How to Overcome Life’s Biggest Obstacles: 7 Steps to Breakthrough Success

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Hiker roping tangled vines on misty peak.
Hiker roping tangled vines on misty peak.

Overcoming life’s biggest obstacles is basically my full-time unpaid gig right now, man. Sitting here in my Seattle shoebox, radiator hissing like it’s pissed at me, cat hair on everything, and I just burned toast again because I zoned out scrolling job listings. Last week I totally ate it in a Zoom interview—froze up, said “um” like 12 times, then my mic cut out mid-sentence. Classic. But yo, beating the crap outta challenges? That’s the deal. I’m no life coach; I’m the dude who still can’t parallel park and cries at ASPCA commercials. Let’s get into the 7 things that actually dragged me outta the hole, even if I keep digging new ones.

Why Overcoming Life’s Biggest Obstacles Feels Like Getting Punched by Monday

2022 was a dumpster fire. Lost my job, girl bailed, car crapped out in a blizzard on I-90. Sat there for hours eating stale jerky, watching wipers freeze. Thought I was done. Then I realized: overcoming life’s biggest obstacles ain’t waiting for sunshine. It’s crawling through mud with a hangover. I’ll preach “stay positive” then doomscroll till 4am. Hypocrite? Yup. American? Double yup.

Cluttered desk with crumbs and exploded pen.
Cluttered desk with crumbs and exploded pen.

Step 1: Write the Ugly Truth (No Filter)

Grabbed a legal pad at 2am, wrote “I’m broke, scared, and kinda hate my reflection.” Ink bled, hand cramped, cat walked across it—paw prints and all. But damn, seeing the mess on paper? That’s where smashing through walls starts. Don’t pretty it up. I tried. Backfired.

  • Any paper. Receipt backs work.
  • Worst fears. All of ‘em.
  • Read it. Out loud. Cringe city.

This Psychology Today thing backs it up (kinda): https://www.psychologytoday.com/us/blog/the-clarity/202101/the-power-self-reflection

Step 2: Get People Who’ll Drag You (Even If They Suck Sometimes)

Solo mode = death. I tried. Ended up talking to my houseplant. Now I got:

  • College buddy who sends “apply or I’ll unfriend you” texts
  • Reddit stranger who’s weirdly good at résumés
  • Coworker who calls me “dude” when I flake

They annoy me. I ghost. They drag me back. Dealing with real shit needs witnesses.

Step 3: Trick Your Brain (It’s Gullible)

Started muttering “I got this” in the mirror. Felt like a tool. Toothpaste on chin, cat judging. Kept doing it. Now? I kinda believe it 60% of the time. Still yell at slow walkers, though. Progress.

Atomic Habits wrecked my excuses: https://jamesclear.com/atomic-habits

Step 4: Do One Stupid Thing. Now.

Applied to a job I sucked at. Got laughed at. Applied to another. Got an interview. Wore mismatched shoes. Still waiting. Point: motion > perfection. Set a 10-min timer. Go.

Leaping over question potholes in chaotic city.
Leaping over question potholes in chaotic city.

Step 5: Screw Up Loud, Fix It Quiet

Bought a “moon” crypto. Watched it crater. Ate ramen for a week. Wrote down every dumb move. Now I Google first. Pushing past the bs means eating crow and keepin’ it movin’.

Forbes gets it: https://www.forbes.com/sites/forbescoachescouncil/2021/05/12/learning-from-failure-15-ways-to-turn-mistakes-into-success/

Step 6: Show Up (Even Hungover)

Walk every morning. Rain. Shine. Hungover. Shoes squish, podcast skips, whatever. Miss a day? Restart. No drama. Getting that win is just not quitting 51% of the time.

Step 7: Reward Yo’ Self (Don’t Be Stingy)

Landed a gig. Bought a $7 burger. Ate it in my car like a raccoon. Took a pic. Sent it. Got roasted. 10/10. Celebrate or you’ll burn out.

Steamy mirror victory fist grin.
Steamy mirror victory fist grin.

Anyway, overcoming life’s biggest obstacles is ongoing. I’m still a mess. Still late. Still eat cereal with a fork sometimes. But I’m here. Try one thing. Tell me how it goes—I actually check comments. What’s kicking your ass rn? Spill.

(left “obstical” uncorrected in draft #3. whoops. fixed now. mostly.)