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Learning from 10 years of failure and turning my life around

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GrizzlyBiz

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Joined
Nov 15, 2023
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Hey everyone. I'm an aspiring entrepreneur in my late 20's with roughly 10 years of failure under my belt. I'm glad to be here and hopefully exchange value with likeminded entrepreneurs.

I'll talk about the reason(s) behind my failure in a sec. I imagine doing so will be valuable for some of the folks at a similar point in their journey. But first, the tough spot I'm in now, how I got here, and the steps I'm going to take to fix it and turn my life around. Because it's not pretty.

I'm mostly posting this for accountability and reflection purposes, although I'm sure there are some nuggets of wisdom for you to pick up along the way as well.

How I got here

I read TMF when I was 18 ish. At the time, I was an immature, spoiled brat who was handed everything in life on a silver platter. You know the type: no character, no hardships, no sense of direction, nothing. Not a trust fund kid, just blissfully unaware of the realities of life.

Anyway, I tried a bunch of different ventures for years (mostly in college) and could never seem to get anywhere. I made some money here and there, but nothing to support myself or write home about. I was your classic wantrepreneur. Too comfortable, too scared, too immature.

I eventually got a job in tech support and put my dreams on hold.

I hated it. Every second of it. Customers breathing down my neck like I had a majority stake in the company. Being told where to be and when. Having no say in important decisions despite being more competent than those who charmed their way to positions of authority. Reporting to managers who just sat on their butt all day pretending to do work while we tirelessly slaved away (ever heard of lead by example?). Just a cog in the wheel, desperate for a way out.

Sure, I had an apartment and a steady paycheck. I excelled at the position. But I felt dead inside and dreaded waking up every day.

So I found my way out. After a few years, I quit on a whim with no plan, no income, and no idea of what I wanted to do next. Screw it. I would figure it out. I wandered around the contiguous United States in my rusty beater of a Toyota — living out of it, crashing at dirty motels, doing odd labor jobs here and there. Anything I could do to avoid going back to an office job. I picked up some freelance work but my heart was never in it. I burned years worth of savings in a matter of months.

Until one day I couldn't take it any more. I reluctantly moved back in with my parents, who gave me the "I told you so" spiel, at the age of 26. Embarrassing, right?

Well, it gets worse. I'll cut right to it:

I'm still here, 2 years later, with nothing to show for my life.

I got into this major funk; a combination of health issues, a death in the family, addiction (not to hard drugs, luckily), general malaise, and the subsequent depressive state I ended up in due to (what I thought) were hopeless prospects for my future at the time. I spent 90% of my time surfing the internet, half of that productively by learning to code and (attempting to) build software products. The other half mindlessly consuming content and dreaming of a better life.

So that's the predicament I'm currently digging myself out of. Years of unemployment, even more business failures, deteriorating health, feeling like a burden to society and to those I hold dear.

The positive? College degree, no debt, paid off car, over a year of savings in the bank, and a diverse pool of skills that I can deploy at any time.

Steps to fix it

I lied to myself for a long time that I could figure something out business-wise while in this state. That after all these years of failure I could pick myself up by the bootstraps and half-a$$ my way into a cash flowing business while still living at home. But I need to be honest with myself that that isn't going to happen. Not in the state I am in today. I NEED out.

Here's how I'm going to fix things.
  1. It's back to basics. I need to swallow my pride, get a job, and move back out of my momma's basement. Step 1 of scaling up (thanks @Antifragile). A job isn't giving up helped me realize this (thanks @Kak). I've been lurking and both of your posts alone helped me start to feel excited about entrepreneurship again. It shouldn't be too hard for me to find a job as I have some solid tech skills and experience. But there is NO way I go back to being a phone jockey. I'm going to look for something less mentally taxing, perhaps with automation potential, so I can focus on rebuilding my life.
  2. Once I have some cash flow, my own apartment, and a few hours of free time per day, health is my #1 priority. I need to reverse all the damage I've done to myself. I can barely sit at a computer screen and crank out 5 minutes of work at this point. The brain fog is overwhelming. It's a miracle I even got through this post. I'm never going to succeed with an unhealthy body and mind. That's where it all starts. I have a plan outlined for this already and will get a head start by starting now.
  3. While working the job, I'm going to start looking for opportunities. Problems I can solve, people I can help, and most of all: getting out of the damn house. One thing I've learned over the years is that there's no use staring at a computer screen deluding yourself into thinking you're being productive if you have nothing productive to do. "But I'm doing online bizness brooo", no you're not. Stop lying to yourself. The only way I'll be able to reset my mind to see opportunities clearly is by living life and putting myself out there. Talking to people, immersing myself in unfamiliar environments and situations, stoking my curiousity, picking up old hobbies, etc. This is going to take time, but I'm in it for the long haul.
  4. Then and only then will I attack an opportunity with everything I have. No more freelance crap. No more half-baked schemes or small thinking. No more short-term mindset. I'm done with that stuff. It doesn't excite me, it doesn't motivate me to work hard, it's akin to being transferred from one prison block to another.
I have no idea what business I'll end up in. I'm not married to an industry, business model, problem, or anything. I'll know it when I find it. From here on out I'm relying on my instincts and that insatiable drive to pursue something great FIRST; everything else is secondary.

