Are You Playing The Should Game? - Daily Love with Mastin Kipp

Are You Playing The Should Game?

“Go confidently in the direction of your dreams. Live the life you’ve imagined.”

– Henry David Thoreau

I gave up the should game in 2007. That’s when I quit my finance job in NYC and promised myself I would lose the shoulds and focus on the life I wanted rather than what others thought I should be doing.  Since that decision I moved to Santa Monica, CA (aka paradise for me) and changed my career to do what I love. It wasn’t always easy but the path is definitely easier when you are living from a place of authenticity and truth. Please note, this doesn’t mean everything is perfect — living your truth simply means you are giving yourself the opportunity for personal success.

I let go of the shoulds when I was honest with myself and realized that everybody else’s shoulds weren’t making me happy. It takes courage and strength to listen and honor your inner truth. The mindset shift starts when you become aware that you have choices and these choices impact your life differently. It’s a process, not magic. Regardless of your situation, living your truth and dropping the shoulds is always an option.

Let’s be honest, we all deal with shoulds in our life. They can be big or small….

I should workout regularly.

I should write for two hours every day.

I should drink less.

I should take “that” job because it’s a good company.

I should go to “that” event.

I should get married.

I should have kids.

I should be more social.

I should volunteer.

I should spend more time with my family.

I should go to bed earlier.

I should eat healthier.

Sound familiar? If your answer is yes, you’re not alone. There are lots of things we should do. Should moments do not come from the heart, but rather from external pressures and opinions of others. Having a should moment is nothing special. The shift happens when you become aware of a should in your life and then change how you respond.

The next time you have a should moment, ask yourself these six questions to decide your next steps:

1. Does the “should” align with your values, your heart, and what you want or someone else?

2. Why is the “should” important?

3. Are you willing to make the “should” a priority in your life?

4. What will happen if you dump this “should?”

5. Is this “should” helping you or preventing you from moving forward in your life?

6. Does the “should” make you happy?

How you respond and the actions you take are your choice.

Top 1% Bottom Line: My best advice: honor yourself and shift your perspective from focusing on what you should do to focusing on what YOU want to do from your heart. Use your internal compass rather than society’s external one. To live you best life, you have to choose to honor your dreams rather than your shoulds.

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Alissa is a Professional Life Coach, motivational speaker, and author of “Living in Your Top 1%: Nine Essential Rituals to Achieve Your Ultimate Life Goals” available on . To learn more about coaching with Alissa and to take the Living in Your Top 1% quiz, please visit or, or

Please join Alissa in her 4-week online class on Living in Your Top 1%  and achieving your goals starting this September.