Are You Playing to Win or Playing Not to Lose?

We get it: No one wants to gamble on their career. But by playing it too safe you could be leaving fulfillment on the table.

The "At Least I Did Something" Trap

You've been there before. It's that day you promised yourself - for the umpteenth time - that you'd crush a workout. But when the moment arrives, you opt for a casual walk instead, consoling yourself with the thought, "At least I did something!" Sure, you get points for moving and racking up some steps, but let's be real: you didn't go for the win. You did the bare minimum to get by.

Sound familiar? This mindset isn't just about fitness. It sneaks into every corner of our lives, especially our careers.

As someone whose job involves holding others accountable to their highest potential, I'll be the first to admit – I struggle with this too. It's a constant mental tug-of-war to keep playing to win instead of merely playing not to lose.

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The Corporate Conundrum: A Real-World Example

Let's put this into a work context with a real-life scenario: I recently worked with a C-suite executive at a mid-sized company undergoing significant changes. Given his position, my client had insider knowledge and was savvy enough to read between the lines – the future didn't look promising, and his position might be at risk. We agreed it was time to explore new opportunities. That's when his confidence took a nosedive. "Maybe I should target VP roles," he suggested. "Perhaps a senior director position at a larger company makes sense. Should I step out of leadership and transition into consulting? I think I should cast a wide net."

'Here we go again,' I thought. While I'm never surprised, I'm always disappointed when this happens. Here I am, sitting across from a brilliant, driven, highly accomplished C-suite exec, and just because his employer is taking an unexpected turn, he's suddenly questioning his worth and status.

The Million-Dollar Question: Are You Playing to Win, or Not to Lose?

So, I posed the million-dollar question to him: "Are you playing to WIN? Or are you playing not to lose?" It's a powerful inquiry, one that my own coach frequently asks me.

Now, I'm turning it to you: Are you playing to WIN? Or are you playing not to lose? Let me break it down for you, as I did for him:

• Volunteering to step down a few rungs on a ladder you've already climbed? That's playing not to lose.

• Searching for a lower-level role through a lower-risk job hunt? Playing not to lose.

• Taking a pay cut to avoid competition? Definitely playing not to lose.

Playing not to lose means accepting less than you deserve, which is a guaranteed 'L' by any meaningful measure.

Strategies for Playing to Win in Your Career

So, how can you shift gears and play to win instead? Here's the game plan:

1. Leverage Your Experience: Use your current position as a springboard, not a safety net. For my C-suite client, this means utilizing his executive experience to land an even better position.

2. Aim Higher When Faced with Adversity: If circumstances threaten to bring you down, that's your cue to aim even higher. Don't settle for not losing – kick it up a notch!

3. Define Your Ultimate Goal: What do YOU really want? Consider these possibilities:

   • A job at a larger organization with higher pay, excellent benefits, and more support.

   • A position that fosters growth and prepares you for the next level

   • A seat at the table with increased visibility and a chance to make a name for yourself.

   • An opportunity to make a significant impact and leave a lasting legacy.

   • A role that values your expertise more than your time, allowing you to prioritize life outside of work.

The Entrepreneur's Dilemma: Niching Down vs. Casting a Wide Net

For those running their own businesses, especially in service-based industries, there's another subtle way of playing not to lose – avoiding specialization.

The temptation is to cast a wide net, diluting expertise to appeal to the broadest possible range of clients and services. This might seem like a safe bet, but it's actually playing not to lose. Winning means working with ideal clients to do ideal work.

Let me share another case study: Tia, a former powerhouse executive turned entrepreneur, was eager to sell her expertise as a turnaround specialist for large companies. However, as doubt crept in, she began accepting any consulting contract she could land, regardless of whether it aligned with her core strengths. She quickly became overwhelmed, scattered, and began to resent her business. By the time she sought my help, the damage was done, but she recognized where she had stopped playing to win and started playing not to lose, resulting in a diluted brand and mediocre results.

It took several months, but Tia managed to wrap up work with less-than-ideal clients and refocus her outreach on playing to win. She started attracting the clients she truly wanted and engaging in work that excited her. As a result, her revenue skyrocketed.

This story illustrates a crucial point: Aiming short of your ultimate potential isn't entirely your fault. We've been conditioned to believe that winning isn't everything. While I don't advocate pushing yourself to the point of burnout, most of us underestimate our own abilities and err on the side of caution.

The Hidden Costs of Playing Not to Lose

Playing not to lose might seem easier, but it comes with hidden costs:

1. Erosion of Self-Confidence: Consistently aiming low chips away at your belief in your abilities.

2. Missed Opportunities: You'll never know what you could have achieved if you don't try.

3. Stagnation: Playing it safe often means staying in your comfort zone, which limits growth.

4. Unfulfillment: Operating at a 'not to lose' level can leave you feeling unsatisfied and restless.

Practical Tips for Shifting Your Mindset to Playing to Win

1. Set Ambitious Goals: Challenge yourself to aim higher than you think possible.

2. Embrace Failure as Learning: Reframe setbacks as valuable lessons on the path to success.

3. Surround Yourself with Winners: Your environment influences your mindset. Connect with people who inspire you to aim higher.

4. Continuously Upskill: Invest in your personal and professional development to stay competitive.

5. Celebrate Small Wins: Acknowledge your progress to build momentum and confidence.

6. Visualize Success: Regularly imagine yourself achieving your goals to reinforce your commitment.

7. Take Calculated Risks: Step out of your comfort zone regularly to grow and learn.

The Choice is Yours: Decide to Win

It's up to you. What do you want to WIN? Challenge yourself to go after that. Too many people mistake aiming lower for taking the easier, less risky route. But remember, playing not to lose never truly wins. Whether you're climbing the corporate ladder or building your own empire, the principle remains the same: Play to win. It might be intimidating, it might be challenging, but it's the only way to truly succeed and find fulfillment in your career and life.

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Laura Berman Fortgang is an award-winning coach known internationally as a pioneer in the personal coaching field. Laura is also a best-selling author, sought-after speaker, TV personality (Oprah and All National Morning Shows), corporate spokesperson, interfaith minister and performer. Her TedX talk currently boasts over 2 million views.

She’s known for her unique career clarity “Now What?®” methodology and her A-List Coach Business Mentoring Program.

If you’re running your own service business and want a strong start in the new year, join Laura for a not-to-be-missed intensive for coaches in January, 2025.

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WEDNESDAY DECEMBER 11, 4pPT/7pET: Join us for a later version of Conversationality, a biweekly conversation we hold to talk about news impacting the Future of Work, and with the movers and shakers that help us get there. This week: We speak with habit-formation expert Connie Kwan, who helps us prepare for the Resolution Season with a new approach to self-improvement.

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