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Which weakness is your greatest asset?

This question was posed at a dinner, an exercise in framing.

Our mind is brilliant at creating new definitions, but they’re not always to our advantage — especially when it comes to self. Thoughts can easily turn negative, centering on weakness and deficient. Doubt can color even the most promising of opportunities.

Over any length of time, a constant may acquire a new meaning. For instance, that particular quirk that first drew you to a lover may become irritating and tiresome. The reason you accepted the job in the first place has now become a mundane task. Did the person change? Did the job change? Possibly, but most often our perspective has transformed.

When you can start pinpointing these adjustments in thought, you can use them to your advantage.

Try viewing a particular weakness as a strength; then play the reserve to see how a strength might pose a weakness. Such mind flexibility can spill creative power into design, production, relationships, your work.

The rebellion of questions

As a school girl, I found myself in detention for asking questions. I was threatened to be kicked out of academic programs for challenging authority. You were permitted one question after your name was called, and superiors always had the last word. Too many questions meant insolence, disrespect and delinquency.

The problem is the greatest inventions arise from asking questions. When we dare to ask why, archaic systems can improve and new ways of doing things emerge.

Questions can take courage, and perseverance is sometimes needed to find the right answers. Honest leadership will welcome such speculation and discussion.

Inconvenience yourself.

New Yorkers and scheduling is borderline ridiculous. I spend more time than I care to admit orchestrating calendars, slotting calls, finding common days for in-person meetings. While there are plenty of automated tools to streamline this process, I’ve found that each person’s needs and requests are very different, and the act of scheduling itself can reveal underlying issues. Each day I’m forced to reassess my priorities and make decisions accordingly.

Yet with all of this scheduling and compartmentalizing, is there space for magic?

We spend so much time making sure things go according to plan. If something falls through the cracks, it’s a fault in the system — our system. The slightest tip of the scale can throw off an entire day, delaying planned meetings and cramping scheduled “me” time. Minor inconveniences (a late train, a forgotten document) suddenly become huge problems.

Ever pause to evaluate whether your intense regimen is adding to your anxiety rather than helping? Consider your definition of inconvenience and flirt with alternatives.

What would happen if you intentionally take the later train, let someone step in front of you, choose the slowest checkout line?


I stopped trying.

I’m still trying to wrap my head around this, as it is completely counterintuitive to me.

The moment I stopped trying and quit everything is when things became clear.

I’m not saying I don’t have challenges and that life is always easy, but my day-to-day isn’t filled with as much strife. There’s less struggle as I move about the world.

I think of how difficult momentum seemed in the past. Once I landed back into the grooves of authenticity, people began to take notice. It’s then that I raised money for a few scholarships, attracted over 30k views on Medium, and found myself speaking on HuffPost (look at 13:30).

I’m not doing anything drastically different. I’m simply living my life by letting passion lead the way.

I’m wondering if this principle has worked for you, too.

What if WORKING HARD didn’t equal SUCCESS? What if you stepped out of the car, allowed your excitement to take the wheel, and put frustration, anxiety, and white-knuckle-decision-making in the backseat? What if by relaxing, you allowed your “best self” to emerge?

If you’re having to work really hard to make something right, I’m wondering if it’s right in the first place.

Tweet me. I want to hear what you think.

Honoring the pivot

A pivot can be one of the most powerful moves on the basketball court. Performed correctly, one step can leave an opponent grasping at air, move a player out of a sticky situation, and provide a better perspective of the game.
The move is also recognized as a strategy for entrepreneurs, transforming a borderline idea into a championed achievement (think PayPal, Instagram, Groupon, Nintendo).
In relationships, in business, in career, true success often requires a reroute — or several. Flexibility in thought can mean the difference between mediocrity and a grand slam; however, switching gears isn’t always easy. Anyone who has “abandoned ship” knows ego and pride are at stake. It takes the hearty soul to admit error and take necessary steps to get back on track.
Reframing the abandonment of past work into an advantageous step can pave the way towards long-term gains and a promising future. Course corrections don’t necessarily mean failure. In fact, intentional pivots can lead to a stronger, more resilient, more creative return.
Questions to ask before making a pivot:

  • What is driving the move? Is it hard facts, instinct, boredom, temporary circumstance?
  • If “I win,” what happens? What does success look like to my business, my relationship, my product, myself?
  • Am I making the kind of progress I’d like? Is subpar acceptable or am I looking to go the distance?
  • Am I afraid of failing? Of admitting I’m wrong?
  • What am I holding onto and why?

Big visions require determination and gumption. Inevitably, uncertainly accompanies change. The trick is to remain grounded while altering your course, keeping one foot rooted in place while the other finds new ground.
Start something, figure out what isn’t working, and use what is to move forward. In the end, you won’t know until you try.