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The 5-Year Journey That Changed My Life (Lessons + Regrets)

Five years, gone in a blink—kinda wild when you really think about it. That’s 1,825 mornings waking up, making a bunch of choices (some smart, lots dumb), screwing up, learning, and just plain refusing to quit. No fairytale stuff here. It’s been all grit, and yeah—a whole circus of questionable decisions.

Flashback to the start: I was basically a walking zombie, clocking in to a job that sucked the soul outta me. Seriously, I had zilch for plans. No million-dollar idea. Not even a crisp vision board. I just knew one thing—I wanted OUT. Out of the boring rat race, out of living for weekends, out of snooze-button purgatory. More freedom, more purpose, and hell, just a little more “me” in my life.

Now? Total plot twist. I’ve got my own online gig. I work when (and if) I want. I actually out-earn my old job, which still makes me laugh a little. But oh man, was it a mess getting here. Nothing smooth. No finish line ribbon and happy montage. Mostly flailing and face-plants.

So, here it is—my totally unfiltered five-year saga, with the good, the regrets, and all the brutal honesty I wish someone had served me on a platter.

Year One: “Wtf Am I Doing?”
The Meltdown
I cracked. Like, actual Sunday-night dread, can’t-sleep, questioning-why-I’m-even-alive meltdown. Every weekday? Copy-pasted misery. My coping mechanism was Googling stuff like, “how to not hate your job” and “can I just do YouTube full time?” And wow, the internet is a rabbithole. Suddenly, I found this whole universe: online hustles, freelancing, dropping passive income buzzwords I barely understood. Instant lightbulb moment.

Takeaway:
You gotta see it to believe it. I legit needed proof that escaping cubicle-jail was possible before I could even dream it for myself.

And real talk—even if you’re clueless, just start moving. Curiosity and a sliver of guts—that’s step one.

Regret?
I lurked for ages, just mindlessly consuming “how-tos” instead of actually doing anything. Paralysis by overthinking. Classic.

Year Two: “Throw Everything at the Wall!"
Trying Literally Everything
Started a blog (no one read it). Tried dropshipping (lol, negative profits). Tossed my hat on Upwork (crickets). Made an Insta account (felt like screaming into the void). It was chaos. I was throwing myself at anything that sounded legit, hoping something would stick. But, hey, I actually picked up skills: copywriting, SEO, haphazard Canva wizardry. That stuff came in handy, go figure.

Big Lesson?
Stop planning forever. Jump. Learn to swim after you’re already flailing.

Skills stack up, even if the “epic idea” flops. I still use half of what I bombed at back then.

And honestly? Most people quit like two seconds before they’re about to hit gold. Glad I didn’t.

Regret?
Total FOMO syndrome. Spread myself thinner than cheap pizza dough. Got okay at a bunch of stuff, but a master of nada.

Year Three: “Wait, This Might Actually Work?”
The Breakthrough
Picked a lane. Writing blog posts for small businesses—super specific. I built a basic portfolio and bombarded folks with emails. Landed my first $500 client, and suddenly it snowballed: $1.5k/month, then $5k, then referrals. My brain kept whispering: “Uh, are we…making money?” Yup. Wild, right?

Major Takeaway:
Obsess over one thing. When you focus, stuff starts moving.

Crystal-clear offers win clients. People want to know what they’re buying, period.

Just keep showing up. Consistency’s the boring secret weapon.

Regret?
Should’ve charged way more, way sooner. Worked myself ragged for too little, too long—because imposter syndrome is a jerk.

Year Four: “Success? Kinda…but Why Am I Dead Inside?”
Boom—Then Burnout
My business exploded. Client list grew. Launched some digital stuff. Grew my audience—living the “laptop lifestyle” that Instagram gurus blab about. From the outside? Killing it. Inside? Totally fried. Couldn’t even enjoy it.

Key Lesson:
If there’s no boundaries, there’s no life. Hustle without balance eats your soul.

Get help, like actually outsource and stop being a control freak. Smart systems, automations—not the sexy stuff, but the only way to scale without losing it.

Say “no” more. You can’t do everything, even if every opportunity feels like “THE ONE.”

Big Regret?
Didn’t ask for help nearly soon enough. Thought if I brought someone on, I’d lose money. Joke’s on me—it cost me time, sanity, creativity. Oops.

Year Five: “Let’s Actually Make This Fun Again”
Realignment Mode
This was the year I stopped hustling for the sake of it. Trimmed out misaligned clients. Focused my offers. Built stuff around what I actually valued—freedom, helping people, chilling on random weekdays. Launched a group program. Wrote a newsletter. Worked less, earned more (no, that’s not a myth).

Ultimate Lesson:
Success = money + sanity. It’s about your life, not just your bank account.

People vibe with realness. The moment I stopped pretending, things fell into place.

Honestly? For the first time, I started actually enjoying where I was at, instead of obsessing over what’s next.

And if you’re reading this, thinking you missed your window? Nope. My advice: get messy, start ugly, and keep going. The journey’s the best part.
 

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