What No One Ever Tells You About Starting Over, After 50…

Empty highway with focus on yellow line down the middle

The five points of starting over, after the age of 50, that no one ever talks about.

Sure, all of the information ever created by mankind is at your fingertips, all of the time.  

It’s amazing, and sometimes overwhelming.

thousands of books

There are workshops, support groups, self-help books – by the gazillions – for every issue, diagnosis, conundrum and problem…not to mention the millions of jerks out there, whose sole focus in life is to scam you out of some money, in one shiny, dazzling way or another. 

But do any of them actually tell you what to expect when you’re starting over after the age of 50

Not really, and I’ve looked and looked…

…Because that’s exactly what I’m doing.

This is the sign you've been looking for neon sign

I was desperate for information…guidance…ANYTHING that would help me figure out what to do, when to do it and — most importantly — HOW to start over.  

I ran one search after another. 

One thing is for sure; I felt as if I was the only person that had ever woken up one day to realize they were over 50 years old and had to find a way to start over.

I. Felt. So. Alone.

man alone on rock at sunset

Each search offered a little information here or there, but none were very straight forward, and it seemed like each was written by someone who had an attorney looking over their shoulder, saying, “Oh, no…don’t write that.  It’ll seem like you’re giving advice, and you’re not licensed.” 

To be clear, the only license I hold is a driver’s license.  

I’m not a counselor.  I’m not a therapist.  I’m not a doctor.  

I’m not giving you advice.

I’m telling you what I did to start over, and how it helped me. 

This post addresses the five points — that I’ve discovered — that no one ever talks about, when starting their lives over, after the age of 50.

Fair enough?

Let’s talk about what no one tells you. . .

woman with finger to her lips

1. Address the negative, so we can focus on the positive:

First, I think we can collectively agree that starting over, in general, SUCKS; But doing it, after 50, really sucks

Oh, and it’s difficult.  I mean it.  It really, truly sucks, and it is truly difficult. 

If it wasn’t super sucky and difficult, everyone would be doing it, wouldn’t they? 

People would be all psyched out, texting each other about how super stoked they are that they’re “starting over,” right? 

But the reality is they’re not.  And the reason they’re not is because it sucks, and it’s one of the hardest things you’ll do in this lifetime.

man with hands interlocked behind his head

Or…if you’re like me…several times…

I’m convinced this is why people stay in bad marriages and jobs. 

It’s easier to just stay where you are and deal with it, because people crave stability and fear change.  I get that. 

But right now, let’s stick to the first topic, and we’ll delve into creating stability for ourselves later. 


yellow pull-down door with ok on it

Right now, I want you to go back and reread those first two lines about it sucking and being really difficult, please. 

I’ll wait. 



We’re all agreed on those two points.  It sucks.  It’s difficult. 


And also…those will be the ONLY two negative points, from here forward. 

Good vibes only sign


Because when we focus on the negative, we compound the negative.  You know this.  I know this.  Everyone knows this. 

Forcing yourself to go through something emotionally and mentally difficult – to stand up and face the music and just do it – is tough.

There’s really good news, though.

Would you like to hear it?

Here it is:

Investing in yourself…It’s always worth it.

seedlings growing through grate

2. No one tells you what “Starting Over” means:

Starting over may mean something completely different to you than it does to me. 

  • For you, it could mean that you’re newly divorced or widowed and looking for companionship or love. 
  • It may mean that you’re looking for a new career – for whatever reason – and unsure if you should go back to school or hit the pavement running with the experience you already have.
  • It may mean that you’re starting over financially – for whatever reason – and unsure of how to do that with the “limited time” we’ve got left. (Kinda grim implying that we’re all going to die, but it’s a fact we are all much more aware of at this age.)
  • It may mean that you’re moving to a new city or area of the country, away from your family and friends.

You get the idea. 

lightbulb in hands

Starting over means that, due to life’s every-changing circumstances, you’ve been forced to face the fact that you’re now going to have to start over – at something or somewhere – and you’re unsure of how to do it, let alone where to start. 

Here’s the good news:  No matter which of the above scenarios fits your particular situation, this is your opportunity to reinvent you

This is your opportunity to learn from your previous mistakes and not “eff it up” again. 

This is your opportunity to move forward. 

Starting over can be gloriously positive.

highway center line

3. No one tells you that you’re in this on your own:

Even if you’re married or have a significant other, most people are dealing with their starting over issues, pretty much, on their own. 

Meaning, you’re not on a team with a bunch of supportive collaborative folks, all collecting and sharing information, all focused on one goal/effort; Assisting and supporting you while you’re starting over. 

family at beach at sunset

Sure, your kids, family and friends may be supportive, and that’s great. 

