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Home » 3 Questions to Ask Yourself Before Pursuing Early Retirement
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3 Questions to Ask Yourself Before Pursuing Early Retirement

arthursheikin@gmail.comBy arthursheikin@gmail.comJuly 6, 2025No Comments5 Mins Read
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This as-told-to essay is based on a conversation with Brad Barrett, who hosts the ChooseFI podcast. Business Insider has verified his professional history.

My journey to financial independence, or FI, started long before I had heard of or read about this term.

I’m a Certified Public Accountant, and I began my career at a big accounting firm. I lived at home with my parents when I got my first job and started saving big chunks of my salary. I was frugal and made decisions in the service of a life I wanted in the future.

In 2013, I read the Mr. Money Mustache blog, and it all made sense to me. His post on the “shockingly simple math behind Early retirement” has become one of the seminal articles in our community. The article was a thunderbolt in my life, and my reaction was: “Oh, wow, I can actually do this.”

I left my full-time job in early 2015, at age 35, about 13 years after I started working. Since then, I have gone on an entrepreneurial journey and have worked on a travel rewards website, a newsletter, and a podcast called ChooseFI, which I have been running for nine years.

To me, FI is not only about quitting your job early and never working again. It’s about reaching a point where we can control the most important and finite aspect of our lives, which is our time.

FI can be a yearslong journey that requires making changes and sacrifices. From talking to people on my podcast and answering questions at FI events, here are three questions I wish everyone would ask themselves before starting their journey to FI.

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1. Are you ready to make a change?

One of the biggest issues people have is that they are ashamed of their financial lives. They feel that they’ve made mistakes and are stuck. My question to them is, are you ready to make a change? If you’ve messed up financially, are you ready to stop beating yourself up about past mistakes? I’ve made calamitous money mistakes, but I’ve still reached FI.

If you are working toward building a nest egg, are you willing to think long term and forgo everyday convenience in exchange for building a better life in the future? It’s about not succumbing to instant gratification like buying fancy cars and going out to dinner all the time. It’s also about the little things, like planning a week’s worth of meals that you can cook at home, so you don’t end up getting fast food just because it’s 6 o’clock on a Tuesday evening and no one’s eaten yet.

On the other hand, if you are someone who has a significant savings rate, are you willing to spend more of it to ensure you are making your life better?

2. Can you rethink what ‘afford’ means?

In modern American society, saving money is seen as countercultural and unusual. And that’s ridiculous.

In order to live a functioning life, you need to have a savings rate. And you need to account for that rate every time you ask yourself whether you can afford something.

Some people make $5,000 a month and think that means they can spend up to $5,000 that month. That mindset needs to change to, “Hey, I need a savings rate. Can I afford this if I’m ever going to retire or have any kind of financial security?” If you decide your savings rate is 30%, that means you only have $3,500 to spend a month.

This doesn’t mean you’re depriving yourself. It’s about prioritizing spending on what is most important to you and saving to have freedom in the future.

3. Are you ready to have conversations about money?

While no one should stuff financial independence down other people’s throats, you have to have conversations about money with your family or partner.

I’ve seen every combination of FI relationships work — many where one partner is working and the other has retired early. Those were the result of significant conversations that weren’t just, “Hey, I’m retiring today, but can you still pay the bills?”

Getting on the same page financially is important for any couple, whether in the FI community or not, because we know, money is one of the biggest stressors in life and in relationships.

It’s OK to date somebody who has significant debt, because that happens. But are you on the same page? Are they trying to pay that debt off?

There’s, of course, no requirement that you have this certain net worth to date somebody in the FI community. But is it going to go well if you have a 50% savings rate and the person you’re dating is going more and more into debt every month? No.



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