12 Career Lessons That Catapulted Me to Early Retirement

CEO Tips - Career Lessons

I changed careers three times.

I failed with two businesses.

But I STILL retired at 36.

Did I get lucky? Absolutely.

But I also created a heck of a lot of my own luck. Here’s how:

1. Early in Your Career, Just Say “Yes”

Say a lot of “yes” now, so later on you can say “no!”

Take opportunities others won’t.

One of the first things that I did when I started my career was I took all the crap tasks that no one else wanted to do.

I copied and pasted thousands of emails, I sent out marketing emails even though I didn’t know HTML, and then I built a website even though I had no idea how to.

I said “yes” to any opportunity and it earned me a raise within three months.

And sometimes opportunities don’t come your way, so then you have to push for them.

Push to take on more work once you have a handle on your current load

It doesn’t matter what the job, EVEN cleaning dishes, just say “yes!”

2. Forget About Your Major

The minute you graduate, it DOESN’T matter anymore!

If it turns out you don’t love your first job, pivot.

Even though I took on a lot at my first job, I realized pretty quickly it wasn’t what I wanted to do.

Your major is a sunk cost – so if you aren’t happy, change things up!

So I started a side hustle, that I worked on during nights/weekends, and that business eventually led to a full-time gig in another industry.

Try again and KEEP trying!

3. Don’t be Afraid to FAIL!

As Albert Einstein said, “Failure really is just success in progress.”

Failure leads to learning AND growth.

Show me a failure that you have not learned from in some way. I dare you.

But I already know the answer –> you can’t find one.

The lessons you learn from failure will DRIVE your eventual success.

4. Focus on effectiveness, NOT efficiency

Long hours DOESN’T mean you are getting more done.

The more hours you work, the more time you are likely to squander.

Leverage the 80/20 principle to maximize time & effort.

I can firmly say in my career as a manager, that promotions and raises go to people who get sh*t done. FULL STOP.

5. If You Don’t Ask, You Don’t Get

Don’t be afraid to ask!

  • Ask for a raise
  • Ask for more work
  • Ask for a promotion

Just ask!

The worst you’ll do even if they say “no” is earn a little respect.

I once went in and asked for a 45% raise – and got it.

Just imagine what would have happened had I not asked. Absolutely nothing. It is always worth the ask!

6. Don’t Be Afraid to Pivot Careers

So you made a mistake?

You don’t need to stick with it forever.

Just like your major, any career is a sunk cost.

Even if you are a Doctor or a Lawyer, you can and should leave it all behind if your heart is not in it.

Careers are meant to evolve

I majored in finance.

Then I got my first job in marketing.

Then I taught myself to code and became an engineer!

Later on, I learned to be a manager.

Careers evolve and change!

7. Take Calculated Risks

You can’t get anywhere without taking on some risk.

Take a risk in your job by doing something new.

Or take a risk by changing jobs to increase income.

Take a risk to start a business (even if it fails).

Or take a risk to ask for a raise or promotion.

If you don’t take risks, others will and they will benefit while you suffer.

8. NEVER Stop Learning

Learning doesn’t stop after school!

Read books and blogs that support your job.

Listen to industry podcasts.

Teach yourself new and relevant skills.

Even if not career-relevant, continue to build on your skills!

9. Be Sure to Network (A Little)

Your network WILL land your next job.

Go to industry events and mingle.

Try to eat lunch with at least 1 person a week (especially those at your company).

Meet with those at the next level to find out how they got there –> then stay in touch!

10. Get 7-9 Hours of Sleep!

Sleep supports a healthy body and mind:

  • You’ll have more brain power and less sickness
  • You’ll make better decisions
  • Your productivity will skyrocket

If you don’t sleep, you won’t be functioning at a high level. PERIOD.

11. You Don’t HAVE to Work Long Hours

Hours worked DOES NOT translate into wealth.

Remember: Effectiveness > Efficiency.

Show you are productive -> then set boundaries. Because it turns out that working fewer hours will increase your productivity.

Schedule in-depth blocks for deep work.

Believe it or not, I only ever worked 40 hours or less, even as a CEO.

It turns out that the more hours you work just for work’s sake, the MORE time you are probably wasting!

12. Vacations are NECESSARY!

You can’t go at it all of the time -> you NEED to rest

Schedule your vacations in advance (and use all of it)

• Remind everyone when it is coming

• Disconnect, unwind, and DON’T work during them

You’ll come back energized, and more productive!


Follow these lessons, and you too will take your career to the next level!

But most of all you will be creating your own luck.

Will it work every time? NO.

There are always obstacles. But careers are anything but linear. Life is anything but linear.

Just keep going and rewards will eventually come your way!

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