The 6 Ways I’m Failing In Life And Lessons You Can Use To Avoid Them

Hopefully my failures can lead to your success.

5 min readMay 17, 2023

Life isn’t all rainbows and butterflies.

Everyone has good times and everyone has bad times.

But we seem to only focus on the good.

We’re pumped to share vacation photos, new accomplishments, and exciting life stories.

But when it’s time to share the low moments or the failures we all tense up and look the other way.

Well hide no more.

Because today I’m going to share what every other creator seems too afraid to share.

All progress isn’t in a straight line.

Progress and success will be tough, difficult, and have many lows.

For every successful person you see on a high of greatness, there was at least 6 lows and failures that came before it.

And that goes for everyone.

Including me.

So today I’m going to share 6 ways I’m personally failing in life.

But because we’re all about growth and progress, I won’t just leave it there.

I’ll share the 6 ways I’m failing in life but also add the lessons you can use to avoid them.

Let’s get into it.

Failure 1: Living at home with my parents at 27 years old.

I’m 27 years old and still living at home with my mom.

I’m not paying any rent or mortgages.

I’m just the same kid that use to ride the bus to school every morning except now I’m heading to work.

It’s a major failure that at nearly 30 years old, I haven’t established my independence and given my mom some kind of financial relief.

Lesson: Don’t get comfortable depending on anyone. It only leads to co-dependence.

If I took some initiative at a younger age to branch out on my own, maybe I wouldn’t have become so comfortable living at home.

Now that I’ve created a 27 year habit, it’s only getting harder to leave.

Don’t get comfortable anywhere for too long.

You’ll only end up very dependent.

Failure 2: Making $0 in personal income.

I’ve never in my whole life had a real job.

That’s a cute little flex but it’s also a horrible failure.

In other words, I’m so sheltered and again comfortable that I’ve made 0 initiative to get out on generate income to survive.

I know I have the skills because I used to do freelance video work.

But now, I live extremely below my means and just accept that I’m making 0 dollars to personally live off.

Lesson: Getting what you want is always 100x harder than getting what you need.

I know I’ll be rich one day.

But the problem is I want it more than I need it.

If I was forced to live on my own at 18 or had a serious financial emergency, there’s no doubt I would find a way to make money.

But because I want income, and I don’t need it, the results are simply lacking.

Failure 3: My only transportation is an old rusty van.

Another travesty is that my only form of transportation is extremely unreliable and shady.

My old Ford 2000 van needs lots of work and gives me lots of anxiety whenever I drive her.

Because of that I don’t leave the house or go out at all.

But I’ve always been a homebody that likes to stay home.

It’s just sad that if I needed to get somewhere fast and reliably, I would be stuck with Uber or asking a friend.

Lesson: Pay yourself first.

I’ve generated over a million dollars in revenue but have never been able to purchase a reliable car.

And when I was gifted a car from my parents years ago, I just turned around and gave that car away to my younger sister instead.

The key here is learning to pay myself upfront and early for my efforts.

If you only ever pay it forward, don’t be surprised when you’re stuck in place.

Failure 4: Zeroing out investment accounts.

I may not have had steady personal income but I’ve always invested any extra money I had.

Those investments were my foundation to build a nest egg for future me.

But through a series of bad spending decisions, I’ve virtually zeroed my investment accounts out.

Whether it’s paying for nice cruise vacations or unexpected emergencies, the spending has led me to fall all the way back to square one.

Lesson: Don’t keep up with the Joneses.

If I didn’t try to spend out of my league, I wouldn’t have overspent into my investment accounts.

And because I’m trying to spend like others, I’m losing money that I needed.

If I stayed in my lane, not compared myself, and not spent from my investments I wouldn’t be failing so bad financially.

Spending like others always leads to bad results.

Failure 5: Letting go of my entire content team.

In December of last year, I had to let go of everyone on the content team.

The economy was really bad and our sales were at an all time low.

We just weren’t able to pay our team members what they required anymore.

It was a major failure to cut ties with the team that has put in countless hours into the success of our company.

It was the last thing I wanted to do and has since been my biggest failure as an entrepreneur to date.

Lesson: Be prepared for the best and worst case scenario.

If I had more foresight as a leader I would of been able to see months prior that our revenue was sliding.

Instead I was short-sighted and only focused on day to day tasks.

As a leader, it is my job to keep my eyes ahead and be prepared for good and bad situations alike.

Always be prepared for the worst and the best.

Both are possible.

Failure 6: Losing office space because we can’t afford the rent.

Just last week I had to break our lease for our office space.

3 months ago we doubled the size of our office space because we thought it would allow for more use cases.

Fast forward to now and we never utilized the extra space.

And because we unnecessarily increased our overhead costs, we have to get rid of the office altogether.

Lesson: Don’t pay for things before you need them.

Instead of increasing expenses for something we wanted, we should of waited until it was something we needed.

We increased our expenses for virtually no reason.

And that’s bad financial planning.

Instead we should of rolled with the smaller office space until we were stuffed and then upgraded at the last second.

You’re not a fortune teller.

Don’t pay for things you need until the moment you need it.

Those are 6 ways I’m currently failing in life.

They suck and they’re actually affecting my day to day life.

But at least I get to learn from these lessons.

Hopefully you can learn from these mistakes as well.

See you in a few months when I turn these failures into wins…

In progress,

Tim Lightwork

Read my personally written insightful letters on growth every other day at




28 year old Cofounder of seen on SharkTank). Sharing my best startup tactics on growth for FREE. Founder? Join us at