If You Looked Back at Your Life in 10 Years, Would You Be Happy?

Jay Gross
8 min readJan 6, 2021

I shot out of bed sweaty. Nauseated. Sick to my stomach.

I’d had this dream for months.

No, it was a nightmare.

It had become horrifying to wake up and realize what had just happened.

That I was reliving my failure.

My failure to get the woman I wanted. The career I wanted. The life I wanted.

The funny thing is, I was only part of the way through my journey. I was only in my late twenties.

And yet, the nightmares persisted.

Did my subconscious know something I didn’t?

Were my dreams trying to tell me something?

Why did they visit me so often?

Meet Jim

Jim is 30. He’s single and works as a low-level manager at a large corporation. He could lose 10 pounds, but he’s not in bad shape.

It’s Monday. Jim snoozes his alarm clock for about 20 minutes, jumps out of bed, and scrambles to get ready for work. He doesn’t have time to make breakfast, so he stops at McDonald’s for a few Sausage and Egg McMuffin’s. It’s $12 and 1,500 calories, but he makes alright money and isn’t ‘out of shape,’ so…not a huge deal.

He gets to work 15 minutes late. Not a big deal, people notice, but he stayed late one day last week. He does enough at work to keep his job secure, but he’s not setting the world on fire, either. Like most, he avoids work if he can — after all, if they want “extra” work out of him, they can pay him more.

He didn’t bring a lunch, so he runs across the street to Taco Bell for a few taco supremes and a diet soda. Oh, and a bottle of water. He figures the diet soda isn’t so bad, and the water is healthy. So lunch isn’t that bad.

He gets home around 5:00 and throws on Netflix while he tosses a frozen dinner into the oven. It’s not a healthy meal, but it isn’t so bad.

He thinks about the woman he likes. His best friend. It may just be the woman he loves.

He wants so badly to do something about their relationship, but he doesn’t want to ruin the friendship. So he pines.

Besides, they talk every day, so maybe something will come of it one day. For now, he’s content being in the friend zone.

And yet he pines, so to get his mind off the subject, he searches elsewhere. He opens Tinder and starts swiping. He matches one and sends the same generic message he sent to the last ten matches.

Maybe this is the one that will let him forget about the woman he does love.

He thinks about the opportunity he has to join his friends in starting a business. It sounds great. But it would require he make less money initially, have worse benefits, and relocate, away from his friends and family. And away from the woman he may love.

But he’s comfortable. Why work harder?

That’s too much to think about right now.

He watches a little more TV, then decides he better clean up. So he washes his dishes and pays a few bills before getting ready for bed.

What did Jim do to improve his life today?

Now consider this — Tuesday through Friday are very similar days.

What did Jim do to improve his life all week?

A Day in Your Life

It is not the years in your life but the life in your years that counts.
~ Adlai Stevenson

Imagine your average weekday.

Let’s take yesterday (unless something unusual happened).

Consider the following questions:

  • What did you eat and drink?
  • Did you exercise?
  • What did you do socially?
  • Are you single? Did you find anyone to ask out on a date?
  • Are you in a relationship? Did you do anything to enhance your relationship?
  • Did you learn anything that would be useful in your future?
  • Did you do anything to advance your career or increase your income?

Now imagine being stuck in a loop — living your day over, and over, and over again.

Now imagine living that week over and over again.

Now that year — over and over.

For ten years.

Now you’re getting the picture.

The worst part is, you may be stuck in this vicious cycle and not even know it…

My Vicious Cycle

If you haven’t figured it out — Jim was me.

Is Jim you, too?

Walking my path, everything I wanted — I didn’t get.

But even worse was that mostly I didn’t even try.

It was a crushing realization, and it still hurts and haunts me to this day. Because it was all right there; even if I had failed, at least I would’ve tried.

When some harsh realities forced me to look back over my life, I realized something that sent shock waves through me:

Not much was different in a day from the day I turned 25 to the day I turned 35. Sure, the aesthetics had changed. But my life was, mostly, the same.

