Plant Your Flag: A Defining Moment in EntrepreneurSHIP
Why deciding first unlocks better advice from mentors and investors
Let’s say I’m sailing around the world and I discover a beautiful island.
There’s a reef that creates a natural anchorage. A perfect beach. Turtles gliding under crystal-clear water. Sea life everywhere. I drop anchor, take a flag, and head ashore.
I walk the beach. I look around. I choose a spot.
Then, with intention and a little drama, I drive the flagpole deep into the sand. I let go. I step back. The flag snaps in the wind.
It’s a big ginger-colored flag with a stick-figure smiling face on it.
That moment matters.
Because planting the flag is not about claiming the island forever.
It is about deciding, “This is where I’m standing right now.”
This spot is mine.
What Planting the Flag Actually Means
Planting your flag means you have made a decision.
Not the final one. Not the perfect one. Just a decision.
You have chosen a direction. You have picked a spot. You have said, “Based on what I know today, this is what I believe.”
That decision gives shape to your thinking. It gives weight to your words. It turns an idea from a cloud into something grounded.
Now picture the same island, but this time I am holding the flag in my hands.
Same flag. Same beach. But now I am hesitating. Shoulders slumped. Looking around, hoping someone else will tell me where it belongs.
That hesitation sends a signal, whether you intend it to or not.
It says, “I haven’t decided yet. I need you to decide for me.”
Why This Is So Hard Early On
This is hard precisely because you are early.
You do not have all the information. You do not know what you do not know. You are still figuring things out. Keeping the flag in your hands feels safer.
If you never plant it, you cannot be wrong.
You can float ideas. You can hedge. You can say, “We are kind of thinking about…” or “One option might be…”
And maybe the person you are talking to will help you figure out where it goes.
That instinct is understandable.
But it is the wrong move.
When you do this, you are asking someone else to orient themselves inside your uncertainty. Most people cannot do that well, even if they want to.
This is your island. You have spent more time here than anyone else.
Plant First. Then Invite Perspective.
When you are ready to talk with people outside your inner circle, the move is simple.
Plant the flag before you ask for advice.
Show them where it is.
Explain why you planted it there.
Share what you think this spot is best for.
Now the conversation changes.
Instead of “What do you think I should do?”
It becomes “Here is what I am doing. What am I missing?”
That shift creates specificity.
People can react. They can challenge you. They can sharpen your thinking.
And sometimes you will hear something and think, “Ah, that makes total sense.”
That is learning.
And yes, your flag moves.
How This Works With an Investor
With an investor, planting your flag looks like clarity.
You do not say, “We are exploring a few markets.”
You say, “This is the market we are focused on right now, and here is why.”
You do not say, “We could monetize a few different ways.”
You say, “This is the model we believe makes sense at this stage.”
Investors do not expect certainty. They expect decision-making.
A planted flag shows that you can choose, explain, and adjust when needed.
How This Works With a Mentor
With a mentor, planting your flag shows respect for their time.
You are not asking them to imagine your idea from scratch. You are inviting them to respond to a decision you have already made.
You say, “Here is where I am planted, and here is why.”
Now their experience has something to work with.
They can say what they have seen succeed, what they have seen fail, and what they would pressure-test if they were you.
That is mentorship at its best.
How This Works With a Potential Client
With a potential client, planting your flag builds trust.
You are not asking them to design your solution. You are showing them what you believe solves their problem.
Here is what we offer.
Here is who it is for.
Here is the value we think it delivers.
Their feedback becomes real because it is grounded in something concrete.
Even a no becomes useful, because you know exactly what they are reacting to.
Your Island. Your EntrepreneurSHIP.
Here is the part that matters most.
The flag always stays with you.
You can pull it out of the sand.
Move it three inches.
Plant it again.
Each pivot.
Each iteration.
Each version.
When you sail to your island on your EntrepreneurSHIP, you are allowed to choose where you stand.
So plant the flag. In the sand. With intention.
Plant your flag.
Get advice.
Adjust, and re-plant your flag.
Rinse and repeat.
As you build your EntrepreneurSHIP, make decisions, learn, and move the flag at will.
It is your island.