Winning the Game: How To Shift from “Should I” to “I Can” in Your Career

What Table Tennis Teaches Us About Speaking Up, Taking Risks, and Advancing in Your Career

My daughter taking the shot with a high-risk move

My 11-year-old daughter plays table tennis competitively and competed in the US Open and US Nationals. As I watch my daughter compete, I am constantly fascinated by her mindset. One of the hardest decisions in table tennis is choosing whether to loop an incoming ball with backspin—a high-risk but potentially game-winning move—or to play it safe and push the ball back defensively. It is high stakes and requires a split-second assessment of skill, position, and confidence.

For my daughter, the decision is simple. She watched the ball and asked herself: “Can I do it?” If she believes she can loop it back, she does it. There is no overthinking, no second-guessing, just an instinctual execution of skill and confidence.

In contrast, my husband, who also plays table tennis, has a different decision-making process. When the opportunity to loop arises, he asked himself: “Should I do it?” He hesitates, thinking about the potential of making an error, and in that brief moment of doubt, the opportunity to win the point slips away.

Watching this dynamic unfold made me reflect on something far deeper than table tennis. It mirrors how many of us, particularly Asian women professionals, navigate opportunities in our careers.

The "Should I" Mentality: A Product of Cultural Conditioning

From an early age, many Asian women are raised with deeply ingrained values that emphasize humility, respect for authority, and not taking up too much space. We are taught to consider whether we have something truly valuable to contribute before speaking up, to weigh whether we are overstepping before asserting ourselves, and to ensure we are deserving before going after opportunities.

This cultural conditioning results in a persistent inner dialogue of shoulds:

• Should I speak up in this meeting?

  
  

• Should I ask for that promotion?

  
  

• Should I advocate for myself?

  
  

In many cases, these "shoulds" do not serve us. Instead, they trap us in a cycle of hesitation, causing us to miss opportunities that were well within our reach, just like my husband missing the chance to execute a game-winning loop. In fact, the higher the stakes, the more likely this “Should I?” paralysis sets in.

The Cost of “Should I” in the Workplace

The “Should I” mindset manifests in different ways in the professional world. How many times have you been in a meeting where you had an idea but held back, only to hear someone else share the same thought moments later and receive recognition for it? How often have you seen a less qualified colleague get a promotion because they confidently put themselves forward while you debated whether you were truly ready?

“Should I” mindset costs us in tangible ways:

• Missed promotions: While we weigh whether we are 100% qualified, someone else is already in the process of negotiating their next step.

  
  

• Lower visibility: If we are not actively contributing, we are less likely to be seen as leaders or innovators.

  
  

• Fewer opportunities: By waiting until we feel completely prepared, we often miss out on stretch assignments that could accelerate our growth.

  
  

Just like in table tennis, career success often comes down to split-second decisions. The women who get ahead are not necessarily the smartest or most skilled; they are the ones who believe they can and take action.

When "Should I" is Necessary

While overthinking and hesitation can hold us back, there are times when asking "Should I" is the right approach. Strategic thinking, ethical considerations, and long-term planning all benefit from thoughtful deliberation. Asking "Should I" can be helpful when:

• Assessing risks and long-term consequences: Certain decisions, such as changing careers, making financial investments, or taking on a leadership role, require careful evaluation.

  
  

• Considering ethical and integrity concerns: When faced with decisions that impact others, it is crucial to reflect on what is right and fair.

  
  

• Formulating a strong strategy: Sometimes, pausing to strategize leads to better execution and a better plan.

  
  

The problem arises when we let "Should I" turn into analysis paralysis—overthinking to the point where we spiral into inaction and miss opportunities we are fully capable of seizing. The key is to differentiate between productive contemplation and hesitation driven by self-doubt.

Shifting to an "I Can" Mindset

So how do we shift from an "Should I" mindset to an "I Can" mindset?

1. Reframe The Risk

Instead of focusing on the potential negative outcomes (What if I fail? What if I embarrass myself?), shift your perspective to what you stand to gain. Ask yourself:

• What’s the best that could happen?

  
  

• What’s the worst that could happen?

  
  

• What’s the likely outcome if I take this action?

  
  

Often, you will find that the worst-case scenario is not as catastrophic as your mind makes it out to be, and the best-case scenario is well worth the risk.

2. Act Before Doubt Creeps In

Indecision is often the result of overthinking. When you find yourself hesitating and thinking about “shoulds”, challenge yourself to act quickly before self-doubt has a chance to take over. This could mean raising your hand in a meeting before you have the chance to talk yourself out of it or applying for a job the moment you see it rather than debating whether you’re ready.

3. Be OK With Imperfect

Many Asian women struggle with perfectionism, feeling that they must be over-prepared before taking action. But in table tennis, as in life, waiting for the perfect opportunity often means missing the shot altogether. Instead, aim for progress, not perfection. Remind yourself that growth comes from taking action, even if it’s not flawless.

4. Embrace "I Can" Thinking

Before executing a move, my daughter does not ask herself whether she should—she simply assesses whether she can. If she believes she can, she acts. Adopting this mindset in your career means training yourself to think:

• Can I contribute something valuable? If yes, speak up.

  
  

• Can I learn and grow in this role? If yes, apply.

  
  

• Can I handle this challenge with effort and support? If yes, take it on.

  
  

By shifting from "Should I" to "I Can," we reduce hesitation and increase our chances of success.

Final Thoughts: Trusting Your Instincts

Watching my daughter play table tennis has been a powerful reminder that confidence and decisiveness are key to winning, both in sports and in life. The women who get ahead are not necessarily the most qualified, but they are the ones who take action when the opportunity presents itself.

If we can cultivate a more childlike mindset—one that assesses capability rather than getting stuck in shoulds—we may find ourselves landing far more of the shots we take.

So the next time you find yourself debating whether you should do something, pause and ask yourself a different question:

Can I?

If the answer is yes, go for it.

P.S.: This article was first published at deniseang.substack.com/p/icanmindset. Subscribe at deniseang.substack.com for free to receive new posts and support my work.