Why I’m Not Afraid of Failing


This is Year 3 on my journey to early financial independence. I officially started in January 2012, beginning that year earning exactly $0/month in passive income. I first conducted research on early FI in November 2011, and initially thought that the entire plan would take about 10 years from Inception to Finale. My original early retirement date from the cubicle life was slated for 2021, when I would be 37 years old.

I’ve made a lot more progress than I originally anticipated for, which is why I’ve been reining in the date over these past two years. Should everything go according to plan, I realistically do see myself walking away from the corporate world sometime next year (2015), at the age of 30.

Everything that’s happened so far has occurred at a blistering speed. Never in my wildest dreams could I have imagined any of this being possible in such a short period of time. By no means am I finished working, but sometimes I do have to pinch myself when I stop and think about how I already own five rental properties… Not long ago, I thought being able to buy just one house in my lifetime would be pretty awesome!

As I’ve become more successful with my investments, I’m realizing that I’m less scared today than I was when I first started. Should this be a natural feeling? I’m not entirely sure, but here are the reasons why I’m not afraid of “failing”:

If You’re Going to Screw Up…

… Do it while you are still young, or relatively young. I’m 29 years old, and I’ve worked extremely hard in my 20’s to save up as much money as possible. I’ve been frugal, living below my means, and a diligent saver. Not only have I invested in retirement accounts (401k and Roth IRA), but I’ve also dabbled in dividend stocks and rental properties.

I make a good (not amazing) salary, so I’ve been very fortunate in this regard. As a result, I’ve been able to accelerate my progress towards financial freedom more so than a good majority of my friends and peers. The best part is that I’ve been able to get through my 20’s without feeling like I’ve been sacrificing the entire time. Quite frankly, I earn more in a given month than I could ever spend… Yes, this is a good problem to have.

The way I look at it is this — I could lose EVERYTHING tomorrow, and I still wouldn’t be much worse off than a lot of people who are also 29 years old. I have friends who are 29 and haven’t saved a penny since they’ve started working full time. Some of these people still owe student loans and have negative net worth.

To be clear, I am not knocking on anybody (we don’t all have the same blessings and opportunities), but when I look on the flipside, I’m just not all that scared. Crashing and burning before I’m 30 and having to hit the reset button would NOT be the worst thing that could possibly happen to me.

Starting over at 30 would still give me ample time to recover and rebuild my wealth empire. I would have the experience and know how of what to do and what NOT to do the next time around. Should I have to start all over again at 30, I really still couldn’t imagine it taking me until 65+ to reach financial freedom… I would probably take less risks since I would be older, but even the most conservative plan wouldn’t require 35 years to finish.

Just having the opportunity to be on the journey to early financial independence is a wonderful blessing. I’ve been able to pursue something that many can only ever dream about…

I Grew Up Poor

Having money is something that will most likely never feel natural for someone like me. I grew up in a poor family and I had to struggle most of my life. I started working at 14, and bagged groceries for minimum wage throughout high school to make ends meet.

Since life has always been a grind, I’m used to not having much, or expecting too much in return. No, I will never be “royal”. 🙁 I just need the basic necessities and my own freedom to do as I please. To me, absolute freedom is the most wonderful possession of all.

I don’t need nice toys. I don’t need flash, or bling. I would even prefer to not have my own car so that I could avoid paying: gasoline, registration, insurance, smog checks, oil changes, etc.

I’m a person who tries their best to stay humble and grounded. I value true friendships and the simple things in life. So, the investments that I do have and the passive income that I collect don’t influence my day-to-day life.

If I didn’t know any better, it would appear to me that my life today really isn’t all that much different from the life I lived when I was still going to school in college. And I’m not complaining, so good news for me. 🙂 Life only needs to be as complicated as you want to make it.

Life Isn’t Binary

Real life isn’t full of 1’s and 0’s and the world we live in isn’t just black and white… There are also a million shades of grey. In the previous paragraphs, I spoke about failing as it being this all or nothing proposition.

It’s not.

In life, failing can, and does entail just about anything. What does it mean to fail? In my mind, it doesn’t mean that you have to lose EVERYTHING and start over again with ZERO.

Let’s suppose that I do attempt early FI at 30 and things just don’t work out. I miscalculated my numbers, and I find myself needing to work again to fully make ends meet…

Big deal. I’ll get a part-time job, or even another full-time job, and keep marching on. I’ll still have my assets and passive income. Even if the market tanks, my assets won’t lose all their value… Am I any less of a person just because I attempted something and wasn’t 100% successful?

I don’t think so… You succeed in life by being open to new ideas and always remaining adaptable. Learn from your mistakes and attempt to do better the next chance you get. Life doesn’t have to be so dramatic. Failing is OK and a natural part of the human experience. It is entirely possible to “fail”, yet still be better off in spite of it. How can you grow as a person if you never experience anything else but success all the time?

