7 Life Lessons From A Frank Sinatra Song You’ll Never Forget

I tend to find inspiration in unusual places. For instance, Jack White once inspired me to give up my cell phone for a day. I discovered sage work-life balance advice from Ferris Bueller, shared PR advice I learned from Mr. T, and I once doled out user-generated content lessons I learned from Dick Cheney. Today I am wondering if Frank Sinatra could have had a second career as a career coach or motivational speaker.

I say yes, but you be the judge.

All my life I have had a fascination with Sinatra. I remember buying my first Sinatra tape in high school (yes, a cassette tape) and loving how his effortless singing style blended in with the big band sound of his day. Frank is timelessly cool and I’m often told I am an old soul, so it worked.

My friends were not into Sinatra, so I mostly played his music stealthily in my car. Occasionally after a night of crooning along I’d mistakenly leave my tape in the deck. The next day, when my friends and I got in the car, the music would start up when I turned the ignition. “…that’s Life, that’s what all the people say…” would blare from the speakers.

I received many odd looks and some teasing.

“Their loss,” I would say as I sang along.

At the time, I loved the music, but at 16 I failed to notice that Mr. Sinatra often doled out stellar advice in his songs. The advice was there, I just wasn’t hearing it at that time of my life.

A few weeks ago, while taking a walk down memory lane with Sinatra, the song “That’s Life” came on and two things came to mind as I listened to him croon:

  • Sinatra could have fallen back on motivational speaking or career coaching if the singing thing hadn’t worked out!
  • I must share his sage wisdom!

Without further ado, a few life lessons I learned from singer/career coach/motivational speaker Frank Sinatra:

(For best results, let the song/video play as you continue reading…)

Life Lesson #1: There will be ups and downs and that ok. Actually, that’s life!

“You’re riding high in April, shot down in May

But I know I am gonna change that tune when I’m back on top in June”

– That’s Life, Frank Sinatra

He’s right, there are ups and downs in every career and that’s part of work life. We all need to get used to it because it’s not going to change. And, here’s the cool part for us normal folks, even Frank (and the original writers of the song) has a bad day now and then. That’s life.

Life Lesson #2: You’ll have to work with some real jerks and that’s OK. In all truth, that’s Life!

“Some people get their kicks stomping on a dream, but I don’t let it get me down, because this fine old world, it keeps a’ spinning around”

– That’s Life, Frank Sinatra

Don’t I know it, Frank! Sad but true, so many people in the world like it when others get knocked down or are having a bad day. While part of me thinks this is a little sad and pitiful, I guess it’s human nature. When others fail it reassures us that we don’t have it too bad and that we all have problems. That’s life.

Life Lesson #3: You’ll do a lot of things in your career and that’s OK. You know what they call that? Life! (That’s Life)…

“I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king…”

– That’s Life, Frank Sinatra

First off, he should add motivational speaker to the list. Second, there are dual meanings on this line. On one hand, we have the literal translation of this lyric – we should remind ourselves that we may need to try many jobs before we find a perfect fit. On the other hand, the implied meaning in this lyric – we’ll all be the little guy, the pawn, the jester now and then, we can’t always be the king. Not even if you’re Frank Sinatra. That’s Life!

Life Lesson #4: Sometimes you’ll be knocked down and that’s OK. You just need to get back up, because, that’s life!

“I’ve been up and down, and over and out and I know one thing, each time I find myself flat on my face I pick myself up and get back in the race”

– That’s Life, Frank Sinatra

Dammed if you aren’t right, Frank. We need to remember that no matter how bad things seem, no matter how many times you get knocked down we need to get up and fight another day. You know why? Because that’s Life.

Life Lesson #5: You’ll want to quit and that’s OK. But sometimes you’re going to need to push through, because, that’s life.

“I thought of quitting, baby, but my heart just aint gonna buy it”

– That’s Life, Frank Sinatra

When you are lying there, on the ground, wind knocked out of you, you’ll want to quit. But, you just need to get up, no matter how badly you want to lie down and quit. Get up! Why? That’s Life.

Life Lesson #6: OK, sometimes you really do need to quit, and that’s OK. When something just isn’t working out, you can quit. Don’t feel bad about it, that’s life.

“If I didn’t think it was worth one single try, I’d jump right on a big bird and then I’d fly”

– That’s Life, Frank Sinatra

Ok, so let’s say you’ve been knocked down a hundred times, and you don’t see it getting better. You’re not happy, not advancing and things are bleak. Then, you just might need to quit, fly off and do what’s right for you. Just do it knowing you tried your best. Keep your pride, never burn bridges, hold your head high and fly baby, fly. Because, that’s life!

Life Lesson #7: You’re going to need a sense of humor to get through. Because, sometimes when things go wrong, all you can do is laugh and say, “that’s life.”

“If there’s nothing shaking this here July, I’m gonna role myself up in a big ball and die!”

– That’s Life, Frank Sinatra

Frank wasn’t really going to lie down and die. All he is trying to say is that we need to have a sense of humor about our selves. We need to laugh things off and move on. Because, you guessed it, that’s life.

So, there you have it, 7 valuable life lessons. In general these are great lessons, but the simple fact that they came to us from the Chairman of the Board, Frank Sinatra, makes them all that much better. Or at a minimum, that much cooler.

I’m curious, where have you unexpectedly found inspiration?