Failure Resume? No. Cover Letter? No…More Like Confessional.

Infographics for Entrepreneurs
All of the above.

I don’t know if anyone has noticed but I went down from posting 3 times a week two months ago to 2 times a week. It’s not a big change, I never felt like I needed to explain my reasoning. After a year of healing, I wanted to shift my focus to improving what made me think hiding out in the blogging world was a good idea in the first place (and yes, it was a very good idea!)


I got fair grades (not that grades matter!) I graduated university early and my GPA was a 3.7. I know it’s rare for a 21-year-old to find overnight, meteoric success online and pretty much unheard of if you came from the poor side of the tracks like I did but…but…but I really thought I hit *something* by 26.

OK, don’t laugh. I was young and dumb. I expected some success by 25. I really thought I would be rich by now (and I don’t mean rich in life or rich off my husband.)

Apparently the highest percentage of where people find entrepreneurial success is in their 40s. If I’m 26 now so then I have 15 years to a lifetime or so of complete, utter failures ahead of me.

Wunderbar. -_-


I have had a lot of startup failures…actually only failures in my mind.

And that’s not an exaggeration. I think my husband is afraid of me for my constant tries that cost $$ and never works out. Both of our stress levels shoot through the roof all the while during which it becomes detrimental to his overall work performance.

I also know it’s more nature rather than nurture. I didn’t receive nurture from my parents in this aspect. They were content people. But I was nursed and inspired by the two years I was dating Mr. Executive at an interesting time in my life. He told me how he quit Oogle even though working at Oogle was great and he excelled at it. He had more faith in himself and his gambles.

My husband, on the other hand, is very different…the total opposite of me…in this aspect. He is the type of person who, if given the chance and no repercussions, would spend every single day of his life playing video games and not want anything more. He’s so happy-go-lucky! His early retirement dream is to spend his days playing games and dad-ing his (someday) kids. He is more loving and emotionally “sweet” than Mr. E. I couldn’t hold a conversation with Mr. E for 5 minutes and not want to strangle the guy (which is not a good sign.)

My husband enjoys a working environment where he is set with clear goals and objectives. His manager noted his lackluster performance in ambiguity was completely opposite of his performance under areas of structure. That’s a dead-on observation.

He loves stability. I mean, who doesn’t love a stable paycheck?!

He has immense loyalty. His grandfather was once the head executive at PG&E. His father followed in grandpa’s footsteps and stayed at PG&E his entire career too. It’s the “one spouse, one God, one company for life” philosophy that my husband picked up. He was brought up by his grandfather and his father to be steadfast and loyal.

Related: How Dumb Luck Made My Husband a Rich Man


Some of the worst fights I’ve ever gotten in with my husband were over our respective careers – it was never was about money – but more the support (or lack of support) I get from him.

My husband and I would be FI/RE by the time I’m even 35. So I struck a deal with him – if I do NOT end up successful in my own right by the time I’m 35 years old, I will break every single entrepreneurship bone in my body and go back to being a pleasant and non-stressed out spouse, mother and caregiver.

(Ha! Tricked him, as if that’s an option for someone bitten…seriously, it’s like an annoying tick.)

Don’t you think I rather be a happy housewife? I said before I have an easy life. I don’t have to worry much and it’s more than what I deserve. I’m not blind, I understand and see my privilege just fine. I’m sure there are tons of people who would take my place or my husband’s place. But that tick is stupidly strong.

I was watching some clip where these Filipino women dig scraps of food from the garbage that restaurants throw out and they recook the garbage to eat it, daily. There are a lot worst things out there than unfulfillment. So I’m not trying to rock the boat over to drown here. The relationship, our well-being, and our future matters more of course.

Before you misunderstand and think that My Darling Hippo is a traditionalist clout, please know that…he works for me 😛 He also works 10 hour days already. After work, his mind is jello. They pay him the big bucks to problem solve and his brain is fried at the end of the day.

He still tries to help when he can. He is actually coding something for me right now that could benefit some bloggers and marketers out there. Only…there is a lot of Red Tape to break first. I think everyone who can, should reach financial independence first and then start going to work for themselves.


Anyway, when we first met, we had the whole housewife and 9-to-5er deal worked out. Unfortunately for him he accidentally roped himself with someone who had reckless concepts, bad planning, and a complete lack of understanding about herself.