And like Wayne Gretzky said, “you miss 100% of the shots you don’t take.” In baseball, if you can just get a base hit 3/10 at bats, you’re batting at an all-star level. 4/10 would put you in the Hall of Fame…

No Regrets

Life is too short to have to live through and have regrets at the end. If I’m going to go out, I’m going to go out on my own terms. I know that the 9-5 lifestyle just isn’t suitable for me, so I’m going to do everything that I possibly can to get out of it as soon as possible.

Ideally, 2015 will be the last year I ever have to work for someone in my life. Once I retire from the workplace, I very much want to continue working in the future, but only for myself. Just like with this blog, I want to be able to set my own rules, hours, schedule, and availability.

But whether or not I succeed in reaching early FI next year, I will have no regrets. The journey to early FI has already been a tremendous experience, and I’ve had a ton of fun on this ride so far. Thanks to all the readers and bloggers who have been following along! 🙂

Financial freedom is the target destination, but it’ll be ok if I don’t get there on time… There’s no need to sweat every last detail, and I’m sure there will be another train just around the corner if I’m late. Besides, I was never good at operating on a fixed schedule, anyway…


Are you afraid of “failure”? How is your journey to early FI going? Does it get easier or more difficult with time?

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Retire Before Dad
6 years ago

Fear of failing definitely limited some of the risk taking I did when I was younger. I read a lot about risk taking by successful entrepreneurs who say to do it in your twenties before you have a family, so I think you are right on with this. But just think when you reach FI, you can still take risks, with any leftover money that you aren’t living off of. At that point, you’re expenses are covered, so you aren’t putting your lifestyle at risk.

JC @ Passive-Income-Pursuit

I always hear the what if you fail remark but I just don’t buy it. I’m not sure if people are that risk averse or that striving for early FI is just so far out from the societal norms that causes the hesitance but what’s the worst that can happen? You live in FI for a few years doing as you please and then if you somehow lost absolutely everything you go back to working full-time? Wouldn’t even a few years of being FI be better than none?

6 years ago

My dad likes to remind me that you only live once. So does the fact that I have a friend from college who was diagnosed with cancer a few years ago. Same age as me. Pretty scary. That’s part of how my boyfriend and I started dating, realizing that if one of us kicked dead the next year, I would have been pretty upset with myself for not giving things a try. And it has worked out so splendidly so far! As for my journey to FI, I grew up in a family where the money came from a business… Read more »

Joe S.
6 years ago

Failure and defeat are just not you, always remember this. I am predicting that you will even make more income and grow your net worth faster while being financial free.

Regards and wish I was you!!,


6 years ago

Great article FI and great attitude and that is what will give you the energy and drive to succeed. Started similar to you, messed up my 20’s and early 30’s… i’m 12 yrs older than you and i started way later – it’s all about focus.

Keep it up!


Very inspirational post! My favorite quote recently: “Doubt kills more dreams than failure ever will” Unfortunately, I am someone who fears failure and will rarely take a leap of faith…especially now that I have a family to support. But sometimes, you do need to take chances…I don’t want to live a life with regrets! As for FI…I think my main obstacle is living in a high cost of living area…but I don’t plan on moving.

6 years ago

It’s amazing how far you come when you only started like 2 yrs ago to your financial freedom. Look forward to your documentation of the journey after you hand in your towel at work. I’m going to work hard away at my stock portfolio and paying down my one rental property hoping to retire earlier than not.

The First Million is the Hardest

Especially with a goal like reaching FI at a young age you have to overcome some fears and take chances. Letting a fear of failure prevent you from ever starting will only guarantee that you fail at reaching those goals!

No Nonsense Landlord
6 years ago

Failure is not an option, making a business decisions to divest or liquidate is a sound business practice. It is not failure.

You have already overcome the fear that strikes many investors, including myself.

Tom @ FinanceandFlipFlops

I can’t believe you’re going to be 7 years ahead of schedule to financial independence! It gives me a lot more hope that I won’t have to work until my late 40’s when I look at my current financial situation. I just started my new job and while its interesting, I’m still left with this gut feeling that I could never do this for decades. I honestly don’t know how people work for a company until they are 65. I’m 31 years old and all I can think about now is how I can shorten my time to financial independence… Read more »

Dividend Mantra
6 years ago

FI Fighter,

Great post.

I completely agree with you in regards to failure. You almost can’t go wrong with the path you’re on. Your upside is freedom for the rest of your life, while your downside still puts you in a position better than all of your peers. It’s a great spot to be in when “failure” isn’t really failure at all.

2015 sounds like a great year to take that leap. I’ll be rooting for you!

Best wishes.

Done by Forty
6 years ago

I love your attitude towards the whole FI process, and real estate in particular. As you know, your attitude has been contagious and is nudging us towards finally buying an investment property, or four, this year. We can’t thank you enough.


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