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When Is the Best Time to Start Something New? (#208)

TCL Illustration 208

The Confident Leader

BOOST YOUR LEADERSHIP IN UNCERTAIN TIMES


Four years ago this week, I started a weekly newsletter. Mistakenly, I had refrained from launching it for three, maybe four, years. I labored under a series of misperceptions many leaders experience. 

“The only thing worse than starting something and failing is not starting something.”

―  Seth Godin (teacher and author)

This Week’s Edition

Happy 4th birthday – The Confident Leader newsletter!!! Check out the first edition here.  

Are you failing to start something? Is your failure to “go” consuming vast mental cycles? Here is how to think about your situation.

Clarify Your Thinking


Just before sitting down to write this week’s newsletter, I joined a virtual call with a group of leaders in our community. Before the call started, one leader made a special note to re-introduce herself. 

She proceeded to thank me for writing The Confident Leader every week, emphasizing: 

  • The impact of the content
  • The timeliness of the 4:00 p.m. Sunday delivery and 
  • Her “Robin’s Leadership Tips” folder where she archives the emails.


To say I was honored is an understatement. Wow! 


Her input was timely, as I was already set to write about how leaders fail to start things. Initially, I hesitated to write a weekly newsletter believing that everyone subscribes to weekly newsletters, but most people rarely read any of them.

In contemplating such a weekly endeavor, my objective was to support people through the challenging journey of leadership. I did not want to spam them with another newsletter they felt obligated to read but never found time to consume. 

After interviewing 50 leaders, I found out I was wrong. The demand for leadership guidance was high, and they indicated they would commit five minutes a week to read it if it was convenient, informative, practical, and easily applicable. 

My initial hesitation did not account for the demand for the content OR the potential impact as evidenced by the gracious leader who thanked me on that call. 

Let this newsletter’s topic be the catalyst for you to maximize your influence to start something new by overcoming the natural hesitations leaders experience when contemplating jumping into something new. 

Thoughts Lead to Actions

Leaders fail to start things for many reasons:

The window of opportunity has passed. The door is closed.

  1. Someone has already done it.
  2. It must be perfect to launch it.
  3. Not enough time to dedicate to it.
  4. The competition is too far ahead. We’ll never catch up.
  5. The window of opportunity has passed. The door is closed.

Here is my coaching response to each of these hesitations/misperceptions:

  1. Someone has already done it.
  2. It must be perfect to launch it.
    • No, it doesn’t.
    • Ship it and iterate based on market feedback.
  3. Not enough time to dedicate to it.
    • It is either a priority or it’s not.
    • You make time for things that are a priority.
  4. The competition is too far ahead. We’ll never catch up.
    • It’s not a competition regarding time.
    • Your creativity and innovation will win the day.
  5. The window of opportunity has passed. The door is closed.
    • No, it hasn’t. There is always time for greatness.
    • Kick that door open. Make it happen.


In a coaching session the other day, a smart savvy CEO said to me, “Robin, we should have started it four years ago.” 

“How do you think about that now?” I asked.

He offered a brilliant response, “The best time to start the project was four years ago. The second-best time to start the project is now.”

Boost Your Performance

So, 208 editions later with a sizable audience and readership stats that out-pace the industry norm, I am proud of the body of work we have published each week for four years. More importantly, I am honored you would spend 5 minutes a week reading what we have curated for you. 

Watch this week’s video to be encouraged about how to move beyond hesitation and start something new.

What’s Your Opinion?


What is something you are struggling to start? Share it with me at robin.pou@robinpou.com.

If you are going to be a leader, you might as well be a good one. Don’t let doubt count you out. Have a confident week!

Robin Pou, Chief Advisor and Strategist

We live to make bad leadership extinct so forward this newsletter to others who strive to be confident leaders. 

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What is “The Confident Leader”?

During the Covid-19 Pandemic, I began a video series called “Panic or Plan?” It was designed to equip leaders to navigate the doubt they experienced and to rise in the confidence they needed to lead during turbulent times. It took off. I then started this newsletter to equip leaders in the same fashion each week for the doubt that crashes across the bow of their leaderSHIP.