On Failure, Optimism, and Success

Updated: August 23, 2020

Six years ago, I tendered my resignation letter for the very last time.

I say that it was “the very last time” because I’ve made up my mind that I’m leaving the corporate world for good.

It wasn’t because I am tired of working, nor I hated my job. But quite simply, I decided that it was time for me to discover the world of freelancing and entrepreneurship.

I must admit that it was one of the scariest things I ever did. It felt like I was jumping off a luxury cruise ship for a small fishing boat, where I’ll be alone tending for myself and finding ways to survive the vast ocean.

Nevertheless, despite the fear in me, I knew I had to do it back then or I’ll never going to have another chance.

But what made me decide to do it? Wasn’t I aware of the risks? Wasn’t I afraid to fail?

Jumping off the boat

Honestly, I didn’t know how much risk was really involved in my decision until a few weeks after I resigned. Since I’ve done several freelance work before, I thought that the transition wouldn’t be so hard. And earning money wouldn’t be a problem.

Also, I didn’t think that my new business was going to fail. Yes, I was afraid, but the idea of being a miserable failure in the end never crossed my mind.

I knew it would be hard but I did my best to banish the idea that I would end up with negative net worth. That I’d be living off an allowance from my parents while I look for a new job that will take me back to the corporate world.

Fast forward to today, I look back and see how far I’ve gone since jumping off to that small fishing boat. Thankfully, I have managed to survive several years without a paycheck and I plan to survive the rest of my life without one.

And as I recall those years when I struggled to get to where I am today. I realize that there were several times that I failed.

Miserable failures that sent credit card collection agencies after me, weeks of asking my parents for money, and a couple of businesses closed down because they simply didn’t make any money.

And in all those times, I learned that optimism is not about believing you wouldn’t fail, but believing that you can get back up and try again when you fail.

The journey towards financial freedom is difficult and risky. That’s why not many people want to do it. But one has to get over that fear and be willing to fail if you want to succeed.

In my experience, I learned that indeed, the worst-case scenario can happen. But it’s usually not as bad as I thought it would be. And tomorrow is always an opportunity to start again.

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  1. Thank you for sharing this inspirational experiences.

    I am impressed with your braveness to take such kind of opportunity which can change your whole financial life from comfort zone to uncertain situation. Truly speaking, I haven’t had that braveness in my today’s life, eventhough sometimes I really think over it.

    I should learn a lot of thing from you – I think, you are two steps ahead from me in this matter.

  2. Grabe six years ka na.. ako 1 year and 3 months pa lang without a paycheck. Hahabulin kita! hehehe πŸ˜›

    @Tyrone – may tama ka! πŸ˜€

    “Failure is not the enemy of success, it is a teacher – a harsh teacher – but the best!”

    Yan ang life quote ko eh.. hehehe πŸ˜€

  3. Congrats Fitz! I’m sure you feel a sense of fulfillment. Tama ka, there would always be ups and downs. But what matters is how you pick yourself up when you fall. πŸ™‚

  4. Nice blog.. coz right now i am really thinking about doing that and it scares the hell out of me especially now that im planning to start a family! My job requires me to be away from the life that i love for 8-9 months then spend 3 months with them.., it pays good but really, it’s not living.. it’s just surviving!

    hope i can get out from this “rat race”! will be looking forward for your blogs and advices soon.. πŸ™‚

  5. Very inspiring, Fitz. I had my last resignation letter a year ago, and it was 9th one. Right now, I am looking for a job but I hope I can find a better source of income instead. There’s a great difference between the two, you know.

    Anyway, I really plan to have my last resignation letter as my last one. But if I have no choice, I will be back in the corporate world but temporary only.

    Maintaining a business is now my target because I know it’s my only way of escaping poverty.


  6. nice and inspiring posting…i truly believe in having much fear on facing financial freedom but the result is worth it…right now i’m still in active and semi-passive income status…it may be hard sometimes but i know when i get the hang of the passive income the active income will be given up…your experience has given us hope that either in corporate or business world there is always tomorrow to start all over again…congrats…

  7. I’ve been with this site several times but this post moved me to do a comment. Very inspiring and brave. I hope I can survive too. Thanks for posting.

  8. Just like in your story, I submitted my resignation letter last night. I was also about to say bye bye to the corporate world permanently to pursue making money doing the things I really like. I am overly optimistic that I CAN DO IT!

    My boss didn’t accept my resignation and he wants me to think about it before I take the big plunge. Thank you for sharing and making me wake up to reality that I must also know how I can get back up in case I fail. Your blog is very helpful.

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