I truly hope they are!  

But they have lives and responsibilities of their own, and you’ve got to do this. 

You’ve got to figure this out.  You’ve got to take this one to the finish line by yourself. 

Oh, and by the way …  

You’ve got this.   

yeah neon sign

It’s easy to say, “You’ve got this.” 

Trust me. 

I just did it. 


You Got This Just Do It GIF by Victoria's Secret PINK

Saying something, versus actually doing something, isn’t quite the same.  One is easy as hell, and the other is actual work. 

When I say “You’ve got this,” I truly mean it. 

thumbs up among plants

However, the only way that you actually do that is by practicing honesty, responsibility and by doing the real work.

  • You’ve got to own your mistakes. 
  • You’ve got to take responsibility for your words and actions/inaction. 
  • You’ve got to forgive yourself.
  • You’ve got to stop blaming others.  
  • You’ve got to be willing to admit when you need help. 
  • You’ve got to do the work. 
  • You’ve got to start moving forward.

Everyone focuses on the mountains in front of them and forgets about the mountains they’ve already climbed. 

We’re a little older, and hopefully wiser.  We’ve learned from our mistakes (Again, hopefully.) 


We now have the luxury of not giving two shits about what other people may think about us, which is not only liberating, it’s downright exhilarating.  

At this point in our lives, if you mess with us, we’ll set you straight, right quick. 

The point is, each of us has had to overcome something tragic, somewhere along the way. 

brown eyes crying

And if you’re reading this right now, hopefully, you’ve figured out that you’re not in this totally alone. 

You also know that every time you achieve one of your goals, it not only feels really freakin’ good – that action means you’re actually doing it.

You don’t have to see the whole staircase, you just have to be brave enough to take the first steps.

large staircase

4. No one tells you how overwhelmed you’re going to feel: 

At first, it’ll feel downright frightening. 

You’ll second guess yourself. 

Then you’ll second guess yourself some more. 

Scared In The Cut GIF by Bounce

And yet again. 

That unforgiving, negative loop will play in your head.  You know the one…we’ve ALL had it playing, at one point or another in our lives. 

it's all in your head neon sign

For some reason, my negative loop plays 80’s hairband music while I berate the shit out of myself.

(I just thought I’d throw in that truth about me.)

david coverdale 80s GIF

We are ALL our own worst enemy. 

However…once we hit the STOP button on that negative loop that’s been playing for days, or even years, and actually start to take action – however minuscule that first action may be – we are, at that very point in time, beginning to move forward. 

I truly believe this.

“These mountains you are carrying, you were only supposed to climb.”

mountain range with yellow brush in foreground

Your first action may be just about anything:

  • Making a list of what you want to accomplish tomorrow
  • Setting your short-term, medium-term and long-term goals and placing them somewhere that you’ll see them several times a day
  • Signing up for a dating site or agreeing to go on that blind date
  • Consulting a divorce attorney
  • Joining LinkedIn or Indeed or Career Builder or Monster and setting up job alerts
  • Making the call to Consumer Credit Counseling or setting up the bankruptcy consultation that you’ve been putting off
  • Rewriting/updating your resume
  • Contacting a realtor and looking for a new place to live
  • Joining a gym and hiring a trainer and actually going
  • Calling the person you’ve been putting off and having an honest conversation

If you’re a procrastinator, as I am, actually following through with one of the things that you’ve been putting off – while beating yourself up for putting it off, in the first place –  is MONUMENTAL

black and white photo of waterfall

Believe me, once you accomplish and cross off just one of the things on your list, it sparks your internal motivation to keep the momentum going – even if you’re a lifelong procrastinator. 

This was where I started starting over. Yes, it’s stupid simple:

Writing a list was my starting point.

journal with coffee ring stain on it

This is you starting to start over. 

It’s where I shifted from being so overwhelmed that I did nothing – to my absolute detriment – to compiling and forming at least the beginning of a plan. 

Stop Talking Action Plan GIF by ScreenCloud

It didn’t have to be a perfect plan. 

It didn’t even have to be a complete plan.

We all fail.

We all have to restart at some point, somewhere. 

We all have to start at zero.

Don’t get hung up on your age, as you restart your life.

Focus on the fact that you are brave enough to actually restart.

Right now, just set your overwhelmed feelings aside, and jot down a list. 

empty journal with two pencils and crumpled up paper

Whatever your particular version of starting over looks like, make a list of the general “hot topics” or goals that you deem necessary to, you know…start over.  (You can subcategorize and get as detailed as you’d like later.) 

to do paper GIF by furrylittlepeach

In fact, later – as you start crossing off these initial items of your list – you’ll find that each item sparks a thought of something else that you need or want to accomplish. 

