Reinventing your life after four decades can feel daunting. But, you owe it yourself to take on this quest. Here’s how to successfully start over in your 40s.

+++

When I was a kid, I wanted nothing more than to be a play-by-play sports announcer. 

I was obsessed with sports.

I’d watch the local newscasts and study how the sports anchors presented the highlights of the day in only a few short minutes.

The mornings were dedicated to SportsCenter on repeat. It was the “Big Show” with Dan Patrick and Keith Olbermann with catch phrases and hilarity. They were rockstars.

When my father would work late nights, I’d call him up and give the play-by-play as I watched the Orlando Magic back in the Shaq and Penny Hardaway days of glory. 

In my senior year of high school, I took the role of public address announcer for the basketball team and was invited to do the same for the spring football game. 

Sports was my passion. It was my hobby. And I was going to do everything I could to make sports my career.

In college, I went to Florida State University and took my goal to the next level. Sports editor of the campus newspaper. Sports anchor of the college-run local newscast. Lead sports reporter for the student-run weekly sports magazine show. 

And that hard work paid off when I got hired right out of college to my first television news station in Macon, Georgia. Eventually I got to work in Jacksonville, Florida, too.

I was set. I was living my dream.

Until one day … that dream just simply faded.

It was shortly after losing my father to cancer, but the warning signs of my eventual distaste for the industry were already presenting themselves.

In 2009, I gave it all up. 

The work of putting in countless hours for minimal pay while bouncing around multiple cities and states to maybe, hopefully, one day get a shot at play-by-play work was just not worth the sacrifice of what I truly wanted: more freedom and a fulfilling life with a great family.

Fast forward to today.

That dream from my 20s is a distant memory and I’ve got my family (wife and two beautiful kids) while living in my dream city (New York) in my 40s.

But now I’m feeling an additional itch. A pull to do something more with my life and my career and how I approach my content.

In short, I think at the age of 44 that I’ve finally figured out what I want to be when I grow up. 

If you’re anything like me and you’re wondering how to start over in your 40s and build a more fulfilling life, then let me be the one to tell you that it is possible. 

Let me show you how I’m doing it so you can do the same.

+++

Ever find yourself wondering how the hell you got here and how the hell you could possibly get out of this purgatory?

Seemingly too old to transition to a new career. 

Yet too young to hang it up and retire. 

Wondering if this is it: You’re just going to settle for less than what you’d dreamed for as a kid and life will just be a mediocre slog wondering “what if” all the time.

I reject this notion.

Because I’ve been there myself. 

Spending countless hours trying to figure out what it is that I could do that would provide a bit more spark and meaning into my days.

Dreaming about a better way to make an income. 

Journaling about how I’d like to be more present with my family and how if I could only figure out that one thing I’m missing.

But how the hell can I do this after the age of 40?

We’ve been conditioned since an early age to follow the process.

Study hard in your teenage years so you can go to college.

Kick ass in college so you can nail down that well-paying career path.

Work your ass off in your 20s so you can find mid-level management in your 30s.

By your 40s, it’s time to start reaping the rewards of all that hard work as you earn more money. Even if that means working even more to do it.

Eventually, somewhere down the line, we’re promised a reprieve from all of this back-breaking work and will be allowed to settle down. Maybe even retire, if we’re lucky.

But you and I both know that dream is dead.

Instead, it’s up to you to create a new way for yourself. And yes, you can and should do this even if you are in your fourth decade of life.

Imagine a life well-lived on your own terms

A life where you’re excited to wake up in the morning and do the thing. The thing that you’ve dictated is important, not one decided by a non-playable character boss that doesn’t give a shit about you.

The thing that has been calling you for years, perhaps decades, but you never gave yourself enough credit that you could actually achieve it.

It is possible. It doesn’t matter how old you are. But you do have to make a plan and commit to it.

Yes, this will be scary. And you’re likely going to mess up a lot. This is all part of the journey. 

You level up a character by gaining experience. Throughout that journey, you will have battles that you win, lose and some that you draw. 

Reinvention is the same exact process.

You will write crappy pages before your first chapter starts to make sense.

That product you want to design will probably suck at first. Until you help more people with it, get some feedback, iterate more and then apply the learnings.

