When “Start With Why” Doesn’t Work

Derrick Duplessy
WORTHY
Published in
3 min readFeb 23, 2018

Simon Sinek’s original TED talk has been viewed 15 million times.

He says “start with why.”

I say “start with who.”

It’s become clearer to me that I can’t get excited or scared enough about a big goal that focuses on my own benefit.

My DNA doesn’t map to becoming personally wealthy, healthy or happy.

Personal goals do give me an initial burst of energy, but I find that dies down over time.

Once I start meeting obstacles, I find that my personal “why” isn’t enough to keep me going.

This vicious cycle of initial strong bursts of starting and eventually ending shortly afterward has made me say,

“What’s wrong with me?”

Let me give you an example.

I’m putting together an online conference for entrepreneurs at the margin.

The whole concept is to help master self awareness via interactive exercises and deep dives in our businesses. I am targeting women, minorities, immigrants and artistic startup entrepreneurs.

My “why” is super strong.

One late night at the office, all I could think of was jumping in front of the train the next morning. I needed to release the emotions I had kept inside of me.

It was time to create a safe space where I could be real about my business.

So I organized a rooftop scream.

A whole bunch of startup entrepreneurs showed up. We screamed, shared vulnerabilities, and at the end, had some breakthroughs.

As soon as I shared the plans for my online conference with a very successful mentor, all of my obstacles and weaknesses came to the forefront.

His questions hit me like boulders in the chest.

How are you going to earn the kind of money to make this sustainable or profitable?” Boom.

“You are making the conference free and asking for $500 for a year-long accountability and support group membership? You can’t do much with $500 per person.” Thud.

His questions were completely valid.

It was at that point that my “why” and enthusiasm immediately disappeared in a sea of doubt.

Then the question appeared again: “What’s wrong with me?”

Another way to maintain motivation

Thankfully, I found another way to maintain motivation toward your goals.

  • Picture someone you have helped by tapping into your unique zone of genius.
  • Picture someone who has benefited greatly from observing you struggle through each phase of learning.
  • Picture someone who will follow your example and therefore change the lives of many people.

I did.

There are three real people who fit these descriptions for me.

When I meet that 1st, 2nd or 3rd obstacle, I keep going for them.

Print out their photos, write down their names, or spend some time with the actual people.

Do whatever you can to remind yourself that your contributions to the human experience go beyond your personal benefit.

Sometimes when you “start with who” your drive begins with them and ends with you.

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Derrick Duplessy
WORTHY
Writer for

Sales coach to women, immigrant, and minority entrepreneurs. Follow stories of self-improvement and sales.