Sometimes You Have to Be Brave and Start Over

I had this friend.

Let’s call him S. Amazing human. We shared a love for 400-page books and deep conversation. I used drive him home after work. We talked about the pressures of his ultra-academic family. His rebellious, troublemaking times. That time he ran away and was homeless. That time he became top of his class. That time he was engaged but never married. That time he was truly, deeply in love.

His favourite book was Don Quixote and he knew all the Simpsons episodes by heart. Once, as a gift, he gave me a copy of The Brothers Karamazov by Dostoevsky. I still have it. It’s one of my favourite books. We lost touch. I think of him from time to time and wish him well.

S was an accomplished man. A brilliant, driven engineer in his early thirties who had the opportunity to make partner in his firm. He would have been the youngest partner in the whole company. Had his own secretary. Patent under his belt. Six-figure salary with a taste for expensive watches, suits, and ties. Hadn’t looked at price tags for years.

He had, above all, a divine appreciation for cars. Those beautiful machines.

S was very impressive, perhaps even intimidating. And envy-inducing to some, I’m sure.

But my favourite thing about him had nothing to do with his intelligence or accomplishments.

It was the way he took such innocent delight in new beginnings.

He was so unafraid of starting over.


See, most of us hate starting over. We hate having to start from scratch, from nothing. Because it makes us feel like nothing. Beginnings are hard and humbling and awkward. We have no pedestal to place our egos upon. We don’t have anything to be proud of: no accomplishments, no status, no power, no recognition.

Frankly, being a beginner at anything usually means you suck.

But throughout life, we’ll find that sometimes, we have to start over, start new. Careers end, businesses end, relationships end. Life happens in seasons and cycles, in days and nights. And sometimes, it just becomes time to walk away from everything we’ve known and done. Sometimes, we just have to take a deep breath, and wipe that slate clean, and start all over again.


He decided to give it all up and go back to school.

He walked away from the partnership. He walked away from the six-figure salary and all the success. He walked away from the rich life he had already built — a life many people only ever just dream of having — a life many people would think he was crazy to stop living — so that he could go back to school full-time, get another degree, and start another career.

Still engineering, sure. But still, different this time: Mechanical.

I asked him my favourite question:

“Why?”

Because — as great as he was with all the buildings and bridges — as much money as he was already making — as much prestige he had already received from doing the work he already did so well — the truth is, what he really wanted to do with his life, his days, his hands, his hours?

Was to work with cars.

Those beautiful machines.


I loved this about him. I thought he was so brave. Because he was just being so damn honest. Which can be the absolute hardest thing to do sometimes in a world that often rewards you so well, if you only know how to tell it the right kinds of lies.

And especially if you buy into its own.

In a society that more often than not, still values climbing that proverbial ladder — not stepping down, or stepping off — so many people would consider starting over again in something new, or at least something different, a big, risky — if not foolish — step backward. A mistake.

But is it really?

If you’re finally going in the direction you really want to go towards the life you really want to live, isn’t that a step forward, from any perspective?

Isn’t any other step but that step the real step backward?

Isn’t any other step but that step, at the very best — a step sideways?

Isn’t any other step but the one you really want to take towards the life you really want to live—just another form of distraction, stagnation, procrastination?

Because whether it’s backwards or sideways:

Any step you take that doesn’t move you in the direction you really want to go — is just another step of avoidance.


We often avoid who we are by trying to be someone we think we should be.

And we don’t always know we’re doing it.

All these things we chase in life, all these arbitrary images and definitions of success, these notions of accomplishment and power and status and honour and money and notoriety. All the awards and accolades and recognition. All the likes and recommends and tweets and shares. All the deeply symbolic, external validations we could ever possibly imagine having.

Do we know why we want these things? Do we really know?

Do we want them because our hearts want them, or has someone told us to want them? Made us think we want them, need them?

Can we untangle ourselves at all from the wishes of the outside world, to reveal our own, very real, and very important, inner world of wishes?

Have we unconsciously bought into the dream of what we’d finally have once we climb that ladder, that great mountain beckoning to us: that we would finally have...what? Value? Worth? Acceptance? Admiration? Respect, fame, glory?

