreneurship experiment by one year, but instead of just doing more and better-paid freelance work, I built something I cared about: Four Minute Books. Ultimately, I also made $20,000 in year number two, except now half the money came from something I truly loved.

As I grew my income over the years, I went back and forth between doing work I genuinely wanted to do and work that was good in a financial sense. This is normal in any career but especially in entrepreneurship, where you face the constant tradeoff of diversification vs focus.

A few weeks ago, however, I reflected on 2020, and I realized: “You’re making way more than enough, and yet, you’re still grinding. When will this end?” It was time to — once again — shift more towards work I truly love. I quit several projects and a part-time job and decided to focus exclusively on writing. It might not be the last, but that was my third retirement.

Finding work you love is a hard problem. You must defy society’s expectations. You must get by financially and still make time to experiment. Once you find your thing and trust your gut, however, it is your duty to follow your heart.

That’s true retirement, and the only way to achieve it is to do work you love. It can’t happen when your bank account hits an arbitrary number because the excuse of “I want more money” will never go away.

Don’t give up. Finding your passion isn’t just exploration. It’s creation. It takes time, but it’ll be worth the effort. As the saying goes, “Choose a job you love, and you’ll never work a day in your life.”

Retire from distraction. You know what you must do, so follow your true north.

“Retirement starts when you stop sacrificing today for some imaginary tomorrow.” That’s a great way to put it.

When it comes to society’s expectations, you’ll never be able to live up to all of them, and even if you were, no one would give you a prize for it. No matter what you do, people will judge you — the imaginary tomorrow never comes. Retire from their expectations, and you’ll be free to find your own path.

Money works in opposition to retirement: If you overindulge today, you’ll automatically sacrifice tomorrow. Live below your means, and you’ll never spend your days working to pay off bills for things you don’t need. Have the discipline to own today, and you’ll also own tomorrow.

Finally, no matter how rich you’ll become, you’ll never feel like you truly have enough. You must decide that you have enough, and only once you do are you free to spend your time and energy on doing what you love — and thus helping not just yourself but others.

The truth is you’ll retire many times in life, and there is no reason to wait until you’re 65 for any of them to roll around. You are the architect of your life. As long as you’re retiring from the right things, you might as well start today.

I write for dreamers, doers, and unbroken optimists. For my best articles & book updates, go here:

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