The 7 Deadly Wins: When Winning Is Actually Losing In Life And Business

The “seven deadly sins” are:

1. Pride

2. Greed

3. Lust

4. Envy

5. Gluttony

6. Wrath

7. Sloth

Got it.

But what about deadly wins?

When is winning actually losing?

In life and business, short-term gains are often long-term losses. I’ve experienced this first-hand. It’s ridiculous.

It happens in organizational cultures that emphasize politics over progress. It happens when people backstab to get ahead. It happens when people are more focused on looking good than actually being good at what they do.

The disturbing thing about these deadly wins is that, you often don’t realize you’re losing. Or, you’re not willing to admit it. Deep down, you know what you’re doing is wrong and will create negative long-term repercussions. But that doesn’t stop you. You’re willing to go-on your destructive path, hoping everything will be ignored and brushed under the rug.

Here’s the truth.

Nothing stays ignored forever.

Consequences eventually come forth.

Eventually, your house of cards comes crumbling down.

Here’s a breakdown of the 7 deadliest “Wins” in life and business. If you prefer maintaining your image over doing what’s right, you’ve probably committed some of these wins.

If you prefer short-term gains, you’ve probably committed a number of these wins.

If you’re fine sabotaging others for your own gain, you’ve probably committed some of these wins.

If your organization prefers profits over people, you’ve probably committed these wins.

Here they are:

1. Reaching the top of the ladder.

“If the ladder is not leaning against the right wall, every step we take just gets us to the wrong place faster.” — Stephen R. Covey

Gaining an edge by stepping on others, engineering results by hiding behind the curtain of committees and politicking your way to the top is never a win. Every time I go into a company and witness lives shattered by toxic management, hidden agendas and politics, I’m grateful to be an entrepreneur.

Remember who is holding your ladder when you step on others to climb your way to the top; the bottom will be kicked out from under you.

It’s like one of those human pyramids. The longer the leader in a ladder-climbing organization stays on top, the weaker the management and staff below become. Eventually, the whole empire crumbles like a house of cards.

2. Saving money by cutting people out.

Accountants put people on a P&L statement as an expense because of GAAP; bad managers do the same thing — creating a gap.

People are your greatest asset. While accountants may expense people in their cubicle, a leader puts them on her “balance sheet” as an investment.

Finding, nurturing and employing great talent is an art in relationship building, not a number to manipulate.

Partnerships fall apart, employees become disenfranchised and bosses look for shiny new people/programs to save money because of the scarcity mentality. They feel like if they can cut someone out, they’ll get a larger piece of the pie.

Life and business isn’t a pie. Life and business is a cake.

The right people doing the right things at the right time in the right place create bigger, better “batter” for all to enjoy the cake. When as an abundance mentality is employed, the cake is baked right. When a scarcity mentality is employed, the cake is half-baked.

Note: An investment in people doesn’t have to be financial. Take a moment to actually talk to your people Show them you care. Ask them about their vision and see how it fits with your vision. Work together, not in silos. An investment in kindness costs nothing, but the return on investment is endless.

3. Getting what you want, but with something to hide.

You can do all the engineering you want to create your desired outcome. When you get it, you may have strategized to have everything look clean to keep your cover. Nothing illegal or ethical may have ever be done, but the secrets you kept from others to manipulate the outcome will always come back to haunt you. It’s called karma.

When people are powerless they have two choices:

1. Fight the system / go around the system.

2. Exploit the system.

The ones you must be the most careful around are the ones that exploit the system. Those who fight the system or go around may not be liked by many, but they are in the open and often transparent about change-making. Those who exploit the system, find power by gaming the system. These policy-and-procedure-mongers capitalize on rules to justify bad behavior, gain undue influence and disenfranchise their best people for personal profit.

4. Fighting for what you want by back-stabbing.

A punch in the gut comes from an enemy. A stab in the back comes from a friend.

Some would say if you’re gonna fight, fight dirty. Others would say, all’s fair in love and war. The ones you have to be the most scared of are the ones that stab people in the back “for the long-term good of the business.”