Stop being afraid of these failures. Embrace them. It’s great feedback that builds knowledge and wisdom. That experience leads to better skill acquisition. 

That’s exactly what you need in order to start over in your 40s, level up and eventually knock this out of the park.

And you can absolutely do this. 

No. Let’s rephrase that. You absolutely must do this. 

Life is meant to be lived and experienced and you owe it to yourself to spend the next six months, 12 months, 12 years working towards that thing that is calling you.

Because it is calling you for a reason.

Imagine finally enjoying this journey with loved ones, instead of living for the weekend, only to get anxiety because the weekend isn’t long enough and Monday is right around the corner.

Maybe it’s financial freedom.

Something you won’t realize by working paycheck to paycheck praying that the NPCs at your corporate HQ finally appreciate you enough to give you more than a cost of living raise. Or a piddly little bonus.

Maybe it’s not about your career, but you need a bit more fun in your mundane life to destress and flex your creativity. 

It doesn’t always have to be about making money and starting businesses. 

You’ve got what it takes to make this happen. 

So let’s set the stage for you to start over in your 40s, 50s and beyond.

Reinventing yourself is possible. It starts with you.

The narrative is that by the time you are in your late 20s, the vast majority of your belief systems have been baked in. Which is why there’s this myth that you can’t change or start over or learn new tricks as an old dog.

Fuck that.

The biggest obstacle that will prevent you from success is your own head. If you start now with a process to reinvent yourself and finally level up, you will not fail unless you give up.

But look, I get it. 

As a 44 year old who’s gone through a similar journey, I know firsthand that the limiting beliefs can wear you down harder than the humidity in a Florida summer. 

Your ego craves comfort. It feeds off of complacency. It rejects change. 

The ego is going to get in the way and tell you that you don’t have time or money or energy or the patience to see this through.

And all of this is true. If you let it be true.

Which is why you must look for more than just motivation to find success. 

You must develop a plan and a set of systems that allow you to build momentum.

How the hell do you start over in your 40s

Like any goal, the path to victory is to get really fucking clear on that goal. Be specific as possible.

What the hell do you want? 

No, like seriously. What the hell do you want out of life?

Is that 9-to-5 job (that’s really more like a 7-to-midnight job) kicking your ass and you want to break free of that corporate capitalist ladder? 

Do you feel like a sluggish troll all day that can’t even get down on the floor to play with your kids and you dream of a way to finally feel energetic and healthy?

Maybe you have this dream of starting a business or writing a book or just being able to travel the world a bit more without having to worry about your stupid “Out of Office” message working so your dumbass colleagues will leave you alone?

Get super clear on what you want.

This might not be an overnight process. 

You might need to go on long walks. Meditate. Journal. Have conversations. Read some books. Be bored as hell for a while (if you’ve got the time to even be bored). 

Maybe you need to get clear on what the hell you don’t want first, which might shed more light on how to get away from that trap.

Once you’ve figured out what you want to do, to start over in your 40s, you’ll need a specific action plan to get there.

If you’ve been here a while, you know how fond I am of video games. I played them as a kid and then shamed myself out of doing so as I transitioned into my professional career paths. 

But now that I’m in my 40s, with two kids who love gaming, I’ve rediscovered my love for all things role playing games (RPGs). 

Life is like an RPG. 

You should go through that article and read it before continuing here. 

To reinvent your life in your 40s, it’s all about finding the right side quests to level up your skill set.

I believe there are four skills that are the pillars of designing a more fulfilling life. 

• One to challenge your body
• One to challenge your mind
• One that deepens your relationships 
• One for play and relaxation

At minimum, you should find about 15 minutes per day developing each skill category. That’s one total hour per day. 

It doesn’t have to be all at once. 

You can challenge your body with microworkouts and minimalist training.

Cultivating better relationships with your loved ones can simply mean committing to one phone call (yes, talking to someone!) or a text to someone in your contacts per day. 

And then a habit of putting the phone away at dinner time with your family.

Play and relaxation should be a daily ritual for you. 

For me, I shut down my work at 4:00 p.m., fire up my PlayStation5 and play a video game for about 30 minutes before I pick up my kids from their afterschool programs.