That we would finally have love, or be loved?

That we would finally love ourselves?

That we would finally be happy?

Because here’s the trouble:

What if we aren’t?
What if we don’t?

What if we get to where we’ve always wanted to go and find that we still aren’t truly, deeply happy with where we are, and what we have?

What if we do and become everything we always thought we wanted to do and become, only to realize we still don’t love our lives?

What if we still don’t love who we are?

What if we’re finally living the life we’ve always dreamed of and we still don’t feel alive?

What if what we truly want is still missing? What if who we truly are is still missing?

What then?

My answer isn’t as depressing or discouraging or frightening as you might think:

I think we would just have to be brave.


Be brave. And honest.

And if you need to — start over.

Just like S.

Start all over again, however you must, and trust — that you can have everything you truly want. Maybe not everything you’ve been told to want, and maybe not everything you might think you want, but everything that you truly want, deep within your own, very real, and very important, inner world of wishes.

Because the truth is, all the things you truly want are already yours — somewhere else in time.

All you have to do?

Is start taking that first step forward. The one that might feel backward. It’s not. It’s not. Because it is the step you really want to take. Take that step. Start from zero. Hell, start from less than zero. Start with absolutely nothing at all. Just start where you are.

Start— so you can finally stop messing around and going in circles and merely toying with the idea of what you truly want out of life. To actually, finally, just start living that life. To start getting to the place—the purpose—the person — you truly want to become. The person you truly are inside.


We can run all we want, but we never can run from who we really are. We carry who we are at all times, whether we want to accept it — all of it, all of ourselves — or not.

On paper, life may appear linear, or seem like it should be. But it’s not. Life is not merely a path we walk, from womb to grave, from conception to final breath. Life is not a plotted journey we make from point A to point B, plodding forward on some one-dimensional line.

Life is a wandering. A traveling. An exploration. An excavation, even — of everything we really are. We aren’t just meant to move forward, in one direction always. We evolve. We spiral out, like a galaxy. And our direction is outward.

We often hear that life is not a sprint.

But it ain’t a marathon either.

Rather — life is an EXPANSION.

For we exist as humans in endless, eternal evolution. We are moving, growing, spiraling, evolving. Summoning all that exists within us to the surface of our physical plane. Manifesting everything compressed inside — to be expressed as who we are outside.

Our direction is outward.


I wondered why S seemed so unafraid, and almost excited, to walk away from the successful life he had built.

The answer was easy:

Because he knew it wasn’t enough.

Not because he didn’t appreciate what he had. And not because he greedily wanted more for no reason, either. He just knew he wanted something different. He could do it all and have it all and reach the very top of this ladder, this great mountain he’d been climbing, but deep down, he knew: It would never be enough.

Because it wasn’t the mountain he wanted to climb in the first place.

But…wasn’t he afraid?

Of failing? Of losing it all? Of making a mistake?

“I started from the bottom once,” he said simply.

“I know I can do it again.”

That statement wasn’t arrogance.

It wasn’t peppy self-talk either.

It was just…trust.

Trust in what he knew he could accomplish. Trust in what he believed he could still accomplish, had yet to accomplish.

And with that trust — there was also the thrill of a new adventure.

This time, it was the one he’d always wanted to have.


Don’t be afraid to start over.

Whatever it is you’re struggling with right now: maybe a dead-end job, a career you no longer want, an unhappy relationship, a lifestyle you’ve outgrown, a place that no longer feels like home, a floundering identity, a belief system that no longer works…

If you know deep in your heart something in your life isn’t what you really want or need — maybe it never was, maybe it used to be, maybe it just isn’t anymore — if you know deep in your heart that you’re meant for something more — or at least something else, something different —

Don’t be afraid to walk away from what isn’t enough.

Don’t be afraid to start over.

You are not running from what isn’t working.

You are walking towards what will.

Because ultimately?

All the things in your life that aren’t right for you — are just keeping you from the things that are.

Don’t be afraid to start over.

Be afraid of never starting at all.

Be afraid of never knowing who you really are.

Be afraid of living someone else’s dreams.

Be afraid of losing your own.

Be honest.

And above all:

Be brave.

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