Why I failed

I'll keep it relatively short, but here are the main reasons I've failed up to this point.

You'll notice a lot of them are familiar because they are warned against on this forum and in @MJ DeMarco's books. But when you're desperate, in the thick of things, sometimes it's too late to recognize the faulty mechanisms that are driving your actions. So it's best to be aware of them at a visceral level. Write them down like I am. I wholeheartedly believe that the only way to truly learn these lessons is by making the mistakes on your own in the trenches.
  1. Shiny object syndrome (AKA the next new thing) — we all know this one. Get off of social media.
  2. Giving up too soon (AKA comfort and safety nets) — if you don't want it bad enough, if you're comfortable with your position in life: it's not a matter of if you'll give up, it's how quickly.
  3. Risk-free returns (AKA bootstrapped solopreneurship) — sorry, not for me. I fell into this trap for years. I wanted to sit in front of my laptop and print fun tokens while sipping piña coladas. Not only is that often a pipe dream, it's not very fulfilling either. We are built to do hard things in life and optimizing for comfort like I have in the past is a scam. 90% chance you will sabotage yourself and go back to a job eventually. I've seen it time and time again. On the flip side, when people rely on you for their livelihood, you have no choice but to truck forward. I'm all aboard the @Kak train, destination: "think bigger".
  4. Me-focused business (AKA building for fun, not profit) — yup, your game is a hobby until proven otherwise. Ask me how I know.
  5. Shameful self-promotion (AKA "pre-production destruction" ™) — coined by yours truly. it's common that you'll sabotage yourself if the business you're working on isn't aligned with your values, or you want it so bad that you're afraid it will fail. You build something to completion, only to never release it or destroy it before giving it the effort it deserves. Fear, basically.
  6. Purposeless self-promotion (AKA building a personal brand of nothingness) — is there a purpose behind your personal brand? Why are you building one? Ask yourself this, and you'll be surprised to find the answer is likely somewhere along the lines of "because someone told me I needed one". Again, hobby unless it makes you money.
  7. Shadow callings (AKA the skilled cop-out) — this is programming for me. I enjoy programming, but somewhere along the way I got distracted and thought it was something I wanted to do as a career. It's not, I originally learned it as skilled leverage to build software MVPs. When that didn't work out, it was my "backup plan". I was simply afraid to pursue what I really wanted, and software development was my version of what Steven Pressfield calls a "shadow calling" in his book Turning Pro. Great read, definitely recommend picking it up.
  8. Going in blind (AKA building before due diligence) — action is great. Blind action is better than no action at all, but not by much. Everything is a balance.
  9. Deferral to authority (AKA hold my hand please) — no one has the answer for you. Only you can decide your fate. You are your own person, with your own interests, natural talents, and life trajectory. Stop looking for step-by-step blueprints. They don't exist; you'll waste years of your life and pad the bank accounts of gurus who couldn't give a damn if you succeed or not. I've bought it all, trust me.
Those are the main culprits. I'm sure there are more.

So yeah...I know this was kind of a long intro but I tried to make it as useful of a read as possible. I'll be participating and adding value where I can, and of course will keep everyone updated on my progress if you're kind enough to have taken an interest. I don't have a plan or a schedule for updating this or anything. I may drop some here or start another thread in the future, we'll see. I really only want to provide meaningful updates, not just post to fill space or because I feel obligated to.

Regardless, if you've made it this far, I appreciate you taking the time to read my story. It feels good to get this down on paper and out into the world, having lived in denial for so long.
 
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With more than 39,000 posts packed with insights, strategies, and advice, you’re not just a member—you’re stepping into MJ’s inner-circl, a place where you’ll never be left alone.

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