Winning vs. Losing vs. Quitting

“Winners never quit, and quitters never win!”

Whenever I hear that line the voice I hear saying it is some gruff high school football coach trying to motivate his team.

“Now get out there and hit ‘em where it hurts, crush ‘em, bang ‘em up, chew them up and spit them out!”



This just reeks of everything toxic that myself and others are writing about when it comes to masculinity and teaching our younger generations how to deal with life. But the reality is…

That coach may be right!

Sometimes in sports and sometimes in life as well.

In sports, you either win or you lose. I mean in some sports you can tie but really does that mean both teams win or both teams lose? Does it even matter?

Unless it’s soccer, in which case they just keep adding more time to see if someone will finally score.

Or Boxing, when one of the fighters is literally getting the life beaten out of him when their coach throws the white towel.

Sometimes life reflects sports in that it can be win or lose, but often there is that same third result. Quitting.

Winning vs. Losing

You can vie for the affection of the one your heart desires, or whom you simply lust after.

You can show interest, you can flirt with them, ask them out, ‘woof’ at them, swipe right or go old school and court them with romantic gestures. In the end you may win their love, or at least get the first date. Or just the hookup and be satisfied and hit the grid again. All of those are a win.


Maybe he/she simply isn’t interested and turns you down with every advance you make.



Maybe you don’t take no for an answer and continue to be persistent in your pursuit,

and eventually they break down and take the bait.


Then again:

Maybe they keep being persistent and you finally realize you can’t win over this person, even just to hit the sheets with. They are just not interested. Oh the shame! How do you deal with that? Simple really.


Losing vs, Quitting

Do you live in shame having quit something like this or is it saving yourself from embarrassment by giving up before you look like a complete fool? I mean really, we have all crossed that line at some point, haven’t we?

If standing outside their window with your boombox overhead playing some sappy ‘80’s song doesn’t do it, maybe it is time to throw in the towel.

In business it’s a bit different.

If you are working towards that promotion but you are convinced your colleague will be looked at as better qualified what are you going to do?

Quit your job? Quit striving for excellence? Quit trying to be noticed for your efforts?

That’s absurd. In this case quitting isn’t the answer. Work your ass off and show the boss just exactly why you deserve that promotion, raise, bonus over anyone else. And if he still awards that to someone else…well yeah that’s a loss.

But that’s their loss. And if you think your career path is being stifled maybe it is time to quit. But only after doing your best work and consistently going unnoticed and under-appreciated. If you like your job and your company you put in all your effort regardless. Give it your passion, if it is your passion. And prove, at least to yourself, that you are the best you can be at that company. But if they don’t recognize it, screw them.

Time to quit.

Quit your job, and find a new one and put the same effort into a company where you will be appreciated.

That’s when quitting can turn into a win.

Winning vs. Quitting

In the case of your job above, quitting and going somewhere better suited for you is really a win.

In fact, there are lot of times where you go after what you want and put in a tremendous amount of effort, and energy, and time, and keep reaching for that win.

Three things can happen:

You can realize what you are going after just isn’t worth the pain and sacrifice of what you are giving up to get it.

You can realize that the collateral damage to your win is too great.

Or, you can actually win and realize it may not have been worth the price.

That one is the hardest. What if we are talking about that love interest.

Your time, your money, your energy, your emotions, your entire life may be consumed in pursuing ‘the dream girl’

Or ‘the dream guy.’ Whether it’s the Marlboro Man or the British Dancer, what happens when you win them over?

Do they fulfill your dreams? Do they live up to the Marlboro man ‘masc af’ vision that you had? Are you even compatible with this person? What if that British Dancer is a control freak or demands all your medicine cabinet space for her makeup and Mary Kay products that she’s suddenly selling out of your living room?

Was it all worth it?

Sometimes you have to be damn certain of what you want.

The old saying goes ‘Be careful what you wish for, because you just might get it!’

There’s a reason that line is called a cautionary tale. Because dreams are made in our heads, and can turn into nightmares in the real world.

This can happen in the career world too. You can be hell bent on being a lawyer and spend ungodly amounts of money and time working on your law degree, your masters and doctorate, studying for the bar and getting everything in line for that dream goal of full partnership at the most prestigious firm in town. Until you read some motivational Instagram post. You know the ones:

“Live YOUR dreams”

“Find YOUR passion”

“Listen to the universe, watch for the signs and be brave enough to follow them!”

We’ve all seen them.

We’ve all scrolled by them.

Until we stop one day and our mind drifts…and our eyes glaze over… and our head tilts back and we stare at the white tiles in the drop ceiling in our not-exactly-the-corner-office-I-expected half-wall cubicle we are were dropped in until we ‘earn our chops’.

What if there is something else out there for me? Is this truly my passion?

When you add up the time, money, years and dues you’ve paid working through your career to get to the point you are at and are still not satisfied, what then?

Maybe you did reach the corner office? But maybe it’s overlooking the parking lot and not the scenic vista on the other side of the building. Or maybe that corner office comes with a type of role/responsibility you hadn’t imagined.

“But I don’t want to be a managing partner, I just want to practice law.”

Well that’s what comes with the corner office.

Or maybe you work your craft, study your passion for acting and audition and audition and audition and do commercials and guest spots as ‘guy with knife in head’ on Grey’s Anatomy. And then you get discovered and boom you’re a movie star but…really the celebrity and notoriety are not at all what you can handle because…

“I just want to act”

Is it a lose to quit the firm and start your own yoga studio?

Is it a lose to leave the glitz of Hollywood and go off-grid and do summer stock in the Poconos?

That depends, are you satisfied? Is your life enriched by the fact that you are doing what you love?

Granted not everyone can just leave it all behind and quit the corporate rat-race to stage homes for sale, not if they have a mortgage and kids and bills, and debt. But you can do it, in time, with planning.

But you have to want it. You have to know what you are getting yourself into. And you have to be true to yourself and your passion.

And when you do find it, go all in! Go for the win, do what it takes, get in there and chew them up and spit them out!

I mean that metaphorically, but whatever you are doing, give it your all, and if it is truly your passion and you know it, never quit.

Win at something that matters.

The point here is, just like masculinity, winning, losing and quitting? It’s not all cut and dry.

There may be 50 shades to each of those as well.

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