‘If you didn’t make it in your 20s, wait for 40s!’

by Dylin Redling

If it happened that I didn’t make it in my 20s, is there still hope of ever becoming successful?


I say this because that scenario definitely describes my life:

In my 20s:

Age 22:

Graduated college, got a job selling industrial maintenance products (glorified cleaning products), and quit after 6 months of boredom & hating my job.

From 22 – 24:

Got a job at a Mexican restaurant and then an Italian restaurant in Columbus, OH. Realized I was spinning my wheels and decide to move to NYC.

Mid 20s:

This was actually a lot of fun but totally slacker — worked as a bartender in a dive bar, then as a bar back in a fancy strip club, and finally as a server in a big theme restaurant in Times Square (where I met my future wife – Allison).

From 26 – 28:

Allison and I moved to San Francisco on a whim (hey, why not, we’re young). We worked low level jobs like food server, customer service, and admin assistant.

From 28 – 30:

I tried my hand at acting – did extra work on some Robin Williams’ movies, local plays, and low budget films. Lots of fun but realized I didn’t want to be a starving actor the rest of my life.

In my 30s and 40s:

Early 30s:

Married Allison, got a job at a tech startup, started investing money, and bought our first home (you can read about our RE adventures here)

Mid 30s – Early 40s:

Got a better job, Invested more, Bought a better home – Rinse and Repeat several times.

Age 43:

Retired! How? Read here.

And we lived happily ever after!

Lesson: If you’re in your 20s and slacking off, you have plenty of time to turn it around.


Dylin Redling is currently retired and financially independent.

To stay engaged and for enjoyment, he runs two websites: RetireBy45 and Experiencify.
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2 Comments on “‘If you didn’t make it in your 20s, wait for 40s!’”

  1. Exceptional post however I was wondering if you could write a
    litte more on this subject? I'd be very grateful if you could elaborate a little bit more.

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