I didn’t want to retire. I am retired. The days I’m not productive in building is a day of forced retirement. For someone who is 26, that’s not an accomplishment.

Related: 3 Profound Things I Wish I Knew Before Adulthood

He has seen me pull 15 hour days (not showering, not eating) trying to squeeze everything I can accomplish in. He’s also seen me depressed with barely 1 hour of work in.

It’s embarrassing because I’m a pretty proud person. I’m also very strict with the definition of personal success. If something was successful for a time but succumbed to failure, that’s still an utter failure.

I inherited this straight shooter mindset from my mom, lovely person, impossible to please. I got my pride from her as well which makes talking about failed things in detail awkward for me.

I don’t want to get into my failure resume…like ever…but out of the 7+ straggling projects I’ve doughed out since I was 18 years dumb – none have been successful. The first few years was the same problem: I didn’t know who I was or what motivated me.

Those don’t sound like business questions you need to answers but, trust me, if you want to be an entrepreneur, you need to find the answer to those.

(Noooo, not write what you think your answers are. It’s not that easy. I mean, you need to FIND out for yourself what your answer is. And you will know when you find the answer because your heart will tell you. It’s going to beat fast and you’re going to say “it was right in front of my eyes.”)

That’s about as much as I want to share now. Mainly…because I fear the possibility of failure and exposing failure. I already have enough problems getting up from falls. This is going to make it worse if I make it remotely public. And I’m sure a good percentage of people out there understand exactly what I’m talking about so I’ll save my breath.


..…………okay, you caught me I wrote this post because there was no cell in my body that wanted to talk about personal finance today. Hahaha 😛 I just didn’t feel like writing about frugality or saving money!

This post was inspired by a recent guest interview with by Jim (from Wallet Hacks) over at Millennial Revolution. Although not directly related to my pursuits (or even yours probably), entrepreneurship does share much of the same vein and that interview was the kind of good ol’ pep talk that gets a girl going. Oh and also check out Pete’s (Do You Even Blog) 40+ failure resume. We’re try-hard stupid little bunnies!!!

32 thoughts on “Failure Resume? No. Cover Letter? No…More Like Confessional.”

  • i would count writing good content like this as a success. i think it’s like an apprenticeship where you’re working out and building the writing and blog ownership muscles. at least you’re not a heavy drinker like me and soap, so there’s that.
    freddy smidlap recently posted…Don’t Be Like Ivan Osokin

  • Thanks for sharing such honest thoughts, Lily! I’m sure everyone has their own failures. Some try to forget about them and only show their success. Some remember such failures and never stop trying. I think it’s great you always try to pursue your goals and your dreams. Many people would look at your AirBnB and blog and see them as great success both in terms of finance and influence.

    I myself have a series of failures in my life. I still think about them every once in a while and can’t help feeling like a loser/failure. But as you mentioned, it can be worse, so we should just be happy with what we have and never stop trying for something better 😉
    Ms. Frugal Asian Finance recently posted…Top 5 Financial Mistakes In My 20s

    • Agree with everything except this blog isn’t successful! I wish! If this blog is successful what are Joe and Sam and J$ and PoFs of the world!!

  • That #1 is it for me. I can’t deal with a boss anymore now that I know what self employment is like. It sucks to work for the man.
    You sounds like my dad. My dad is a serial entrepreneur too. He loves coming up with ideas and projects. Most of them didn’t work out. Even if it worked out, he’d get bored with the steady pace. Good luck. I think you’re doing it right. Shoot for the star while you’re young. You also have safety net so you don’t have to worry about failure much. Just keep at it.
    Joe @ Retire by 40 recently posted…My Unglamorous Early Retirement Lifestyle

    • Thank you Joe, this is very sweet and your opinion always means a lot to me. I could only hope I come up with something successful and see if I am able to stick with it. I’m thankful Jared’s a strong safety net, we smoosh together well.

  • I can’t comprehend someone having that much self knowledge at 26. I’m a Boomer, we were never taught to spend any time thinking about ourselves. Life was about our jobs, raising our families and providing for them. Our own level of contentment really wasn’t relevant to…anything. I was lucky and spent my life very content and enjoying my work as an employee and eventually as the boss but I could tell I was a rare a bird for my age group and most of my peers were not that happy at what their lives had turned out to be. It will be fascinating to see if your generation, with such a different mindset and different goals, will do better or worse. I certainly hope better! Great vulnerable and passionate post Lily, you are gifted at this.
    Steveark recently posted…Why Do Rich Boomers Work Until They are 70 (and Why I Did Not)

    • Omg you just made a girl’s day! Geeeez louis I’m a happy camper. One thing struck out to me that has so many layers – “Our own level of contentment really wasn’t relevant to…anything.” That’s very interesting, I think I get that vibe from my own boomer father in law. Content and responsible indeed but…something missing.