Content.

Comfortable.

And without realizing it — always pining for more.

I was mostly fine. But it’s not like I loved my job. I just did it for the money.

It’s not like I loved where I lived. I lived there because it was comfortable and it was easy.

It’s not like I loved my girlfriend. It just worked. The person I had loved was long gone, and being in a relationship is just what you did.

Yeah, I was comfortable.

But I wasn’t happy.

But at 35 and looking back ten years, what had I done to change my state of contentment? To change to a happier or more successful state?

Not a damn thing.

“We waste a lot of time crying over wasted time “
~NF

I could have sat back and wondered, “why did this happen to me,” but in the end, nothing happens to you. Everything that happens is a result of your actions and the decisions you’ve made.

The Two Culprits

woman hiding in a box for comfort from the fear around her

The only thing I can chalk that up to is my old friend’s comfort and fear.

Comfort in the life I was living. While it wasn’t great by any means, it wasn’t bad either. And hell, everyone else I knew was living the same life.

Fear of change. Change is often scary. Why rock the boat?

Why spend my life to take a chance with a new (and excellent) job offer in Chicago when I can stay here and be relatively okay. Not happy, but getting by.

Why start that business when life is fine right now? You have to put yourself out there; you’ll have to work very hard for a while, and…it’s unknown. What if you — gulp — fail?

Why go for the girl of your dreams when you could get hurt, instead of just being okay as you are now?

What I Learned

If you want more in this life, if you’re going to be happier and more successful, you can’t sit around in contentment.

Get outside your comfort zone.

Take chances, have ambitious goals, and go hard for the things you want.

Looking back, I had always been thinking about things wrong. I had always been asking myself the wrong question:

Why go for something great when your life is adequate?

Thinking about it like that, the choices I made seem insane.

Always go for great.

Every. Single. Time.

Always go for Great

What if I told you that ten years from now, your life would be exactly the same? I doubt you’d be happy. So, why are you so afraid of change?
~Karen Salmaonsohn

Most people don’t realize that where they are today is the sum of the decisions they made 3–5 years ago.

And when you stay in your comfort zone, afraid of change, you will stay stagnant. It’ll start with a day. Then it’ll be a week. Then a year.

And then you’re going to look at your life in 10 years wondering where it all went wrong.

It all starts with one decision in one day.

So what are you doing today that will change where you’re going to be in 3–5 years?

You don’t have to take a big and bold step every day.

Just a small step can have a significant impact later on in life.

Look at your day today, and just do something.

It doesn’t matter how big the step, as long as you’re going in the right direction.

When Will You Be Happy?

woman being happy

Pretend you’re sitting in a room with just one other person.

You.

But you from 10 years in the future.

Now ask Future You if he or she would be happy with your day today.

And whenever you have a big decision to make, go back into that room, and ask Future You if he or she would be happy with your decision.

It will change your view immensely.

Because now that you know, now that Future You knows, it’s no secret, and you will judge every decision you make.

So the next time you’re facing a critical or life-altering decision, sit down and talk to your new friend.

What would he or she think?

Stop the Loop — Stop the Nightmares

woman sleeping sound on the moon

I wish I had seen it when the nightmares persisted — but eventually, even they gave up on me.

I wanted a better life, but I did nothing to get there. I thought I had plenty of time but never did a damn thing with it.

I never did a thing to live this “better life” I wanted.

You can easily glide along in this life, being content — living the same day over and over again.

Because hey, it’s alright most of the time.

But if you think about it, do you consider yourself as successful as you could be?

Do you consider yourself as happy as you could be?

If not, my friends, it’s time to break that vicious cycle.

Stop repeating the same day over and over, and decide to be bold, step outside your comfort zone, and change.

Make Future You proud.

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Jay Gross

Jay Gross is a writer, podcast host, lives to travel, with an unhealthy mango obsession. Focused on personal growth. Find him at www.lifenextlevel.com.