The most challenging circumstances rarely come from distant enemies, they come from those once-thought allies

When you play the long game, you learn that short term gains never outperform the long term side effects of short term actions. Stabbing others in the back to get what you want creates too much collateral damage.

Victims of business-back-stabbing become confused on whether they should fight back or protect their friend for the good of the business. Short-term actions like backstabbing are unsustainable.

Eventually, the offender finds himself in a lonely leadership position. S/he is all alone…wondering why everyone has become “yes-men” and no one is willing to share their true feelings.

Lower management doesn’t want to be the next victim. Further, no one comes to the victims rescue because they got bills to pay. The leadership in these situations who have lower-level back-stabbing management never actually never really know what is happening in the organization because they receive reports from middle management.

As a result, the backstabbing leader becomes an expert on “how to lose friends and alienate people” (an article I’m working on for another time). The leader eventually becomes the victim himself (Et tu, Brute?) or leaves because he can’t get anything significant done in that environment.

If you feel like your organization is toxic, have the leaders manage by walking around. Have them chat with those on the front lines. Make sure there is a safe environment to speak the truth without backlash from whistle-blowers. Above all, talk with the executive assistants and secretaries. They are the ones that really run the business and know what is happening.

5. Maintaining the status quo.

Many leaders and managers pretend to want innovation, change and creativity, yet cut off the heads of anyone who pops their head up. You know what I’m talking about.

Maintaining the status quo is never a win. You may spend all your time and money to keep things the way they are (because it’s working, it’s tradition, it’s the way we’ve always done it), while at the same time giving lip-service to disruption.

I call these people “hierarchal hypocrites.” Hierarchal hypocrites never cease to amaze me when they pretend to have a vision and share with stakeholders and then return to their corner office to play online poker. Hierarchal hypocrites attempt to save face and be the face by only showing face; there is no body to the talking head. No substance to the blabber. (That’s why they play with digital face cards…but I digress.) :-)

Soon enough, conditions and circumstance will force you to change. You’ll be too slow to know what happened, forgotten by those you thought had your back and only heard of in rumor.

6. Saving something for a special occasion.

“Don’t save something for a special occasion. Every day of your life is a special occasion.” — Gordon B. Hinckley

Why not use that fancy silverware tonight? Why not do your best work today? Why save that idea for later?

Life is short. Just because that saying is cliche, doesn’t make it any less true. Many people save their best projects for later, only to never start them at all and never to see them come to fruition. The future is elusive, people!

Imagine if a rose stayed a bud because it wanted to save the petals for an unknown time in the future. When do budding entrepreneurs, artists, leaders actually do stuff?

Aren’t you sick of all the lip-service to entrepreneurship, art and leading by those who don’t do actually make, create or take people by the hand and lift them to new heights?

Too many thought-leaders and internet marketers don’t do anything at all (or got lucky once) and market it like they know what they’re doing. Kinda gross.

Time to step up your game.

The most successful people don’t wait to do their best work. They don’t save up for a special occasion. In fact, the happiest lives are lead by those who create greatness daily and build each project on top of the others. Successful people create a body of work instead of a capstone experience (tombstone experience).

To become an expert you have to have experience and to get experience you have to experiment.

7. Recognizing your wins (while ignoring your losses).

If you’re an optimist like me, you’ll tend to focus on your wins and brush over your losses. However, while modern day management gurus will tell you to focus on your strengths (not weaknesses), there is something to say about turning your weaknesses into strengths.

We all have blind spots.

We are all human (unless you’re a robot indexing this article). Some of us our devastated when we get feedback (and some of us brush it off).

This isn’t about right or wrong reactions, this is about strategy.


If you want to improve your life and business, look at the trail of blood you may have left around you in the past. Listen to the feedback people give you. More importantly, look to the feedback that your losses give you and do something about it.

The outcomes you create will tell you more about how you’re winning at life or business than anything else. Don’t wait for someone else to pick you as a winner; pick yourself…despite your losses. Don’t let winning obsess you so much that your wins are actually losses.

In the end, take 100% responsibility for your life (both wins and losses) and watch the magic happen.

Call to Action

If you’re a millennial and are ready to live your dreams, download my 9-page Millennial Checklist (power sheet): How to Prove them Wrong and Win at Life.

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