You’ll add that to the list. 

Things to do before I die list

Sometimes, you’ll cross off one item and add two more. 

And as this happens – and whether you realize it or not – this is you making progress and moving forward. 

The positive momentum keeps on going!

For now – as overwhelming as it may seem – just write a simple, five-to-seven-item list.  

desk with laptop, coffee mug, pens, notebook,

5. No one tells you how humbling it is.

When I “started” over, I had no idea of what to do or where to start. 

So I did nothing. 

I did nothing for so long and with such vigorous denial of my circumstances that I eventually lost track of which way was up or down. 

I was in complete and total denial. 

not an entry sign on blue door

For the first time in my life – I’m talking EVER – I had to ask for help.  But since I’m not married and don’t have a significant other, I felt utterly alone, stranded and desperate. 

I Need Help Support GIF by YouTube

Sure, I researched online, and I read the feel-good stories of the people who sold everything and moved Honduras or Argentina to write freelance articles, help the needy and lived happily ever after.   

I read the bankruptcy stories of how they rebuilt their lives and became multi-millionaires, too. 

Mercedes car

We all have, haven’t we?

But I was so freaking far from that, I couldn’t even imagine an outcome that didn’t involve my car being repossessed, let alone that had me moving to another country and wandering the sandy beaches all day, every day.

The only person I knew…the only person that even rarely interacted with me…was my ex. 

outstretched hand and arm

Yep, I had to ask my ex for help. 

Can you even imagine? 

I mean, seriously. Can you?

Surprised-faced little boy

To his credit, he reluctantly came through for me, when no one else did.  He let me and my two dogs live with him, so we wouldn’t have to live in my car. 

You want to talk about humbling? 

My business that I’d started — two years previous to this five-alarm shitstorm — had gone under. All of the work that I had lined up was put off for at least a year, or altogether called off.

Sorry we're closed sign in door window

I’d been laid off in May of 2020 (Yep, the Coronavirus killed my job), and I wasn’t able to find any jobs in my previous line of work – I’m talking absolutely nothing.

The house I had been renting was sold by the owners, and they never said a word to me – just a two-week notice that the house was sold for cash.   

sold on chalkboard

Months of being laid off with no income, I watched my teeny-tiny savings quickly dwindle away, and I knew I was rapidly approaching the point of no return.

And still … I did nothing.

Complete and total, ostrich-with-its-head-in-the-sand, flat-out denial.

ostrich face mouth open

I had nowhere to go and time was running out.

I was flat-ass broke, and I was homeless. 

I put the majority of my belongings in a storage unit, and I moved in with my ex.

orange pull-down door

With MORE than $100K of credit card debt eating me alive, creditors hounding me nonstop and the local Sheriff’s office serving me with not one but TWO summons for court appearances, I had enough money left – to my name – to file Chapter 7 bankruptcy…so that’s what I did. 

bankruptcy lawyer scrabble letters

I accepted a remote job that paid $13/Hour.  That hurt, but income is income, and I desperately needed it. 

I set my ego and pride to the side, and I worked that remote, soul-sucking job, while I diligently searched for a better job.

Before my business went under, and before I was laid off, I was making six figures and spending money like I had my own personal money tree in the backyard…

twenty-dollar bill on tree branch

…I was living way beyond my means with little to nothing in savings.   

Ouch.  I’m embarrassed to even write that, but it’s the truth.   

woman with hands over her face

Like I said, owning these truths is humbling

Believe it or not, this is a good thing. 

After falling so low and now having to find a way to slowly climb my way out of the hole I dug for myself, I had no choice but to take responsibility for all of my bullshit. 

I’m talking…ALL OF IT.

raised arm with fist

I had to own my choices, own my actions, as well as my inaction, and I had to accept that my current place in life was the direct consequence of my choices, my procrastination and my denial.


These are difficult, but necessary, life lessons. 

writing in journal

I wish I had learned them earlier in life, but here I am floundering around at the ripe, old age of 50.   

Key Point:  The reason why I say that I had to accept that this is my current place in life is because I am positive that this is not my permanent place in life. 

man standing at shore alone on rocks

To me, this is incredibly important. 

We all fail. 

Every success arrives after one – or many – failures. 

man with outstretched arms at sunrise

Regardless, I am thankful that I was overwhelmed.

I am thankful for being humbled. 

I am thankful that I was eventually forced to act. 

I am thankful that I am figuring this out on my own. 

I am thankful that I am starting over. 

thank you neon sign


One last thing…Today, I’ll be crossing this item off of my original “starting over” list:


(And I cannot even begin to tell you how satisfying that is.)

Restart. Refocus. Reinvent.

More soon,


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