  • I do think there’s a vein of entrepreneurship that does run through the FIRE community. Whether it’s people who do side hustles, starting their own business, etc., I’ve seen it crop up quite a bit. I’ve started countless failed business ventures, as has Mr. Picky Pincher. I think the difference between us is that I try not to spend ANY money on ventures unless I see profit. 😛
    Mrs. Picky Pincher recently posted…How to stop procrastinating by optimizing your life

    • Oooh there’s some good stories there I bet. You twos partnered up in crime, my partner is best as the getaway driver when I am done or screwed up 😛 <3

    • I do keep telling myself “you just need one and that’s probably going to be 9 more failures ahead of the ONE success.” Arguh. My blog is totally not a success. I have no idea what I’m doing……

  • I’m going to tell you what my husband tells me when I write about fear, stress and squirrels, “Let’s get you some sleep….mmmk Pumpkin?”

    Again, in all seriousness – these posts need to happen! It’s a way to process thoughts, and help get your action plan on paper. Annd leaves the reader wanting more! Keep doing them!

  • You only have to answer one question: “what do I want to be when I’m 60”, and then go be that. There are no failures, only journey, learning and choices on the way to 60.

    • Yes that’s very true. Someone asked me what I would be proud of on my death bed and that hit home with me on what I should do/want to do.

  • I need to write my complete failure resume someday. You’d laugh and maybe relate.

    Have you heard the story about the door…where they guy (or gal) keeps pulling on it to open it but it needs to be pushed instead? (or maybe it’s vice versa) but anyway, you get the idea. Sometimes we pull too hard when we really just need to push with 1/10th the effort. 🙂

    • Haha oh you mean the mistake that I make every single week?! Yes I know that embarrassing move!! What’s something I can push…is it one of those things that’s right in front of my eyes – like my husband was?? Argh stop trolling me Universe!!!

      (Oh and thanks Amy :D)

  • I love it. I have failed many, many … many times in different areas of entrepreneurship. Some have come out netting zero, some lost, a few had small gains, but I have learned a bunch. So long as I am failing and learning some new aspect of starting a business, then I am happy. I always tell my son, it’s good to fail… but only once.

    And you guys are pretty funny. My wife is technically a stay-at-home-mom, but she has NEVER had any less than 3 side gigs going on. At times I have to laugh because we are working hard for FI/RE so that we can fully immerse ourselves in our side gigs 🙂

    Keep inspiring!


  • One of best things that I was said to me when I came back to brag to my mentor, thinking I was the sh!t when I fluked my first £100k in a month.

    “Success is boring. Tell me of your failures, your struggles, those are the interesting parts. Tell me where you failed, the fear, the doubt, the blood, sweat, and tears. When you show them, others know that they’re not alone when they stumble and fall. The most inspiring thing to see is that we were never Superman or Wonder Woman, only human.”

    …And just like that I was cut to size. 😅

    So I see none of these as failures, in fact they’re inspirational, giving me more encouragement to keep moving forward. So keep up that stubbornness, and keep encouraging people along the way. 👌

    • Holy…….seriously how did I miss this. Will that’s like the BEST thing I’ve heard ALL month! Who is your mentor? What does he do?

      I’ll show everybody (actually just my subscribers) how much I failed and exactly after I find some success so I’m not a weeping, sweeping…loser. <3

  • Do you notice that there are very few entrepreneurs who are interested in FIRE? Because they are already FIRE’d pretty much (well, once they get their company going and all). You don’t have to answer to anyone, your time is flexible, you can do what you want because you earn your money how you want. Girl you are already FIREd with your Airbnb and dog walking hustles!
    GYM recently posted…GYM Book Review: The Dhandho Investor: The Low-Risk Value Method to High Returns

    • Oh yeah, because they can’t leave their baby. They raised them up from nothing basically! I don’t wanna FIRE yet!! (Ohhh I see what you mean ahahahahha)

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