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Home » Media and Blogs » Are You Losing Before You Even Start?

Are You Losing Before You Even Start?

July 30, 2025 Ellen Leikind

The 4 Ways You Sabotage Your Own Success (Without Realizing It)

Most people don’t lose in business or life because they lack skill or talent. They lose because they take themselves out of the game one of two ways:

  1. Folding too early, before they’ve even played the hand.
  2. Doubling down on hands they know are losers, hoping for a miracle.

Both drain your chips, energy and time and neither moves you closer to winning.

Here’s how it shows up and how to stop the sabotage spiral:

1. Assuming “No” Before You Ask

You want the raise, the bigger role, the flexibility. But you never ask because you “know” the answer will be no. You wait for the “right time” … and it never comes.

How to fix it: Stop deciding for other people. Make the ask clearly and confidently with proof of your value. Even if it’s no, you’ve marked yourself as someone who knows their worth. That sticks and will build your confidence to do it again the next time.

2. Letting One Bad Hand Define You

You missed a sale. Froze during a presentation. Got passed over for a project. Instead of learning, you retreat. You fold not just the hand, but the whole game.

How to fix it: The best players don’t avoid mistakes; they use them. Review, recalibrate, and ante back in. Resilience wins more pots than perfection.

3. Waiting for Perfect Cards

You hold off on pitching the idea, launching the service, or making the introduction because the timing isn’t perfect. Meanwhile, others move first and take your win.

How to fix it: Play the hand you’ve got. Perfect is a trap; momentum is a weapon.

4. Getting Involved in the Wrong Hands

Self-sabotage isn’t just about quitting too soon—it’s also about saying yes to the wrong things in the first place. We commit to toxic partnerships, time-sucking projects, or deals that were bad bets from the start, hoping they’ll magically turn around.

How to fix it: Learn to spot the odds before you sit down. If the deal, project, or relationship doesn’t have a real chance of paying off, don’t ante up. Protect your time, energy, and reputation for the opportunities that actually move you forward.

Before your next big decision, ask yourself:

Am I folding because I’m scared to play… or betting because I’m scared to walk away?

Play strategically. Enter and fold wisely. And when you’re in be all in.

That’s how you win.

Filed Under: Articles

About Ellen Leikind

Ellen Leikind is the founder of PokerDivas, the groundbreaking leadership program that uses poker strategy to build confidence, sharpen negotiation skills, and transform the way professionals lead. A former Fortune 500 marketing executive at Pfizer and L’Oréal and author of PokerWoman, she has been featured in CNBC, Forbes, and Crains for her fresh take on business strategy. Ellen blends real-world corporate expertise with poker strategy to help people win in business and life. Learn More

What Clients Are Saying

This is an entertaining and enlightening book. And dangerous. Take the title seriously: It really is written to give women an advantage in virtually every area of life, from poker to business to personal relationships. Which is the reason every male and female poker player, and non-poker player, should read it. Ellen Leikind analyzes the games of poker and life in a straight-forward manner, with many examples, to make the lessons easy to apply. The transitions can be fascinating. Take ‘Playing with Fire: Trading on Attraction,’ Read it, if only in self-defense.

– Nelson Rose, Editor and Chief, Gaming Law Review

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