When Did Hard Start Feeling Like Failing? (#302)
The Confident Leader
BOOST YOUR LEADERSHIP IN UNCERTAIN TIMES
“Our numbers aren’t great. The team is tired. I might need to pull the plug.”
“If you don’t know where you are going, you will end up someplace else.” – Yogi Berra
This Week’s Edition
Leadership is hard. We shouldn’t make it harder by not defining success and letting our feelings dictate in the moment.
This edition walks through how to define the win before you start, so when the work gets hard, you can have an objective measurement.
Clarify Your Thinking
here may be a sentence playing in your head about something you started few months ago.
This isn’t working. Things aren’t going the way I expected. Why aren’t we further along?
That voice in your head might be building a case for declaring the effort a failure. Declaring you a failure.
On Sunday morning before the final round at the Masters golf tournament, Rory McIlroy was frustrated that he had blown a record lead the day before. His caddy stopped him cold.
He said, “On Thursday you said if you were in the final pairing on Sunday that would be a win. Here you are in the final pairing.”
Because Rory had defined success before he started the tournament, his caddy was able to pull him out of feeling defeated in the middle of the “process.”
Don’t let your mind play tricks on you.
Old Thinking: If it feels this hard at this stage, it is probably not working.
New Thinking: Hard is the work. The mark I set is what tells me whether it is working.

Thoughts Lead to Actions
Think about it this way, as smart and experienced as we are, our ability to gauge how difficult something will be or when we will achieve success by a certain time is imprecise at best – definitely not certain.
Define success from the outset and the milestones of success along the way.
Step 1. Name the initiative you may be doubting.
Step 2. Pull up what you said success would look like when you launched it. The plan. The internal memo. The board slide. Whatever you have.
Step 3. If nothing exists, write what progress should look like right now. At sixty days. At six months. At twelve months. Specific. Numbered. Dated.
Step 4. Define success not by the outcome, but by your effort.
- Complete the plan
- Assemble the team
- Launch the initiative
- Conduct bi-monthly sprint check-ins
- Complete milestone 1 by ____
Difficulty is part of the price. Failing is missing a mark you set.
Hard is the price. Failing is the mark you didn’t set.
Boost Your Performance
You can feel crummy about what you’ve accomplished so far. Sadly, that would be a waste. You are in the game doing things. Don’t draw the line of success too early. Give yourself credit. Define success a different way. Watch this week’s video to learn how.
What’s Your Opinion?
What’s one recurring thought you’ve had to reframe in your leadership journey? Send me a note: 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.