The mind can be enriched by spending time learning.

If building a new business is your goal, spend 15-20 minutes per day learning the proper levers to pull to actualize that dream.

Or spend that time actually taking action on that dream. 

Ideally, you’d like to get to 60 daily minutes of focused work towards that big goal. 

Can you do it in the morning before the kids get up? 

Or maybe 30 minutes here and there? 

Whatever it is, this is your life’s work. You owe it to yourself to get real.

This is exactly how I did it with two kids in the house. 

I’d spend my mornings writing and learning and researching how to transition from a corporate job to my own business. 

Then I did it again when realizing that my business wasn’t as fulfilling as I’d liked and needed to pivot a bit more to start creating the content that really gets me excited to wake up in the morning.

Here’s how you’re going to reinvent yourself and start over in your 40s

Pick a side quest that will allow you develop in each area:

Health

Your fitness and nutrition should now be taking a priority if they’re not already. 

What good is crushing all of your dreams if you end up too sick and lethargic and out of shape to truly enjoy this more fulfilling life?

At minimum, you should be strength training, walking and just eating more balanced meals on the regular.

The exact simplistic approach that I teach in my Lean4Life program.

Mind

Graduation from school is not the end game of learning. You need to do more. 

Find the books, courses and lectures that allow you to do expand your brain a bit.

If you want to start a new business, you’ll need to learn copywriting, marketing and sales to successfully sell your products or services. 

Even writing a book means learning how the publishing industry works. 

Finding a new career requires additional knowledge about said new career.

You need to learn. And keep learning.

But I get it. Look, if none of that is your goal, you still shouldn’t let your mind just atrophy.

Find something new and interesting and start learning about it every single day. 

Relationships

There’s this premise that you can block out six months to a year and be anti-social and emerge as some Phoenix from the ashes that crushes life and earns $10,000 a month in revenue. 

They call this Monk Mode. 

It’s dumb and unnecessary.

You need relationships. 

Just like your health, what good is all of this starting over in your 40s to reinvent yourself if you’re going to end up as a miserable curmudgeon toiling away all alone?

Build up your relationships with loved ones. 

Make it a point to network more and utilize that network if possible to help strengthen this reinvention project. 

Reconnect with your buddies instead of just sharing memes about sports in your group chat (I’m guilty of this myself).

Go on that girl’s trip with your friends. No kids or husbands allowed. 

And if that’s not possible because your husband is a douche who can’t watch the kids for more than two hours alone, it’s time to work on that relationship, too.

Play

We’re starting over to build a more fulfilling life. Play is a major part of that life we’re trying to build. 

Find those activities that you truly enjoy. 

Channel your inner child and revisit some of the things that really got you excited to get out of bed in the mornings of your youth. 

For me, I rediscovered my passion for playing video games, particularly role playing games, which is where the theme and title of the LevelUp Letter came into reality.

You’ll be less stressed, more energetic, happier and healthier as a result of finding some areas of enjoyment if you make that a priority every day … or at least weekly.

Some ideas:

• Play a sport
• Dance
• Video games
• Paint
• Puzzles
• Cooking classes
• Baking
• Book clubs

Get creative. It’s your life. 

Do the thing that makes you smile and laugh and helps you get lost for a few minutes or hours. Something not related to work or parenting or business and side hustle building. 

One year. Give yourself at least one year to make this reinvention happen.

One year will be enough to see meaningful progress and results that propel you forward for the rest of your life.

But, in all honesty, this should be your life’s work. 

Focus on the four pillars for skill acquisition to successfully start over in your 40s. 

If you build up those skills, it will include everything you need to Level Up.

I hope you found this useful. If so, I’d appreciate it if you sent this newsletter to one person you think would benefit from my writing today. 

And if you’re new here, be sure to join the party and grab my weekly doses of awesome by signing up for my regular newsletters at the form below.

If you’ve gone down the path to reinvent your own life, shoot me a note and tell me your story, I’d love to connect.

I answer all of my emails at pete [at] petecataldo [.] com … Hit me up with the subject line “start over in your 40s” and I’ll answer any questions you have to make this work for you.

Until next time,
Pete